Overview
The Loop is the central business district of Chicago, bounded by the Chicago River to the north and west, Harrison Street to the south, and Lake Michigan to the east. It contains the tallest members of Chicago's skyline and much of the city's finest architecture, holding within them much of the city's working stiffs; for visitors, it also has the glitzy downtown theater district, and the biggest annual music festivals.
31 sights · 16 things to do · 10 places to eat · 7 bars & cafés · 13 places to stay
Updated from Wikivoyage on 1 October 2026 · Something wrong or missing? Improve it on Wikivoyage
Best things about Loop
Art Institute of Chicago
One of the premier museums in the U.S. — and with the opening of the sensational new Modern Wing, it's one of the largest, too. Set aside a whole day and arrive early! Iconic pieces on display include "American Gothic" b…
Federal Reserve Bank Money Museum
Currency wonks can study various denominations and practice counterfeit detections. Guided tours every day at 1PM.
Museum of Contemporary Photography
A stimulating and innovative forum for the collection, creation, and examination of contemporary image-making in its camera tradition and in its expanded vocabulary of digital processes. Affiliated with Columbia College …
Spertus Institute
A museum dedicated to Jewish culture and learning, in a dramatic, newly remodeled facility. There's a children's center, which promises hands-on exhibits, and a regular slate of exhibits and events on Jewish art, culture…
Grant Park
Right at the center of Chicago, this has been a park space for almost the entire history of the city. Most citywide events and festivals (see below) are held in Grant Park and the Petrillo Bandshell. The centerpiece of t…
Millennium Park
Long before it opened, Millennium Park had become notorious for delays and cost-overruns, missing its titular date by a wide margin. However, when it was finally finished in 2004, the biggest shock of all came when it tu…
Plan your trip
Best time to visit & weather
Most comfortable: May–Oct. Summer highs reach about 85°F; winter lows dip to about 20°F. Cold months (Jan, Feb, Dec) can bring snow and ice; check road conditions. Wettest: May and Jun. (climate data from nearby Chicago)
Blue bars: average daily high and low (°F). Purple columns: average monthly rain and melted snow (inches).
Getting there
- From you: to see whether to drive or fly, and how long it takes.
- MDW Chicago Midway International Airport, Chicago — 9 mi away (major hub). Directions
- ORD Chicago O'Hare International Airport, Chicago — 15 mi away (major hub). Directions
In Chicago, all tracks lead to the Loop. The astonishing, creaky elevated tracks of the CTA come in from virtually every corner of the city, and through the smoother commuter rails of Metra and Amtrak, from the rest of the Chicagoland area and the country beyond.
Full “Get in” guide ↓Budget & where to stay
- Places to stay listed here: about $29–$259 a night (typical $200), from 13 listed prices.
- Typical meal: about $10 per person at listed restaurants.
- Estimated daily budget per person (room, two meals, local transport and an activity): budget ~$60, mid-range ~$260, comfortable ~$380.
Options are grouped as Budget, Mid-range, Splurge in the Sleep guide ↓.
Sample 3-day itinerary
Day 1
- Morning Art Institute of Chicago, Chicago Architecture Foundation, The Fine Arts Building
- Lunch Osaka Express
- Afternoon Museum of Contemporary Photography, Spertus Institute
- Dinner Russian Tea Time
- Evening Exchequer Restaurant & Pub
Day 2
- Morning Chicago Architecture Center, Carbide and Carbon Building, Vietnam Veterans Memorial
- Lunch Pizano's
- Afternoon Chicago Cultural Center, Millennium Park
- Dinner Garrett Popcorn
- Evening Emerald Loop
Day 3
- Morning Federal Reserve Bank Money Museum, The Rookery, 311 S Wacker Dr
- Lunch Luke's Italian Beef
- Afternoon The Skydeck, The Gage Group
- Dinner Cellars Market
- Evening Elephant & Castle
Stops are grouped by area so each day needs little backtracking. Check opening hours before you go.
Food for you
It's easy to find cheap food during the day — this is where most of Chicago works, so this is where most of Chicago eats lunch. However, most of those places close when the work day ends, so it's more difficult to keep costs down at night, when it's gourmet or bust. There's a sizable food court at Ogilvie/Northwestern Station (Canal and Madison) if you're on your way in or out of town.
In general, it's wise to avoid the restaurants right by major tourist attractions (e.g., the Art Institute, Millennium Park, etc.), as the quality of service and food tends to improve with distance from these one-time-visitor hot spots. There are some gems in the Loop, but you should also consider a quick cab ride west to one of downtown Chicago's premiere dining strips in Greektown.
Cuisine (tap to filter)
What to ask about, for your diet
Diet labels come from each listing's description and cuisine; “likely” means the cuisine usually has good choices, not a promise. Check with the restaurant. Open the food finder
Photos
Map
Every listing with a location. Tap a pin for its Google Maps link.
Understand
The Loop is the center of Chicago and without a doubt the most iconic section of the city. If you've never been to Chicago, begin here. Whether on an official architecture cruise along the Chicago River, or an unofficial one along the veritable river of elevated trains, only the most jaded could shake that feeling of awe at the canyons of LaSalle and the cliffs of Michigan Avenue. Moreover, the Loop contains a world-class collection of public art, in the form of huge street-side statues by many of the 20th century's most famous sculptors.
The Loop initially got its name from the looping route of streetcars that served as the transit hub of early downtown Chicago, but the name has come to be defined by the modern era's looping route of elevated train tracks, serving seven CTA lines, which ensures the continued prominence of the area as the center of Chicago's working world. Despite the gradual northwards shift in the city's center of gravity and the centrifugal force of suburbanization, all tracks lead here and accordingly the Loop remains the most attractive location in the city for major businesses, and for most of the city's visitors.
On a work day, you won't have to walk around long to realize you are at the center of things. Busy-looking people in suits hurry in and out of tall buildings, major theaters hawk their big-name productions on neon marquees, and every block has a reminder of a scene from Ferris Bueller's Day Off, The Dark Knight, or another Chicago movie. The Loop is the United States' second largest central business district, owing largely to its historical position as the financial hub for the Midwest and the modern world's biggest futures market. Many of those suits walking by (as you stand and gape) work for one of four major financial exchanges, the largest of which is the 2007 merger between the Merc (the Chicago Mercantile Exchange) and the Chicago Board of Trade. The CBoT was the world's first modern futures exchange, set up principally to serve the needs of the Midwest agriculture market, and along with the other major exchanges in Chicago, pioneered the massive modern derivatives industry. Not too long ago the streets sagged under the enormous profits, as the Merc and CBoT traded over nine million contracts daily, worth over $4.2 trillion. Today's economic outlook has soured, though, and the ranks of those suits have been thinned by layoffs, golden parachuting, and other extreme sports.
Forget work, though — the fun of Millennium Park and the festivals of Grant Park are here, and the Art Institute is fantastic. A walk by the Sears Tower and the Chicago Board of Trade is a requisite Chicago experience, but the Loop is eclipsed by other parts of the city in terms of nightlife, shopping, and dining. Being as it is first and foremost a business district, things shut down when the commuters punch the clock and hop on the train, so even if you have a room at one of the Loop's classic old hotels, don't plan to spend all of your time here — even though your camera will likely receive no finer work-out anywhere else.
Get in
By train
In Chicago, all tracks lead to the Loop. The astonishing, creaky elevated tracks of the CTA come in from virtually every corner of the city, and through the smoother commuter rails of Metra and Amtrak, from the rest of the Chicagoland area and the country beyond.
Two CTA lines run through downtown Chicago as subway lines, and do not loop around Chicago's downtown area. Both travel out of the Loop area in two directions:
The CTA Red Line runs along the lakefront neighborhoods on both the North and South sides of the city. From the north, it begins in Rogers Park, and from the south, it begins on the Far Southeast Side. In the Loop, it runs as a subway under State Street, with key stops at Lake, Monroe, and Jackson.
The Blue Line arrives at downtown from the northwest, beginning at O'Hare International Airport on the Far Northwest Side, and from the west, beginning in the suburb of Forest Park and traveling through the West Side (including a stop at UIC's campus). The Blue Line also runs underground through the Loop along Dearborn, offering free connections with the Red Line at Jackson.
Five other CTA lines (Brown, Purple, Green, Pink, and Orange) ride the elevated tracks that travel through the Loop in, well, a loop. All except the Green Line enter and leave the Loop in only one direction:
The Brown Line also comes in from the north and northwest, though it runs east of the Blue Line, beginning in North Lincoln and running closer to the lakefront starting in Lakeview.
The Purple Line, which runs downtown only during peak hours, comes in from the north, beginning in suburban Wilmette.
The Green Line comes in from Oak Park and the West Side to the west and Bronzeville to the South. It is the only one of these five lines that enters and leaves the Loop in two different directions.
The Pink Line comes in from suburban Cicero and the West Side, including Pilsen.
The Orange Line arrives downtown from the Southwest Side, where it begins at Midway Airport.
Transfers between all six of these lines are possible in the Loop. The CTA's only line not served by the loop is the Yellow Line, a shuttle between suburban Skokie and the Red and Purple Lines in Rogers Park.
From the suburbs, Metra commuter trains arrive at Union Station (Canal St and Jackson Blvd), Ogilvie/Northwestern Station (Canal St and Madison St), LaSalle Street Station (LaSalle St and Congress Pkwy), and Millennium Station (Michigan Ave between South Water St and Randolph St), all of which are within easy walking distance of the Loop and the CTA elevated lines. From beyond the suburbs, Amtrak connections from across the region and the country arrive at Union Station.
By bus
Several dozen CTA bus lines travel through the Loop, but given the traffic, only a few will be useful for visitors traveling from the rest of the city.
- 20 Madison heads west down Madison St, ideal for reaching the United Center on the Near West Side.
- 147 Express runs through the Near North before running express on Lake Shore Drive to Rogers Park.
By car
Do not drive to the Loop if at all possible. It is not a very automobile-friendly place, and traffic is abysmal. You're unlikely to relish the memory of having driven through the Loop, but plenty of people do it every day. Michigan Avenue offers a scenic — if slow as mud — trawl through the east end of the Loop, marking the end of the commercial area and the beginning of the parkland along the lake. Lake Shore Drive provides an equally lovely — and equally slow — route through the Loop. I-90 lets out at Jackson Blvd, at the west end of the Loop.
If you do come by car, there are four underground parking garages near Grant Park and Millennium Park. Rates vary by garage and are more expensive for special events, but the East Monroe garage (near Millennium Park) is the cheapest ($13 up to 12 hours, $16 12–24 hours).
See
Itineraries
- The Loop Art Tour will take you down the Loop's main roads through Millennium Park and the downtown city plazas, all in the name of art.
- Along the Magnificent Mile is a one day and night itinerary that connects the Loop with the Near North for shopping, food, skyscrapers, parks, and amazing views of Chicago from high and low.
Museums and galleries
See Art Institute of Chicago
One of the premier museums in the U.S. — and with the opening of the sensational new Modern Wing, it's one of the largest, too. Set aside a whole day and arrive early! Iconic pieces on display include "American Gothic" by Grant Wood (the stoic farm couple), "Nighthawks" by Edward Hopper (the late-night diner), Georges Seurat's pointillist masterpiece "Sunday Afternoon on the Island of La Grande Jatte". The Art Institute also boasts the world's best collection of Impressionist painting outside of France. But there's a lot more to discover, including a great selection of early 20th-century painting, architecture, and photography, as well as archaeological finds covering 5,000 years of art and cultural history.
See Spertus Institute
A museum dedicated to Jewish culture and learning, in a dramatic, newly remodeled facility. There's a children's center, which promises hands-on exhibits, and a regular slate of exhibits and events on Jewish art, culture, and social issues, with points given for range that includes the Israeli-Palestinian Comedy Tour and lectures on Jewish-Catholic relations. The Asher Library, also on-site, keeps different hours (Su-Th afternoons).
Parks and monuments
See Grant Park
Right at the center of Chicago, this has been a park space for almost the entire history of the city. Most citywide events and festivals (see below) are held in Grant Park and the Petrillo Bandshell. The centerpiece of the park is Buckingham Fountain (10AM-11PM), which is sometimes accompanied by music and colored lights (8-11PM, May-Sep). There are also tennis courts, softball fields, and a walking trail near the lake. Millennium Park is to the north and the Museum Campus is to the south, so there is a large area to wander.
See Millennium Park
Long before it opened, Millennium Park had become notorious for delays and cost-overruns, missing its titular date by a wide margin. However, when it was finally finished in 2004, the biggest shock of all came when it turned out to be quite nice. Aside from plenty of grass and open space, it has modern sculptures in steel and glass, including Chicago's newest must-photo for visitors, The Bean (properly known as Cloud Gate), and the Frank Gehry-designed Pritzker Pavilion for outdoor concerts. Kids will love getting wet in the Crown Fountain (mid-April to the end of summer) at Michigan and Monroe, in which the giant projected faces of Chicago residents spit water into a shallow reflecting pool where everyone is welcome to splash around. Look for tents offering guides to the park near the entrances at Randolph and/or Washington. From mid-November to early March there is an ice skating rink open to the public (weather permitting) on Michigan Avenue between Washington and Madison Streets. The McCormick Tribune Ice Rink opens at noon on weekdays and 10AM on Saturdays and Sundays with free admission (skate rental is $12, locker rental is $1).
See Vietnam Veterans Memorial
Designed in coordination with the National Vietnam Veterans Art Museum in the Near South, this waterfront plaza features a timeline from the war, a list of Illinois veterans who were killed in action, and a nice vantage point toward a few iconic buildings down the river. After crossing over the river from the Near North, turn and take the stairs down to the lower level.
Visitor centers
See Chicago Cultural Center
Built in 1897 as Chicago's first public library, the building now houses the city's Visitor Information Center, galleries, and exhibit halls. Worth a visit to see the beautiful interior — the ceiling of Preston Bradley Hall includes a 38-foot Tiffany glass dome, and the north wing includes the impressive Grand Army of the Republic Rotunda. Of late, amid various city-approved art and music events, some surprisingly good theater has been performed here.
See The Skydeck
Once the tallest building in the world, the Sears Tower (officially renamed the Willis Tower) now has to settle for second-highest in the Americas alone, behind New York City's One World Trade Center (and even those are after a semantic battle with Toronto and the CN Tower). The Hancock Observatory (see Near North) has a nicer view of the city, but the Sears Tower offers an incredible view of its own from "The Ledge", which lets visitors walk out in a transparent balcony suspended 1,353 feet above the street. To avoid the crowds, visit after 4PM.
Architecture
Most of these buildings are not fully open to the public, although some may be accessible through tours by the Chicago Architecture Foundation. Security procedures will, of course, vary. For some, you won't be able to make it past the lobby; for others, a purposeful stride can take you anywhere you want to go.
See Chicago Architecture Foundation
Runs numerous river cruises and themed architecture walks covering the Loop and other parts of the city, with offerings suitable for general audiences and people with specific interests. There are some small, informative exhibits inside their 224 S Michigan headquarters and a gift shop. Walking tours are usually $15, $12 for students/seniors.
Buildings
Some of Chicago's greatest buildings, like the Chicago Board of Trade and the Auditorium Theatre, have major attractions inside to draw the appreciative eyes of visitors. Many other masterworks, though, don't have a specific attraction associated with them, so you'll have to seek them out.
See Carbide and Carbon Building (Burnham Brothers, 1929)
A beautiful Art Deco tower covered in dark green terra cotta and adorned with a gold terra cotta leaf at the pinnacle. It is rumored that the architects (the sons of city planner Daniel Burnham) intended the building to resemble a bottle of champagne. It's in great condition today, and can be visited through one of the bars in the lobby of the hotel inside.
See Federal Center (van der Rohe, 1964/1975)
This plaza includes Mies' Dirksen Federal Building and Kluczynski Federal Building (built eleven years apart), with a low-rise post office enveloped in their sleek black lines. But the buildings are not quite as famous as the gigantic red constructivist flamingo statue by Alexander Calder in the plaza in front of the post office. An adventurous raccoon may have set a raccoon world climbing record by reaching the scaffolding on the 36th floor in 2006.
See The Fine Arts Building (Beman, 1885)
A Michigan Avenue charmer built in 1884-85 whose worn stone walls looks even older. Even though few artists could afford to keep studios on Michigan Avenue these days, it still has a creative air, thanks to the fanciful carvings on the walls.
See The Gage Group (Sullivan/Holabird & Roche, 1898-1902)
Louis Sullivan designed the northernmost (18) of the three buildings here, and the team of Holabird & Roche added the next two (24 & 30). The roots of Mies-style modernism are easily apparent in the immaculate proportions here, although Sullivan's piers overflow like water-pipes with ornament at the top, and Holabird & Roche's two make an interesting contrast with the master.
See The Haskell Building (Van Osdel, 1877)
Designed by John Mills van Osdel, the city's first accredited architect after the Chicago Fire, this four-story building is one of the oldest in the Loop. The two bottom floors were remodeled by Louis Sullivan in 1896, adding some interesting cast-iron designs for its use as a department store.
See The Jewelers' Building (Adler & Sullivan, 1882)
Louis Sullivan was only a draftsman at the time this was built, but there are some interesting designs nestled into expressive façade and the classic, powerful masonry walls.
See Marquette Building (Holabird & Roche, 1894)
It's partially obscured by renovations, but this first-wave skyscraper still makes an immediate contrast with the modern Federal Center across the street. The lobby is decorated with Tiffany mosaics and bronze carvings of Pere Marquette, an early French explorer. There is plenty of first-floor retail to allow trips inside.
See Monadnock Building (Burnham & Root, 1891)
Named appropriately for a mountain in New Hampshire, the Monadnock was the last tall building to be supported by its own walls (not a metal frame, although the 1893 addition by Holabird & Roche does use one). It's a masterpiece of simplicity and power in form. The block-long hallway that serves as a lobby has incredible ambiance: it's always kept at a level of brightness that suggests gas lamps, and the small stores on the first floor (a coffee shop, a shoe-shine, a restaurant) are all turn-of-the-century tile-and-polish.
See The Reliance Building (Root/Atwood, 1890/1895)
A then-unprecedented amount of glass was used in this early skyscraper, bewildering a public still used to masonry walls. Note the difference between the first two floors and the ones above: hold-outs among the previous building's tenants forced developers to build the foundation and the first two floors under the top three floors from the old building, and then knock off the top three when their leases had expired. It was restored when it became the Hotel Burnham (see below) in 1999, and can be explored with a stop at the Atwood Cafe (also below).
See The Rookery (Burnham & Root, 1888)
The Rookery is gorgeous to the point of absurdity, with delight to be found in details in the rustic lower walls and the triumphant upper walls. (Note the helpful street names carved in the corners.) Named for pigeons' habit of roosting in the then-new skyscrapers, this was the first Loop building to be granted preservation status in 1972. The lobby was remodeled in 1907 by enfant terrible Frank Lloyd Wright, adding his own touch to the interior.
Skyline
Other buildings, however, you will not need to seek out — Chicago's tallest skyscrapers are attractions for anyone who happens to look up! For more information about the many buildings that make up the skyline and where best to view them, be sure to check out the Chicago skyline guide.
See 311 S Wacker Dr
961 ft. For a time this was the tallest building in the world without an official name, although locals know exactly what to call it: The White Castle Building. It is distinctive for its "crown," which is brightly illuminated at night. If you are nearby, head into its lobby to see its enormous indoor garden and fountain.
See Aon Center
1136 ft. Built as the Standard Oil Building, the Aon Center is America's sixth tallest building from base to roof, after the Empire State Building in New York City, and fifteenth tallest in the world by architectural detail. It was built in 1972 by architect Edward Stone and initially was faced with marble, but the windy city began to blow the marble off the sides of the building. The entire building had to be refaced with granite — a costly job at one-half of the entire building costs! A walk around the base can be particularly gratifying to admire the uninterrupted views straight up the shear walls and the "musical sculptures.".
See Aqua
823 ft. The biggest American project ever to be headed by a woman, Jeanne Gang's skyscraper was named the world's best new building by Emporis when it opened in 2009 (four spots ahead of the Trump Tower across the river). Its most distinguishing feature is its series of undulating balconies, which extend as far as twelve feet from the building's walls, giving the building a surreal "rippling" effect. It uses an unforgettable curtain wall that compliments wavy balconies. Though impressive from any angle, it's best viewed relative to the water — either from a boat tour or the riverwalk over in the Near North.
See AT&T Corporate Center
1007 ft. Built by Adrian Smith in 1989, the granite-clad AT&T Corporate Center is one of the city's more distinctive skyscrapers for its massive size, spiked roof pinnacles, and a style evocative of both Gothic and Japanese architectural styles. It's not well-known, but it is the eighth tallest building in the U.S.
See Chase Tower
850 ft. Located at the exact center of CTA's Loop transit system, this building is distinctive for its vertical curve. It has been renamed for each of the successive banks that have bought out its previous tenants — for example, it was the BankOne Tower until 2005. The plaza outside is more interesting than the interior — it is home to an enormous mosaic by renowned Russian painter Marc Chagall.
See Daley Center
648 ft. The 1965 Daley Center is Chicago's principal civic center and boasts a gigantic Picasso statue on the adjacent plaza. A true Chicago landmark, the Daley Center was featured in The Blues Brothers, who drive across Daley Plaza and crash through the glass walls of the building. The Mies-esque design was intended to age visibly: the color has faded in a rust-like direction from exposure to the elements.
See Metropolitan Correctional Center
287 ft. While not very tall, this 1975 brutalist structure is one of the most distinctive and curious in the Chicago skyline. As its name suggests, it is a vertical prison skyscraper and its sharp triangular shape is designed to minimize the amount of time that it takes to patrol its corridors. Its prisoners have some of the prison world's best views as their exercise yard is on top of the roof, although the narrow slits serving as windows do not allow such nice views from the cells. The prison houses male and female convicts of all security levels, waiting for transport to the courthouse nearby.
See Crain Communications Building (Diamond Bldg)
582 ft. Anyone who has seen Adventures in Babysitting should immediately recognize this 1984 building, as its slanted roof (lit up at night) played a very important role in the film's climax. It's a hard building to miss, as it is just across the street from Millennium Park.
Trains
Although they're across the river in the West Loop, Union Station and Ogilvie/Northwestern Station are very much a part of the daily commute in the Loop. Union Station (1925) is a classical behemoth, lined with marble colonnades, and beautifully efficient on the inside. Ogilvie (1987), designed by Helmut Jahn, is tidy and efficient on the inside as well, with waterfalls of blue steel on the outside. If you'd like to compare a third era of Chicago transit, head over to the Near South and check out Dearborn Station (1885), which no longer serves trains.
If you're taking the elevated train around the Loop, the Quincy stop may be worth a look, as it's done up like an old-timey station, complete with vintage advertisements. You can step off the train, have a look around the platform, and get on the next train without paying again.
Do
In the old days, the Loop was the theater district in Chicago. Few of the originals survived the demolition wave of the 1960s, but most of the ones that did are now part of the Randolph Theater District. The Broadway in Chicago consortium stages big-budget shows there, most of which are in previews before their Broadway debut (hence, the name). Tickets for hot shows are snapped up in droves, so inquire with your hotel concierge about dinner-and-a-show packages.
The Chicago Cultural Center is also a theater destination — see above.
Do The Auditorium Theatre
Dankmar Adler and Louis Sullivan's masterpiece. Frank Lloyd Wright, who served as an apprentice on the project, called it "The greatest room for music and opera in the world — bar none." If the current production isn't worth seeing, take a tour of this gorgeous, acoustically-perfect theater instead. Tours are available at various times and days depending on the season.
Do CIBC Theatre (Shubert Theater)
Another Broadway in Chicago theater. Founded in 1906 to attract a classier vaudeville crowd, it saw performances from Harry Houdini, and was run by New York theater impresario Sam Shubert for more than forty-five years. In modern times, Monty Python's Spamalot and High School Musical have played here.
Do Lyric Opera
Extraordinary productions of major operas, in the impressive Civic Opera House, overlooking the river; local legend has it that the back-story behind business magnate Samuel Insull's decision to build it was the inspiration for the opera scenes in Citizen Kane. Although highly acclaimed today, there was a minor controversy among purists when they began to project English titles above the stage for non-English operas.
Events & Festivals
The Loop is ground zero for Chicago festivals, and the festivals run long and large. Take note of these dates, as hotel reservations will become more difficult to find and prices will rise.
Do Saint Patrick's Day Parade
Chicago has a large Irish-American population, and it's one that punches above its weight — St Patrick's Day is a huge affair in the Windy City. The endless parade takes place on Columbus Drive along the Chicago River, which is dyed green for the occasion. The river dyeing is at 10:45AM, and the parade starts at noon. These festivities take place on the Saturday before the holiday.
Do Blues Fest
Top national and local blues musicians perform all day long throughout the festival just a couple miles from where modern blues was born. This is the world's premiere blues festival, and the list of greats who have performed here (like Albert King, B.B. King, Buddy Guy, Chuck Berry, Etta James, John Lee Hooker, Memphis Slim, Stevie Ray Vaughan, Willie Dixon) gets more impressive each successive year. Admission is free and the performances are spread out across six stages throughout Grant Park.
Do Taste of Chicago
An outdoor showcase of Chicago restaurants, vendors, and performers, plus big name concerts. The specifics of the scheme vary from year to year, but generally, you buy a roll of tickets and then trade in those tickets for beer, drinks, food, and desserts. It's a great chance to sample the range of Chicago cuisine (at steeper prices). Also a great opportunity to watch Independence Day fireworks from the park and lakefront, but beware: it gets crowded.
Do Grant Park Music Festival (Grant Park Symphony Orchestra)
Chicago is spoiled for free music in the summer – the excellent Grant Park Symphony Orchestra plays in Millennium Park's Pritzker Pavilion about three times per week June–August, usually W,F Sa. The symphony is hardly the only free show at the Pritzker Pavilion, though, and it's worth walking by on any night around 6:30PM to see if any other classical, dance, etc. performances are running.
Do Jazz Fest
The great Chicago Jazz Festival was inaugurated in 1974 just weeks after Duke Ellington's death to commemorate his life's work, and has since become one of the world's largest annual jazz festivals, pulling some of the biggest names in the jazz world each year. And this one is free. If you have the means, you might want to come earlier in the week — there are usually a host of jazz-related events in the run up to the festival.
Buy
The Magnificent Mile ends at the Chicago River, but there are still more than a few places to shop in the Loop, particularly on and east of State Street. The two landmark department stores that once anchored the area, Marshall Field's and Carson Pirie Scott, are both gone. The Carson's building, designed by Louis Sullivan, has remodeled to serve as office space on its upper floors, and now houses a Target on its two lower floors.
The fate of Marshall Field's is a somewhat thornier one. Marshall Field himself was one of the original Chicago aristocracy, and his gorgeous store on State Street defined Chicago retail for several generations. In spite of its ties to Chicago culture and identity, when New York retailer Macy's bought the chain, they announced plans to rebrand all Field's stores as Macy's. Amid shock and uproar (among Chicagoans) and dire warnings (among industry analysts), Macy's executives assured reporters that focus group research had suggested people would, in fact, come to prefer the new brand. Today, sales have plunged, workers have been forced to take a sharp pay cut, and the interior is like a tomb. Ain't corporate hubris great?
Today, there are a few discount department stores, a few big stores for national chains like Old Navy and H&M, and a few amusingly shady joints on the streets under the elevated tracks.
Shop Central Camera
As the name suggests, this is a centrally-located place to deal with fussy cameras or upgrade to better ones. They've been in business since 1899, and have an awe-inspiring amount of spare and obsolete parts from over the years in storage, so don't be shy about asking for something you can't find anywhere else.
Shop Nordstrom Rack
The outlet store for the Near North retailer. There's plenty of heavily-discounted merchandise, but shoes are where the serious mania lies.
Shop Wabash Jewelers Mall
The other bastion of Jeweler's Row, with several stores that specialize in loose diamonds.
Eat
It's easy to find cheap food during the day — this is where most of Chicago works, so this is where most of Chicago eats lunch. However, most of those places close when the work day ends, so it's more difficult to keep costs down at night, when it's gourmet or bust. There's a sizable food court at Ogilvie/Northwestern Station (Canal and Madison) if you're on your way in or out of town.
In general, it's wise to avoid the restaurants right by major tourist attractions (e.g., the Art Institute, Millennium Park, etc.), as the quality of service and food tends to improve with distance from these one-time-visitor hot spots. There are some gems in the Loop, but you should also consider a quick cab ride west to one of downtown Chicago's premiere dining strips in Greektown.
Budget
Eat Boni Vino
Boni Vino, in addition to its pasta dishes, serves what is probably the best Chicago style thin crust pizza downtown — a good option if you want pizza, but fear the cholesterol-laden stuffed pizzas at Bella Bacino's. In addition to good pizza, this restaurant has lots of character and surprisingly low prices.
Eat Garrett Popcorn
Whether Garrett's shout-out-loud delicious popcorn is the cap to a good lunch or composes the entire meal is up to you and your conscience. "The Mix" is equal parts caramel- and cheese-coated popcorn; strange as it sounds, the combination is addictive. Sales went mad after an appearance on Oprah, so expect lines. There are a few other Loop stores, including 26 W Randolph and 2 W Jackson, but this is the most centrally located. Nice as it would be, signs warn that you can't bring Garrett's into the nearby theaters with you.
Eat Luke's Italian Beef
Luke's is where it's at for Italian Beef sandwiches in the Loop, and it's right next to the Sears Tower. The quality is a little unreliable at Luke's, but when they're on, they serve some of the best beef in the city. Hold the enormous portions of fries though, if you have any sympathy for your circulatory system.
Eat Osaka Express
A counter on a corner of Michigan Avenue with good, cheap seafood and vegetarian sushi. Be prepared for blank stares if you try ordering in Japanese, though.
Mid-range
Miller's Pub and Exchequer in the Drink section serve food worth considering for a mid-range lunch.
Eat Cellars Market
A hidden gem serving breakfast and lunch only, this cafeteria closes soon after the trading floors upstairs do. Made-to-order deli sandwiches, homemade soups, a large salad bar, and daily specials prepared on-site. The turkey club sandwich is enormous, especially if you're polite and cheerful toward the person making it.
Eat Petterino's
Petterino's is a classic Chicago restaurant, serving high quality steaks, salads, and seafood dishes. The restaurant caters to the theater-going crowd, and reservations for dinner are wise.
Eat Pizano's
Deep dish pizza that has roots in the family that produced UNO's and Lou Malnati's, but will serve a worthy thin-crust, too.
Splurge
Eat Atwood
Popular restaurant with a bar in the classic Hotel Burnham. Good location and atmosphere for dinner before a show.
Eat Russian Tea Time
This is the place to try Russian cuisine in Chicago! Easily one of the best Russian restaurants in the world with an inventive menu and excellent management. Ask to be seated in the front section. Afternoon tea runs from 2:30-4:30PM.
Eat Vivere
One of Chicago's top Italian restaurants, with very creative decor and a romantic ambiance.
Drink
The cost of real estate in the Loop means that most dives are priced out of the area, sending most of the after-work crowd to the places noted below. Friday nights after work can be a mob scene — if you're with a group, either make a reservation or be prepared to split up for a little while.
Drink BIG Bar
Don't expect an intimate atmosphere or anything resembling a classic Chicago experience. Do expect all things comically out of proportion. The bar is 160 feet long and the margaritas can get so big that they actually mix them in a cement mixer. And the view is great.
Drink Elephant & Castle
English-ish pub chain with the requisite fish & chips and other mid-range pub food, long hours, and a second location at 185 N Wabash. It's a good place for a long stay.
Drink Emerald Loop
Irish-style pub in an elegant setting, with large tables to accommodate business lunches. The food's good, breakfast included.
Drink Exchequer Restaurant & Pub
Family-friendly pub with pizza and ribs, under the L tracks and covered in Chicago memorabilia.
Drink Miller's Pub
Established in 1935 and bursting with faded celebrity photos, Miller's Pub serves ribs, steak, and sandwiches with its list of beer, wine, and martinis. It's a little too formal to sprawl out and relax, but perfect if getting a beer is a task of equal import to dinner.
Drink Plymouth Restaurant & Bar
The Plymouth Restaurant is merely an adequate cafe serving diner-style food, but come here instead for the rooftop bar. Sipping a cocktail while gazing off the balcony at the Harold Washington Library and various Louis Sullivan masterpieces is a fine way to cap off a day of sightseeing, provided that the blaring music doesn't drive you away.
Drink Stocks & Blondes Bar & Grille
Stocks & Blondes, aside from the frightening pun, is a rarity in the Loop in that it is "just a bar." No fake Irish pub gimmickry, no failing attempts at trendiness, just a bare-bones bar atmosphere and good beer on tap.
Sleep
Although this is the most expensive real estate in Chicago, the hotels in the Loop are slightly cheaper than those in the Near North simply because so much of the area shuts down at night. Still, these are some pretty nice digs, and being in the Loop makes transportation to any part of the city easy.
Budget
Stay Congress Plaza Hotel
The Congress Hotel has seen visits from most U.S. presidents since it was built in 1893. Today, other hotels have overtaken the Congress in the glamour class, leaving it behind as a great deal with a colorful past. Ask for a room with a view of the lake — if Buckingham Fountain is running, you will be treated to a magnificent view. The workers of the Congress hotel staged the longest hotel strike in history from 1993-2013.
Stay Hostelling International Chicago (J Ira & Nicki Harris Family Hostel)
Right in the middle of the downtown college ruckus, HI Chicago is not far from Union and Ogilvie, but will take some navigating from either airport into Chicago. Available 24 hours a day, 365 days a year. No curfew, no age restrictions (under 18 must be accompanied by adult). Ask for the coupon which gives $3 off the Chicago Architecture Foundation tours.
Mid-range
Stay The Royal Sonesta Chicago Downtown
Located on the Chicago River at Wacker Drive and Michigan Avenue with an impressive view, right on the border of the Near North.
Stay The Allegro Royal Sonesta
This lovely, Art Deco hotel calls itself a boutique, probably in reference to its friendly, full four-star service, designer decorated rooms and prices that are the same, or just a little bit more than you would pay for a blander three-star place just north of the river. Suites and some rooms have a double jacuzzi.
Stay Silversmith Hotel & Suites
The Silversmith boasts an enviable location, good value, and perfectly adequate suites, but light sleepers should be sure to ask for a room away from the noisy L lines. Don't miss the dessert hour: free high quality cake, cookies, and coffee/tea in the lobby M-Th 9PM-10PM.
Splurge
Stay Hotel Monaco
The Monaco provides a bit better than four-star comfort at a bit less than four-star prices, though they are a little higher than at sister hotels like the Allegro or the Burnham. What you get for the extra money is a number of specialty services geared for business travelers, so if you are traveling for pleasure go for the Allegro.
Stay Hyatt Regency Chicago
2,000 guest rooms in two towers, a riverfront location, and what the management claims is the largest freestanding bar in the U.S. It's a favorite for convention groups, and is connected via covered walkways to the Illinois Center, which is a major business complex.
Stay The Palmer House
With over 1,600 rooms and no shortage of luxuries, the Palmer House is one of Chicago's most memorable hotels. The first Palmer House was built by business magnate Potter Palmer for his socialite wife Bertha. This one is the third version of the Palmer House — the first opened two weeks before the Great Chicago Fire. (Can't beat that for timing.) The current version, overlooking State Street, enjoyed an extravagant renovation in 2008, with tasteful 1920s-style guest rooms and a magnificent lobby bar (with magnificently overpriced drinks).
Stay safe
Most streets west of Clark St. can be hit or miss. After 7pm, the Loop can easily be a ghost town (more so in colder months). Many homeless people still walk around, but are usually just trying to find shelter and are easy to avoid. You must also watch out for pickpockets in crowded areas. Just use common sense and if you find yourself walking in a seedy part of the Loop at night, stick to well lit streets or use the CTA to get to your destination.
Go next
The Loop is rivaled only by the Near North as Chicago's principal tourist destination. But the city has riches far beyond the tourist lure of downtown skyscrapers and big museums; to experience what makes Chicago ‘’Chicago’’, venture into the neighborhoods where Chicagoans actually live.
The good news is that there is convenient public transportation from the Loop to virtually every corner of this massive city. Here are a few easy excursions if you are staying in the Loop that will really show you some of the city beyond the major tourist attractions:
- Take the Metra Electric Line or the #6 bus south from Millennium Park to spend half a day visiting the excellent museums or visiting the University of Chicago and the local independent bookstores in Hyde Park.
- Head south on the CTA Red Line to Chinatown for a delicious Cantonese dinner.
- Take the CTA Red Line north to Lawrence Avenue in Uptown for a night of jazz at the historic Green Mill.
- Hop on the CTA Blue Line to Damen Avenue in the epicenter of the ever-popular Wicker Park neighborhood, where you will find better dining options, way better bar options, and some eccentric shopping.
- Take the CTA Brown/Purple lines north to Lincoln Park and Old Town to visit Chicago's top comedy clubs and celebrity chefs, or to head into lovely Lincoln Park, home of the Lincoln Park Zoo and the famous North Avenue Beach.
- Visit the heart of Mexican-American Chicago in the Little Village (aka "La Villita") or in Pilsen (18th Street Pink Line stop).
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