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Chicago: walking tour of the Loop

While we were taking a well-deserved break at our hotel bar during our stay in Chicago, another hotel guest came up to talk to my husband and I.

This must have been her twentieth visit to the city, she told us, but it was the first time she was visiting with her husband.

She had made a point of showing him the various works of art found in the Loop and, from memory, noted these on a map.

This circuit being done, she gave us the map so that we could in turn discover the district, which we did the next day with great pleasure.

Chicago Loop Walking Tour

Now it’s my turn to share this tour with you. I’ve also added some of the city’s iconic buildings in this walking tour.

At every corner, a surprise awaits you. Don’t hesitate to enter the buildings, you will always be welcomed and the entrance halls are often breathtaking!

I hope you enjoy the walk as much as we did, which alternates between artistic and architectural treasures.

Good tips for a stay in Chicago

The Elevated Train or "the L" in Chicago

Before you start this walking tour, here are 3 additional good plans for a perfect stay in Chicago:

If you’re going to Palm Springs, you could also like this itinerary to see the mid-century homes.

20-stop walking tour of the Loop

Map of the walking tour in the Loop

Walking tour of the Loop

Here is the circuit. It should take you between 1 hour to 1h20 on foot to complete this circuit, not counting the time if you decide to stop here and there.

Itinerary in the Loop in Chicago, alternating between works of art and not to be missed iconic buildings.

1. Beginning of Route 66

Let’s start the itinerary at the Route 66 sign, on Adams Street between Michigan Avenue and Wabash Avenue. This is where the mythical road that crosses the United States to California begins.

2. Chicago Athletic Association Hotel

12 S Michigan Avenue
Go north on Michigan Avenue to the Chicago Athletic Association Hotel

Chicago Athletic Association
Photo: Facebook @ChicagoAthleticAssociation

What is now a hotel was, in 1893, a private club reserved for the elite of Chicago at the time of the World’s Fair. The exterior of the building reminds of the Venetian palaces but it is really the interior that deserves the visit.

Even if you are not a client, you can visit several rooms that have been extensively renovated and that have kept their original character. It’s a guaranteed trip back in time.

Not to be missed: the grand staircase, the drawing room, the Cherry Room and The Game Room.

3. Cloud Gate

Millennium Park
Return to Michigan Avenue to cross the street. Walk north to the Cloud Gate. On your way there, you will pass the Crown Fountain.

Cloud Gate at night and during the day - Millenium Park - Chicago
Cloud Gate at night and during the day

Known as the “Bean”, the Cloud Gate is a sculpture by British artist Anish Kapoor. Shaped like a silver drop, it is the most popular place to take a picture. But beyond the tourist photo, you must take the time to admire the work on which the city is reflected. If you pass underneath, you will have a whole new perspective… of you!

4. Chicago Cultural Center

78 E Washington St
Go back to Michigan Avenue and head north. Turn right onto Washington Street.

Chicago Cultural Center

One of the main reasons for visiting the Chicago Cultural Center, a magnificent Beaux-Arts building, is its Tiffany stained glass dome, the largest in the world.

But while you’re there, you might as well take the opportunity to visit the exhibits in what was, at its inauguration in 1897, the Chicago Public Library.

5. Aqua Tower

200 N. Columbus Dr.
Return to Michigan Avenue and continue north to E Randolph St. Turn right on Randolph and left on N Columbus Dr.

As you walk up N Columbus Dr, you will pass the Aqua Tower. This building, which was completed in 2010, stands out with its undulating balconies that recall the waves and the topography of the Great Lakes.

It won the Emporis Skyscraper Award for Skyscraper of the Year in 2009.

6. Riverwalk Park

Continue on N Columbus Drive to the end.

Riverwalk - Chicago

This is where you’ll have access to Chicago’s Riverwalk, a 1.25-mile pedestrian promenade along the Columbus River. Of course, it’s a little busier in the summer when the shops and restaurants are open.

7. Tribune Tower

435 Michigan Avenue
Turn left to continue on E Upper Wacker Dr to the next bridge.

Chicago Tribune Tower
Photo : Eric Allix Rogers – Chicago Architecture Center

On your way to the DuSable Bridge, you will pass by the Chicago Architecture Center, which is worth a visit for its exhibition of buildings in Chicago and around the world.

From the DuSable Bridge, you can cross the river to leave the Loop and admire the Tribune Tower. The Gothic Revival building was completed in 1925 and houses the offices of the Chicago Tribune.

8. Wrigley Building

400-410 N Michigan Ave
Go back the way you came and return to Michigan Avenue. Cross the street to the Wrigley Building.

Wrigley Tower - Chicago - Loop Walking tour

The building, with its tower inspired by the Giralda in Seville, is simply magnificent. There are many details to admire, including the footbridge that joins the two buildings and the small interior courtyard. The building is also worth a visit at night, when it is all lit up.

9. LondonHouse Chicago Rooftop Bar

85 E Upper Wacker Dr
Head south on N Michigan Ave and turn right on E Upper Wacker Dr.

It is now time to cross the bridge again to return to the Loop district with a short stop on the roof of the LondonHouse Chicago hotel, recognizable by its dome.

In the summer, the place serves as a bar with a beautiful terrace. In winter, you can go there simply to admire the view of the surrounding buildings, including Marina City.

10. Marina City

300 N State St

Marina City - Vue du London House Chicago
View from the LondonHouse

Located on the other side of the river, these 2 towers, also called the corncobs, are part of the iconic buildings of Chicago.

Moreover, another good plan if you are in Chicago is to take a cruise on the river which will allow you to admire the city from another angle.

11. Chicago Theatre

175 N State St
Head southwest on E Upper Wacker Dr (toward N Wabash Ave) and turn left on N State St.

Chicago Theater de nuit

Another good photo opportunity is in front of the Chicago Theater sign.

12. The Oriental Theatre

24 W Randolph St
Head south on N State St to W Couch Pl and turn right on W Randolph St.

Oriental Theater - Chicago

Opened in 1926 as a luxury movie theater, this theater is now owned by Broadway Chicago. It is another of Chicago’s iconic buildings that lights up the street day and night.

13. Monument to the standing beast by Jean Dubuffet

100 W Randolph St
Head west on W Randolph St toward N Dearborn St.

Jean Dubuffet's Monument with Standing Beast - Chicago

The Loop looks like an open-air museum with artworks scattered here and there in the neighborhood. The monument to the standing beast, a sculpture by Jean Dubuffet located in front of the James R. Thompson Center, is a good example.

14. Chicago Picasso by Pablo Picasso

50 W Washington St
Head east on W Randolph St (toward N Clark St), turn right on N Clark St then turn left on W Washington St.

Chicago Picasso by Pablo Picasso - The Loop

Even Picasso has left his mark in Chicago with his statue that stares at the bustle of the street. Is it a “Picasso-style” woman or a creature? No one knows for sure. Bonus: it’s located right in the heart of the Christmas market that takes place during the holiday season in Daley Plaza

15. Joan Miró’s Miss Chicago

77 W Washington St,
Cross Washington St.

Miss Chicago de Joan Miró - Le Loop

Almost opposite the Picasso statue is the Catalan artist Miro’s Sun, Moon and Star, also known as Miss Chicago.

16. Marc Chagall’s Four Seasons

10 S Dearborn St
Continue on Washington St to N Dearborn St and turn right on N Dearborn St.

Chagall's Four Seasons - Chicago
One of the stops of the Chicago Loop walking tour

Chagall’s Four Seasons mural is another of the artistic gems found in the Loop. Take the time to admire both sides of this mosaic, a universe of shapes and colors.

17. Alexander Calder’s Flamingo

50 W Adams St
Head south on S Dearborn St to W Monroe St. Turn right on W Adams St.

Flamingo de Calder - Chicago

Alexander Calder’s Flamingo, a red steel stabile, contrasts with the black buildings that surround it and makes the Federal Plaza blaze.

18. Rookery Building

209 S LaSalle St
Head west on W Adams St to S Clark St, turn left on S LaSalle St.

The Rookery Building - Chicago

Built in 1888, it is one of the oldest buildings in the city. It is difficult to guess from its austere façade that this building hides a large luminous hall, covered by a glass roof and designed by Frank Lloyd Wright several years after its construction.

19. Chicago Board of Trade Building

141 W Jackson Blvd
Head south on S LaSalle St (toward W Quincy St) and turn left on W Jackson Blvd.

Chicago Board of Trade Building
Photo: Eric Allix Rogers – Chicago Architecture Center

On top of the imposing Chicago Board of Trade, the statue of the goddess of agriculture Ceres overlooks the street.

20. Willis Tower

233 S Wacker Dr
Head west on W Jackson Blvd to S LaSalle St.
Turn right on S Franklin St. then turn left on W Adams St

Willis Tower - Chicago
Photo: Wikimedia

Here we are at the last stop of the tour, the Willis Tower. It is the highest tower in Chicago and stands at 442 meters high. You can go up to the 103rd floor to observe the city either on the skydeck or in the glass cubes that float in the void.

If you don’t feel like waiting in line, you can also have a drink at the Signature Room, located at the top of the John Hancock Center at the very end of the Magnificent Mile (another great ride!).

And while you’re at it, take a ride on the L Train!

Enjoy the visit :)

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