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10 things not to miss on a trip to Chicago

10 things not to miss when traveling to Chicago< /p> UPDATE DAY

CHICAGO, ILLINOIS – While many look to New York for a fall getaway, others consider Chicago instead. A stunning city in the Midwest of the United States, Chicago seduces with its rich culture, impressive architecture and excellent restaurants. 

Only 2h30 by plane from Montreal, Chicago has the merit to offer a multitude of activities. 

You can decide to spend your day in a museum in the city center before having dinner in a trendy restaurant in Wicker Park or even landing on a beach and admiring the architecture of the city in the distance. 

Note that you will need at least three days to enjoy all that the city has to offer.

Here are some of the things to put on your itinerary:

Get caught pictured in front of the 'Bean' at Millenium Park

Millennium Park artist Anish Kapoor's reflective 'Cloud Gate' sculpture has quickly become a Chicago icon.

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Nicknamed the “Bean”, this sculpture is popular with both locals and tourists. 

In fact, Jaume Plensa's interactive 'Crown Fountain' is nearby and well worth a visit.

Scar the Skydeck >

A climb to the top of Chicago's giant skyscrapers is a must. 

To experience the total, we encourage you to go to the Skydeck. Located on the 103rd floor of the Willis Tower, this observatory features a series of retractable boxes that jut out of the structure to provide an unparalleled view of Chicago. 

A ticket costs $38.50 US (about $50) for people 12 and over.

Walk along the Riverwalk

In the center- city ​​of Chicago, the Riverwalk, or simply The Walk, offers a public space known for its tree-lined promenade that runs along the Chicago River. 

A walk allows you to enjoy the water of the river and look up to admire the architecture. 

It is the architect Daniel H. Burnman who is at the origin of part of the town planning of the city. His goal was to make Chicago a “Paris of the Prairies”. 

Thus, a little magic is felt when walking along the Riverwalk. 

Several restaurants and bars are also located on the Riverwalk.

Walking around the Wicker Park neighborhood

Wicker Park is a residential enclave in Chicago. 

It was actually founded when Chicago gained city status in 1837. Wander the streets and be sure to take photos of the pretty Brownstone homes. 

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You'll feel like you're part of the city on your ride. 

The Jay Pritzker Pavilion in Millennium Park, Chicago. OCT 4, 2022 Credit: Naomi Auger

Bet on North Milwaukee Avenue to experience its vibrant nightlife, restaurants and numerous entertainment venues.

Have a drink on a rooftop terrace

After a busy day of sightseeing, there's nothing better than a terrace to unwind. 

Bet on the city center to find raised terraces where to end the evening. 

The Up Room, on the 13th floor of The Robey (2018 W North Ave), features “mid-century modern” decor and is often frequented by city dwellers. Otherwise, the rooftop of the Aba (302 N Green St 3rd Floor), a Mediterranean restaurant, is the talk of the town thanks to its pretty decor and its extensive list of wines, beers and cocktails.

Admire the painting by George Seurat at the Chicago Art Institute

“A Sunday Afternoon on the Island of La Grande Jatte” is a painting by Georges Seurat, exhibited at the Art Institute of Chicago. 

A bit like in the movie “Ferris Bueller's Day Off”, it is impossible not to remain captivated by the many brushstrokes (pins ) on the canvas.

The museum houses several cult works including a “Self-Portrait” by Van Gogh, “The Water Lilies” by Monet, “Saint Martin and the Beggar” by El Greco, “Nighthawks” by Edward Hopper, and the “American Mona Lisa, American Gothic,” by Grant Wood.

Shopping in Andersonville

Rated #2 on the list of “World's Coolest Neighborhoods” Time Out in 2021, Andersonville is a must-see neighborhood in Chicago.

What characterizes it is the extraordinary concentration of shops, cafes, art galleries and restaurants found there. 

Foursided, ENJOY, Early to bed, Chicatolia, Andale Market (adorable bodega) and Galleria on Clark Street are must-sees. 

Also, the neighborhood is home to one of the largest LGBTQ+ communities in Chicago. Inclusion is therefore a flagship value of the neighborhood and is felt. 

If you are planning a trip to Andersonville, we advise you to leave room in your suitcases, they may fill up quickly!

Stroll on the beach

< p>Overlooking Lake Michigan, several beaches stretch near downtown Chicago. 

They stand out for their soft white sand. Our favorites are Montrose Avenue Beach (the largest beach in Chicago), Oak Street Beach and North Avenue Beach. Depending on the season, the water temperature allows swimming.

Eat a “deep dish” pizza

A cult favorite in the city, a visit to Chicago wouldn't be complete without sampling deep dish pizza. 

Deep dish pizza at Giordano's, Chicago. OCT 4, 2022 Credit: Naomi Auger

This is a thick pizza prepared in a hollow pan. This is served in the middle of the table on a stand and is perfect for sharing. 

Flanked by rising edges, the pizza consists of a thin and crispy dough, generously topped with cheese and a tomato sauce with a pronounced herbal taste. The best places to enjoy a “deep dish” in Chicago are undoubtedly Giordano's, Uno's and Pequod's (the latter being by far the favorite of city dwellers). 

Note that the pizza takes 45 minutes to cook properly. Better not be in a hurry!

Spend the evening at a blues or jazz bar

Chicago's nightlife vibrates to the sounds of blues and jazz. Thus, there is no shortage of nightlife hotspots in the city. 

Buddy Guy's Legends (700 S Wabash Ave, Chicago) remains THE blues temple in the city. Otherwise, the Green Mill (4802 N Broadway, Chicago) is a bar adored by jazz lovers.


There are many restaurants in Chicago. Here are a few of our favorites:

– Avli, for its Greek specialties and martini shakes.

Avli Greek Restaurant, Chicago. OCT 4, 2022 Credit: Naomi Auger

– Girl and The Goat, for the refined dishes of chef Stephanie Izard.  

-Venteux, for its $1 oysters on Tuesdays.

– Big Star, for tacos that bring crowds to the Wicker Park district.

– Eataly, for fresh pasta and Italian specialties to eat in or take out 

– Hinoki Sushiko , to test the Omakase experience, a 15-course meal off the beaten track prepared in front of you.

– Dear Margaret, for French-Canadian cuisine with super nostalgic flavors.

At Tanta restaurant in Chicago. OCT 4, 2022 Credit: Naomi Auger

– Tanta, for her dishes to share that combine Peruvian and Japanese influences.

Getting around< /p>

Public transportation (bus, train, subway) remains your best option for getting around Chicago easily. 

You can check the schedules on the Transit Chicago website or at using the Citymapper, Transit and Moovit mobile apps.


Located near Millenium Park and in the heart of the Loop (downtown), Boutique Hotel Pendry is a great option for a short stay in Chicago. Inaugurated in May 2021, in a 37-storey building, the hotel offers an excellent restaurant and a café on the ground floor. 

We love it for its historic cachet, its Artistic decoration decor, tastefully appointed rooms and accessibility.

* This trip was made possible thanks to Choose Chicago.

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