10 things not to miss on a trip to Chicago

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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 captivates with its rich culture, impressive architecture and excellent restaurants. 

Only 2h30 by plane from Montreal, Chicago has the merit of offering 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 sit on a beach and admire 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:

Taking a photo in front of the “Bean” at Millenium Park

Millenium Park artist Anish Kapoor's reflective Cloud Gate sculpture has quickly become a Chicago icon. Nicknamed the “Bean”, this sculpture is as popular with locals as it is with tourists. Incidentally, Jaume Plensa's interactive 'Crown Fountain' is nearby and well worth a visit. >

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 unparalleled views of Chicago. A ticket costs US$38.50 (about $50) for people 12 and older.

Walk the Riverwalk

In downtown 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 the sky 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 in the Wicker Park district

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Wicker Park is a residential enclave in Chicago. It was also founded when Chicago acquired city status in 1837. Stroll through the streets and be sure to take pictures of the pretty Brownstone houses. You will feel like you belong in the city during your walk. Bet on North Milwaukee Avenue to experience its lively nightlife, restaurants and numerous entertainment venues.

Have a drink on a rooftop terrace

After a busy day of sightseeing, there is nothing better than a terrace to decompress. 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 Aba (302 N Green St 3rd Floor), a Mediterranean restaurant, is talked about 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 film “The crazy day of Ferris Bueller”, 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

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Ranked second on Time Out's 2021 “Coolest Neighborhoods in the World” list, 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 space in your suitcases, they may fill up quickly!

Stroll on the beach

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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 dish in the city, a visit to Chicago wouldn't be complete without sampling some deep dish pizza. It 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 it takes 45 minutes for the pizza to cook properly. Better not be in a hurry!

Spend the evening at a blues or jazz bar

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Chicago's nightlife vibrates to the sounds of blues and jazz. Thus, the high places of nightlife are not lacking 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.

PRACTICAL INFORMATION

 Enjoy

The restaurants are plentiful in Chicago. Here are some of our favorites:

– Avli, for its Greek specialties and martini shakes

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

– Venteux, for her $1 oysters on Tuesdays

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

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

– 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 hyper-nostalgic flavors

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

Getting around

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 using the Citymapper, Transit and Moovit mobile apps.

Accommodation

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 Art Deco decoration, its tastefully furnished rooms and its accessibility.

* This trip was made possible by Choose Chicago.