How to Spend a Luxury Weekend in Chicago, Illinois

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Curated By

Oluwaseyi Aladeselu

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  • USA

  • Illinois

  • Chicago

  • Arts & Culture

  • City Travel

  • Domestic Travel

  • Luxury Travel

  • Bougie

  • Foodie

  • Music

City Skyline in Chicago
Curator’s statement

Chicago, Illinois is a truly unique city with unexpected gems all around. Though dubbed the "Windy City," Chicago also comes alive in the summer. Stop by a neighborhood fest, relax along the Riverwalk, or enjoy a glass of wine on your favorite rooftop. You can also hit a festival: Pride, Puerto Rican parade, Taste of Chicago, Lollapalooza, blues fest, etc. You won't be disappointed with a Chicago Summer, but the city also has a lot to offer during the winter (especially around November through January.) So if you don't mind a little cold, add a Chicago winter escape to your list.

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Insider knowledge

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Where to stay in Chicago, Illinois

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Four Seasons Hotel Chicago

Best-of-the-best on the Magnificent Mile, with standout service and unmatched views of Lake Michigan and the cityscape.

Fora Perks
  • $100 food / beverage or spa credit

  • Breakfast daily

  • Upgrade whenever possible

The Langham, Chicago

A Chicago icon set apart by its Mies van der Rohe-designed building, Chicago River and city views, and sleek mid-century style.

Fora Perks
  • When you book Langham with a Fora Advisor, you will enjoy exclusive Preferred Partner amenities. Reach out to your Fora Advisor to learn more.

The Ritz-Carlton, Chicago

In the Gold Coast district, this family favorite delights with oversized rooms, Lake Michigan views and four excellent eateries, including the 12th-floor Italian steakhouse and alfresco bar.

Fora Perks
  • $100 food / beverage credit.

  • Breakfast daily for two guests per bedroom.

  • Upgrade & extended check-in/out based upon availability at check-in.

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Unlock perks by contacting Oluwaseyi to book your trip.

Things to do in Chicago, Illinois

The bean in Chicago

Chicago is a vibrant city with many activities to offer. You might have heard about the Willis Tower, previously called the Sears Tower. Scale the roof to take in breathtaking views of the city. You can also book a city helicopter tour to view the city from above. When you’re back on the streets of Chicago, head to the Museum of Contemporary Art for some incredible exhibitions and to spend the day neighboring some of the best art in the world. When you’re done with that, get your shopping in at the Magnificent Mile

Looking for something more active and nature-related, start off the day with early morning kayaking on the river. You can also spend the day on North Ave Beach and enjoys the swoon-worthy views of the lake. Head to the Shedd Aquarium to see some marine life too. Finally, a movie in the park under the stars is a lovely way to end the day. Chicago also offers a plethora of shows including comedy, music, and plays. 

For a relaxing afternoon, head to AIRE Ancient Baths and indulge in the spa.

Eat & drink in Chicago, Illinois

Happy hour in Chicago

Tanta: Go here for bottomless brunch or happy hour to enjoy its spirited libations. 

WoodWind: American restaurant with an inventive take on traditional dishes.

Cabra: Peruvian-inspired restaurant with excellent ceviche and fun weekend brunch.  

sushiDokk: Best sushi in town, perfect for date night dinner. 

Aikana: Central and South American-influenced cuisine with a handcrafted beverage program. 

Aba: Delicious Mediterranean restaurant perfect for dinner for its spectacular rooftop views. 

3 Arts Club Café: A charming joint for afternoon coffee and/or evening wine. 

Nobu: Chic rooftop restaurant and bar with a fantastic view. 

The Violet Hour: Come here for inventive cocktails. 

Floriole Cafe & Bakery: A bit of a sweet tooth? Stop by here for dessert.

Garrett's Popcorn: Grab a local-favorite popcorn here. 

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Travel Advisor

Oluwaseyi Aladeselu

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