Chicago Must-Sees

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Advisor - Abby Kulwicki
Curated By

Abby Kulwicki

  • Luxury Travel

  • Boutique Travel

  • Food & Wine

  • Arts & Culture

  • Family Travel

  • Bachelor Party Destinations

  • Bachelorette Party Destinations

  • Birthdays

  • Group Travel

  • Foodie

  • Nightlife

  • Architecture

  • Comedy Club

  • Lakefront

  • High-end

Sky touching buildings in Chicago
Curator’s statement

Chicago is a wonderful destination for foodies and art lovers! Enjoy amazing meals and big city life. Chicago is a place to treat yourself and live luxuriously.

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Where to stay in Chicago, IL

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Things to do in Chicago, IL

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Chicago Art Institute

Chicago Architecture tour

($42/pp, 90 min boat ride)

The Chicago Lakefront

Rent divvy bikes or walk along the Chicago Lakefront trail. Great spot for sunset! If you're visiting in the summer, rent a boat and enjoy the playpen

Second City

See a show at the famous Second City comedy club! Grab a drink at Utopian Tailgate before your show.

Places to eat & drink in Chicago, IL

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The Weathervane Cafe: The chickpea wraps and the chai latte with oat milk, add orange blossom syrup (iced or hot.)
Queen's Eleven: Iced oat milk latte (the best!)
Thump Coffee: The smashed avocado on an everything bagel.
Honey Hill: The lattes,


Blue Moon Brewery: The grilled cheese with tomato soup and the pretzel bites.
Stueben's Uptown: For brunch, make sure to get the crispy smashed potatoes and the Wake Up & Rage breakfast cocktail.
Root Down: Carrot cake french toast, the lamb burger, and the veggie burger sliders.
Marczyk Fine Foods: Specialty grocery store - head to the deli counter for delicious sandwiches and prepared foods.


Daughter Thai Kitchen & Bar: Pad See Moa and the vegetarian crispy roll.
Ash'Kara: Whipped feta and the chocolate tahini brownie.
Linger: Chili garlic edamame, the carrot falafel plate and the bao buns.
Postino Wine Bar: The Boards and the grilled cheese.


Redeemer Pizza. Best for slices! Rotating specialty slices available daily.
Blue Pan pizza. award-winning Detroit style, thicker crust.
White Pie - Options include New Haven style crust (thin, similar to a flatbread) and Sicilian style (thicker, square pan pizza.)

Cocktail Bars

Lady Jane: Chai Town or Blood Magic.
Room for Milly: The SS City of Paris or Top Side.
Honey Elixir Bar: Honey Bear or RiNo Shrub.
The Tatarian: The Senator or Saturn.

Need to Know

Looking for more travel inspiration? Check out my guide, Explore Mallorca: 3-Day Itinerary.

Advisor - Abby Kulwicki

Travel Advisor

Abby Kulwicki

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This guide is part of our ongoing series on travel to Chicago.