A Rain or Shine Guide to the Windy City: Chicago, Illinois

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Advisor - Jordan Schack
Curated By

Jordan Schack

  • Chicago

  • Active Travel

  • Arts & Culture

  • Boutique Travel

  • Food & Wine

  • Foodie

  • Local Culture

  • Sightseeing

A view of the Chicago train and railroad with a tall skyscraper in the background.
Curator’s statement

Visit Chicago this July and you'll get why some people say that a summer in Chicago is the best season in the world (it is). The city that I call home goes toe to toe with the best in the world, blending international flair with local charm, Michelin star restaurants with dive bars slinging hand made tamales. Chicago has forged its unique identity, filled with Midwestern charm, a food scene second to none and world-class attractions. Come for the deep dish, fall in love with the architecture, but don't you dare put ketchup on your hotdog.

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Insider knowledge

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Where to stay in Chicago, IL

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Things to do in Chicago, IL

A view of a river cruise boat on the Chicago river with skyscrapers in the background.

Chicago Architecture River Cruise: A must-do for first timers and locals alike. Find out for yourself why Chicago’s architecture is talked about around the world.

Chicago Lakefront Trail: Check out the Chicago skyline on the Lakefront path, an 18-mile long trail that hugs the coast of Lake Michigan.

The Second City: Where Tina Fey and Chris Farley cut their teeth. The gold standard of improv comedy.

Art Institute of Chicago: Snap a pic of the bronze lions out front while you’re at it.

Museum of Contemporary Art: Just off Michigan Ave, MCA houses one of the world's largest museums dedicated to contemporary art.

Wrigley Field: Bleacher seats, a cold beer and a hotdog “run through the garden”. Thank me later.

The Salt Shed: The enormously popular new music venue housed within the iconic Morton Salt boasts a lineup of legends. Arrive early for a sampling of local food truck options at the outdoor Fairgrounds space.

North Avenue Beach: There’s a beach in Chicago? There’s a beach in Chicago!

Places to eat & drink in Chicago, IL

A picture of a steakhouse bar with blue tiling, warm tones, and an assortment of alcoholic bottles lit up on the shelves hanging above.

Breakfast & Brunch:

Lula Cafe: Definition of a neighborhood gem. Brunch is first-come, so get in line!

Kasama: A Michelin starred bakery? Say no more.

3 Arts Club Cafe: Housed inside Restoration Hardware in Chicago’s Gold Coast neighborhood. Come for the candied bacon, stay for a post-meal nap on a cloud couch.

Lunch:

J.P. Graziano Grocery: Best sandwich in town, hands down.

Superdawg Drive-In: Is a hotdog a sandwich? If so, might need to reconsider ^.

Taqueria Chingón: Tacos that give Mexico City a run for its money.

Dinner:

Bavette’s: If you’re here for a special occasion, this is where you’re going.

Monteverde: Pasta heaven.

Akahoshi Ramen: More than just a humble ramen shop.

Athenian Room: Get the Kalamata Chicken. Or the Skirt Steak. Or the gyros. What am I saying? Get it all. Cash-only.

Chilam Balam: A family run Mexican outfit in the Lakeview neighborhood. Bring a good bottle of tequila for some house-made margs. Don’t skip the ribs or the peanut butter empanadas.

Drinks:

Kumiko: There’s a reason it’s a top 25 bar in the world.

The Green Mill: Smooth jazz and a stiff old fashioned. Say no more.

Scofflaw: A must for gin-lovers, like me.

Bungalow by Middle Brow: Natural wines, house beers and some of the best bar pies in town. Great patio for summer days.

Advisor - Jordan Schack

Travel Advisor

Jordan Schack

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This guide is part of our ongoing series on travel to Chicago. Looking for more travel inspiration? Check out my guide, A Complete Guide to Mexico's Culinary Capital: Oaxaca.