Found in 1879, this is one of the oldest and largest art museums in the world.

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Art Institute of Chicago

One of the world's largest contemporary art venues.

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Museum of Contemporary Art 

Chicago's natural history museum, found in 1893.

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Field Museum

Spend a day at the largest science center in the Western Hemisphere. 

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Museum of Science and Industry

Explore public art, exhibitions, gardens, and more. 

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Millennium Park 

Enjoy live performances at this legendary theatre company.

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Steppenwolf Theatre Company

There's plenty to explore in this cosmopolitan Midwestern city. Visit world class museums, vibrant parks, and renowned restaurants.

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Chicago

Visit Wrigley Field and experience iconic Chicago baseball. 

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Cubs Game

The perfect place to spend a summer day; relax in the sand with a view of the Chicago skyline.

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Oak Street Beach

Watch a show at this iconic comedy club, comedy theater, and school of improvisation known for its many famous alums.

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The Second City

Spend 90 minutes aboard a boat on the Chicago River and learn about the city's fascinating architecture.

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Chicago River Architecture Tour

A free 35-acre zoo founded in 1868, making it the fourth oldest zoo in North America.

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Lincoln Park Zoo

A 1.25 mile walk along the Chicago River; explore cafes, shops, restaurants, and more.

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Chicago Riverwalk

Sip martinis at Ralph Lauren's iconic Chicago restaurant.

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RL Restaurant

A Japanese dining bar known for its creative cocktails and hip atmosphere.

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Kumiko

An elevated tiki bar experience in River North.

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Three Dots and a Dash

At over 100 years old, this jazz and cocktail lounge is simply iconic. Note - they only accept cash.

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Green Mill

Soho House's public restaurant and bar is a terrific place to meet for drinks.

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The Allis

Artisinal cocktails and pre-prohibition libations are served in this Wicker Park bar.

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The Violet Hour

Known for its incredible Italian fare and impeccable service, Monteverde is a go-to choice for visitors and locals alike.

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Monteverde

Chicago is known for its steak, and this lively, yet intimate spot is perhaps our favorite steakhouse in the city. 

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Bavette's Bar & Boeuf

What's a trip to Chicago without deep dish pizza? Opt for Lou Malnati's, a local favorite.

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Lou Malnati's

This gorgeous French-Vietnemese restaurant is housed in a Gold Coast row house.

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Le Colonial

Renowned Chef Izard's creation, Duck Duck Goat offers terrific Chinese-American fare.

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Duck Duck Goat

Enjoy thoughtful Greek food in an earth-toned, indoor-meets-outdoor space. 

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LÝRA

Also by Chef Izard, this is her diner featuring creative, gourmet takes on comfort food classics.

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Little Goat Diner

Italy meets Croatia at this industrial-chic restaurant in the historic Fulton Market district.

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Rose Mary

Enjoy elevated Mediterranean fare and creative cocktails at this rooftop restaurant.

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Two-Michelin star chef Danny Grant brings us an unforgettable culinary experience. 

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Maple & Ash

7 levels of shopping and restaurants anchored by Bloomingdale's.

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900 North Michigan Shops

Established in 1875, this pharmacy features upscale and unique brands like Santa Maria Novella, D.R. Harris & Co, and more.

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Merz Apothecary

Luxury shopping in Chicago's Gold Coast. Visit Chanel, Prada, Hermes, Morgenthal Frederics, and more. 

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Oak Street

Visiting during the holidays? This traditional holiday market is a must-visit, drawing over 1 million visitors per year.

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Christkindlmarket

Antique housewares and and vintage goods sourced from auction houses and European markets. 

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P.O.S.H.

Located just north Chicago, in Lake Forest — shop a perfectly curated selection of high end women's clothing, jewelry, and more.


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The Lake Forest Shop

This stunning luxury hotel offers gorgeous views of the Chicago River and Lake Michigan.

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The Langham

This luxury hotel is ideally located just a block away from the Museum of Contemporary Art and Water Tower Place.

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The Peninsula

Located in iconic Gold Coast, the Thompson is comfortable, modern, and sophisticated.

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Thompson

A more trendy stay in the heart of Fulton Market District.

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The Hoxton

This elegant hotel has large rooms and is found in a great location.

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Waldorf Astoria

Step into a 1929 art deco building in the Loop, paying a perfect tribute to both the past and present.

Chicago

Gray's Guide to

Chicago