Chicago City Guide

Editor's Choice: Discover Chicago restaurants, activities, hotels & maps.

Trip by Skyscanner's Chicago travel guide is the best way to discover the coolest places to go in Chicago. Whether you're planning a vacation or simply exploring, Trip by Skyscanner offers insider reviews and photos for the best hotels, restaurants, and places to go in Chicago. Named Editor's Choice on Google Play, and featured in New York Times Travel, Conde Nast Traveler, Travel + Leisure, CNN Travel, Huffington Post, Outside and more.

Trip by Skyscanner's Chicago City Guide offers the best personalized guide to Chicago. Affectionately referred to as “The Windy City” by locals and tourists alike, Chicago rests along the southwestern coast of Lake Michigan and possesses perhaps one of the most picturesque skylines in the United States. The city's combination of office-laden skyscrapers and rail and steel industries help give the city a cosmopolitan feel with blue-collar sensibility. Visitors inevitably hang out in The Loop with its high-rise hotels and iconic attractions like the Sears Tower, the world-renowned Art Institute of Chicago, and the Museum of Contemporary Photography and Millennium Park, which showcases the city's architecture, art and music. Head indoors -- especially in the brutal winter months when an arctic wind whips off Lake Michigan-- for Chi-town's other famous offerings: jazz clubs, theater (including the famed Second City improv troupe) or, of course, sports. Name a sport and Chicago has a team: the Chicago Bulls, Chicago Cubs, Chicago White Sox, Chicago Bears and the Chicago Blackhawks, winners of the 2010 Stanley Cup. Dieters might want to skip a week here; Chicago's signature dishes include deep-dish pizza, hot dogs and infinite forms of sausage.

What users love about the Trip by Skyscanner Chicago Travel Guide:


✓ EXPLORE Chicago to the fullest.

✓ PLAN your next trip easily and discover where friends have been!


✓ BOOK a hotel on the go with just a tap.


✓ CREATE stunning photo postcards and reviews of places you've visited.


✓ GET INSPIRED with postcards and reviews by friends and travelers like you


✓ JOIN a community of passionate travelers from around the world.

TRIBES

Trip by Skyscanner Tribes are communities of travelers who share common interests. Are you a trail-blazing jet-setter with an adrenaline addiction? The Adventure Tribe may be for you. Feel at home in high-end hotels in exotic locations? Check out the Luxury Tribe for great tips. Always on top of the latest local hotspots? The Trendsters Tribe and Nightlife Tribe is where you'll find your groove. With 19 Tribes, and more on the way, travel advice has never been more personal!

POSTCARDS

Share your experiences with your friends. Turn your photos into digital postcards and customize them with filters to make them look beautiful. You can share your postcards with friends via Facebook, Twitter, email or SMS. You can also browse beautiful postcards from around the world on the "Featured" feed.