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Cheap Flights to Chicago

All that Jazz...


First time to Chicago? The cheapest flights to Chicago generally land at Midway Airport, although you can find some great deals to O’Hare International Airport as well. From there it’s an easy taxi or train ride straight into downtown Chicago.

The home of blues and jazz, Chicago boasts an eclectic mix of cutting edge architecture, top notch theatre, world class museums, major league baseball, fantastic shopping and a buzzing night-life.

Take a stroll through downtown Chicago and enjoy the view of the Windy City as some of the tallest skyscrapers in the world rise out of Lake Michigan. Pay a visit to the Art Institute of Chicago to see some of the country’s best art collections, or Millennium Park famous for its architecture and landscape design. Shop till you drop on Magnificent Mile and rest your wary feet over a renowned deep dish pizza in Pizzeria Uno. Take a train to Wrigley Field to watch the Chicago Cubs and finish your night at Buddy Guy’s Legends to listen to some Chicago blues at its best. Ready to go? Skyscanner can also help you find a hotel in Chicago. Or, if you want to expand your search, have a look at cheap flights to Illinois.

Find cheap airfares using Skyscanner's flight search engine. Browse the best travel agents and over 600 airlines, worldwide. Skyscanner is simple and fast! We make it easy to browse for airline tickets then book your flights to Chicago direct, by clicking through to travel agency and airline sites. Find inspiration for your next adventure: try searching on Skyscanner from your chosen departure airport to "everywhere". Please look through our flight offers below, or use the search box to enter your travel information and let us find airline tickets to Chicago, or wherever your next adventure may take you!


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from $65 return

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