When Chicagoans start to shed their winter layers and Chi-beria is nothing but a distant memory, it usually means spring is here and the city is ready to get its party started! Spring and summer are wonderful seasons to be in Chicago, besides the nice weather, because of the numerous festivals and events that dot the local calendar, including a couple of firsts for the City of Big Shoulders: the NFL Draft and the 25th James Beard Foundation Awards (first time this event is held outside New York City). In addition, there are twice weekly fireworks over at Navy Pier between Memorial Day and Labor Day, the 35th Taste of Chicago, Lollapalooza, the Chicago Blues Festival, the Air & Water Show (billed as the largest free show of its kind in the U.S.), and much more.

If you’ve never experience Chicago at its best, perhaps it’s time to pay the Second City a visit with one of the amazing fares the deal experts at Fly.com have found. In addition, we also have great fares to other destinations including Florida, New York City, Los Cabos and more.

Cheap Flights to Chicago

The prices below represent a savings of up to $100 off typical roundtrip prices. These fares are not part of an airline sale and may disappear at any time, so book ASAP!

Availability varies by route. Click on the Fare Calendar links below to find the best dates to travel through June 9, unless otherwise noted (blackouts may apply). All prices roundtrip, including taxes:

More Cheap Flights

If Chi-town’s plethora of events aren’t enough to draw you in, we have more low fares to other destinations including Florida, New York City, Los Cabos and more.

The prices below represent a savings of up to $200 off typical roundtrip prices. These fares are not part of an airline sale and may disappear at any time, so book ASAP!

Availability varies by route. Click on the Fare Calendar links below to find the best dates to travel through June, unless otherwise noted (blackouts may apply). All prices roundtrip, including taxes:

Cheap Domestic Flights

Cheap International Flights

Don’t see fares from your hometown? Browse Today’s Best Fares from your city. And for hotel suggestions, check out Fly.com/hotels for deals and offers.

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Featured Image: Chicago Skyline from North Avenue Beach (Shutterstock.com)

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Kim has been hunting flight deals and writing travel articles for over 13 years. His articles have appeared in the Boston Herald, Chicago Daily Herald, and Frommer’s Budget Travel, among other publications. Amsterdam, Bangkok, Rome, and Sydney are some of his favorite destinations and he aspires to one day live in Italy. La dolce vita!

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