Summer is by far the best time to visit Chicago not just for the agreeable weather, which allows for spending time on the beach (people often forget there are over 20 miles of lakefront park and beaches in Chicagoland), but also the opportunity to partake in the summer festivals including the Taste of Chicago and Lollapalooza, both in July. There are also endless shopping, dining (from hole-in-the wall joints to Michelin rated options), and several world class museums, including the Art Institute of Chicago, which was the number 1 museum in the world in 2014’s TripAdvisor’s Travelers’ Choice awards, beating out other world renown museums including the State Hermitage Museum in St. Petersburg, Musee d’Orsay in Paris and the Metropolitan Museum of Art in New York City.
But don’t just take our word for it, and find out for yourself with these great, low fares the experts at Fly.com have found that will save you up to $100 off roundtrip prices. So whether you’re a Chicago virgin or its been a while since your last visit, now’s a good a time as any to take in all that the Windy City has to offer!
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 August to November, unless otherwise noted (blackouts may apply). All prices roundtrip, including taxes:
- $98-$117 — Raleigh (through Aug. 31)
- $117-$127 — Philadelphia (through June 22)
- $118 — Las Vegas (through June 18)
- $137 — Houston
- $145 — Washington, D.C. (Aug. 18-Sept. 30)
- $157 — Tampa
- $198-$208 — Los Angeles (Aug. 18-Oct. 19)
- $198-$228 — San Francisco (Sept. 1-Oct. 18)
- $237-$247 — San Diego
- $267 — San Antonio (Aug. 25-Oct. 27)
- More Flights to Chicago
More Cheap Domestic Flights
Chi-town’s not the kind of town for you? Don’t fret as we have 10 hot fares to various U.S. destinations including Denver and Florida.
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 August, unless otherwise noted (blackouts may apply). All prices roundtrip, including taxes:
- $77-$137 — Charlotte to Philadelphia
- $78-$97 — Phoenix to Denver (through Aug. 5)
- $81-$119 Minneapolis to Denver (through June 23)
- $87 — Kansas City to Houston (through June 23)
- $97 — Los Angeles to Denver (Sept. 1-Dec. 9)
- $98 — Atlanta to Miami (June 2-July 27)
- $107 — Baltimore to Myrtle Beach
- $117-$147 — Cleveland to Fort Lauderdale
- $118 — Chicago to Las Vegas (through June 16)
- $145 — Seattle to Denver (Sept. 1-Oct. 6)
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.
Fly.com Updates
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Featured Image: Oak Street Beach, Chicago (Shutterstock.com)
