Chicago Flights as Low as $158.99
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
It's time to fly. What's waiting for you in Chicago?
Perhaps you’re searching cheap flights to Chicago for a much-needed vacation or you simply have to roll in to see the relatives. Either way, we say rock that family reunion. Tell one too many stories at the hotel bar. Traveling for work? Crush it. If you lie back and relax without your cell phone, we won’t tell.
In the end you want to score a great deal and have a fantastic time, right? Flying is a small part of the whole adventure. We get that. Wherever you’re excited to go – or get away from – start this story with Hotwire’s cheap flights to Chicago.
Not sure how to get the best price on plane tickets to Chicago?
We know there are some airline aficionados out there. If you don’t know the industry like the back of your hand, don’t worry. You can make spending less look good with our booking tips.Search certain days of the week for Chicago flights
For better savings, consider departing on a Wednesday, Thursday or Saturday. Return on a Sunday, Tuesday or Wednesday. International deals are often available when departing Monday through Thursday.Change up your days for cheaper weekend getaways
Jetting off on Thursday and returning on Sunday is generally less expensive than flying on Friday and returning on Monday.Stay a Saturday night to play more
Spending the weekend at your destination will generally result in lower airfares. We’re all for that.Consider alternate airports when searching Chicago flights
Other nearby airports may offer different fares from your current search results. Clicking “Nearby Airports” after your initial search will give a list of the closest options.See a fare that you like? Pounce!
Coordinate with your travel buddies before searching and you’ll be able to act quickly when it’s time to book. Airline ticket prices often change in minutes. We know you’re combing for the best prices but so is everyone else! If the deal is right, snag it and feel the sweet satisfaction of booking victory.Fly during the off-peak season
Certain travel destinations have especially high volume during particular seasons. For example, Europe, Hawaii and Alaska are big hits in the summer. Florida, New Orleans and Southern California are the most popular in springtime. Winter is prime for Mexico and the Caribbean, as well as ski and snowboard destinations like the Colorado Rockies. In the autumn, Northern California, the Pacific Northwest and New England draw visitors. Flying during less popular periods can mean extra money in your wallet – yes, please!Save more. Do more.
Flights to Cities Near Chicago
Our Favorite Destinations
- Flights to Las Vegas
- Flights to New York
- Flights to Orlando
- Flights to Los Angeles
- Flights to San Francisco
- Flights to Chicago
- Flights to Miami
- Flights to Honolulu
- Flights to Boston
- Flights to Atlantic City
- Flights to San Diego
- Flights to Seattle
- Flights to New Orleans
- Flights to Myrtle Beach
- Flights to Fort Lauderdale
- Flights to Anaheim
- Flights to Atlanta
- Flights to Nashville
- Flights to Key West
- Flights to Denver