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Cheap flights from Chicago

Compare flights from Chicago from hundreds of providers

Find a cheap flight deal from Chicago to anywhere, anytime

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Fast facts on flights from Chicago

Closest airportsChicago Midway, Chicago O'Hare International
Cheapest route foundChicago - Atlanta, C$52
Cheapest month to flyJune
Most popular airlineAmerican Airlines
Most popular destinationToronto

The best flight deals leaving from Chicago soon

Save on your flight fare, so you can spend more when you get there. Here are the best domestic and international flights from Chicago departing soon.
Atlanta.C$52 per passenger.Departing Tue, Jun 4, returning Wed, Jun 5.Round-trip flight with Spirit Airlines.Outbound direct flight with Spirit Airlines departing from Chicago O'Hare International on Tue, Jun 4, arriving in Atlanta Hartsfield-Jackson.Inbound direct flight with Spirit Airlines departing from Atlanta Hartsfield-Jackson on Wed, Jun 5, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$52, select.
San Juan.C$146 per passenger.Departing Tue, May 7, returning Tue, May 14.Round-trip flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departing from Chicago O'Hare International on Tue, May 7, arriving in San Juan Luis Munoz Marin.Inbound indirect flight with Spirit Airlines, departing from San Juan Luis Munoz Marin on Tue, May 14, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$146, select.
Cancun.C$251 per passenger.Departing Sun, May 5, returning Wed, May 8.Round-trip flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departing from Chicago O'Hare International on Sun, May 5, arriving in Cancun.Inbound direct flight with Frontier Airlines departing from Cancun on Wed, May 8, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$251, select.
San Jose.C$276 per passenger.Departing Tue, May 7, returning Wed, May 15.Round-trip flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departing from Chicago O'Hare International on Tue, May 7, arriving in San Jose Juan Santamaria.Inbound indirect flight with Spirit Airlines, departing from San Jose Juan Santamaria on Wed, May 15, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$276, select.
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Booking flights from Chicago: Frequently Asked Questions

The best price we found for a round-trip flight from Chicago to Atlanta is C$52. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
After crunching the numbers on our flight calendar, we found that the cheapest date to fly out of Chicago is Tuesday, June 4, 2024, to Atlanta Hartsfield-Jackson.
It's easy with us. Look for cheap flights and flight offers from Chicago to anywhere using Everywhere search – it'll show you the lowest fares for your chosen time period.

You can also set up Price Alerts for flights you'd like to keep an eye on. We'll let you know when a particular fare from Chicago goes up or down so you can book when it's cheapest.
Sure – our flight search allows you to check for outbound flights from Chicago O'Hare International Airport departing the very same day. But if you want the cheapest fare, we recommend you book around 30 days before departure. On average, this is the time when fares are cheaper.
Of course! Just select "one way" when you search with us. And here's an extra tip: Sometimes, searching for a one-way ticket from Chicago, and another one-way back home, can yield cheaper tickets than a round-trip fare with an airline.
It's best to arrive at the airport at least 2 hours before the time of your flight departure, so you have enough time to check in any luggage, clear security and find your gate.
The cheapest flight from Chicago we found in the next 1 year is to Atlanta Hartsfield-Jackson for C$52. It departs from Chicago O'Hare International Airport on Tuesday, June 4, 2024. There are also cheap flights from Chicago to San Juan Luis Munoz Marin for C$146 and Cancun for C$251.

How to find cheap flights from Chicago in 2024

Looking for cheap tickets from Chicago? Round-trip flight tickets from Chicago start from C$52 and one-way flights from Chicago start from C$26.

Whether you are flying one-way or round-trip, here are a few tips on how to score the best price and make your flight journey as smooth as possible.

  • Enter your destination and hit "search." We've compared flights from all major airlines and online travel agents to find the cheapest flight tickets from Chicago. And with us, there are no hidden fees – what you see is what you pay.
  • Compare flight deals from Chicago from over 1,000 providers. Then choose the cheapest or fastest plane tickets. Flight tickets from Chicago start from C$26 one-way.
  • Search flights everywhere. Not sure on the destination just yet? You can easily browse available places to travel to from Chicago by searching flights to "Everywhere."
  • Flex your dates to secure the best fares for your flight from Chicago. If your travel dates are flexible, use Skyscanner's "Whole month" tool to find the cheapest month, and even day to fly from Chicago.
  • Set up a Price Alert. We price-check with over 1,000 travel companies so you don't have to. You can easily track the price of your tickets from Chicago by creating an alert. Whenever prices go up or down, you'll get an email or push notification to help make sure you get the best possible flight deal.
  • Look for direct flights. Only interested in non-stop flights from Chicago? Make sure to check "Direct flights" when performing a search. If there are direct flights from Chicago available, these will appear in the results.
  • Find the cheapest Business class flights from Chicago. We scour the Internet for the best Business, Premium Economy and First Class flight fares from Chicago, too. Check the difference in price as you search – you might just chance upon a last-minute low fare.
  • Include nearby airports in your search. Widen your search for flight deals from Chicago by selecting the "add nearby airports" option. This will allow you to see flight prices for all the nearest airports at your departure and destination point and could help you save money.
  • Search for cheap flights from Chicago on the go. To get the best flight booking experience when out and about, download the app and search for plane tickets from Chicago whenever you want.

Combine your flight from Chicago with hotels and car rental

Once you've secured your plane ticket from Chicago, discover the best prices and exclusive rates for hotels in, or close to, your destination. Compare hundreds of car rental companies all at once so you get the best car rental deals for your trip.