Find cheap flights to Chicago
Good to know
|February||Best time to beat the crowds with an average 3% drop in price.|
|December||Most popular time to fly with an average 6% increase in price.|
Average price of a round-trip
|$227||(avg. price over the last 2 weeks)|
Good deal for a round-trip
Top tips for finding cheap flights to Chicago
- Looking for cheap airfare to Chicago? 25% of our users found round-trip tickets to Chicago for the following prices or less: From New York $125, from Boston Logan Intl $134, from Los Angeles $152
- Book at least 3 weeks before departure in order to get a below-average price.
- High season is considered to be June and July. The cheapest month to fly to Chicago is February.
- When purchasing flights to Chicago, travelers have two main airport options: the larger and newer O’Hare International Airport (ORD) and the more budget-friendly Midway International Airport (MDW). O’Hare is located on the northwest side of Chicago and offers direct flights to over 200 destinations across the world. Once known as the “busiest square mile in the world”, Midway is now predominantly serviced by low-cost airlines.
- For those yogi travelers out there, Midway International Airport has yoga rooms ready for your vinyasas. Located in Concourse C, it is open daily from 6:00 a.m. to 10:00 p.m. and has complimentary mats available for your use.
- “The "Kids on the Fly" (KOTF) exhibit at O’Hare International Airport is an educational and excitement-filled place for kids and parents to relax and have a bit of a fun before or after their flight.
- If you are looking at flights to Chicago, an alternative to ORD and MDW is the Gary/Chicago International Airport (GYY). Technically just outside Gary, Indiana, the airport is actually only 30 minutes away from downtown Chicago and provides another option for travelers to consider.
- Public transit in Chicago conveniently links up directly with both O’Hare International Airport and Midway International Airport. For O’Hare, the CTA Blue Line is located right within the airport and will get you to downtown Chicago in around 40 minutes while costing you about $5. At Midway, the CTA Orange Line can be found within the airport and will take around 20 minutes to get you downtown and will cost around $3.
FAQs - booking Chicago flights
Which airlines fly to Chicago?
How much does it cost to fly to Chicago?
What are the cheapest months to fly to Chicago?
Which is the cheapest day to fly to Chicago?
How long is the flight to Chicago?
Which Chicago airport is closest to central Chicago?
Which Chicago airport is closest to downtown?
How to get to the Loop from Chicago’s airports?
What to do in O’Hare International Airport?
How far are the Chicago airports from each other?
How does KAYAK’s flight Price Forecast tool help me choose the right time to buy?
Top airline flying to Chicago
Scores according to KAYAK customer reviews
Book Cheap Chicago Plane Tickets (Round-trip)
Book Cheap Chicago Plane Tickets (One-way)
Flights to Chicago
We attempt to get accurate prices, however, prices are not guaranteed.
We’re not the seller.
At KAYAK we don’t set the prices, so it’s not possible for us to guarantee what other companies are selling.
We compile tonnes of data for you
Our service lets you quickly and easily compare results from hundreds of travel sites at once. In this sense, KAYAK is a search engine and we can't guarantee prices we find.
Why aren’t prices accurate 100% of the time?
Prices on airline seats, hotel rooms and car rentals can change frequently. Several people may also be trying to buy the same travel option simultaneously. As a result, you may find, on occasion, that certain prices are no longer available.
If you have more questions or if you have a bad price to report to us,
please send us an email and someone from our team will get back to you promptly.