Cheapest flights from Chicago

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Reviews from verified customers

Aug 13, 2020

Most comfortable flight we’ve eve had! Friendly staff and great food! Would definitely use them again.

May 1, 2020


Apr 2, 2020

Free movies on the flight were great!

Mar 23, 2020

First time on TAP & very impressed 💙🇵🇹

Mar 19, 2020

Got me to my destination w minimal hassle.

Mar 19, 2020

Too hot during flight.

Mar 17, 2020

Hoping my trip home is easy as it was coming to Hartford.!!

Mar 17, 2020

Carry on policy not the same for everyone. Don't like it

Mar 16, 2020

All American staff that we encountered were very friendly and helpful

Mar 16, 2020

Airlines are doing a great job

Mar 16, 2020

I am very angry at Expedia. I have an infant daughter I was flying with. I asked Expedia to add a lap infant to my ticket. I was told that it was impossible, I need to cancel my booking, buy a new ticket which will cost EUR 3000. This is definitely a discriminatory behavior. I was also told that United Airlines cannot do that, so the only option is to pay EUR3000. Then, I contacted United. Without asking me further questions, they added a lap infant for EUR 300. What Expedia has done is not only discriminatory but also predatory. I demand an apology

Mar 16, 2020

The staff was amazing! Also- the seats were comfortable. I will fly with them again anytime.

Flights from Chicago: Essential Travel Information

Cheapest flight from Chicago$31 (roundtrip)
Best airlines to fly from ChicagoSpirit Airlines, Frontier Airlines, Delta, United
Cheapest month to fly from ChicagoDecember
Chicago IATA codeCHI
Chicago Country/StateIllinois
Airline ticket deals from Chicago$31 - $218


How to Find Cheap Flights from Chicago

How much is a flight from Chicago?

This week, flights from Chicago are available between $31 - $218. 

How to find cheap flights from Chicago?

Expedia makes it easy to compare cheap flights from Chicago to many destinations. Check out excellent deals on both domestic and international flights from Chicago. Once you select an offer, use our filters and sort by ‘Price (Lowest)’ to see the cheapest and most suitable options. 

How can I get the best deal on flights from Chicago?

Expedia gives you access to all the hottest deals on plane tickets so you can get the most amount of value for the lowest price possible. An excellent strategy for finding the best deal on flights is to be flexible with your dates. Within each offer, you can compare prices for similar timeframes using our ‘Show flexible dates’ feature. Depending on your destination, direct flights from Chicago may be more expensive. Airlines with strict bag policies or fees can also impact your costs. 

What is the best airline to fly from Chicago?

At Expedia, we give you all the available options from our reputable partners. Select the airline that best suits your preferences and membership loyalties. You can fly from Chicago with: Spirit Airlines, Frontier Airlines, Delta, United. 

What is the best month to fly from Chicago?

The cheapest time to fly from Chicago airport(s) is December, based on the current list of flights available now. Prices on plane tickets vary considerably throughout the year due to availability and seasonal demand.

When is the best time to book flights from Chicago?

ARC & Expedia Group historical data suggests that booking flights from Chicago three weeks out and on a weekend, usually on a Sunday, can save you up to 20% or more on your fare. *

Are there any last-minute flights from Chicago?

Expedia is the place to find last-minute flights from Chicago, making it easy for you to compare prices on flights in the near future for different combinations of travel dates and from multiple airlines. We source the best deals for you and display the best offers available over the next 2-weeks. 

Why booking with Expedia?

Booking flights from Chicago with Expedia is the obvious choice to get low prices, save money, and see more value from every dollar spent. We show you the best deals happening right now and provide a vast inventory of airlines and flight routes to choose from. You can customize your journey to your timeline, route preferences, budget, rewards programs, and more. Not only will you get a stellar deal, but you’ll also get rewards points back and the opportunity for additional discounts when bundling with a hotel or car rental.

Can I change/cancel my flight?

Some flights can be changed or canceled, but fees and refunds will depend on the unique terms of your flight agreement. Airlines have different rules and restrictions for exchanging or refunding flights. For more information, go to your itinerary or visit our customer service portal. We recommend choosing flights with no change fees for the most amount of flexibility. Filter by ‘Flexible change policies’ to see flights with no change fees.

*Data specialists from both ARC and Expedia Group analysed ARC’s global flight data to distil actionable information to help people save money on travel. While it’s impossible to guarantee when to find the lowest prices, after examining the variables, we were able to observe trends. Analysis based on ARC, round-trip flight data between 1 October 2017 – 30 September 2018 for Economy and Premium cabin ATPs on a global basis.