WAS - CHI

£102 Find Cheap Flights from Washington, D.C. to Chicago

This is the cheapest return flight price found by a KAYAK user in the last 72 hours by searching for a flight from Washington, D.C. to Chicago departing on 16/8. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Washington, D.C. to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Washington, D.C. to Chicago, as well as popular online travel agencies
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Flights Deals

Cheap Flights from Washington, D.C. to Chicago (WAS-CHI)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for return flights from Washington, D.C. to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent return flight deals from Washington, D.C. to Chicago

Sat, 16 Aug - Sat, 16 Aug
United Airlines Logo
06:15 - 07:30BWI-ORD
2h 15mdirect
United Airlines Logo
20:20 - 23:24ORD-BWI
2h 04mdirect
£102United Airlines
Find Deal
Thu, 14 Aug - Tue, 19 Aug
United Airlines Logo
06:15 - 07:30BWI-ORD
2h 15mdirect
United Airlines Logo
10:45 - 13:48ORD-BWI
2h 03mdirect
£109United Airlines
Find Deal
Tue, 16 Sep - Wed, 17 Sep
Southwest Logo
10:25 - 21:30BWI-ORD
12h 05m2 stops
Southwest Logo
13:50 - 16:55ORD-BWI
2h 05mdirect
£120Southwest
Find Deal
Tue, 23 Sep - Mon, 29 Sep
Southwest Logo
10:35 - 11:50BWI-ORD
2h 15mdirect
Southwest Logo
11:25 - 23:35ORD-BWI
11h 10m1 stop
£121Southwest
Find Deal
Sat, 26 Jul - Sat, 2 Aug
Spirit Airlines Logo
05:45 - 16:57BWI-ORD
12h 12m1 stop
Spirit Airlines Logo
16:37 - 23:49ORD-BWI
6h 12m1 stop
£127Spirit Airlines
Find Deal
Thu, 14 Aug - Mon, 18 Aug
Delta Logo
06:00 - 10:20DCA-ORD
5h 20m1 stop
Delta Logo
13:30 - 20:46ORD-DCA
6h 16m1 stop
£145Delta
Find Deal
Wed, 13 Aug - Tue, 19 Aug
Delta Logo
09:50 - 12:45IAD-ORD
3h 55m1 stop
Delta Logo
09:10 - 16:31ORD-IAD
6h 21m1 stop
£145Delta
Find Deal
Mon, 24 Nov - Thu, 27 Nov
JetBlue Logo
09:40 - 17:27DCA-ORD
8h 47m1 stop
JetBlue Logo
08:40 - 18:01ORD-DCA
8h 21m1 stop
£149JetBlue
Find Deal
Sun, 14 Sep - Fri, 19 Sep
JetBlue Logo
06:25 - 12:10DCA-ORD
6h 45m1 stop
JetBlue Logo
13:36 - 19:21ORD-DCA
4h 45m1 stop
£153JetBlue
Find Deal
Sat, 26 Jul - Sat, 2 Aug
Spirit Airlines Logo
22:11 - 16:41BWI-ORD
19h 30m2 stops
Spirit Airlines Logo
16:37 - 23:49ORD-BWI
6h 12m1 stop
£166Spirit Airlines
Find Deal
Expert advice

Expert advice for your flight from Washington, D.C. to Chicago

 
Snippets provided in this section are AI-generated based on a summarisation of KAYAK-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airports
DCA

DCA offers convenient access to downtown D.C., just 4 miles away, making it ideal for quick trips.

Read more about DCAby Stefanie Waldek
IAD

For quick access at IAD, use the AeroTrain to navigate between terminals efficiently, especially during peak travel times.

Read more about IADby Stefanie Waldek
ORD

Take the CTA Blue Line from ORD to reach downtown Chicago in about 45 minutes, avoiding traffic delays.

Read more about ORDby Stefanie Waldek
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on ORD, DCA and IAD

Stefanie Waldek

Stefanie Waldek

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or out at sea, likely en route to Antarctica or the Arctic.

Read more
Useful Info

KAYAK's insights & trends for Washington, D.C. to Chicago flights

Get data-powered insights and trends into flights from Washington, D.C. to Chicago to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Washington, D.C. to Chicago flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Washington, D.C. to Chicago.

Our data shows that the cheapest route for a return flight from Washington, D.C. to Chicago cost £169 and was between Washington, D.C. Reagan-National Airport (DCA) and Chicago O'Hare Intl Airport (ORD). On average, the best prices are found if you fly this route. The average price for a return flight for this route is £169.

What is the cheapest month to fly from Washington, D.C. to Chicago?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Washington, D.C. to Chicago, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Washington, D.C. to Chicago is September, where tickets cost £157 (return) on average. On the other hand, the most expensive months are April and May, where the average cost of round-trip tickets is £201 and £201 respectively.

How far in advance should I book a flight from Washington, D.C. to Chicago?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Washington, D.C. to Chicago, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Washington, D.C. to Chicago, you should book around 3 weeks before departure. For the absolute cheapest price, our data suggests you should book 11 weeks before departure.


Good to know - Cheap tickets from Washington, D.C. to Chicago

Low seasonJanuary
High seasonAugust
Best time to beat the crowds (10% less expensive on average)
Most popular time to fly (5% more expensive on average)

When to book flights from Washington, D.C. to Chicago

Are your dates flexible? Find out the best times to travel from Washington, D.C. to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated return price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or returns with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Washington, D.C. to Chicago

  • What is the cheapest flight from Washington, D.C. to Chicago?

    In the last 3 days, the lowest price for a flight from Washington, D.C. to Chicago was £59 for a one-way ticket and £139 for a return.

  • Which airlines offer Wi-Fi service onboard planes from Washington, D.C. to Chicago?

    Only American Airlines offers inflight Wi-Fi service on the Washington, D.C. to Chicago flight route.

  • Which aircraft models fly most regularly from Washington, D.C. to Chicago?

    The Airbus A319 is the aircraft model that flies most regularly on the Washington, D.C. to Chicago flight route.

  • Which airline alliances offer flights from Washington, D.C. to Chicago?

    oneworld, and Star Alliance are the airline alliances operating flights between Washington, D.C. and Chicago, with Star Alliance being the most commonly used for this route.

  • On which days can I fly direct from Washington, D.C. to Chicago?

    There are direct flights from Washington, D.C. to Chicago on a daily basis.

  • How does KAYAK find such low prices on flights from Washington, D.C. to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Washington, D.C. to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Washington, D.C. to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Washington, D.C. is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Washington, D.C. to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional return ticket. You could then fly to Chicago with an airline and back to Washington, D.C. with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Washington, D.C. to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Washington, D.C. up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Washington, D.C. to Chicago

  • Looking for a cheap flight from Chicago to Washington, D.C.? 25% of our users found flights on this route for £338 or less one-way.

Prefer to fly direct from Washington, D.C. to Chicago?

Find which airlines fly direct from Washington, D.C. to Chicago, which days they fly and book direct flights.

Direct departures

Washington, D.C. to Chicago

Monday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Tuesday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Wednesday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Thursday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Friday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Saturday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Sunday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

See more direct flights

Direct returns

Chicago to Washington, D.C.

Monday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Tuesday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Wednesday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Thursday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Friday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Saturday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Sunday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

See more direct flights
See more direct flights

Top airline flying from Washington, D.C. to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Washington, D.C. to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Washington, D.C. to Chicago? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
5.9
FrontierOverall score based on 3295 reviews
6.2Boarding
4.8Food
6.8Crew
5.6Comfort
4.5Entertainment
Airline reviews

Book with frontier airlines with the mentality that they'll cancel your flight, kick you off and lose your luggage. Anything besides that is a win. Compare prices with other airlines (to include luggage) and if frontier is still worth it, book it but know all of their policies.

8.0 ExcellentTy, Jun 2025DFW - TPA
Read more Frontier reviews

Book with frontier airlines with the mentality that they'll cancel your flight, kick you off and lose your luggage. Anything besides that is a win. Compare prices with other airlines (to include luggage) and if frontier is still worth it, book it but know all of their policies.

You get what you pay for nothing essentially but a hard uncomfortable seat that doesn’t recline and kids screaming all around you and chaotic boarding and limited check bag weight allowance when compared to other airlines

I never got to experience the flight because they delayed my first flight and I missed this one. Then Frontier didn't want to help me rebook a flight to get me to my final destination.

The Boarding process in Denver was chaotic, and since the line was so long, we were lined up very far from the gate. If there were any announcements from the gate staff, we didn't hear them. The flight attendants were spectacular. The only negative part of the flight was sitting by a 2 1/2 year old who was unruly and unfortunately had parents that matched his behaviors. Also, the restaurants in Denver on the E concourse, they didn't have food (passengers could only order 1 item on the entire menu) or the restaurants had 12-14 people waiting for orders to be prepared and another 6 people waiting to order. If you have a layover in Denver and need to grab food, be prepared to visit the shops with pre-packaged sandwiches, or you can visit another concourse but it may take a while to transit throughout the airport.

I liked the turn-style feature at gate 209B at LAX. Very efficient process. The gate staff also made several, clearly directed announcements so I felt very informed.

Although an hour and a half early was told by staff at check in they had overbooked and could not check us in for the flight.

The crew was delayed because they came on another flight that was delayed due to weather 10pm flight left at 1.30 am The airline made no effort to align alternate crew

Plane was down graded and I lost my uncharged exit row with more leg room. No mention or offer of refund from podium. Flight attendant was nice to explain this happens often and that I could request a refund via online form submission. I did this and have heard nothing back.

Worst airline experience. They were rude and kept changing our seats and/or giving our seats away so our family didn’t get to sit with each other. Almost everyone we dealt with at both airports with this airline was rude. The app kept giving us wrong information making things take longer. Dealing with them before TSA can take close to an hour…longer than I’ve ever had to deal with before. Never using this airline again.

Horrendous. I do not recommend Frontier. The passengers lack manners and decency, and the flight attendants lack professionalism. If I wasn’t in a bind to fly with 48 hours notice for a job interview, I would not have selected a flight with Frontier and I never plan to fly with them in the future.

Everything you need to know for your flight from Washington, D.C. to Chicago

Cabin class types available on flights from Washington, D.C. to Chicago

Cabin classes available on flights from Washington, D.C. to Chicago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability are not guaranteed.

Compare transportation modes for Washington, D.C. to Chicago

Transportation modeAverage priceAverage duration
Flights£3392h 13m
Trains£20617h 40m
Buses£11721h 08m

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