WAS - CHI

$89 Find Cheap Flights from Washington, D.C. to Chicago - Compare and Save

This is the cheapest one-way 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 9/25. 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, 0 bags

Save 21% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Everything you should know

Cheapest round-trip
$184
Typical prices: $217-$308
Southwest
Sun 9/6Sat 9/12
DCA - MDW • Non-stop
Cheapest non-stop
$184
Typical prices: $246-$382
United Airlines
Wed 9/9Fri 9/11
IAD - ORD • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
United Economy Plus adds up to six inches more legroom than standard economy.
Southwest free carry-on beats bag fees, while American adds early boarding.
Expert advice
Expert advice
Expert advice
Expert advice
Nonstop flights
You can fly direct with American Airlines, Southwest and United Airlines. Average duration is 2h 14m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $179 (round-trip)
Shortest trip • 3h 41m (one-way)
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 4 weeks in advance save around 52% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 17% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
Flight Deals
Booking Insights
Expert advice
Flight 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 round-trip 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 round-trip flight deals from Washington, D.C. to Chicago

Sun, Sep 6 - Sat, Sep 12
Southwest Logo
11:50 am - 12:45 pmDCA  Washington, D.C. Reagan-National-MDW Chicago Midway
1h 55mnonstop
Southwest Logo
11:15 am - 2:05 pmMDW  Chicago Midway-DCA Washington, D.C. Reagan-National
1h 50mnonstop
$184Southwest
Sat, Sep 12 - Mon, Sep 14
Frontier Logo
6:00 pm - 12:23 amDCA  Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl
7h 23m1 stop Denver Intl
Frontier Logo
6:30 am - 9:59 pmORD  Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National
14h 29m1 stop Denver Intl
$184Frontier
Fri, Oct 30 - Mon, Nov 2
United Airlines Logo
9:30 am - 10:50 amDCA  Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl
2h 20mnonstop
United Airlines Logo
6:00 am - 8:56 amORD  Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National
1h 56mnonstop
$184United Airlines
Fri, Sep 11 - Mon, Sep 14
United Airlines Logo
9:30 am - 10:47 amDCA  Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl
2h 17mnonstop
United Airlines Logo
7:00 am - 9:59 amORD  Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National
1h 59mnonstop
$184United Airlines
Sat, Sep 5 - Tue, Sep 8
American Airlines Logo
10:16 pm - 11:37 pmDCA  Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl
2h 21mnonstop
American Airlines Logo
9:56 am - 12:57 pmORD  Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National
2h 01mnonstop
$184American Airlines
Wed, Sep 2 - Sat, Sep 5
American Airlines Logo
5:23 pm - 6:54 pmDCA  Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl
2h 31mnonstop
American Airlines Logo
6:00 am - 9:16 amORD  Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National
2h 16mnonstop
$184American Airlines
Tue, Sep 29 - Fri, Oct 30
Southwest Logo
6:00 am - 12:05 pmDCA  Washington, D.C. Reagan-National-MDW Chicago Midway
7h 05m2 stops Orlando Atlanta Hartsfield-Jackson
Southwest Logo
11:10 am - 2:00 pmMDW  Chicago Midway-DCA Washington, D.C. Reagan-National
1h 50mnonstop
$185Southwest
Sun, Sep 6 - Fri, Sep 11
Frontier Logo
8:39 pm - 7:53 amIAD  Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl
12h 14m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
8:55 am - 4:30 pmORD  Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl
6h 35m1 stop Detroit Metropolitan Wayne County
$185Frontier
Sun, Sep 6 - Fri, Sep 11
Delta Logo
6:10 am - 9:17 amDCA  Washington, D.C. Reagan-National-MDW Chicago Midway
4h 07m1 stop Detroit Metropolitan Wayne County
Delta Logo
4:30 pm - 10:40 pmMDW  Chicago Midway-DCA Washington, D.C. Reagan-National
5h 10m1 stop Atlanta Hartsfield-Jackson
$197Delta
Sun, Sep 6 - Fri, Sep 11
Delta Logo
12:33 pm - 4:59 pmDCA  Washington, D.C. Reagan-National-MDW Chicago Midway
5h 26m1 stop Detroit Metropolitan Wayne County
Delta Logo
11:35 am - 6:28 pmMDW  Chicago Midway-DCA Washington, D.C. Reagan-National
5h 53m1 stop Atlanta Hartsfield-Jackson
$197Delta
Booking Insights

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.

How much is a round-trip flight from Washington, D.C. to Chicago?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Washington, D.C. to Chicago departing in September.

Flight prices are below average for this route right now.

Flights to Chicago from Washington, D.C. usually cost between $200 and $352 in September.
The lowest price found in the past 5 days was $184 on American Airlines (Sep 11-Sep 14).

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

Data is based on round-trip flight searches on KAYAK over the past month.

The absolute cheapest return flight from Washington, D.C. to Chicago costs $163 on the route between Baltimore (BWI) and Chicago O'Hare Intl Airport (ORD). However, over the past month, flights between Washington, D.C. Reagan-National Airport (DCA) and Chicago Midway Airport (MDW) were, on average, 6% cheaper than other Washington, D.C.-Chicago routes. The most popular route is between Washington, D.C. Reagan-National Airport (DCA) and Chicago O'Hare Intl Airport (ORD).

What’s the cheapest day of the week to fly from Washington, D.C. to Chicago?

The average price of all round-trip flights from Washington, D.C. to Chicago clicked on KAYAK for each day over the last 12 months.

When flying from Washington, D.C. to Chicago, you should consider leaving on a Thursday and avoid Mondays if you are looking for the best rates. For your return to Washington, D.C., you’ll find the best rates on Fridays and the most expensive ones on Tuesdays.

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 October, where tickets cost $272 (return) on average. On the other hand, the most expensive months are June and July, where the average cost of round-trip tickets is $393 and $377 respectively.

Can I save money by flying with a layover from Washington, D.C. to Chicago?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $356 on average.

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 4 weeks before departure, which saves you about 52% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 17 weeks before departure.

Expert advice

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

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on United Airlines, ORD, DCA and IAD

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 on the sea, likely en route to Antarctica or the Arctic.

Blane Bachelor

Blane Bachelor

Expert on Southwest

Blane Bachelor is a journalist and editor specializing in travel and aviation who writes regularly for top global outlets. Born and raised in Florida, Blane has worked and lived in four countries, including the Netherlands, where she’s currently based with her family. Her favorite way to get to know a new destination is by running or riding a bike around town – or hearing a spooky ghost story about local history. She will always choose the window seat.

Harriet Baskas

Harriet Baskas

Expert on American Airlines

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Good to know

Low season

February

Cheapest flight

$89
Best time to beat the crowds with an average 19% drop in price.
Most popular time to fly and prices are also 18% lower on average.
Flight from Reagan Washington National Airport to Chicago O'Hare Airport

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 round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips 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

  • How do I get downtown from Chicago O’Hare Airport?

    There are a few public transport options available, including the CTA Blue Line “L” train, which is a 24-hour rapid transit service between the airport and downtown Chicago. Metra’s North Central Service commuter train has a weekday service connecting Union Station to the north central suburbs, while Pace buses (250 and 330) offer regular services downtown from Chicago O’Hare ATS Station in remote Parking Lot E.

  • I’m traveling with a baby. What facilities are available at the airports in Washington and Chicago?

    If you’re traveling with a baby or infant, BWI Marshall Airport has lactation stations located in each concourse. Rocking chairs can also be found around the terminal. At Chicago O’Hare in Illinois, Mother’s Rooms allow parents to feed and change infants in a private, comfortable environment.

  • Are there any pet relief areas at Baltimore-Washington International Airport?

    If you’re traveling with pets or service animals, there are two convenient pet relief areas at BWI Airport, located past the security checkpoint.

  • What is the closest hotel to Chicago O’Hare Airport?

    The Hilton Chicago O'Hare Airport Hotel is within walking distance of the domestic terminals. Facilities include comfortable guest rooms, conference facilities, a barber shop, a fitness center, and a number of restaurants.

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

    In the last 5 days, the lowest price for a flight from Washington, D.C. to Chicago was $89 for a one-way ticket and $184 for a round-trip.

  • Do I need a passport to fly between Washington, D.C. and Chicago?

    A passport is not required to fly from Washington, D.C. to Chicago.

  • Which airports will I be using when flying from Washington, D.C. to Chicago?

    There are 2 airports in Washington, D.C. (Washington, D.C. Reagan-National and Washington, D.C. Dulles Intl) and 2 airports in Chicago (Chicago Midway and Chicago O'Hare Intl). The cheapest flights are generally found on the Washington Dulles Airport to Chicago Midway Airport flight route.

  • 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 Boeing 737 MAX 8 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?

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

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

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

  • Which is the best airline for flights from Washington, D.C. to Chicago, Southwest or Delta?

    The two airlines most popular with KAYAK users for flights from Washington, D.C. to Chicago are Southwest and Delta. With an average price for the route of $320 and an overall rating of 8.0, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $335 and an overall rating of 7.8.

  • 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 round-trip 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? 25% of our users found flights on this route for $206 or less one-way and $317 or less round-trip.
  • Flights from Washington to Chicago depart from three airports in the Washington, D.C. area. Baltimore-Washington International Thurgood Marshall Airport is about 45 miles south of downtown Washington and is served by Amtrak and the Maryland Commuter Rail, both of which offer services from Union Station to the airport. Dulles International Airport is located 26 miles from Washington in Chantilly, Virginia. Taxis and shuttle buses are the most convenient way to get to the airport. Ronald Reagan Washington National Airport is located in Arlington County, Virginia, about 4 miles from downtown Washington. This airport is the most convenient for those staying in the heart of the city and is accessible via the Yellow or Blue Line Metro.
  • Direct flights from Washington to Chicago O’Hare International Airport are served by a number of airlines, including American Airlines, Spirit Airlines, and United Airlines. The non-stop route takes a little over two hours.
  • While you’re waiting for your flight to depart from BWI Marshall Airport in Washington, visit the Observation Gallery on the upper level before the security checkpoint. Exhibitions include a 28-foot-tall sounding rocket provided by NASA and a half-sized model of the Parker Solar Probe spacecraft. There is also a small playground and children will enjoy using the binocular viewers to have a closer look at the arriving and departing aircraft. The Sky Azure bistro serves cocktails, craft beer, and snacks.
  • It’s easy to stay active before your flight from Baltimore-Washington International Airport. Located next to gate D1, the ROAM Fitness gymnasium offers complimentary workout gear and is equipped with machines for cardio, weights, and resistance training. Passengers can also enjoy some light exercise by walking the 20-minute Cardio Trails around the terminals before taking off.
  • If you’re looking for a way to relax before your flight from Washington, passengers have access to a private meditation room at BWI Marshall Airport. This space is located behind the Delta ticket counter on the side closest to the D/E security checkpoint.

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

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying 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

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

Other airlines flying from Washington, D.C. to Chicago

Flights from the other most popular airlines that fly from Washington, D.C. to Chicago according to KAYAK users. Prices are the lowest found on KAYAK over the last 7 days. Price and availability are not guaranteed.