WAS - CHI

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

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Everything you should know

Cheapest round-trip
$177
Typical prices: $270-$459
Southwest
Wed 9/26Fri 9/28
BWI - MDW • Non-stop
Cheapest one-way
$89
Typical prices: $146-$317
Southwest
Sat 9/15
DCA - MDW • Non-stop
Nonstop flights
You can fly direct with United Airlines, American Airlines and Southwest. Average duration is 2h 19m
Direct flights
+1
Direct flights
+1
Top routes
Cheapest • 33% average savings
Most popular
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 7 weeks in advance save around 50% compared to booking last minute.
Insights
Insights
When to travel
Cheapest • 15% price drop
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Cheapest • Avg $182 (round-trip)
Shortest trip • 4h 09m (one-way)
Insights
Insights
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Flight Deals
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Expert advice
Flight Deals

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

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Washington, D.C. to Chicago

Sat, Oct 24 - Mon, Oct 26
Frontier Logo
10:22 am - 6:31 pmBWI  Baltimore/Washington-ORD Chicago O'Hare Intl
9h 09m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
6:00 am - 9:03 amORD  Chicago O'Hare Intl-BWI Baltimore/Washington
2h 03mnonstop
$177Frontier
Fri, Oct 9 - Tue, Oct 13
Frontier Logo
9:58 am - 11:21 amBWI  Baltimore/Washington-ORD Chicago O'Hare Intl
2h 23mnonstop
Frontier Logo
7:40 am - 8:17 pmORD  Chicago O'Hare Intl-BWI Baltimore/Washington
11h 37m1 stop Houston George Bush Intcntl
$177Frontier
Wed, Oct 28 - Sat, Oct 31
United Airlines Logo
6:10 am - 7:29 amBWI  Baltimore/Washington-ORD Chicago O'Hare Intl
2h 19mnonstop
United Airlines Logo
6:29 pm - 9:42 pmORD  Chicago O'Hare Intl-BWI Baltimore/Washington
2h 13mnonstop
$177United Airlines
Mon, Oct 19 - Wed, Oct 21
United Airlines Logo
7:10 pm - 8:29 pmBWI  Baltimore/Washington-ORD Chicago O'Hare Intl
2h 19mnonstop
United Airlines Logo
3:00 pm - 6:13 pmORD  Chicago O'Hare Intl-BWI Baltimore/Washington
2h 13mnonstop
$177United Airlines
Wed, Sep 30 - Thu, Oct 1
Southwest Logo
2:50 pm - 3:50 pmBWI  Baltimore/Washington-MDW Chicago Midway
2h 00mnonstop
Southwest Logo
8:55 pm - 11:45 pmMDW  Chicago Midway-BWI Baltimore/Washington
1h 50mnonstop
$177Southwest
Thu, Oct 1 - Sat, Oct 3
Southwest Logo
6:15 am - 7:15 amBWI  Baltimore/Washington-MDW Chicago Midway
2h 00mnonstop
Southwest Logo
4:50 pm - 7:40 pmMDW  Chicago Midway-BWI Baltimore/Washington
1h 50mnonstop
$177Southwest
Thu, Oct 8 - Tue, Oct 13
American Airlines Logo
7:17 am - 8:45 amBWI  Baltimore/Washington-ORD Chicago O'Hare Intl
2h 28mnonstop
American Airlines Logo
9:12 pm - 12:16 amORD  Chicago O'Hare Intl-BWI Baltimore/Washington
2h 04mnonstop
$177American Airlines
Tue, Nov 10 - Thu, Nov 26
American Airlines Logo
6:16 pm - 8:04 pmBWI  Baltimore/Washington-ORD Chicago O'Hare Intl
2h 48mnonstop
American Airlines Logo
9:00 pm - 11:58 pmORD  Chicago O'Hare Intl-BWI Baltimore/Washington
1h 58mnonstop
$177American Airlines
Tue, Sep 29 - Sat, Oct 3
Delta Logo
6:10 am - 9:07 amDCA  Washington, D.C. Reagan-National-MDW Chicago Midway
3h 57m1 stop Detroit Metropolitan Wayne County
Delta Logo
4:30 pm - 11:44 pmMDW  Chicago Midway-DCA Washington, D.C. Reagan-National
6h 14m1 stop Atlanta Hartsfield-Jackson
$184Delta
Tue, Dec 29 - Thu, Jan 7
Delta Logo
7:30 pm - 11:50 pmDCA  Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl
5h 20m1 stop Atlanta Hartsfield-Jackson
Delta Logo
7:00 am - 11:53 amORD  Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National
3h 53m1 stop Detroit Metropolitan Wayne County
$197Delta
Booking Insights

Price, demand and travel trends for Washington, D.C. to Chicago flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights from Washington, D.C. to Chicago with more confidence.

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

Round-trip flights from Washington, D.C. to Chicago start at $177. Prices are below average for this route right now, with typical round-trip fares ranging from $270 to $459. The lowest price found in the past 5 days was $177 on Southwest.

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

Washington, D.C. Dulles Intl Airport (IAD) to Chicago Midway Airport (MDW) is the cheapest Washington, D.C. to Chicago route, averaging $203 round-trip. Other Washington, D.C. to Chicago routes average $338, based on KAYAK data over the past 12 months.

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

Saturday is the cheapest day of the week to fly from Washington, D.C. to Chicago, it is 13% cheaper than the average day. Monday is the most expensive day with flight prices 22% higher than average. Based on deals found by KAYAK users in the last 12 months.

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

  • September is the cheapest month to fly from Washington, D.C. to Chicago at $288 round-trip.
  • June ($377) and July ($356) are the most expensive months.
  • The price difference between flying in the cheapest and most expensive months is 30% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

When are prices from Washington, D.C. to Chicago the cheapest?

Flights from Washington, D.C. to Chicago are cheapest 7 weeks before departure. Booking in this window typically costs about 50% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

Expert advice

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

 
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.

Key details for Washington, D.C. to Chicago flights

Low season

January

Cheapest flight

$89
Best time to beat the crowds but there is an average 3% increase in price.
Most popular time to fly with an average 12% increase in price.
Flight from Washington, D.C. Reagan-National Airport to Chicago Midway 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

Your Washington, D.C. to Chicago flight questions, answered

Find helpful route details based on KAYAK data, including flight times, airports, airlines and booking questions.

  • 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.

  • Which airlines offer extra legroom and free seat selection on Washington, D.C. to Chicago flights?

    Among airlines operating Washington, D.C. to Chicago flights:

    • United Airlines: offers extra legroom; offers free seat selection
    • American Airlines: offers extra legroom; offers free seat selection
    • Southwest: offers free seat selection
    • JetBlue: offers free seat selection

    Extra legroom and free seat selection availability depends on fare class and route.

  • What airlines are available from Washington, D.C. to Chicago?

    3 airlines operate flights between Washington, D.C. and Chicago. The airlines offering nonstop flights on this route include:

    • United Airlines
    • American Airlines
    • Southwest

  • Which airports can I use when flying from Washington, D.C. to Chicago?

    Flights from Washington, D.C. to Chicago may depart from several airports in Washington, D.C. area, including Washington, D.C. Reagan-National (DCA) and Washington, D.C. Dulles Intl (IAD), with arrivals available at Chicago area airports such as Chicago Midway (MDW), Chicago O'Hare Intl (ORD) and Chicago Greater Rockford (RFD).

  • Which airlines include bags at no extra cost on Washington, D.C. to Chicago flights?

    Here are some options for this route, based on selected ticket types and cabin classes:

    • United Airlines: a cabin bag and a checked bag in Economy Class
    • American Airlines: a cabin bag and a checked bag in Economy Class
    • Southwest: a cabin bag and a checked bag in Economy Class

    Bag allowance can vary by ticket type, cabin class, route and airline, so travelers should check the fare details before booking.

  • What cabin classes can I book on flights from Washington, D.C. to Chicago?

    Four cabin classes are available on flights from Washington, D.C. to Chicago:

    • Economy Class
    • Premium Economy Class
    • Business Class
    • First Class

    Prices vary by airline.

  • How much can I save by taking a layover when flying from Washington, D.C. to Chicago?

    On this route, layover flights are cheaper than nonstop options on average. Layover fares average $182 round-trip via Fort Lauderdale (FLL), compared to $341 for nonstop.

  • What is the standard checked-bag allowance on flights from Washington, D.C. to Chicago?

    There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $40–$100 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

  • Which airports do connecting flights from Washington, D.C. to Chicago pass through?

    One-stop flights from Washington, D.C. to Chicago most commonly connect through:

    • Atlanta Hartsfield-Jackson (ATL) - 67% of one-stop connections
    • Detroit Metropolitan Wayne County (DTW) - 11% of one-stop connections
    • Boston Logan Intl (BOS) - 6% of one-stop connections
    • Orlando (MCO) - 5% of one-stop connections

    Atlanta Hartsfield-Jackson (ATL) handles the largest share of one-stop connections on this route.

  • Can I save money by using flexible dates for flights from Washington, D.C. to Chicago?

    On the Washington, D.C. to Chicago route, being flexible with your departure day can save you up to 29%. Saturday is the cheapest day at $297 round-trip on average, while Monday is the most expensive at $415: a $118 difference. Cheaper weekend fares like these are typical of routes dominated by weekday business travel.

  • How are flight departures from Washington, D.C. to Chicago spread across the day?

    Morning is the busiest departure period on Washington, D.C. to Chicago flights, with 41% of flights leaving in that window. Afternoon departures account for 27%, evening flights for 24%, and night flights for 8%.

  • What popular places can I visit in Chicago?

    Some of the most popular sights in Chicago are Magnificent Mile, Grant Park and River North. These are among the most viewed places in Chicago on KAYAK.

  • What are the earliest and latest flights from Washington, D.C. to Chicago?

    These are the earliest and latest flight times available from Washington, D.C. to Chicago:

    • Earliest: departs at 6:00 am and lands at 8:19 am
    • Latest: departs at 10:47 pm and lands at 1:06 am.

    The flight takes about 2h 19m.

  • How expensive are last-minute Washington, D.C. to Chicago flights?

    Last-minute fares on this route - booked within 2 weeks of departure - run 73% above the route average of $338. Book 7 weeks before departure for the lowest fares.

  • How long is a flight from Washington, D.C. to Chicago?

    A nonstop flight from Washington, D.C. to Chicago takes 2h 19m, covering 593 miles.

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

    No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID, or another TSA-accepted form of identification.

  • Have flight prices from Washington, D.C. to Chicago changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $177 to $1,280. That means the highest observed fare was about 7x higher than the lowest one.

  • How are flight prices from Washington, D.C. to Chicago looking right now?

    One-way fares from Washington, D.C. to Chicago are currently lower than usual. Average one-way flight prices are about $89, which is 60% below the typical average for this route.

  • Is it cheaper to take a train or bus instead of flying between Washington, D.C. and Chicago?

    Based on prices from the last 5 days, flying between Washington, D.C. and Chicago is around $177 round-trip, with a flight time of about 2h 00m. Recent bus fares are around $138, with a trip time of about 17h 10m. Compared with flying, recent bus fares are roughly 23% lower. However, taking the bus takes about 15+ hours longer each way.

  • How much time can I save by choosing a different layover airport from Washington, D.C. to Chicago?

    Flying via Detroit Metropolitan Wayne County (DTW) gives the shortest average 1-stop total travel time at 4h 09m, compared with 4h 10m via Lambert-St Louis (STL) and 4h 42m via Charlotte Douglas (CLT).

  • What is the time difference between Washington, D.C. and Chicago?

    Chicago is 1 hour behind Washington, D.C. (Central Time vs Eastern Time). Plan for the time shift when scheduling connections or first-day activities.

  • What car rental options are available in Chicago?

    Since Chicago is served by multiple airports, car rental options and rates can vary depending on which one you fly into.
    Near Chicago O'Hare Intl Airport (ORD) — daily rates from around $17:

    · Routes Car & Truck Rentals
    · Europcar
    · Hertz
    · Dollar
    · Ace

    Near Chicago Midway Airport (MDW) — daily rates from around $32:

    · Hertz
    · Dollar
    · Budget
    · Alamo
    · Rent-A-Wreck

    Near Chicago Greater Rockford Airport (RFD) — daily rates from around $30:

    · Alamo
    · Enterprise Rent-A-Car
    · Budget
    · Avis
    · National

  • How much should I expect to pay for a Washington, D.C. to Chicago flight?

    Round-trip flights from Washington, D.C. to Chicago range from $270 to $459, with an average of $338 over the past 12 months. Anything below $270 counts as a good deal.

  • Which airlines offer Wi-Fi on Washington, D.C. to Chicago flights?

    Two airlines offer in-flight Wi-Fi on Washington, D.C. to Chicago flights:

    • • American Airlines
    • • JetBlue

    Pricing varies by airline and fare class. Some plans are included with the ticket or loyalty program; others are paid add-ons priced by flight length.

Your guide to booking Washington, D.C. to Chicago flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates can be flexible, aim for a Saturday departure instead of Monday. On this route, Saturday flights average $297 - about $118 less than Monday (28% savings) based on the last 12 months.
  • For the best chance at a low fare, aim to book around 7 weeks before you fly. On this route, that window historically saves about 50% versus last-minute pricing (KAYAK booking data, last 12 months).
  • If you can choose when to travel, plan your Washington, D.C. to Chicago trip for September. Fares historically average $288 round-trip in that month - typically $89 less than the most expensive month, which is June (based on the last 12 months).
  • If you have the time, taking a 1-stop flight through Fort Lauderdale Airport (FLL) can be cheaper than flying direct. The cheapest layover option averages $182 round-trip on this route - about $158 less than direct flights (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Chicago Midway Airport.
    - DoubleTree by Hilton Chicago Midway Airport
    - Holiday Inn Chicago - Midway Airport S by IHG
  • 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?

 
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