Cheap flights from Washington, D.C. to Chicago from $93

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Washington, D.C. to Chicago departing on 5/20. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Washington, D.C. to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
6:30 am - 7:35 am
BWI
-
MDW
2h 05mnonstop
Southwest Logo
4:40 pm - 9:45 pm
MDW
-
BWI
4h 05m
1 stop
$202Southwest
Tue, May 26 - Tue, May 26
Multiple Airlines Logo
9:13 pm - 11:01 pm
BWI
-
ORD
26h 48m
1 stop
Multiple Airlines Logo
4:05 pm - 8:18 pm
ORD
-
BWI
27h 13m
1 stop
$202Multiple Airlines
Mon, May 4 - Sat, May 9
Frontier Logo
2:42 pm - 11:59 pm
BWI
-
ORD
10h 17m
1 stop
Frontier Logo
4:28 pm - 12:44 am
ORD
-
BWI
7h 16m
1 stop
$203Frontier
Sun, Apr 26 - Sat, May 2
Frontier Logo
10:10 am - 10:02 pm
BWI
-
MDW
12h 52m
2 stops
Frontier Logo
6:00 am - 7:43 am
MDW
-
BWI
24h 43m
1 stop
$204Frontier
Thu, May 7 - Mon, May 11
American Airlines Logo
5:55 am - 7:24 am
DCA
-
ORD
2h 29mnonstop
American Airlines Logo
12:35 pm - 7:15 pm
ORD
-
DCA
5h 40m
1 stop
$219American Airlines
Wed, May 20 - Tue, May 26
American Airlines Logo
6:36 am - 10:11 am
DCA
-
ORD
4h 35m
1 stop
American Airlines Logo
12:42 pm - 3:45 pm
ORD
-
DCA
2h 03mnonstop
$222American Airlines
Sat, May 16 - Wed, May 20
United Airlines Logo
5:05 pm - 6:27 pm
DCA
-
ORD
2h 22mnonstop
United Airlines Logo
6:00 am - 8:54 am
ORD
-
DCA
1h 54mnonstop
$223United Airlines
Sat, May 23 - Mon, May 25
United Airlines Logo
10:10 pm - 11:21 pm
IAD
-
ORD
2h 11mnonstop
United Airlines Logo
6:18 pm - 9:22 pm
ORD
-
IAD
2h 04mnonstop
$223United Airlines
Thu, Sep 3 - Sat, Sep 5
Delta Logo
1:55 pm - 7:14 pm
DCA
-
ORD
6h 19m
1 stop
Delta Logo
12:15 pm - 6:59 pm
ORD
-
DCA
5h 44m
1 stop
$224Delta
Sat, May 16 - Tue, May 26
Delta Logo
6:05 am - 8:43 am
DCA
-
MDW
3h 38m
1 stop
Delta Logo
10:45 am - 6:28 pm
MDW
-
DCA
6h 43m
1 stop
$224Delta
Wed, May 27 - Sat, May 30

United Airlines flights from Washington, D.C. to Chicago

Our best United Airlines deals on Washington, D.C. to Chicago flight tickets
United Airlines
Jun 3
BWI8:05 pmBaltimore/Washington
2h 24m
ORD9:29 pmChicago O'Hare Intl
Jun 8
ORD9:25 pmChicago O'Hare Intl
2h 08m
BWI12:33 amBaltimore/Washington
$212
United Airlines
May 23
DCA5:05 pmWashington, D.C. Reagan-National
2h 22m
ORD6:27 pmChicago O'Hare Intl
May 25
ORD6:00 amChicago O'Hare Intl
1h 54m
DCA8:54 amWashington, D.C. Reagan-National
$223
United Airlines
May 29
DCA9:30 amWashington, D.C. Reagan-National
2h 20m
ORD10:50 amChicago O'Hare Intl
Jun 2
ORD7:00 amChicago O'Hare Intl
1h 59m
DCA9:59 amWashington, D.C. Reagan-National
$233

American Airlines flights from Washington, D.C. to Chicago

Our best American Airlines deals on Washington, D.C. to Chicago flight tickets
American Airlines
May 20
BWI5:39 amBaltimore/Washington
2h 32m
ORD7:11 amChicago O'Hare Intl
May 26
ORD6:47 pmChicago O'Hare Intl
4h 20m
1 stop
BWI12:07 amBaltimore/Washington
$219
American Airlines
May 16
DCA6:36 amWashington, D.C. Reagan-National
4h 35m
1 stop
ORD10:11 amChicago O'Hare Intl
May 20
ORD12:42 pmChicago O'Hare Intl
2h 03m
DCA3:45 pmWashington, D.C. Reagan-National
$222
American Airlines
May 14
DCA5:55 amWashington, D.C. Reagan-National
2h 29m
ORD7:24 amChicago O'Hare Intl
May 18
ORD9:01 pmChicago O'Hare Intl
1h 56m
DCA11:57 pmWashington, D.C. Reagan-National
$231

momondo Fare Finder

 
Customize your flight search to find flights from Washington, D.C. to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated April 23, 2026.
Use the filters below to find and compare flights from Washington, D.C. to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Tue 5/26

6:30 am-7:35 am

Nonstop2h 05m

Chicago Midway

Tue 5/26

4:40 pm-9:45 pm

1 stop4h 05m

$202

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Mon 5/4

9:13 pm-11:01 pm

1 stop26h 48m

Chicago O'Hare Intl

Sat 5/9

4:05 pm-8:18 pm

1 stop27h 13m

$202

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Sun 4/26

2:42 pm-11:59 pm

1 stop10h 17m

Chicago O'Hare Intl

Sat 5/2

4:28 pm-12:44 am

1 stop7h 16m

$203

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Thu 5/7

10:10 am-10:02 pm

2 stops12h 52m

Chicago Midway

Mon 5/11

6:00 am-7:43 am

1 stop24h 43m

$204

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Wed 5/20

5:55 am-7:24 am

Nonstop2h 29m

Chicago O'Hare Intl

Tue 5/26

12:35 pm-7:15 pm

1 stop5h 40m

$219

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Sat 5/16

6:36 am-10:11 am

1 stop4h 35m

Chicago O'Hare Intl

Wed 5/20

12:42 pm-3:45 pm

Nonstop2h 03m

$222

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Sat 5/23

5:05 pm-6:27 pm

Nonstop2h 22m

Chicago O'Hare Intl

Mon 5/25

6:00 am-8:54 am

Nonstop1h 54m

$223
Quickest round-trip

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Thu 9/3

10:10 pm-11:21 pm

Nonstop2h 11m

Chicago O'Hare Intl

Sat 9/5

6:18 pm-9:22 pm

Nonstop2h 04m

$223

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Sat 5/16

1:55 pm-7:14 pm

1 stop6h 19m

Chicago O'Hare Intl

Tue 5/26

12:15 pm-6:59 pm

1 stop5h 44m

$224

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Wed 5/27

6:05 am-8:43 am

1 stop3h 38m

Chicago Midway

Sat 5/30

10:45 am-6:28 pm

1 stop6h 43m

$224

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Washington, D.C. to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the typical price of a round-trip flight between Washington, D.C. and Chicago?

What is the cheapest month to fly to Chicago?

The month of September is, on average, the cheapest month to fly to Chicago from Washington, D.C., with most prices found around $203. If you’re not able to fly to Chicago in September, then August is your next best option. Flight prices from Washington, D.C. to Chicago during August average around $218.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $387. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Washington, D.C. to Chicago for around $509.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Washington, D.C. to Chicago during this time can be as low as $379. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $423.

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

Fly from Washington, D.C. Reagan-National to Chicago Midway for the best Washington, D.C. - Chicago flight prices

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

You are more likely to see cheaper flights to Chicago from Washington, D.C. when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $370 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Washington, D.C. for as low as $201 on momondo.

What cabin class options are available on Washington, D.C. to Chicago flights?

There are 4 cabin classes available to choose from on Washington, D.C. to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Washington, D.C. to Chicago flights?

You could potentially save up to 2% on your flight if you consider stops on a Washington, D.C. to Chicago flight.

How have Washington, D.C. to Chicago flight prices changed over time?

As of April 2026, prices for Washington, D.C. to Chicago flights are approximately 144% more expensive when compared to flights at the same time last year.

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

Are you open to changing your travel dates? Check out the ideal times to fly from Washington, D.C. to Chicago according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Washington, D.C. to Chicago (WAS to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Washington, D.C. to Chicago

Best Price Found

$177

Fastest flight time

1h 55m

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from Washington, D.C. in the past 72 hours is $177. The best round-trip flight deal from Washington, D.C. to Chicago found on momondo in the last 72 hours is $303.
The fastest flight from Washington, D.C. to Chicago takes 1h 55m
Direct flights go from Washington, D.C. to Chicago every day.
There are 3 airports in Chicago. From Washington, D.C. there are direct flights to Chicago O'Hare Intl (ORD), Chicago Midway (MDW).

Frequently asked questions about flying from Washington, D.C. to Chicago

  • Is flying the fastest way to get from Washington, D.C. to Chicago?

    The quickest way is to book a flight from Washington, D.C. to Chicago, which can be as quick as 2h 05m onboard Southwest. You can also get a train from Washington, D.C. to Chicago, or a bus from Washington, D.C. to Chicago which can take you longer to arrive at your destination.

  • Is flying the cheapest way to get from Washington, D.C. to Chicago?

    The cheapest way is to get a bus from Washington, D.C. to Chicago, which can be as cheap as $158. A flight from Washington, D.C. to Chicago is more expensive than a bus, with prices starting at $202. A train from Washington, D.C. to Chicago is also an option, with an average price of $296.

  • How far is Washington, D.C. to Chicago by plane?

    The straight-line distance from Washington, D.C. to Chicago is 593.1 mi. 1h 55m is a normal flight duration for this route.

  • When did momondo last update prices for flights from Washington, D.C. to Chicago?

    Prices for flights from Washington, D.C. to Chicago are refreshed on a daily basis.

  • How many operators does momondo search for flights from Washington, D.C. to Chicago?

  • How old do you have to be to fly from Washington, D.C. to Chicago?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Washington, D.C. to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Washington, D.C. to Chicago?

  • What is the most popular airline from Washington, D.C. to Chicago?

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

Compare and see reviews for airlines that fly from Washington, D.C. to Chicago with momondo
Airline
Rating
Free Cancellation
Price
Spirit AirlinesPriceFrom $52Free CancellationRating
6.3
8,631 reviews
Search Spirit Airlines flights
FrontierPriceFrom $57Free CancellationRating
5.6
2,981 reviews
Search Frontier flights
SouthwestPriceFrom $134Free CancellationRating
8.0
4,327 reviews
Search Southwest flights
DeltaPriceFrom $149Free CancellationRating
7.9
8,437 reviews
Search Delta flights
United AirlinesPriceFrom $152Free CancellationRating
7.4
9,635 reviews
Search United Airlines flights
American AirlinesPriceFrom $158Free CancellationRating
7.1
11,655 reviews
Search American Airlines flights
  • Southwest Flights From Washington, D.C. to Chicago

    Southwest flies from Washington, D.C. to Chicago around 33 times per week, with 4,327 momondo users rating the airline 8.0/10. The cheapest Southwest deal from Washington, D.C. to Chicago in the last 72 hours was $134 (round-trip), much lower than the average airfare cost of $296 for Southwest flights on this route.

  • United Airlines Flights From Washington, D.C. to Chicago

    The best United Airlines deal for Washington, D.C. to Chicago flight tickets found on momondo in the last 72 hours was $152, round-trip. It should be noted that an average United Airlines flight deal for this route in this time was higher, at $342 round-trip. United Airlines operates 95 flights out of Washington, D.C. into Chicago in an average week, so prices vary by time and availability. 9,635 United Airlines reviews by users on momondo have scored the airline at 7.4/10.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
Crown Point
Monticello
Chesterton
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Washington, D.C. to Chicago?

It is quick and easy to find Washington, D.C. to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

Can I find flights from Washington, D.C. to Chicago with flexible booking policies on momondo?

Flights from Washington, D.C. to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Washington, D.C. to Chicago?

Once you have performed a search for Washington, D.C. to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Washington, D.C. to Chicago right now. Can momondo alert me if prices change?

Price alerts on flights to Chicago from Washington, D.C. are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

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1 adult
Sat 5/23
Sat 5/30

Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago