Cheap flights from Washington, D.C. to Chicago from $99

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 5/26. 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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Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
9:56 pm - 11:12 am
BWI
-
MDW
14h 16m
1 stop
Frontier Logo
6:00 am - 4:26 pm
MDW
-
BWI
9h 26m
1 stop
$209Frontier
Sat, Jun 6 - Sat, Jun 20
Frontier Logo
6:28 am - 11:04 am
BWI
-
MDW
5h 36m
1 stop
Frontier Logo
6:00 am - 3:34 pm
MDW
-
BWI
8h 34m
1 stop
$210Frontier
Sat, Jul 4 - Tue, Jul 7
Frontier Logo
8:36 am - 7:53 pm
BWI
-
ORD
12h 17m
1 stop
Frontier Logo
7:05 am - 6:33 pm
ORD
-
BWI
10h 28m
1 stop
$210Frontier
Tue, Jul 28 - Mon, Aug 10
United Airlines Logo
8:25 am - 9:39 am
BWI
-
ORD
2h 14mnonstop
United Airlines Logo
6:20 pm - 9:26 pm
ORD
-
BWI
2h 06mnonstop
$212United Airlines
Wed, May 27 - Thu, Jun 4
Southwest Logo
9:35 am - 10:40 am
BWI
-
MDW
2h 05mnonstop
Southwest Logo
7:00 am - 9:50 am
MDW
-
BWI
1h 50mnonstop
$212Southwest
Wed, May 27 - Tue, Jun 2
Southwest Logo
7:50 am - 11:00 am
BWI
-
MDW
4h 10m
1 stop
Southwest Logo
12:00 pm - 5:35 pm
MDW
-
BWI
4h 35m
1 stop
$217Southwest
Wed, Jun 24 - Wed, Jun 24
Delta Logo
5:50 pm - 10:36 pm
DCA
-
ORD
5h 46m
1 stop
Delta Logo
2:00 pm - 6:59 pm
ORD
-
DCA
3h 59m
1 stop
$228Delta
Wed, May 27 - Thu, Jun 4
Delta Logo
6:00 am - 8:45 am
IAD
-
ORD
3h 45m
1 stop
Delta Logo
12:00 pm - 8:02 pm
ORD
-
IAD
7h 02m
1 stop
$228Delta
Tue, May 26 - Sat, May 30
United Airlines Logo
6:30 am - 7:46 am
DCA
-
ORD
2h 16mnonstop
United Airlines Logo
6:00 am - 8:54 am
ORD
-
DCA
1h 54mnonstop
$233United Airlines
Wed, Jul 1 - Wed, Jul 8
American Airlines Logo
3:52 pm - 5:25 pm
DCA
-
ORD
2h 33mnonstop
American Airlines Logo
2:57 pm - 6:00 pm
ORD
-
DCA
2h 03mnonstop
$234American Airlines
Sat, Jun 13 - Tue, Jun 16

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
BWI8:25 amBaltimore/Washington
2h 14m
ORD9:39 amChicago O'Hare Intl
Jun 6
ORD3:00 pmChicago O'Hare Intl
2h 09m
BWI6:09 pmBaltimore/Washington
$222
United Airlines
Jul 1
DCA6:30 amWashington, D.C. Reagan-National
2h 16m
ORD7:46 amChicago O'Hare Intl
Jul 8
ORD6:00 amChicago O'Hare Intl
1h 54m
DCA8:54 amWashington, D.C. Reagan-National
$233
United Airlines
May 27
BWI8:25 amBaltimore/Washington
2h 14m
ORD9:39 amChicago O'Hare Intl
May 29
ORD6:20 amChicago O'Hare Intl
1h 57m
BWI9:17 amBaltimore/Washington
$237

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

Our best American Airlines deals on Washington, D.C. to Chicago flight tickets
American Airlines
Jun 30
DCA10:10 pmWashington, D.C. Reagan-National
2h 20m
ORD11:30 pmChicago O'Hare Intl
Jul 3
ORD7:02 amChicago O'Hare Intl
2h 01m
DCA10:03 amWashington, D.C. Reagan-National
$243
American Airlines
Jun 17
DCA7:50 amWashington, D.C. Reagan-National
4h 14m
1 stop
ORD11:04 amChicago O'Hare Intl
Jun 24
ORD6:00 amChicago O'Hare Intl
2h 14m
DCA9:14 amWashington, D.C. Reagan-National
$244
American Airlines
May 28
BWI7:59 pmBaltimore/Washington
2h 45m
ORD9:44 pmChicago O'Hare Intl
Jun 1
ORD9:01 pmChicago O'Hare Intl
2h 10m
BWI12:11 amBaltimore/Washington
$249

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 May 8, 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

Sat 6/6

9:56 pm-11:12 am

1 stop14h 16m

Chicago Midway

Sat 6/20

6:00 am-4:26 pm

1 stop9h 26m

$209

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Sat 7/4

6:28 am-11:04 am

1 stop5h 36m

Chicago Midway

Tue 7/7

6:00 am-3:34 pm

1 stop8h 34m

$210

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Tue 7/28

8:36 am-7:53 pm

1 stop12h 17m

Chicago O'Hare Intl

Mon 8/10

7:05 am-6:33 pm

1 stop10h 28m

$210

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Wed 5/27

8:25 am-9:39 am

Nonstop2h 14m

Chicago O'Hare Intl

Thu 6/4

6:20 pm-9:26 pm

Nonstop2h 06m

$212
Quickest round-trip

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Wed 5/27

9:35 am-10:40 am

Nonstop2h 05m

Chicago Midway

Tue 6/2

7:00 am-9:50 am

Nonstop1h 50m

$212

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Wed 6/24

7:50 am-11:00 am

1 stop4h 10m

Chicago Midway

Wed 6/24

12:00 pm-5:35 pm

1 stop4h 35m

$217

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Wed 5/27

5:50 pm-10:36 pm

1 stop5h 46m

Chicago O'Hare Intl

Thu 6/4

2:00 pm-6:59 pm

1 stop3h 59m

$228

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Tue 5/26

6:00 am-8:45 am

1 stop3h 45m

Chicago O'Hare Intl

Sat 5/30

12:00 pm-8:02 pm

1 stop7h 02m

$228

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Wed 7/1

6:30 am-7:46 am

Nonstop2h 16m

Chicago O'Hare Intl

Wed 7/8

6:00 am-8:54 am

Nonstop1h 54m

$233

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Sat 6/13

3:52 pm-5:25 pm

Nonstop2h 33m

Chicago O'Hare Intl

Tue 6/16

2:57 pm-6:00 pm

Nonstop2h 03m

$234

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 August is, on average, the cheapest month to fly to Chicago from Washington, D.C., with most prices found around $211. If you’re not able to fly to Chicago in August, then October is your next best option. Flight prices from Washington, D.C. to Chicago during October average around $219.

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 $391. 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 $511.

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 $383. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $424.

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

Fly from Baltimore/Washington to Chicago O'Hare Intl 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 $374 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.

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

No. A direct flight is the cheapest option for a flight between Washington, D.C. to Chicago.

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

As of May 2026, prices for Washington, D.C. to Chicago flights are approximately 81% 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

$176

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 $176. The best round-trip flight deal from Washington, D.C. to Chicago found on momondo in the last 72 hours is $309.
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 3h 38m onboard Delta. 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 $203. A flight from Washington, D.C. to Chicago is more expensive than a bus, with prices starting at $209. A train from Washington, D.C. to Chicago is also an option, with an average price of $301.

  • 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 $43Free CancellationRating
6.3
8,638 reviews
Search Spirit Airlines flights
FrontierPriceFrom $57Free CancellationRating
5.6
2,963 reviews
Search Frontier flights
SouthwestPriceFrom $134Free CancellationRating
7.9
4,302 reviews
Search Southwest flights
DeltaPriceFrom $149Free CancellationRating
7.9
8,456 reviews
Search Delta flights
United AirlinesPriceFrom $152Free CancellationRating
7.4
9,694 reviews
Search United Airlines flights
American AirlinesPriceFrom $158Free CancellationRating
7.1
11,667 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 4,302 momondo users rating the airline 7.9/10. 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 $303 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 $348 round-trip. United Airlines operates 114 flights out of Washington, D.C. into Chicago in an average week, so prices vary by time and availability. 9,694 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

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1 adult
Sun 6/7
Sun 6/14

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