Cheap flights from Washington, D.C. to Chicago from $57

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 3/11. 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.
Frontier Logo
4:25 pm - 5:51 pm
BWI
-
ORD
2h 26mnonstop
Frontier Logo
12:25 pm - 3:30 pm
ORD
-
BWI
2h 05mnonstop
$107Frontier
Fri, May 1 - Mon, May 4
Frontier Logo
4:32 pm - 5:59 pm
BWI
-
ORD
2h 27mnonstop
Frontier Logo
1:19 pm - 4:24 pm
ORD
-
BWI
2h 05mnonstop
$108Frontier
Mon, Mar 23 - Thu, Apr 2
Multiple Airlines Logo
5:58 pm - 11:22 am
BWI
-
ORD
18h 24m
2 stops
Multiple Airlines Logo
5:15 am - 8:24 am
ORD
-
BWI
2h 09mnonstop
$115Multiple Airlines
Tue, Feb 24 - Thu, Feb 26
Multiple Airlines Logo
11:30 am - 5:46 pm
BWI
-
ORD
7h 16m
1 stop
Multiple Airlines Logo
5:15 am - 8:24 am
ORD
-
BWI
2h 09mnonstop
$119Multiple Airlines
Tue, Feb 24 - Thu, Feb 26
United Airlines Logo
7:00 pm - 8:35 pm
DCA
-
ORD
2h 35mnonstop
United Airlines Logo
7:40 pm - 10:52 pm
ORD
-
DCA
2h 12mnonstop
$175United Airlines
Sat, Mar 7 - Sat, Mar 14
United Airlines Logo
6:30 am - 7:50 am
DCA
-
ORD
2h 20mnonstop
United Airlines Logo
7:00 am - 9:54 am
ORD
-
DCA
1h 54mnonstop
$177United Airlines
Wed, Mar 4 - Sat, Mar 7
American Airlines Logo
5:33 pm - 7:08 pm
DCA
-
ORD
2h 35mnonstop
American Airlines Logo
8:58 pm - 11:50 pm
ORD
-
DCA
1h 52mnonstop
$182American Airlines
Sat, Feb 28 - Tue, Mar 3
American Airlines Logo
3:21 pm - 4:45 pm
DCA
-
ORD
2h 24mnonstop
American Airlines Logo
11:50 am - 2:41 pm
ORD
-
DCA
1h 51mnonstop
$184American Airlines
Sat, Feb 28 - Wed, Apr 1
Southwest Logo
10:00 am - 11:10 am
DCA
-
MDW
2h 10mnonstop
Southwest Logo
8:30 pm - 11:15 pm
MDW
-
DCA
1h 45mnonstop
$194Southwest
Sat, Feb 28 - Wed, Apr 1
Southwest Logo
7:00 pm - 8:05 pm
DCA
-
MDW
2h 05mnonstop
Southwest Logo
4:20 pm - 7:10 pm
MDW
-
DCA
1h 50mnonstop
$197Southwest
Tue, Apr 14 - Wed, Apr 15

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

Our best American Airlines deals on Washington, D.C. to Chicago flight tickets
American Airlines
Feb 28
DCA5:33 pmWashington, D.C. Reagan-National
2h 35m
ORD7:08 pmChicago O'Hare Intl
Mar 3
ORD8:58 pmChicago O'Hare Intl
1h 52m
DCA11:50 pmWashington, D.C. Reagan-National
$182
American Airlines
Feb 28
DCA3:21 pmWashington, D.C. Reagan-National
2h 24m
ORD4:45 pmChicago O'Hare Intl
Apr 1
ORD11:50 amChicago O'Hare Intl
1h 51m
DCA2:41 pmWashington, D.C. Reagan-National
$184
American Airlines
Apr 11
DCA1:45 pmWashington, D.C. Reagan-National
2h 24m
ORD3:09 pmChicago O'Hare Intl
Apr 18
ORD9:01 pmChicago O'Hare Intl
1h 56m
DCA11:57 pmWashington, D.C. Reagan-National
$185

Frontier flights from Washington, D.C. to Chicago

Our best Frontier deals on Washington, D.C. to Chicago flight tickets
Frontier
May 1
BWI4:25 pmBaltimore/Washington
2h 26m
ORD5:51 pmChicago O'Hare Intl
May 4
ORD12:25 pmChicago O'Hare Intl
2h 05m
BWI3:30 pmBaltimore/Washington
$107
Frontier
Mar 23
BWI4:32 pmBaltimore/Washington
2h 27m
ORD5:59 pmChicago O'Hare Intl
Apr 2
ORD1:19 pmChicago O'Hare Intl
2h 05m
BWI4:24 pmBaltimore/Washington
$108
Frontier
Feb 26
BWI9:19 amBaltimore/Washington
2h 27m
ORD10:46 amChicago O'Hare Intl
Mar 5
ORD5:15 amChicago O'Hare Intl
2h 09m
BWI8:24 amBaltimore/Washington
$112

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 February 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

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Fri 5/1

4:25 pm-5:51 pm

Nonstop2h 26m

Chicago O'Hare Intl

Mon 5/4

12:25 pm-3:30 pm

Nonstop2h 05m

$107

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Mon 3/23

4:32 pm-5:59 pm

Nonstop2h 27m

Chicago O'Hare Intl

Thu 4/2

1:19 pm-4:24 pm

Nonstop2h 05m

$108

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Tue 2/24

5:58 pm-11:22 am

2 stops18h 24m

Chicago O'Hare Intl

Thu 2/26

5:15 am-8:24 am

Nonstop2h 09m

$115

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Tue 2/24

11:30 am-5:46 pm

1 stop7h 16m

Chicago O'Hare Intl

Thu 2/26

5:15 am-8:24 am

Nonstop2h 09m

$119

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Sat 3/7

7:00 pm-8:35 pm

Nonstop2h 35m

Chicago O'Hare Intl

Sat 3/14

7:40 pm-10:52 pm

Nonstop2h 12m

$175

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Wed 3/4

6:30 am-7:50 am

Nonstop2h 20m

Chicago O'Hare Intl

Sat 3/7

7:00 am-9:54 am

Nonstop1h 54m

$177

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Sat 2/28

5:33 pm-7:08 pm

Nonstop2h 35m

Chicago O'Hare Intl

Tue 3/3

8:58 pm-11:50 pm

Nonstop1h 52m

$182

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Sat 2/28

3:21 pm-4:45 pm

Nonstop2h 24m

Chicago O'Hare Intl

Wed 4/1

11:50 am-2:41 pm

Nonstop1h 51m

$184

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Sat 2/28

10:00 am-11:10 am

Nonstop2h 10m

Chicago Midway

Wed 4/1

8:30 pm-11:15 pm

Nonstop1h 45m

$194

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Tue 4/14

7:00 pm-8:05 pm

Nonstop2h 05m

Chicago Midway

Wed 4/15

4:20 pm-7:10 pm

Nonstop1h 50m

$197

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 February is your next best option. Flight prices from Washington, D.C. to Chicago during February average around $226.

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 $381. 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 $502.

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 $356. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $420.

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 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 $334 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 $216 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?

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 February 2026, prices for Washington, D.C. to Chicago flights are approximately 3% cheaper 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

$118

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 $118. The best round-trip flight deal from Washington, D.C. to Chicago found on momondo in the last 72 hours is $220.
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).
  • 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 10m 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 flight from Washington, D.C. to Chicago, which can be as cheap as $107. A train from Washington, D.C. to Chicago is more expensive than a flight, with prices starting at $202. A bus from Washington, D.C. to Chicago is also an option, with an average price of $162.

  • 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 $41Free CancellationRating
6.3
8,430 reviews
Search Spirit Airlines flights
FrontierPriceFrom $57Free CancellationRating
5.7
3,052 reviews
Search Frontier flights
SouthwestPriceFrom $148Free CancellationRating
8.0
4,280 reviews
Search Southwest flights
United AirlinesPriceFrom $154Free CancellationRating
7.4
9,254 reviews
Search United Airlines flights
American AirlinesPriceFrom $158Free CancellationRating
7.2
11,249 reviews
Search American Airlines flights
DeltaPriceFrom $194Free CancellationRating
7.9
8,172 reviews
Search Delta flights
  • Southwest Flights From Washington, D.C. to Chicago

    Southwest flies from Washington, D.C. to Chicago around 26 times per week, with 4,280 momondo users rating the airline 8.0/10. The cheapest Southwest deal from Washington, D.C. to Chicago in the last 72 hours was $148 (round-trip), much lower than the average airfare cost of $298 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 $154, round-trip. It should be noted that an average United Airlines flight deal for this route in this time was higher, at $323 round-trip. United Airlines operates 73 flights out of Washington, D.C. into Chicago in an average week, so prices vary by time and availability. 9,254 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
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Munster
Crown Point
Chesterton
Monticello
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
Tue 3/10
Tue 3/17

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