Cheap flights from Washington, D.C. to Chicago from $97

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 7/29. 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
9:43 pm - 8:03 am
BWI
-
ORD
11h 20m
1 stop
Frontier Logo
1:29 pm - 11:00 pm
ORD
-
BWI
8h 31m
1 stop
$222Frontier
Sun, Jun 14 - Tue, Jun 16
Frontier Logo
6:35 am - 11:04 am
BWI
-
MDW
5h 29m
1 stop
Frontier Logo
6:00 am - 3:33 pm
MDW
-
BWI
8h 33m
1 stop
$224Frontier
Sat, Aug 29 - Sun, Aug 30
Frontier Logo
9:43 pm - 7:55 am
BWI
-
ORD
11h 12m
1 stop
Frontier Logo
6:55 am - 6:30 pm
ORD
-
BWI
10h 35m
1 stop
$224Frontier
Thu, Jun 4 - Sat, Jun 6
Southwest Logo
8:30 pm - 9:35 pm
BWI
-
MDW
2h 05mnonstop
Southwest Logo
10:10 am - 2:20 pm
MDW
-
BWI
3h 10m
1 stop
$226Southwest
Tue, Jun 23 - Wed, Jul 1
Southwest Logo
6:30 am - 7:35 am
BWI
-
MDW
2h 05mnonstop
Southwest Logo
10:20 am - 2:30 pm
MDW
-
BWI
3h 10m
1 stop
$228Southwest
Wed, Jun 3 - Sat, Jun 6
United Airlines Logo
8:15 am - 9:36 am
IAD
-
ORD
2h 21mnonstop
United Airlines Logo
6:30 am - 9:24 am
ORD
-
IAD
1h 54mnonstop
$237United Airlines
Thu, Jun 4 - Wed, Jun 10
Delta Logo
6:05 am - 8:45 am
DCA
-
ORD
3h 40m
1 stop
Delta Logo
11:26 am - 5:15 pm
ORD
-
DCA
4h 49m
1 stop
$238Delta
Mon, Jun 1 - Tue, Jun 2
Delta Logo
10:43 am - 4:56 pm
IAD
-
ORD
7h 13m
1 stop
Delta Logo
5:30 am - 2:10 pm
ORD
-
IAD
7h 40m
1 stop
$238Delta
Sat, May 30 - Tue, Jun 2
United Airlines Logo
6:10 pm - 7:33 pm
DCA
-
ORD
2h 23mnonstop
United Airlines Logo
7:45 pm - 10:52 pm
ORD
-
DCA
2h 07mnonstop
$239United Airlines
Thu, Aug 13 - Sat, Aug 15
American Airlines Logo
1:59 pm - 3:23 pm
DCA
-
ORD
2h 24mnonstop
American Airlines Logo
9:42 am - 12:44 pm
ORD
-
DCA
2h 02mnonstop
$243American Airlines
Fri, Jul 3 - Wed, Jul 8

Delta flights from Washington, D.C. to Chicago

Our best Delta deals on Washington, D.C. to Chicago flight tickets
Delta
Jun 1
DCA6:05 amWashington, D.C. Reagan-National
3h 40m
1 stop
ORD8:45 amChicago O'Hare Intl
Jun 2
ORD11:26 amChicago O'Hare Intl
4h 49m
1 stop
DCA5:15 pmWashington, D.C. Reagan-National
$238
Delta
Jun 1
IAD5:33 pmWashington, D.C. Dulles Intl
4h 36m
1 stop
MDW9:09 pmChicago Midway
Jun 3
MDW6:36 pmChicago Midway
3h 20m
1 stop
IAD10:56 pmWashington, D.C. Dulles Intl
$243
Delta
Jun 2
IAD3:08 pmWashington, D.C. Dulles Intl
6h 18m
1 stop
ORD8:26 pmChicago O'Hare Intl
Jun 4
ORD7:07 amChicago O'Hare Intl
6h 03m
1 stop
IAD2:10 pmWashington, D.C. Dulles Intl
$248

Frontier flights from Washington, D.C. to Chicago

Our best Frontier deals on Washington, D.C. to Chicago flight tickets
Frontier
Jul 15
BWI9:32 pmBaltimore/Washington
11h 21m
1 stop
ORD7:53 amChicago O'Hare Intl
Jul 19
ORD7:05 amChicago O'Hare Intl
23h 31m
1 stop
BWI7:36 amBaltimore/Washington
$222
Frontier
Jun 4
BWI9:43 pmBaltimore/Washington
11h 12m
1 stop
ORD7:55 amChicago O'Hare Intl
Jun 6
ORD6:55 amChicago O'Hare Intl
10h 35m
1 stop
BWI6:30 pmBaltimore/Washington
$224
Frontier
Jul 25
BWI9:32 pmBaltimore/Washington
11h 21m
1 stop
ORD7:53 amChicago O'Hare Intl
Jul 27
ORD7:05 amChicago O'Hare Intl
10h 28m
1 stop
BWI6:33 pmBaltimore/Washington
$225

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 13, 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 - ORD

BWIORD

Baltimore/Washington

Sun 6/14

9:43 pm-8:03 am

1 stop11h 20m

Chicago O'Hare Intl

Tue 6/16

1:29 pm-11:00 pm

1 stop8h 31m

$222

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Sat 8/29

6:35 am-11:04 am

1 stop5h 29m

Chicago Midway

Sun 8/30

6:00 am-3:33 pm

1 stop8h 33m

$224

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Thu 6/4

9:43 pm-7:55 am

1 stop11h 12m

Chicago O'Hare Intl

Sat 6/6

6:55 am-6:30 pm

1 stop10h 35m

$224

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Tue 6/23

8:30 pm-9:35 pm

Nonstop2h 05m

Chicago Midway

Wed 7/1

10:10 am-2:20 pm

1 stop3h 10m

$226

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Wed 6/3

6:30 am-7:35 am

Nonstop2h 05m

Chicago Midway

Sat 6/6

10:20 am-2:30 pm

1 stop3h 10m

$228
Quickest round-trip

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Thu 6/4

8:15 am-9:36 am

Nonstop2h 21m

Chicago O'Hare Intl

Wed 6/10

6:30 am-9:24 am

Nonstop1h 54m

$237

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Mon 6/1

6:05 am-8:45 am

1 stop3h 40m

Chicago O'Hare Intl

Tue 6/2

11:26 am-5:15 pm

1 stop4h 49m

$238

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Sat 5/30

10:43 am-4:56 pm

1 stop7h 13m

Chicago O'Hare Intl

Tue 6/2

5:30 am-2:10 pm

1 stop7h 40m

$238

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Thu 8/13

6:10 pm-7:33 pm

Nonstop2h 23m

Chicago O'Hare Intl

Sat 8/15

7:45 pm-10:52 pm

Nonstop2h 07m

$239

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Fri 7/3

1:59 pm-3:23 pm

Nonstop2h 24m

Chicago O'Hare Intl

Wed 7/8

9:42 am-12:44 pm

Nonstop2h 02m

$243

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 $393. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Washington, D.C. to Chicago for around $514.

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 $385. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $426.

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 $376 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 $198 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 175% 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

$175

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 $175. 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 4h 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 $155. A flight from Washington, D.C. to Chicago is more expensive than a bus, with prices starting at $222. A train from Washington, D.C. to Chicago is also an option, with an average price of $252.

  • 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
8,632 reviews
Search Spirit Airlines flights
FrontierPriceFrom $57Free CancellationRating
5.6
2,952 reviews
Search Frontier flights
SouthwestPriceFrom $134Free CancellationRating
7.9
4,296 reviews
Search Southwest flights
DeltaPriceFrom $149Free CancellationRating
7.9
8,452 reviews
Search Delta flights
United AirlinesPriceFrom $153Free CancellationRating
7.4
9,706 reviews
Search United Airlines flights
American AirlinesPriceFrom $158Free CancellationRating
7.1
11,663 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 4,296 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 $307 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 $153, round-trip. It should be noted that an average United Airlines flight deal for this route in this time was higher, at $350 round-trip. United Airlines operates 112 flights out of Washington, D.C. into Chicago in an average week, so prices vary by time and availability. 9,706 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
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
Fri 6/12
Fri 6/19

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