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Cheap flights from Washington, D.C. to Chicago from $39

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 6/4. 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

KAYAK's recommended round-trip deals from the most popular airlines that fly from Washington, D.C. to Chicago.
Frontier Logo
6:36 pm - 7:43 pmBWI-MDW
2h 07mnonstop
Frontier Logo
2:44 pm - 5:42 pmMDW-BWI
1h 58mnonstop
$88Frontier
Find Deal
Wed, May 28 - Wed, Jun 4
Frontier Logo
1:38 pm - 2:45 pmBWI-MDW
2h 07mnonstop
Frontier Logo
2:53 pm - 5:46 pmMDW-BWI
1h 53mnonstop
$96Frontier
Find Deal
Thu, May 15 - Wed, May 28
United Airlines Logo
7:11 pm - 8:27 pmDCA-ORD
2h 16mnonstop
United Airlines Logo
8:00 am - 10:56 amORD-DCA
1h 56mnonstop
$161United Airlines
Find Deal
Sat, May 24 - Sun, May 25
Southwest Logo
6:45 pm - 7:45 pmDCA-MDW
2h 00mnonstop
Southwest Logo
12:05 pm - 2:50 pmMDW-DCA
1h 45mnonstop
$161Southwest
Find Deal
Sat, May 24 - Sun, May 25
Southwest Logo
5:00 pm - 6:00 pmBWI-MDW
2h 00mnonstop
Southwest Logo
6:35 am - 9:25 amMDW-BWI
1h 50mnonstop
$169Southwest
Find Deal
Sat, May 24 - Sun, May 25
American Airlines Logo
6:00 pm - 7:19 pmDCA-ORD
2h 19mnonstop
American Airlines Logo
1:29 pm - 4:29 pmORD-DCA
2h 00mnonstop
$170American Airlines
Find Deal
Sat, May 24 - Wed, May 28
American Airlines Logo
9:00 pm - 10:11 pmDCA-ORD
2h 11mnonstop
American Airlines Logo
8:17 pm - 11:18 pmORD-DCA
2h 01mnonstop
$171American Airlines
Find Deal
Sat, May 24 - Sat, May 31
United Airlines Logo
10:18 pm - 11:30 pmIAD-ORD
2h 12mnonstop
United Airlines Logo
9:31 pm - 12:30 amORD-IAD
1h 59mnonstop
$179United Airlines
Find Deal
Fri, May 30 - Sat, May 31
Delta Logo
6:05 am - 11:47 amDCA-ORD
6h 42m1 stop
Delta Logo
5:15 pm - 10:10 pmORD-DCA
3h 55m1 stop
$197Delta
Find Deal
Sat, May 24 - Sat, May 24
Delta Logo
6:25 am - 11:47 amIAD-ORD
6h 22m1 stop
Delta Logo
11:23 am - 4:45 pmORD-IAD
4h 22m1 stop
$197Delta
Find Deal
Sat, May 24 - Sun, May 25

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

Our best Spirit Airlines deals on Washington, D.C. to Chicago flight tickets
Spirit Airlines
May 7
BWI2:59 pmBaltimore/Washington
18h 56m
1 stop
ORD8:55 amChicago O'Hare Intl
May 29
ORD10:33 amChicago O'Hare Intl
1h 46m
BWI1:19 pmBaltimore/Washington
Spirit Airlines
May 11
BWI8:10 amBaltimore/Washington
2h 14m
ORD9:24 amChicago O'Hare Intl
May 15
ORD10:33 amChicago O'Hare Intl
1h 46m
BWI1:19 pmBaltimore/Washington
Spirit Airlines
May 18
BWI8:10 amBaltimore/Washington
2h 14m
ORD9:24 amChicago O'Hare Intl
May 20
ORD7:47 amChicago O'Hare Intl
11h 42m
1 stop
BWI8:29 pmBaltimore/Washington

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 24
DCA6:00 pmWashington, D.C. Reagan-National
2h 19m
ORD7:19 pmChicago O'Hare Intl
May 28
ORD1:29 pmChicago O'Hare Intl
2h 00m
DCA4:29 pmWashington, D.C. Reagan-National
American Airlines
May 24
DCA9:00 pmWashington, D.C. Reagan-National
2h 11m
ORD10:11 pmChicago O'Hare Intl
May 31
ORD8:17 pmChicago O'Hare Intl
2h 01m
DCA11:18 pmWashington, D.C. Reagan-National
American Airlines
Jun 7
BWI5:24 pmBaltimore/Washington
2h 16m
ORD6:40 pmChicago O'Hare Intl
Jun 14
ORD1:52 pmChicago O'Hare Intl
1h 56m
BWI4:48 pmBaltimore/Washington

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 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 $208. If you’re not able to fly to Chicago in September, then January is your next best option. Flight prices from Washington, D.C. to Chicago during January average around $229.

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 Wednesday when prices can be found for as low as $402. 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 $495.

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 $337. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $456.

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

Fly from Baltimore/Washington to Chicago Midway 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 6 weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $334 when searching 6 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 $266 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.

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

As of April 2025, prices for Washington, D.C. to Chicago flights are approximately 39% 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

$39

Fastest flight time

1h 55m

Direct flights

Every day

Airports in Chicago

2 airports
The best one-way flight to Chicago from Washington, D.C. in the past 72 hours is $39. The best round-trip flight deal from Washington, D.C. to Chicago found on momondo in the last 72 hours is $88.
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 2 airports near Chicago: 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 1h 55m 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 $88. A train from Washington, D.C. to Chicago is more expensive than a flight, with prices starting at $261. A bus from Washington, D.C. to Chicago is also an option, with an average price of $147.

  • 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 $56Free CancellationRating
6.3
7,942 reviews
Search Spirit Airlines flights
FrontierPriceFrom $58Free CancellationRating
5.9
3,283 reviews
Search Frontier flights
DeltaPriceFrom $99Free CancellationRating
8.0
7,920 reviews
Search Delta flights
American AirlinesPriceFrom $144Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $154Free CancellationRating
7.4
8,685 reviews
Search United Airlines flights
SouthwestPriceFrom $167Free CancellationRating
8.0
4,286 reviews
Search Southwest flights
  • Southwest Flights From Washington, D.C. to Chicago

    Southwest flies from Washington, D.C. to Chicago around 32 times per week, with 4,287 momondo users rating the airline 8.0/10. The cheapest Southwest deal from Washington, D.C. to Chicago in the last 72 hours was $167 (round-trip), much lower than the average airfare cost of $300 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 $330 round-trip. United Airlines operates 83 flights out of Washington, D.C. into Chicago in an average week, so prices vary by time and availability. 8,685 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
Portage
Lansing
Saint Joseph
Schererville
Valparaiso
Munster
Crown Point
Monticello
Chesterton
Griffith
Porter
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.


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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