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Cheap flights from Washington, D.C. to Chicago from $29

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 2/26. 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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Find the cheapest flights from Washington, D.C. to Chicago

Cheap round-trip flights

These are some of the best round-trip flight deals from Washington, D.C. to Chicago that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Washington, D.C. to Chicago.

Cheap last minute flights

Planning a quick getaway from Washington, D.C. to Chicago? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Chicago, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Washington, D.C. to Chicago

Find recent round-trip train or bus tickets from Washington, D.C. to Chicago.

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
5:11 pm - 6:23 pmBWI-MDW
2h 12mnonstop
1:16 pm - 4:11 pmMDW-BWI
1h 55mnonstop
$65Frontier
Find Deal
Wed, Feb 19 - Wed, Feb 26
5:11 pm - 6:23 pmBWI-MDW
2h 12mnonstop
10:26 am - 1:21 pmMDW-BWI
1h 55mnonstop
$66Frontier
Find Deal
Wed, Feb 19 - Sat, Feb 22
11:51 am - 1:09 pmBWI-ORD
2h 18mnonstop
2:50 pm - 5:37 pmORD-BWI
1h 47mnonstop
$133American Airlines
Find Deal
Wed, Mar 12 - Wed, Mar 12
11:51 am - 1:12 pmBWI-ORD
2h 21mnonstop
8:20 am - 11:17 amORD-BWI
1h 57mnonstop
$139American Airlines
Find Deal
Wed, Jan 29 - Wed, Feb 5
8:10 pm - 9:25 pmBWI-MDW
2h 15mnonstop
5:05 pm - 7:50 pmMDW-BWI
1h 45mnonstop
$140Southwest
Find Deal
Tue, Jan 28 - Tue, Feb 4
12:35 pm - 2:00 pmBWI-ORD
2h 25mnonstop
4:35 pm - 7:30 pmORD-BWI
1h 55mnonstop
$140Southwest
Find Deal
Tue, Jan 28 - Tue, Feb 4
7:02 am - 8:20 amDCA-ORD
2h 18mnonstop
6:30 am - 9:32 amORD-DCA
2h 02mnonstop
$191United Airlines
Find Deal
Fri, Jan 24 - Sun, Jan 26
10:09 pm - 11:15 pmIAD-ORD
2h 06mnonstop
9:05 pm - 11:57 pmORD-IAD
1h 52mnonstop
$191United Airlines
Find Deal
Wed, Jan 29 - Sun, Feb 16
6:00 am - 12:42 pmBWI-MDW
7h 42m1 stop
10:57 am - 5:36 pmMDW-BWI
5h 39m1 stop
$196Delta
Find Deal
Mon, Feb 17 - Wed, Feb 26
12:28 pm - 6:21 pmBWI-ORD
6h 53m1 stop
6:45 am - 11:43 amORD-BWI
3h 58m1 stop
$196Delta
Find Deal
Wed, Mar 26 - Tue, Apr 1
5:11 pm - 6:23 pmBWI-MDW
2h 12mnonstop
$29Frontier
Find Deal
Wed, Feb 26
5:11 pm - 6:23 pmBWI-MDW
2h 12mnonstop
$30Frontier
Find Deal
Wed, Feb 26
6:30 am - 7:52 amBWI-ORD
2h 22mnonstop
$69United Airlines
Find Deal
Tue, Feb 18
7:35 am - 8:50 amBWI-MDW
2h 15mnonstop
$69Southwest
Find Deal
Tue, Feb 18
10:35 am - 11:45 amBWI-MDW
2h 10mnonstop
$70Southwest
Find Deal
Wed, Jan 29
6:30 am - 7:52 amBWI-ORD
2h 22mnonstop
$89United Airlines
Find Deal
Fri, Feb 21
8:45 pm - 10:04 pmDCA-ORD
2h 19mnonstop
$97American Airlines
Find Deal
Wed, Jan 29
6:00 am - 8:54 amBWI-MDW
3h 54m1 stop
$98Delta
Find Deal
Wed, Jan 29
11:59 am - 1:17 pmDCA-ORD
2h 18mnonstop
$99American Airlines
Find Deal
Wed, Jan 15
6:00 am - 9:01 amDCA-ORD
4h 01m1 stop
$105Delta
Find Deal
Sat, Feb 1
12:02 pm - 1:06 pmBWI-MDW
2h 04mnonstop
8:20 am - 11:12 amMDW-BWI
1h 52mnonstop
$286Frontier
Find Deal
Fri, Jan 3 - Mon, Jan 6
9:31 pm - 9:54 amBWI-ORD
13h 23m1 stop
8:14 pm - 7:39 amORD-BWI
10h 25m1 stop
Sun, Jan 5 - Tue, Jan 7
9:44 am - 11:02 amDCA-ORD
2h 18mnonstop
3:00 pm - 8:30 pmORD-DCA
4h 30m1 stop
$353American Airlines
Find Deal
Wed, Jan 1 - Wed, Jan 1
10:16 pm - 6:45 pmIAD-ORD
21h 29m1 stop
9:05 pm - 11:59 pmORD-IAD
1h 54mnonstop
$369United Airlines
Find Deal
Fri, Jan 3 - Sat, Jan 4
10:16 pm - 6:45 pmIAD-ORD
21h 29m1 stop
9:05 pm - 11:59 pmORD-IAD
1h 54mnonstop
$409United Airlines
Find Deal
Fri, Jan 3 - Sat, Jan 4
6:55 am - 8:05 amDCA-MDW
2h 10mnonstop
8:15 pm - 11:05 pmMDW-DCA
1h 50mnonstop
$496Southwest
Find Deal
Sun, Jan 5 - Tue, Jan 7
5:15 am - 2:25 pmIAD-ORD
10h 10m1 stop
6:15 am - 3:05 pmORD-IAD
7h 50m1 stop
$501Southwest
Find Deal
Sun, Jan 5 - Tue, Jan 7
7:00 am - 8:27 amDCA-ORD
2h 27mnonstop
8:25 pm - 11:20 pmORD-DCA
1h 55mnonstop
$507American Airlines
Find Deal
Sun, Jan 5 - Tue, Jan 7
6:00 am - 8:50 amDCA-MDW
3h 50m1 stop
6:00 am - 12:49 pmMDW-DCA
5h 49m1 stop
$514Delta
Find Deal
Sun, Jan 5 - Tue, Jan 7
6:00 am - 9:21 amIAD-ORD
4h 21m1 stop
5:45 am - 12:46 pmORD-IAD
6h 01m1 stop
$527Delta
Find Deal
Sun, Jan 5 - Tue, Jan 7
5:11 pm - 6:23 pmBWI-MDW
2h 12mnonstop
1:16 pm - 4:11 pmMDW-BWI
1h 55mnonstop
$65Frontier
Find Deal
Wed, Feb 19 - Wed, Feb 26
5:11 pm - 6:23 pmBWI-MDW
2h 12mnonstop
10:26 am - 1:21 pmMDW-BWI
1h 55mnonstop
$66Frontier
Find Deal
Wed, Feb 19 - Sat, Feb 22
5:11 pm - 6:23 pmBWI-MDW
2h 12mnonstop
12:26 pm - 3:21 pmMDW-BWI
1h 55mnonstop
$80Frontier
Find Deal
Wed, Feb 19 - Fri, Feb 21
4:21 pm - 5:33 pmBWI-MDW
2h 12mnonstop
10:26 am - 1:21 pmMDW-BWI
1h 55mnonstop
$81Frontier
Find Deal
Fri, Feb 21 - Sat, Feb 22
11:51 am - 1:09 pmBWI-ORD
2h 18mnonstop
2:50 pm - 5:37 pmORD-BWI
1h 47mnonstop
$133American Airlines
Find Deal
Wed, Mar 12 - Wed, Mar 12
11:45 am - 1:05 pmBWI-ORD
2h 20mnonstop
4:00 pm - 6:55 pmORD-BWI
1h 55mnonstop
$136Southwest
Find Deal
Tue, Mar 25 - Tue, Mar 25
7:34 am - 8:50 amBWI-ORD
2h 16mnonstop
8:15 am - 11:10 amORD-BWI
1h 55mnonstop
$137American Airlines
Find Deal
Tue, Feb 25 - Wed, Feb 26
9:50 am - 11:00 amBWI-MDW
2h 10mnonstop
5:05 pm - 7:50 pmMDW-BWI
1h 45mnonstop
$139Southwest
Find Deal
Sat, Feb 22 - Tue, Feb 25
7:02 am - 8:20 amDCA-ORD
2h 18mnonstop
7:30 am - 10:43 amORD-DCA
2h 13mnonstop
$191United Airlines
Find Deal
Fri, Feb 7 - Sun, Feb 9
10:09 pm - 11:15 pmIAD-ORD
2h 06mnonstop
9:05 pm - 11:57 pmORD-IAD
1h 52mnonstop
$191United Airlines
Find Deal
Wed, Jan 29 - Sun, Feb 16

Southwest flights from Washington, D.C. to Chicago

Our best Southwest deals on Washington, D.C. to Chicago flight tickets
Southwest
Jan 28
BWI12:35 pmBaltimore/Washington
2h 25m
ORD2:00 pmChicago O'Hare Intl
Feb 4
ORD4:35 pmChicago O'Hare Intl
1h 55m
BWI7:30 pmBaltimore/Washington
Southwest
Jan 25
BWI7:00 pmBaltimore/Washington
2h 10m
MDW8:10 pmChicago Midway
Feb 1
MDW8:35 amChicago Midway
1h 45m
BWI11:20 amBaltimore/Washington
Southwest
Jan 31
BWI5:25 pmBaltimore/Washington
2h 10m
MDW6:35 pmChicago Midway
Feb 1
MDW4:35 pmChicago Midway
1h 45m
BWI7:20 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
Mar 12
BWI11:51 amBaltimore/Washington
2h 18m
ORD1:09 pmChicago O'Hare Intl
Mar 12
ORD2:50 pmChicago O'Hare Intl
1h 47m
BWI5:37 pmBaltimore/Washington
American Airlines
Jan 29
BWI11:51 amBaltimore/Washington
2h 21m
ORD1:12 pmChicago O'Hare Intl
Feb 5
ORD8:20 amChicago O'Hare Intl
1h 57m
BWI11:17 amBaltimore/Washington
American Airlines
Jan 28
BWI7:30 amBaltimore/Washington
2h 21m
ORD8:51 amChicago O'Hare Intl
Feb 4
ORD8:20 amChicago O'Hare Intl
1h 57m
BWI11:17 amBaltimore/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 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 $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 $228.

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 Monday when prices can be found for as low as $249. 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 $303.

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 afternoon. Flights from Washington, D.C. to Chicago during this time can be as low as $254. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $299.

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?

The best time to book a flight to Chicago from Washington, D.C. is 53 days out, which is when prices tend to be around $282. Don’t hesitate to check prices now though because momondo users recently found tickets for as low as $193.

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 72% 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 December 2024, prices for Washington, D.C. to Chicago flights are approximately 32% 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

$29

Fastest flight time

1h 57m

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 $29. The best round-trip flight deal from Washington, D.C. to Chicago found on momondo in the last 72 hours is $65.
The fastest flight from Washington, D.C. to Chicago takes 1h 57m
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 57m onboard United Airlines. 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 $65. A train from Washington, D.C. to Chicago is more expensive than a flight, with prices starting at $190. A bus from Washington, D.C. to Chicago is also an option, with an average price of $192.

  • 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 57m 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
FrontierPriceFrom $58Free CancellationRating
6.0
3,453 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $101Free CancellationRating
6.3
8,106 reviews
Search Spirit Airlines flights
American AirlinesPriceFrom $136Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $152Free CancellationRating
7.4
8,985 reviews
Search United Airlines flights
SouthwestPriceFrom $159Free CancellationRating
8.1
4,707 reviews
Search Southwest flights
DeltaPriceFrom $175Free CancellationRating
8.0
8,540 reviews
Search Delta flights
  • Southwest Flights From Washington, D.C. to Chicago

    Southwest flies from Washington, D.C. to Chicago around 36 times per week, with 4,708 momondo users rating the airline 8.1/10. The cheapest Southwest deal from Washington, D.C. to Chicago in the last 72 hours was $159 (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 $152, round-trip. It should be noted that an average United Airlines flight deal for this route in this time was higher, at $335 round-trip. United Airlines operates 60 flights out of Washington, D.C. into Chicago in an average week, so prices vary by time and availability. 8,980 United Airlines reviews by users on momondo have scored the airline at 7.4/10.


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.


Choose the best way to get from Washington, D.C. to Chicago

Buses

21h 10m
$61 one-way$192 round-trip
Nonstop · from $192

Distance to downtown

ZUN0.7 mi
F990.8 mi

Trains

17h 40m
$95 one-way$190 round-trip
Nonstop · from $190

Distance to downtown

ZUN0.7 mi

Flights

1h 59m
$29 one-way$65 round-trip
Nonstop · from $651 stop · from $84

Distance to downtown

MDW8.6 mi

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Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago