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Cheap flights from Washington, D.C. to Chicago from $35

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 2/15. 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.
2:21 pm - 3:33 pmBWI-MDW
2h 12mnonstop
1:16 pm - 4:11 pmMDW-BWI
1h 55mnonstop
$59Frontier
Find Deal
Sat, Mar 1 - Wed, Mar 5
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
11:25 am - 12:45 pmBWI-ORD
2h 20mnonstop
4:20 pm - 7:15 pmORD-BWI
1h 55mnonstop
$135Southwest
Find Deal
Sat, Feb 22 - Sat, Feb 22
11:51 am - 1:12 pmBWI-ORD
2h 21mnonstop
8:20 am - 11:17 amORD-BWI
1h 57mnonstop
$139American Airlines
Find Deal
Sat, Jan 25 - Sat, Feb 1
11:25 am - 12:45 pmBWI-ORD
2h 20mnonstop
4:35 pm - 7:30 pmORD-BWI
1h 55mnonstop
$140Southwest
Find Deal
Sat, Jan 11 - Tue, Jan 14
11:51 am - 1:12 pmBWI-ORD
2h 21mnonstop
8:20 am - 11:17 amORD-BWI
1h 57mnonstop
$169American Airlines
Find Deal
Tue, Jan 7 - Thu, Jan 9
12:26 pm - 6:14 pmBWI-MDW
6h 48m1 stop
5:05 pm - 11:19 pmMDW-BWI
5h 14m1 stop
$196Delta
Find Deal
Tue, Jan 7 - Sat, Jan 11
12:26 pm - 4:13 pmBWI-ORD
4h 47m1 stop
7:05 am - 12:56 pmORD-BWI
4h 51m1 stop
$196Delta
Find Deal
Tue, Jan 7 - Sat, Jan 11
5:22 pm - 6:40 pmBWI-ORD
2h 18mnonstop
6:15 pm - 9:12 pmORD-BWI
1h 57mnonstop
$208United Airlines
Find Deal
Tue, Feb 4 - Wed, Feb 26
10:05 am - 11:24 amBWI-ORD
2h 19mnonstop
5:50 pm - 8:48 pmORD-BWI
1h 58mnonstop
$209United Airlines
Find Deal
Sat, Jan 11 - Sat, Jan 11
2:21 pm - 3:33 pmBWI-MDW
2h 12mnonstop
$35Frontier
Find Deal
Sat, Feb 15
4:18 pm - 5:22 pmBWI-MDW
2h 04mnonstop
$39Frontier
Find Deal
Mon, Dec 16
8:05 pm - 9:30 pmBWI-ORD
2h 25mnonstop
$69Southwest
Find Deal
Tue, Feb 18
10:05 am - 11:24 amBWI-ORD
2h 19mnonstop
$70United Airlines
Find Deal
Tue, Jan 7
8:10 pm - 9:25 pmBWI-MDW
2h 15mnonstop
$70Southwest
Find Deal
Tue, Jan 7
6:30 am - 7:52 amBWI-ORD
2h 22mnonstop
$89United Airlines
Find Deal
Fri, Feb 28
12:26 pm - 6:14 pmBWI-MDW
6h 48m1 stop
$98Delta
Find Deal
Wed, Jan 8
12:00 pm - 3:43 pmBWI-ORD
4h 43m1 stop
$98Delta
Find Deal
Wed, Feb 5
9:43 am - 11:03 amDCA-ORD
2h 20mnonstop
$105American Airlines
Find Deal
Wed, Dec 11
5:59 am - 7:19 amDCA-ORD
2h 20mnonstop
$116American Airlines
Find Deal
Mon, Dec 30
6:30 am - 11:10 amBWI-MDW
5h 40m1 stop
12:36 pm - 3:28 pmMDW-BWI
1h 52mnonstop
$279Frontier
Find Deal
Mon, Dec 2 - Mon, Dec 9
10:49 pm - 2:31 pmBWI-ORD
16h 42m1 stop
5:11 pm - 10:34 amORD-BWI
16h 23m2 stops
$285Spirit Airlines
Find Deal
Mon, Dec 2 - Wed, Dec 4
2:54 pm - 7:26 pmDCA-ORD
5h 32m1 stop
8:28 pm - 11:24 pmORD-DCA
1h 56mnonstop
$373American Airlines
Find Deal
Fri, Nov 29 - Fri, Nov 29
5:15 pm - 6:55 pmIAD-ORD
26h 40m1 stop
9:10 pm - 11:59 pmORD-IAD
1h 49mnonstop
$419United Airlines
Find Deal
Thu, Nov 28 - Fri, Nov 29
12:40 pm - 2:00 pmBWI-ORD
2h 20mnonstop
3:10 pm - 6:05 pmORD-BWI
1h 55mnonstop
$419Southwest
Find Deal
Mon, Dec 2 - Wed, Dec 4
4:35 pm - 10:00 pmBWI-ORD
6h 25m1 stop
3:10 pm - 6:05 pmORD-BWI
1h 55mnonstop
$428Southwest
Find Deal
Mon, Dec 2 - Wed, Dec 4
1:05 pm - 2:19 pmIAD-ORD
2h 14mnonstop
6:08 pm - 9:00 pmORD-IAD
1h 52mnonstop
$469United Airlines
Find Deal
Mon, Dec 2 - Tue, Dec 31
11:59 am - 1:12 pmDCA-ORD
2h 13mnonstop
12:01 pm - 2:55 pmORD-DCA
1h 54mnonstop
$469American Airlines
Find Deal
Fri, Nov 29 - Thu, Dec 19
7:55 am - 12:21 pmIAD-ORD
5h 26m1 stop
7:00 am - 11:50 amORD-IAD
3h 50m1 stop
$488Delta
Find Deal
Fri, Nov 29 - Thu, Dec 19
6:00 am - 8:50 amIAD-MDW
3h 50m1 stop
9:30 am - 3:35 pmMDW-IAD
5h 05m1 stop
$488Delta
Find Deal
Fri, Nov 29 - Thu, Dec 19
2:21 pm - 3:33 pmBWI-MDW
2h 12mnonstop
1:16 pm - 4:11 pmMDW-BWI
1h 55mnonstop
$59Frontier
Find Deal
Sat, Mar 1 - Wed, Mar 5
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
7:53 pm - 9:05 pmBWI-MDW
2h 12mnonstop
1:16 pm - 4:11 pmMDW-BWI
1h 55mnonstop
$75Frontier
Find Deal
Mon, Feb 3 - Wed, Feb 26
7:53 pm - 9:05 pmBWI-MDW
2h 12mnonstop
10:26 am - 1:21 pmMDW-BWI
1h 55mnonstop
$76Frontier
Find Deal
Mon, Feb 3 - Sat, Mar 1
11:25 am - 12:45 pmBWI-ORD
2h 20mnonstop
4:20 pm - 7:15 pmORD-BWI
1h 55mnonstop
$135Southwest
Find Deal
Sat, Feb 22 - Sat, Feb 22
7:30 am - 8:51 amBWI-ORD
2h 21mnonstop
8:15 am - 11:10 amORD-BWI
1h 55mnonstop
$138American Airlines
Find Deal
Wed, Feb 5 - Wed, Feb 26
11:51 am - 1:12 pmBWI-ORD
2h 21mnonstop
8:20 am - 11:17 amORD-BWI
1h 57mnonstop
$139American Airlines
Find Deal
Sat, Jan 25 - Sat, Feb 1
10:35 am - 11:45 amBWI-MDW
2h 10mnonstop
6:55 pm - 9:45 pmMDW-BWI
1h 50mnonstop
$139Southwest
Find Deal
Wed, Feb 5 - Wed, Feb 26
5:22 pm - 6:40 pmBWI-ORD
2h 18mnonstop
6:15 pm - 9:12 pmORD-BWI
1h 57mnonstop
$208United Airlines
Find Deal
Tue, Feb 4 - Tue, Feb 25
10:05 am - 11:24 amBWI-ORD
2h 19mnonstop
5:50 pm - 8:48 pmORD-BWI
1h 58mnonstop
$209United Airlines
Find Deal
Sat, Jan 11 - Sat, Jan 11

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

Our best American Airlines deals on Washington, D.C. to Chicago flight tickets
American Airlines
Jan 25
BWI11:51 amBaltimore/Washington
2h 21m
ORD1:12 pmChicago O'Hare Intl
Feb 1
ORD8:20 amChicago O'Hare Intl
1h 57m
BWI11:17 amBaltimore/Washington
American Airlines
Jan 7
BWI11:51 amBaltimore/Washington
2h 21m
ORD1:12 pmChicago O'Hare Intl
Jan 9
ORD8:20 amChicago O'Hare Intl
1h 57m
BWI11:17 amBaltimore/Washington
American Airlines
Jan 30
BWI7:30 amBaltimore/Washington
2h 21m
ORD8:51 amChicago O'Hare Intl
Feb 3
ORD8:20 amChicago O'Hare Intl
1h 57m
BWI11:17 amBaltimore/Washington

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

Our best United Airlines deals on Washington, D.C. to Chicago flight tickets
United Airlines
Feb 4
BWI5:22 pmBaltimore/Washington
2h 18m
ORD6:40 pmChicago O'Hare Intl
Feb 26
ORD6:15 pmChicago O'Hare Intl
1h 57m
BWI9:12 pmBaltimore/Washington
United Airlines
Dec 11
BWI5:25 pmBaltimore/Washington
2h 13m
ORD6:38 pmChicago O'Hare Intl
Dec 14
ORD10:46 amChicago O'Hare Intl
1h 57m
BWI1:43 pmBaltimore/Washington
United Airlines
Feb 4
BWI5:22 pmBaltimore/Washington
2h 18m
ORD6:40 pmChicago O'Hare Intl
Feb 28
ORD7:00 amChicago O'Hare Intl
1h 55m
BWI9:55 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 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 $247. 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 $304.

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 $257. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $302.

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 60 days out, which is when prices tend to be around $261. Don’t hesitate to check prices now though because momondo users recently found tickets for as low as $203.

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 82% 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 November 2024, prices for Washington, D.C. to Chicago flights are approximately 23% 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

$35

Fastest flight time

2h 00m

Direct flights

Mon, Tue, Thu, Fri, Sat and Sun

Airports in Chicago

2 airports
The best one-way flight to Chicago from Washington, D.C. in the past 72 hours is $35. The best round-trip flight deal from Washington, D.C. to Chicago found on momondo in the last 72 hours is $59.
The fastest flight from Washington, D.C. to Chicago takes 2h 00m
Direct flights go from Washington, D.C. to Chicago on Monday, Tuesday, Thursday, Friday, Saturday and Sunday. Airlines offering direct flights are: United Airlines, Southwest and Frontier.
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 2h 00m 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 $59. A train from Washington, D.C. to Chicago is more expensive than a flight, with prices starting at $210. A bus from Washington, D.C. to Chicago is also an option, with an average price of $121.

  • How far is Washington, D.C. to Chicago by plane?

    The straight-line distance from Washington, D.C. to Chicago is 593.1 mi. 2h 00m 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
6.1
3,523 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $101Free CancellationRating
6.3
8,172 reviews
Search Spirit Airlines flights
American AirlinesPriceFrom $137Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $152Free CancellationRating
7.4
9,146 reviews
Search United Airlines flights
SouthwestPriceFrom $157Free CancellationRating
8.1
4,979 reviews
Search Southwest flights
DeltaPriceFrom $175Free CancellationRating
8.0
8,730 reviews
Search Delta flights
  • Southwest Flights From Washington, D.C. to Chicago

    Southwest flies from Washington, D.C. to Chicago around 21 times per week, with 4,979 momondo users rating the airline 8.1/10. The cheapest Southwest deal from Washington, D.C. to Chicago in the last 72 hours was $157 (round-trip), much lower than the average airfare cost of $283 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 $332 round-trip. United Airlines operates 71 flights out of Washington, D.C. into Chicago in an average week, so prices vary by time and availability. 9,146 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
$58 one-way$121 round-trip
Nonstop · from $1211 stop · from $83

Distance to downtown

ZUN0.7 mi

Trains

17h 40m
$95 one-way$210 round-trip
Nonstop · from $210

Distance to downtown

ZUN0.7 mi

Flights

2h 00m
$35 one-way$59 round-trip
Nonstop · from $591 stop · from $83

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