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Cheap flights from Washington, D.C. to Chicago from £74

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 23/6. Fares are subject to change and may not be available on all flights or dates of travel.
WAS — CHI
28 Jun — 5 Jul1
1 adult
1 adult, Economy, 0 bags
Cheapflights Tip: The best prices from Washington, D.C. to Chicago are usually found in September or August, booked 90 days in advance, depart on a Tuesday or Friday and return on a Wednesday

Cheap flight deals from Washington, D.C. to Chicago

Enter your travel dates to find the best prices.

Cheapest flights from Washington, D.C. to Chicago
Explore the most affordable flight options available from Washington, D.C. to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 29 May 2026.

Wed 16/914:28
BWI
-
ORD
1 stop5h 17m
Delta
Mon 21/913:50
ORD
-
BWI
1 stop4h 45m
Delta
Deal found 28/5£172
Wed 14/1006:17
BWI
-
ORD
Nonstop2h 12m
United Airlines
Thu 22/1014:15
ORD
-
BWI
Nonstop1h 58m
United Airlines
Deal found 24/5£174
Wed 24/622:10
DCA
-
ORD
Nonstop2h 20m
American Airlines
Sat 27/606:00
ORD
-
DCA
Nonstop2h 14m
American Airlines
Deal found 28/5£176
Tue 23/607:15
DCA
-
ORD
Nonstop2h 14m
United Airlines
Thu 25/606:00
ORD
-
DCA
Nonstop1h 54m
United Airlines
Deal found 26/5£177
Mon 13/706:10
IAD
-
ORD
Nonstop2h 17m
United Airlines
Wed 15/713:30
ORD
-
IAD
Nonstop2h 00m
United Airlines
Deal found 28/5£177
Mon 28/906:59
DCA
-
ORD
1 stop6h 41m
Delta
Wed 30/907:01
ORD
-
DCA
1 stop3h 36m
Delta
Deal found 25/5£177
Wed 19/817:25
IAD
-
ORD
1 stop4h 02m
Delta
Sat 22/813:50
ORD
-
IAD
1 stop5h 15m
Delta
Deal found 24/5£177
Thu 27/819:10
DCA
-
ORD
Nonstop2h 20m
United Airlines
Mon 31/806:00
ORD
-
DCA
Nonstop1h 55m
United Airlines
Deal found 27/5£178
Thu 27/813:10
IAD
-
ORD
Nonstop2h 17m
United Airlines
Mon 31/806:25
ORD
-
IAD
Nonstop1h 58m
United Airlines
Deal found 27/5£178
Thu 6/819:45
DCA
-
ORD
1 stop5h 17m
Delta
Tue 11/806:51
ORD
-
DCA
1 stop3h 37m
Delta
Deal found 29/5£180
Wed 5/820:33
IAD
-
ORD
1 stop12h 20m
Frontier
Mon 10/807:05
ORD
-
IAD
1 stop9h 09m
Frontier
Deal found 26/5£180
Wed 17/613:15
IAD
-
ORD
Nonstop2h 14m
United Airlines
Wed 17/621:55
ORD
-
IAD
Nonstop2h 04m
United Airlines
Deal found 26/5£180

Find flight deals from Washington, D.C. to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Washington, D.C. (WAS) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated 29 May 2026.

Round-trip from

£172

One-way from

£74

Popular in

March

Cheapest in

September

Average price

£238

Good round-trip deal

£252 or less

Good one-way deal

£296 or less
Delta
  • Delta
  • 16/9-17/9
  • 2 total stops
  • 13h 50m total
  • Washington, D.C. to Chicago
Search Deals
Delta
  • Delta
  • 21/7
  • 1 total stop
  • 6h 03m total
  • Washington, D.C. to Chicago
Search Deals
Highest demand for flights based on searches. 6% potential increase in price (£10 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease (£3 potential savings vs. average return price).
Search Deals
Average for round-trip flights in May 2026
Search Deals
Price to beat on a round-trip flight from Washington, D.C. (WAS) to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Washington, D.C. (WAS) to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customise 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, Cheapflights users made 858,174 searches. Data last updated 29 May 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 return flight

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Thu 1/10

12:01-16:48

1 stop5h 47m

Chicago O'Hare Intl

Tue 6/10

05:30-11:08

1 stop4h 38m

£172

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Wed 16/9

12:30-16:14

1 stop4h 44m

Chicago O'Hare Intl

Sat 19/9

13:50-19:35

1 stop4h 45m

£172

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Thu 22/10

14:00-15:15

Nonstop2h 15m

Chicago O'Hare Intl

Mon 26/10

08:00-10:44

Nonstop1h 44m

£178

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Tue 23/6

22:15-23:26

Nonstop2h 11m

Chicago O'Hare Intl

Fri 3/7

13:30-16:30

Nonstop2h 00m

£181

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Thu 25/6

22:20-23:31

Nonstop2h 11m

Chicago O'Hare Intl

Tue 30/6

21:40-00:45

Nonstop2h 05m

£184

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Fri 17/7

22:20-23:31

Nonstop2h 11m

Chicago O'Hare Intl

Wed 22/7

06:30-09:24

Nonstop1h 54m

£184

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Tue 14/7

17:27-20:31

1 stop4h 04m

Chicago O'Hare Intl

Sat 18/7

17:18-23:18

1 stop5h 00m

£186

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Sat 26/9

17:40-20:22

1 stop3h 42m

Chicago O'Hare Intl

Tue 29/9

07:01-11:42

1 stop3h 41m

£189

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Wed 16/9

10:21-14:32

1 stop5h 11m

Chicago O'Hare Intl

Mon 21/9

13:50-19:35

1 stop4h 45m

£189

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Sat 19/9

17:40-20:22

1 stop3h 42m

Chicago O'Hare Intl

Tue 22/9

07:01-11:42

1 stop3h 41m

£189

Flights are sorted by cheapest return flights first.

Deals found on 27/5

Showing 1-10 of 60 resultsSorted by cheapest first
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Best time to book a flight from Washington, D.C. to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Washington, D.C. with our price prediction graph.
Estimated return price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Washington, D.C. to Chicago

What is the cheapest month to book a flight from Washington, D.C. to Chicago?

Currently, August is the cheapest month in which you can book a flight from Washington, D.C. to Chicago (average of £159). Flying from Washington, D.C. to Chicago in February is currently the most expensive (average of £317). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from WAS to CHI?

Find hourly flight availability from Washington, D.C. to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 29 May 2026.

It’s optimal to fly from Washington, D.C. to Chicago in the evening. By choosing this option you can save up to 47% on the cost of your flight, compared to a flight in the afternoon.

Weekly flight availability from Washington, D.C. to Chicago

Explore weekly flight availability from Washington, D.C. to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated 29 May 2026.

The most flights from WAS to CHI are scheduled on a Friday (102 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (47 on average).

How much does it cost for a return flight from Washington, D.C. to Chicago?

How far ahead should I book a flight from Washington, D.C. to Chicago?

Booking 35 days in advance of your planned departure date is, on average, the best time to get cheap flights from Washington, D.C. to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

Related info for your journey

Find useful and relevant information for your journey from Washington, D.C. to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Washington, D.C. to Chicago?

    Delta and United Airlines can get you from Washington, D.C. to Chicago in just under 2h 14m. Your travel time can differ by up to 3h 33m. Washington, D.C. and Chicago are separated by a distance of 610 mi. When browsing for deals, the options you’ll see will be for both direct flights and flights with stops.

  • What is the cheapest airline to fly from Washington, D.C. to Chicago round-trip?

    Our cheapest airline available from Washington, D.C. to Chicago is Frontier. Our recent data shows that you can find tickets from as low as £158 on this airline. Frontier is 21% cheaper than the average price of flights available within the next 90 days to this destination.

  • What are the most popular routes from Washington, D.C. to Chicago?

    While some choose either Baltimore/Washington - Chicago O'Hare Intl or Washington, D.C. Dulles Intl - Chicago O'Hare Intl, Washington, D.C. Reagan-National - Chicago O'Hare Intl is the most popular route from Washington, D.C. to Chicago.

  • What are the most reliable airlines from Washington, D.C. to Chicago?

    No one likes to see their flight delayed. When booking a flight from Washington, D.C. to Chicago consider choosing Ethiopian Air (87%), ANA (81%) or Air Canada (80%) as they are the most reliable in getting you off to your destination on time.

  • Can I find deals for flights from Washington, D.C. to Chicago that include hotel bookings?

    Yes. In addition to deals on Washington, D.C. to Chicago flights, Cheapflights offers holiday packages that include both flights and hotel.

  • How can I find direct flights from Washington, D.C. to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Washington, D.C. to Chicago.

  • Can I find deals for business class flights from Washington, D.C. to Chicago?

    Yes. Cheapflights offers flight deals from Washington, D.C. to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Washington, D.C. to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Washington, D.C. to Chicago (average of £159). Flying from Washington, D.C. to Chicago in February is currently the most expensive (average of £317). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

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Top airline flying from Washington, D.C. to Chicago

Discover the top airline that operate flights from Washington, D.C. to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 858,174 searches. Data last updated 29 May 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest£158Average£158FlexibilityNo cancel feeOn-time62%
Search Frontier flights

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travellers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Washington, D.C. to Chicago?

Cheapflights goes through 900+ travel sites to look for the best flight deals for flights from Washington, D.C. to Chicago. Too many options? Cheapflights also provides filters for things like airlines, price ranges, and number of stops to help you make a decision easily.

Why should you use Cheapflights to find cheap flight tickets from Washington, D.C. to Chicago?

Cheapflights helps you find that perfect flight to Chicago from Washington, D.C. by searching from hundreds of airlines and agencies you know and love. We are also free to use, in case you were wondering!

Can Cheapflights find flights from Washington, D.C. to Chicago with no change fees?

Need flexible booking options for your flight to Chicago from Washington, D.C.? Don’t worry, Cheapflights have you covered. Use our search filter to only show flights with no change fees.

Can Cheapflights notify me if prices for flights from Washington, D.C. to Chicago become cheaper?

Yes, Cheapflights has a feature called Price Alert, which notifies users when flight prices change. Track prices for your flight to Chicago from Washington, D.C. today and book when prices fit your budget.

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