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Cheap flights from Washington, D.C. to Chicago from £66

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 13/5. Fares are subject to change and may not be available on all flights or dates of travel.
WAS — CHI
16 May — 23 May1
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 67 days in advance, depart on a Thursday or Wednesday and return on a Monday

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 16 April 2026.

Sat 6/613:59
BWI
-
ORD
1 stop5h 42m
Delta
Tue 9/611:23
ORD
-
BWI
1 stop4h 56m
Delta
Deal found 14/4£149
Fri 1/506:14
BWI
-
ORD
1 stop6h 18m
Frontier
Mon 4/516:28
ORD
-
BWI
1 stop7h 16m
Frontier
Deal found 15/4£150
Thu 9/719:29
BWI
-
ORD
1 stop5h 24m
Delta
Tue 14/709:45
ORD
-
BWI
1 stop5h 08m
Delta
Deal found 14/4£153
Wed 6/520:30
BWI
-
ORD
Nonstop2h 29m
United Airlines
Sat 9/511:10
ORD
-
BWI
Nonstop2h 03m
United Airlines
Deal found 13/4£153
Tue 19/519:52
BWI
-
ORD
Nonstop2h 31m
American Airlines
Sat 23/521:01
ORD
-
BWI
Nonstop2h 10m
American Airlines
Deal found 11/4£155
Sat 23/518:31
BWI
-
ORD
1 stop6h 36m
Delta
Tue 26/517:19
ORD
-
BWI
1 stop4h 58m
Delta
Deal found 16/4£157
Wed 3/607:30
DCA
-
ORD
Nonstop2h 17m
United Airlines
Mon 8/619:40
ORD
-
DCA
Nonstop2h 09m
United Airlines
Deal found 11/4£161
Thu 14/508:20
IAD
-
ORD
Nonstop2h 17m
United Airlines
Tue 19/512:55
ORD
-
IAD
Nonstop2h 03m
United Airlines
Deal found 12/4£162
Sat 30/505:00
BWI
-
ORD
1 stop5h 02m
American Airlines
Tue 2/606:56
ORD
-
BWI
Nonstop2h 06m
American Airlines
Deal found 13/4£162
Sat 23/518:20
BWI
-
ORD
Nonstop2h 24m
United Airlines
Tue 26/506:20
ORD
-
BWI
Nonstop1h 57m
United Airlines
Deal found 12/4£163
Wed 29/409:40
DCA
-
ORD
1 stop4h 05m
Delta
Wed 6/513:36
ORD
-
DCA
1 stop4h 23m
Delta
Deal found 14/4£167
Sat 2/506:00
IAD
-
ORD
1 stop5h 19m
Delta
Tue 5/508:15
ORD
-
IAD
1 stop4h 49m
Delta
Deal found 14/4£167

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 16 April 2026.

Round-trip from

£149

One-way from

£66

Popular in

March

Cheapest in

September

Average price

£234

Good one-way deal

£103 or less
Delta
  • Delta
  • 6/6-9/6
  • 2 total stops
  • 10h 38m total
  • Washington, D.C. to Chicago
Search Deals
American Airlines
  • American Airlines
  • 13/5
  • Nonstop
  • 2h 34m total
  • Washington, D.C. to Chicago
Search Deals
Highest demand for flights based on searches. 9% potential increase in price (£15 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (£4 potential savings vs. average return price).
Search Deals
Average for round-trip flights in April 2026
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 16 April 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

Wed 29/7

12:33-18:29

1 stop6h 56m

Chicago O'Hare Intl

Fri 31/7

17:18-23:13

1 stop4h 55m

£153

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Mon 4/5

06:15-07:36

Nonstop2h 21m

Chicago O'Hare Intl

Tue 5/5

11:10-14:13

Nonstop2h 03m

£153

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Fri 8/5

19:41-23:59

1 stop5h 18m

Chicago O'Hare Intl

Mon 11/5

17:41-23:46

1 stop5h 05m

£157

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Sat 30/5

06:00-13:10

1 stop8h 10m

Chicago O'Hare Intl

Tue 2/6

14:40-21:55

1 stop6h 15m

£168

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Tue 5/5

09:40-12:45

1 stop4h 05m

Chicago O'Hare Intl

Thu 7/5

07:05-12:59

1 stop4h 54m

£168

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Sat 16/5

10:35-15:30

2 stops5h 55m

Chicago O'Hare Intl

Tue 19/5

11:55-20:00

1 stop7h 05m

£172

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Thu 11/6

12:29-18:29

1 stop7h 00m

Chicago O'Hare Intl

Sat 13/6

11:15-18:59

1 stop6h 44m

£175

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Wed 29/7

06:00-10:10

1 stop5h 10m

Chicago O'Hare Intl

Fri 31/7

17:18-22:55

1 stop4h 37m

£175

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Wed 29/7

17:26-20:31

1 stop4h 05m

Chicago O'Hare Intl

Fri 31/7

09:45-18:26

1 stop7h 41m

£175

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Thu 11/6

06:00-10:45

1 stop5h 45m

Chicago O'Hare Intl

Mon 15/6

17:22-23:14

1 stop4h 52m

£175

Flights are sorted by cheapest return flights first.

Deals found on 12/4

Showing 1-10 of 59 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

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

Use this chart to determine the optimal time to book a return flight from Washington, D.C. to Chicago. Price data was last updated on 10 April 2026.

Booking 67 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.

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 £156). Flying from Washington, D.C. to Chicago in February is currently the most expensive (average of £310). 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 16 April 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 16 April 2026.

The most flights from WAS to CHI are scheduled on a Thursday (91 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (35 on average).

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

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, Southwest, and United Airlines can get you from Washington, D.C. to Chicago in just under 2h 19m. Your travel time can differ by up to 5h 51m. Washington, D.C. and Chicago are separated by a distance of 620 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 £156 on this airline. Frontier is 19% 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 CommutAir (100%), ANA (78%) or Ethiopian Air (77%) 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 £156). Flying from Washington, D.C. to Chicago in February is currently the most expensive (average of £310). 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 16 April 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest£156Average£156FlexibilityNo 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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