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Cheap flights from Washington, D.C. to Chicago from £51

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 17/1. Fares are subject to change and may not be available on all flights or dates of travel.
WAS — CHI
27 Jan — 3 Feb1
1 adult
1 adult, Economy, 0 bags

Cheapflights Tip: The best prices from Washington, D.C. to Chicago are usually found in September or January, booked 83 days in advance, depart on a Monday or Tuesday and return on a Tuesday

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 28 December 2025.

Wed 31/1222:06IAD - ORD
1 stop12h 27mUnited Airlines
Thu 1/113:24ORD - IAD
Nonstop2h 00mUnited Airlines
Deal found 27/12£254
Wed 31/1217:35DCA - ORD
1 stop16h 26mDelta
Thu 1/117:31ORD - DCA
1 stop4h 25mDelta
Deal found 25/12£266
Thu 25/1217:15IAD - ORD
1 stop17h 20mUnited Airlines
Fri 26/1213:24ORD - IAD
Nonstop2h 00mUnited Airlines
Deal found 24/12£275
Wed 31/1211:20DCA - ORD
1 stop8h 26mJetBlue
Sat 31/107:45ORD - DCA
1 stop8h 19mJetBlue
Deal found 27/12£284
Wed 31/1222:17IAD - ORD
1 stop10h 48mUnited Airlines
Sat 31/110:00ORD - IAD
1 stop9h 59mUnited Airlines
Deal found 27/12£287
Sat 27/1222:14IAD - ORD
1 stop21h 11mUnited Airlines
Sun 28/1221:15ORD - IAD
Nonstop2h 00mUnited Airlines
Deal found 25/12£298
Wed 31/1211:20DCA - ORD
1 stop8h 26mJetBlue
Tue 6/110:55ORD - DCA
1 stop5h 39mJetBlue
Deal found 26/12£306
Thu 25/1216:05DCA - ORD
2 stops16h 34mUnited Airlines
Fri 26/1211:15ORD - DCA
Nonstop2h 02mUnited Airlines
Deal found 24/12£326
Tue 30/1222:17IAD - ORD
1 stop10h 48mUnited Airlines
Thu 1/121:15ORD - IAD
Nonstop2h 00mUnited Airlines
Deal found 25/12£335
Mon 29/1207:00DCA - ORD
1 stop9h 57mDelta
Thu 1/107:00ORD - DCA
1 stop5h 11mDelta
Deal found 25/12£338
Sat 27/1216:26DCA - ORD
2 stops15h 04mUnited Airlines
Sun 28/1209:00ORD - DCA
Nonstop1h 58mUnited Airlines
Deal found 27/12£347
Thu 25/1215:00BWI - ORD
1 stop7h 34mDelta
Thu 1/105:30ORD - BWI
1 stop6h 25mDelta
Deal found 25/12£358

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 28 December 2025.

Round-trip from

£90

One-way from

£51

Popular in

November

Cheapest in

September

Average price

£210

Good round-trip deal

£69 or less

Good one-way deal

£56 or less
Frontier
  • Frontier
  • 14/1-19/1
  • 1 total stop
  • 9h 08m total
  • Washington, D.C. to Chicago
Search Deals
Southwest
  • Southwest
  • 17/1
  • 1 total stop
  • 7h 50m total
  • Washington, D.C. to Chicago
Search Deals
Highest demand for flights based on searches. 6% potential increase in price (£8 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease (£2 potential savings vs. average return price).
Search Deals
Average for round-trip flights in December 2025
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 28 December 2025.
Use the filters below to find and compare flights from Washington, D.C. to Chicago that are best for you.

Fly from

Washington, D.C.

Fly to

Chicago

Route

Depart

Return

Price

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Mon 23/2

06:30-07:53

Nonstop2h 23m

Chicago O'Hare Intl

Thu 26/2

11:00-14:01

Nonstop2h 01m

£103

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Mon 2/2

10:05-11:25

Nonstop2h 20m

Chicago O'Hare Intl

Sat 7/2

11:05-14:11

Nonstop2h 06m

£103

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Wed 28/1

10:05-11:25

Nonstop2h 20m

Chicago O'Hare Intl

Tue 3/2

11:05-14:11

Nonstop2h 06m

£103

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Sun 18/1

17:18-18:38

Nonstop2h 20m

Chicago O'Hare Intl

Tue 20/1

11:05-14:11

Nonstop2h 06m

£103

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Thu 29/1

10:05-11:25

Nonstop2h 20m

Chicago O'Hare Intl

Tue 10/2

18:15-21:21

Nonstop2h 06m

£103

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Wed 28/1

17:18-18:38

Nonstop2h 20m

Chicago O'Hare Intl

Mon 2/2

18:15-21:21

Nonstop2h 06m

£103

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Wed 21/1

10:05-11:25

Nonstop2h 20m

Chicago O'Hare Intl

Mon 26/1

11:05-14:11

Nonstop2h 06m

£110

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Fri 6/2

17:18-18:38

Nonstop2h 20m

Chicago O'Hare Intl

Tue 10/2

18:15-21:21

Nonstop2h 06m

£117

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Sun 18/1

07:15-14:45

1 stop8h 30m

Chicago O'Hare Intl

Tue 20/1

11:55-20:50

2 stops7h 55m

£121

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Thu 29/1

06:00-09:41

1 stop4h 41m

Chicago O'Hare Intl

Tue 10/2

07:05-15:38

1 stop7h 33m

£131

Flights are sorted by cheapest return flights first.

Deals found on 28/12

Showing 1-10 of 60 results
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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 26 December 2025.

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, March is the cheapest month in which you can book a flight from Washington, D.C. to Chicago (average of £37). Flying from Washington, D.C. to Chicago in June is currently the most expensive (average of £98). 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 28 December 2025.

It’s optimal to fly from Washington, D.C. to Chicago in the morning. By choosing this option you can save up to 30% on the cost of your flight, compared to a flight in the evening.

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 28 December 2025.

The most flights from WAS to CHI are scheduled on a Saturday (68 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (48 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?

    United Airlines, JetBlue, and Delta can get you from Washington, D.C. to Chicago in just under 2h 23m. Your travel time can differ by up to 6h 15m. 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 £157 on this airline. Frontier is 15% 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 Washington, D.C. Reagan-National - Chicago O'Hare Intl or Washington, D.C. Dulles Intl - Chicago O'Hare Intl, Baltimore/Washington - 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 Egyptair (85%), Air China (84%) or ANA (82%) 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, March is the cheapest month in which you can book a flight from Washington, D.C. to Chicago (average of £37). Flying from Washington, D.C. to Chicago in June is currently the most expensive (average of £98). 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

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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 28 December 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest£157Average£157FlexibilityNo 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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