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Flights from Washington D.C. to Chicago Starting at £30

We've found these cheap flights for you. You can book one-way or return flight tickets.

  • One way
  • Round-trip

Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

Find the best time to fly from Washington D.C. to Chicago

We monitor flight fares to help you find the best deals effortlessly

Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.
Airlines Flying from Washington D.C. to Chicago

Compare prices, find the option that best suits your travel needs, and enjoy a comfortable journey with a trusted airline.

Southwest Airlines
From £30
American Airlines
From £36
Frontier Airlines
From £54
Delta Air Lines
From £61
United Airlines
From £65
Jetblue Airways
From £73
Southern Airways Express
From £81
Sun Country Airlines
From £92
ANA airlines

Find more flights and airlines

Alternative Routes from Washington D.C. to Chicago

Searching for potential routes that might be cheaper and faster? Check out these alternative flights from Washington D.C. to Chicago.

  • Cheapest
    Southwest Airlines
    DCA
    09:00
    2h 15m
    Direct
    MDW
    10:15
    Ronald Reagan Washington National Airport - Midway International Airport
    Wed, Apr 3Southwest Airlines
    £30
  • American Airlines
    DCA
    06:00
    2h 15m
    Direct
    ORD
    07:15
    Ronald Reagan Washington National Airport - O'Hare International Airport
    Tue, May 7American Airlines
    £36
  • Delta Air Lines
    IAD
    19:55
    4h 57m
    1 transfer
    ORD
    23:52
    Washington Dulles International Airport - O'Hare International Airport
    Mon, Apr 29Delta Air Lines
    £62
  • Delta Air Lines
    IAD
    19:55
    4h 57m
    1 transfer
    ORD
    23:52
    Washington Dulles International Airport - O'Hare International Airport
    Mon, Apr 29Delta Air Lines
    £62
    Find More Flights

How do I find the cheapest flights?

  • When are flight tickets from Washington D.C. (WAS) to Chicago (CHI) the cheapest?

    Airlines adjust prices for flights from Washington D.C. to Chicago based on the date and time of your booking. By analyzing data from all airlines, on Trip.com, you can find the cheapest flight prices on Tuesdays, Wednesdays, and Saturdays.
  • How much are flights from Washington D.C. (WAS) to Chicago (CHI) cost?

    According to Trip.com's data, the lowest price is around £207.
  • How long is the flight from Washington D.C. (WAS) to Chicago (CHI)?

    It takes about 2 hours 12 minutes to fly from Washington D.C. (WAS) to Chicago (CHI).
  • What is the transportation method from the main airport to downtown in Chicago?

    • The distance from O'Hare International Airport to downtown is about 25km, by taxi about 40 minutes.
    • The distance from Midway International Airport to downtown is about 14km, by taxi about 30 minutes.
  • What are the most popular airlines that fly from Washington D.C. (WAS) to Chicago (CHI)?

  • What's the most popular airline for direct flights from Washington D.C. (WAS) to Chicago (CHI)?

    Southwest Airlines operates 7 direct flights from Washington D.C. (WAS) to Chicago (CHI).
  • How many airports in Chicago (CHI)?

Flight Information from Washington D.C. to Chicago

Cheapest direct flight price

£29

Cheapest return ticket price

£75

Cheapest month

April

Peak season for travel

September