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Cheap flights from Washington, D.C. to Chicago from £79

WAS — CHI
10 Nov — 17 Nov1
1 adult
1 adult, Economy, 0 bags
Cheapflights Tip: The best prices from Washington, D.C. to Chicago are usually found in January or February, booked 60 days in advance, depart on a Wednesday or Thursday 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

Fri 20/1114:29 -
Nonstop2h 28m
Fri 27/1114:52 -
Nonstop2h 10m
Deal found 6/10£153
Tue 27/1014:06 -
1 stop6h 23m
Wed 4/1113:00 -
1 stop6h 09m
Deal found 8/10£158
Wed 25/1122:05 -
Nonstop2h 10m
Tue 1/1206:00 -
Nonstop2h 00m
Deal found 7/10£158
Tue 27/1012:34 -
Nonstop2h 20m
Wed 28/1007:45 -
Nonstop2h 04m
Deal found 8/10£158
Thu 29/1013:09 -
1 stop7h 20m
Sat 31/1013:00 -
1 stop6h 09m
Deal found 8/10£159
Sat 7/1118:30 -
Nonstop2h 10m
Mon 9/1120:15 -
Nonstop1h 55m
Deal found 8/10£159
Thu 5/1106:10 -
Nonstop2h 21m
Tue 10/1118:29 -
Nonstop2h 13m
Deal found 8/10£159
Thu 12/1111:49 -
Nonstop2h 23m
Tue 17/1106:00 -
Nonstop1h 56m
Deal found 8/10£159
Thu 29/1008:23 -
Nonstop2h 22m
Mon 9/1114:21 -
Nonstop2h 03m
Deal found 8/10£159
Thu 5/1122:05 -
Nonstop2h 10m
Mon 9/1105:05 -
Nonstop1h 50m
Deal found 7/10£159
Thu 5/1112:34 -
Nonstop2h 20m
Mon 9/1116:05 -
Nonstop2h 04m
Deal found 8/10£159
Thu 5/1106:10 -
Nonstop2h 05m
Tue 10/1107:25 -
Nonstop1h 50m
Deal found 8/10£159

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

Round-trip from

£153

One-way from

£79

Popular in

June

Cheapest in

January

Average price

£242

Good one-way deal

£259 or less
Frontier
  • Frontier
  • 20/11-27/11
  • Nonstop
  • 4h 38m total
  • Washington, D.C. to Chicago
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JetBlue
  • JetBlue
  • 9/12-31/12
  • 1 total stop
  • 6h 22m total
  • Washington, D.C. to Chicago
Search Deals
Highest demand for flights based on searches. 12% potential increase in price (£24 potential increase over avg. return price).
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Cheapest flight prices on average. 2% potential price decrease (£4 potential savings vs. average return price).
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Average for round-trip flights in October 2026
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Price to beat on a one-way flight from Washington, D.C. (WAS) to Chicago (CHI).
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Cheapflights Fare Finder

 
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

Washington, D.C.Chicago

DCA Washington, D.C. Reagan-National - ORD Chicago O'Hare Intl

DCAORD

Washington, D.C. Reagan-National

Sat 12/12

09:59-16:47

1 stop7h 48m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

£79

BaltimoreChicago

BWI Baltimore/Washington - MDW Chicago Midway

BWIMDW

Baltimore/Washington

Wed 6/1

07:55-09:05

Nonstop2h 10m

Chicago Midway

Wed 31/12

00:00-01:00

Nonstop0h 00m

£79

Washington, D.C.Chicago

DCA Washington, D.C. Reagan-National - ORD Chicago O'Hare Intl

DCAORD

Washington, D.C. Reagan-National

Wed 9/12

11:20-16:42

1 stop6h 22m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

£79
Fastest return journey

BaltimoreChicago

BWI Baltimore/Washington - MDW Chicago Midway

BWIMDW

Baltimore/Washington

Thu 29/10

21:00-22:00

Nonstop2h 00m

Chicago Midway

Wed 31/12

00:00-01:00

Nonstop0h 00m

£80

Washington, D.C.Chicago

DCA Washington, D.C. Reagan-National - MDW Chicago Midway

DCAMDW

Washington, D.C. Reagan-National

Thu 5/11

21:15-22:20

Nonstop2h 05m

Chicago Midway

Wed 31/12

00:00-01:00

Nonstop0h 00m

£80

Washington, D.C.Chicago

DCA Washington, D.C. Reagan-National - MDW Chicago Midway

DCAMDW

Washington, D.C. Reagan-National

Sat 7/11

14:35-15:40

Nonstop2h 05m

Chicago Midway

Wed 31/12

00:00-01:00

Nonstop0h 00m

£80

Washington, D.C.Chicago

DCA Washington, D.C. Reagan-National - MDW Chicago Midway

DCAMDW

Washington, D.C. Reagan-National

Mon 18/1

21:35-22:40

Nonstop2h 05m

Chicago Midway

Wed 31/12

00:00-01:00

Nonstop0h 00m

£80

Washington, D.C.Chicago

DCA Washington, D.C. Reagan-National - MDW Chicago Midway

DCAMDW

Washington, D.C. Reagan-National

Thu 29/10

15:00-16:00

Nonstop2h 00m

Chicago Midway

Wed 31/12

00:00-01:00

Nonstop0h 00m

£80

Washington, D.C.Chicago

DCA Washington, D.C. Reagan-National - ORD Chicago O'Hare Intl

DCAORD

Washington, D.C. Reagan-National

Tue 29/12

11:51-13:15

Nonstop2h 24m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

£82

Washington, D.C.Chicago

DCA Washington, D.C. Reagan-National - ORD Chicago O'Hare Intl

DCAORD

Washington, D.C. Reagan-National

Mon 18/1

09:36-11:00

Nonstop2h 24m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

£82

Flights are sorted by cheapest return flights first.

Deals found on 10/10

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

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, January is the cheapest month in which you can book a flight from Washington, D.C. to Chicago (average of £221). Flying from Washington, D.C. to Chicago in June is currently the most expensive (average of £297). 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?

It’s optimal to fly from Washington, D.C. to Chicago in the evening. By choosing this option you can save up to 41% on the cost of your flight, compared to a flight in the afternoon.

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

The most flights from WAS to CHI are scheduled on a Friday (99 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (40 on average).

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

Airfare is below average for this route at the moment.
Washington, D.C. to Chicago flights typically cost between £183 and £315 in November.
The cheapest return price found within the last 5 days was £153 on Frontier (20 Nov–27 Nov).

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

Booking 59 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

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

    JetBlue, Southwest, and United Airlines can get you from Washington, D.C. to Chicago in just under 2h 10m. Your travel time can differ by up to 5h 10m. Washington, D.C. and Chicago are separated by a distance of 609 mi. When browsing for deals, the options you’ll see will be for both direct flights and flights with stops.

  • What are the cheapest airlines to fly from Washington, D.C. to Chicago one-way?

    £78 is the cheapest one-way deal found within the past few days, from Delta. You may also be able to find cheap deals on United Airlines and American Airlines, with prices starting from £97 and £103, respectively.

  • 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 (89%), Air China (85%) or Avianca (79%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Washington, D.C. to Chicago?

    Looking at all options, your cheapest flight can be booked for £259. While the most popular route (Baltimore/Washington - Chicago O'Hare Intl) can be booked for £331 on average, our data indicates £259 when flying from Washington, D.C. to Chicago.

  • 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, January is the cheapest month in which you can book a flight from Washington, D.C. to Chicago (average of £221). Flying from Washington, D.C. to Chicago in June is currently the most expensive (average of £297). 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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