Find flights
Deals
When to book
FAQs

Cheap flights from Washington, D.C. to Chicago from £111

WAS — CHI
4 Oct — 11 Oct1
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 55 days in advance, depart on a Friday or Thursday 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

Wed 14/1007:50 -
1 stop11h 41m
Wed 21/1008:04 -
1 stop11h 07m
Deal found 2/9£155
Wed 14/1005:40 -
1 stop6h 52m
Wed 21/1006:00 -
1 stop9h 47m
Deal found 2/9£155
Fri 16/1009:58 -
Nonstop2h 23m
Fri 23/1006:00 -
Nonstop2h 03m
Deal found 1/9£171
Wed 14/1007:00 -
1 stop18h 24m
Wed 21/1006:30 -
1 stop28h 34m
Deal found 2/9£192
Sat 21/1116:49 -
Nonstop2h 44m
Sat 28/1105:45 -
Nonstop1h 57m
Deal found 1/9£209
Wed 14/1007:46 -
Nonstop2h 14m
Mon 19/1007:00 -
Nonstop1h 59m
Deal found 2/9£221
Thu 1/1017:20 -
Nonstop2h 21m
Wed 7/1018:06 -
Nonstop2h 05m
Deal found 1/9£221
Thu 1/1011:55 -
Nonstop2h 20m
Thu 8/1010:49 -
Nonstop2h 09m
Deal found 2/9£221
Tue 29/906:05 -
1 stop11h 54m
Sat 3/1008:25 -
1 stop14h 34m
Deal found 2/9£223
Wed 30/911:44 -
1 stop10h 49m
Wed 7/1009:59 -
1 stop12h 27m
Deal found 2/9£223
Fri 11/912:10 -
Nonstop2h 21m
Wed 7/1019:45 -
Nonstop2h 14m
Deal found 31/8£226
Thu 8/1022:18 -
Nonstop2h 14m
Mon 12/1021:52 -
Nonstop2h 06m
Deal found 3/9£228

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

Round-trip from

£155

One-way from

£111

Popular in

June

Cheapest in

January

Average price

£195

Good round-trip deal

£132 or less

Good one-way deal

£95 or less
Frontier
  • Frontier
  • 14/10-21/10
  • 2 total stops
  • 22h 48m total
  • Washington, D.C. to Chicago
Search Deals
United Airlines
  • United Airlines
  • 8/10-31/12
  • Nonstop
  • 2h 14m total
  • Washington, D.C. to Chicago
Search Deals
Highest demand for flights based on searches. 15% potential increase in price (£29 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 September 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

 
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

Thu 26/11

10:30-11:50

Nonstop2h 20m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

£111

Washington, D.C.Chicago

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

DCAORD

Washington, D.C. Reagan-National

Wed 11/11

11:49-13:15

Nonstop2h 26m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

£111

Washington, D.C.Chicago

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

DCAORD

Washington, D.C. Reagan-National

Thu 8/10

06:30-07:44

Nonstop2h 14m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

£111

Washington, D.C.Chicago

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

DCAORD

Washington, D.C. Reagan-National

Thu 15/10

20:10-21:29

Nonstop2h 19m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

£111

Washington, D.C.Chicago

IAD Washington, D.C. Dulles Intl - ORD Chicago O'Hare Intl

IADORD

Washington, D.C. Dulles Intl

Thu 8/10

08:20-09:38

Nonstop2h 18m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

£111

Washington, D.C.Chicago

IAD Washington, D.C. Dulles Intl - ORD Chicago O'Hare Intl

IADORD

Washington, D.C. Dulles Intl

Thu 15/10

13:10-14:26

Nonstop2h 16m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

£111

BaltimoreChicago

BWI Baltimore/Washington - ORD Chicago O'Hare Intl

BWIORD

Baltimore/Washington

Sat 27/2

07:30-21:37

1 stop15h 07m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

£115

BaltimoreChicago

BWI Baltimore/Washington - ORD Chicago O'Hare Intl

BWIORD

Baltimore/Washington

Sat 31/10

07:20-21:27

1 stop15h 07m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

£115

Washington, D.C.Chicago

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

DCAORD

Washington, D.C. Reagan-National

Mon 1/3

19:30-23:50

1 stop5h 20m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

£118

BaltimoreChicago

BWI Baltimore/Washington - ORD Chicago O'Hare Intl

BWIORD

Baltimore/Washington

Tue 2/3

06:00-08:58

1 stop3h 58m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

£118

Flights are sorted by cheapest return flights first.

Deals found on 3/9

Showing 1-10 of 60 resultsSorted by cheapest first
1
2
3
...
6

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, October is the cheapest month in which you can book a flight from Washington, D.C. to Chicago (average of £204). Flying from Washington, D.C. to Chicago in June is currently the most expensive (average of £291). 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 Wednesday (93 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (42 on average).

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

Airfare is typical for this route at the moment.
Washington, D.C. to Chicago flights typically cost between £136 and £247 in October.
The cheapest return price found within the last 5 days was £155 on Frontier (14 Oct–21 Oct).

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

Booking 54 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?

    United Airlines and Delta can get you from Washington, D.C. to Chicago in just under 2h 20m. Your travel time can differ by up to 3h. 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 are the cheapest airlines to fly from Washington, D.C. to Chicago one-way?

    £76 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 £95 and £101, respectively.

  • 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 Egyptair (92%), Ethiopian Air (75%) or Air China (71%) 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 £95. While the most popular route (Washington, D.C. Reagan-National - Chicago O'Hare Intl) can be booked for £236 on average, our data indicates £217 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, October is the cheapest month in which you can book a flight from Washington, D.C. to Chicago (average of £204). Flying from Washington, D.C. to Chicago in June is currently the most expensive (average of £291). 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

Fly with Cheapflights

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.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.