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Cheap flights from Washington, D.C. to Chicago from £87

WAS — CHI
4 Dec — 11 Dec1
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 Thursday or Friday 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

Tue 1/1212:06 -
1 stop10h 29m
Thu 31/1205:58 -
1 stop8h 15m
Deal found 3/11£178
Thu 17/1215:55 -
1 stop7h 54m
Thu 24/1205:58 -
1 stop8h 15m
Deal found 2/11£182
Thu 17/1207:40 -
1 stop17h 46m
Thu 24/1207:00 -
1 stop13h 59m
Deal found 2/11£192
Thu 26/1107:45 -
1 stop12h 54m
Sat 5/1206:20 -
1 stop10h 39m
Deal found 3/11£196
Mon 23/1117:10 -
Nonstop2h 21m
Fri 27/1119:45 -
Nonstop1h 58m
Deal found 2/11£206
Thu 3/1210:10 -
Nonstop2h 23m
Thu 3/1218:15 -
Nonstop2h 03m
Deal found 3/11£206
Thu 3/1206:10 -
Nonstop2h 05m
Mon 7/1209:15 -
Nonstop1h 45m
Deal found 3/11£206
Tue 1/1208:43 -
Nonstop2h 32m
Thu 31/1219:30 -
Nonstop2h 02m
Deal found 3/11£207
Thu 17/1220:06 -
Nonstop2h 25m
Thu 24/1219:30 -
Nonstop2h 02m
Deal found 2/11£208
Tue 1/1217:40 -
Nonstop2h 25m
Thu 3/1213:30 -
Nonstop2h 03m
Deal found 4/11£208
Thu 26/1107:45 -
1 stop12h 54m
Mon 7/1214:39 -
1 stop6h 52m
Deal found 3/11£209
Tue 24/1109:45 -
1 stop4h 06m
Thu 26/1111:05 -
1 stop9h 55m
Deal found 3/11£209

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

Round-trip from

£178

One-way from

£87

Popular in

October

Cheapest in

January

Average price

£237
Frontier
  • Frontier
  • 1/12-31/12
  • 2 total stops
  • 18h 44m total
  • Washington, D.C. to Chicago
Search Deals
Frontier
  • Frontier
  • 11/12-31/12
  • 1 total stop
  • 7h 54m total
  • Washington, D.C. to Chicago
Search Deals
Highest demand for flights based on searches. 6% potential increase in price (£11 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).
Search Deals
Average for round-trip flights in November 2026
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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

Wed 23/12

15:30-16:54

Nonstop2h 24m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

£104
Fastest return journey

Washington, D.C.Chicago

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

DCAMDW

Washington, D.C. Reagan-National

Wed 25/11

21:00-22:05

Nonstop2h 05m

Chicago Midway

Wed 31/12

00:00-01:00

Nonstop0h 00m

£104

Washington, D.C.Chicago

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

DCAORD

Washington, D.C. Reagan-National

Tue 9/2

19:05-20:35

Nonstop2h 30m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

£104

Washington, D.C.Chicago

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

DCAMDW

Washington, D.C. Reagan-National

Fri 27/11

18:30-19:40

Nonstop2h 10m

Chicago Midway

Wed 31/12

00:00-01:00

Nonstop0h 00m

£104

Washington, D.C.Chicago

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

IADORD

Washington, D.C. Dulles Intl

Fri 27/11

22:47-00:01

Nonstop2h 14m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

£104

Washington, D.C.Chicago

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

DCAMDW

Washington, D.C. Reagan-National

Thu 3/12

20:55-22:10

Nonstop2h 15m

Chicago Midway

Wed 31/12

00:00-01:00

Nonstop0h 00m

£104

Washington, D.C.Chicago

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

IADORD

Washington, D.C. Dulles Intl

Tue 9/2

08:15-09:40

Nonstop2h 25m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

£104

Washington, D.C.Chicago

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

IADORD

Washington, D.C. Dulles Intl

Sat 19/12

22:45-00:01

Nonstop2h 16m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

£104

Washington, D.C.Chicago

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

IADORD

Washington, D.C. Dulles Intl

Mon 7/12

10:10-11:33

Nonstop2h 23m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

£104

Washington, D.C.Chicago

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

IADORD

Washington, D.C. Dulles Intl

Sat 21/11

15:37-17:00

Nonstop2h 23m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

£104

Flights are sorted by cheapest return flights first.

Deals found on 2/11

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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 £223). Flying from Washington, D.C. to Chicago in October is currently the most expensive (average of £299). 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 39% 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 Monday (97 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (38 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 £163 and £297 in December.
The cheapest return price found within the last 5 days was £178 on Frontier (1 Dec–31 Dec).

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?

    Delta, United Airlines, and Southwest can get you from Washington, D.C. to Chicago in just under 2h 10m. Your travel time can differ by up to 8h 13m. Washington, D.C. and Chicago are separated by a distance of 599 mi. When browsing for deals, the options you’ll see will be for both direct flights and flights with stops.

  • 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 (88%) or Copa Airlines (87%) 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, January is the cheapest month in which you can book a flight from Washington, D.C. to Chicago (average of £223). Flying from Washington, D.C. to Chicago in October is currently the most expensive (average of £299). 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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