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Cheap flights from Washington, D.C. to Chicago from £53

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 25/12. Fares are subject to change and may not be available on all flights or dates of travel.
WAS — CHI
7 Dec — 14 Dec1
1 adult
1 adult, Economy, 0 bags

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

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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 7 November 2025.

Sun 23/1110:41BWI - ORD
1 stop13h 25mSpirit Airlines
Tue 25/1105:00ORD - BWI
1 stop11h 43mSpirit Airlines
Deal found 5/11£128
Mon 22/1210:12BWI - ORD
Nonstop2h 18mFrontier
Mon 29/1213:44ORD - BWI
Nonstop2h 07mFrontier
Deal found 7/11£134
Fri 5/1210:20BWI - ORD
Nonstop2h 08mUnited Airlines
Fri 12/1218:09ORD - BWI
Nonstop1h 59mUnited Airlines
Deal found 5/11£135
Mon 22/1210:12BWI - ORD
Nonstop2h 18mMultiple Airlines
Mon 29/1215:26ORD - BWI
1 stop7h 20mMultiple Airlines
Deal found 7/11£141
Tue 18/1116:55DCA - ORD
1 stop4h 57mJetBlue
Thu 20/1108:20ORD - DCA
1 stop5h 39mJetBlue
Deal found 6/11£147
Sat 15/1116:55DCA - ORD
1 stop4h 57mJetBlue
Wed 19/1106:45ORD - DCA
1 stop6h 51mJetBlue
Deal found 4/11£149
Mon 8/1210:20BWI - ORD
Nonstop2h 08mUnited Airlines
Thu 11/1214:30ORD - BWI
Nonstop1h 55mUnited Airlines
Deal found 5/11£150
Thu 4/1217:18BWI - ORD
Nonstop2h 08mUnited Airlines
Tue 9/1218:09ORD - BWI
Nonstop1h 59mUnited Airlines
Deal found 6/11£150
Wed 3/1213:10BWI - ORD
Nonstop2h 09mUnited Airlines
Wed 10/1214:30ORD - BWI
Nonstop1h 55mUnited Airlines
Deal found 5/11£153
Fri 5/1210:20BWI - ORD
Nonstop2h 08mUnited Airlines
Mon 8/1218:09ORD - BWI
Nonstop1h 59mUnited Airlines
Deal found 5/11£154
Mon 8/1213:45DCA - ORD
1 stop6h 58mJetBlue
Wed 10/1211:25ORD - DCA
1 stop8h 38mJetBlue
Deal found 6/11£157
Mon 22/1218:18BWI - ORD
1 stop7h 12mSpirit Airlines
Mon 29/1215:26ORD - BWI
1 stop7h 20mSpirit Airlines
Deal found 7/11£157

Cheap 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 7 November 2025.

Round-trip from

£106

One-way from

£53

Popular in

April

Cheapest in

September

Average price

£202

Good round-trip deal

£71 or less

Good one-way deal

£131 or less
United Airlines
  • United Airlines
  • 3/2-5/2
  • Nonstop
  • 4h 26m total
  • Washington, D.C. to Chicago
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United Airlines
  • United Airlines
  • 25/12
  • Nonstop
  • 2h 20m total
  • Washington, D.C. to Chicago
Search Deals
Highest demand for flights based on searches. 7% potential increase in price (£12 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 November 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).
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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 7 November 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

Sat 14/2

17:14-18:37

Nonstop2h 23m

Chicago O'Hare Intl

Sun 15/2

18:25-21:27

Nonstop2h 02m

£127

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Fri 13/2

06:30-07:53

Nonstop2h 23m

Chicago O'Hare Intl

Sun 15/2

18:25-21:27

Nonstop2h 02m

£134

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Sun 1/2

18:59-23:57

1 stop5h 58m

Chicago O'Hare Intl

Wed 4/2

18:00-23:07

1 stop4h 07m

£135

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Mon 2/3

11:45-16:40

1 stop5h 55m

Chicago O'Hare Intl

Tue 3/3

17:53-00:39

1 stop5h 46m

£135

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Fri 5/12

10:20-11:28

Nonstop2h 08m

Chicago O'Hare Intl

Sun 7/12

14:30-17:25

Nonstop1h 55m

£135

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Fri 23/1

07:15-14:45

1 stop8h 30m

Chicago O'Hare Intl

Sun 25/1

13:45-20:15

2 stops5h 30m

£139

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Wed 4/3

06:00-11:48

1 stop6h 48m

Chicago O'Hare Intl

Tue 10/3

10:00-16:03

1 stop5h 03m

£144

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Fri 16/1

06:15-14:45

1 stop9h 30m

Chicago O'Hare Intl

Sun 18/1

13:45-20:55

1 stop6h 10m

£144

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Sat 14/2

06:35-12:15

1 stop6h 40m

Chicago O'Hare Intl

Sun 15/2

13:45-22:40

1 stop7h 55m

£148

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Tue 18/11

16:55-20:52

1 stop4h 57m

Chicago O'Hare Intl

Wed 19/11

06:45-14:36

1 stop6h 51m

£149

Flights are sorted by cheapest return flights first.

Deals found on 6/11

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 31 October 2025.

Booking 83 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 £38). Flying from Washington, D.C. to Chicago in June is currently the most expensive (average of £101). 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 7 November 2025.

It’s optimal to fly from Washington, D.C. to Chicago in the morning. By choosing this option you can save up to 37% 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 7 November 2025.

The most flights from WAS to CHI are scheduled on a Thursday (75 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (27 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, Delta, and JetBlue can get you from Washington, D.C. to Chicago in just under 2h 23m. Your travel time can differ by up to 3h 44m. 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 £162 on this airline. Frontier is 14% cheaper than the average price of flights available within the next 90 days to this destination.

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

    £53 is the cheapest one-way deal found within the past few days, from United Airlines. You may also be able to find cheap deals on JetBlue and Delta, with prices starting from £65 and £93, respectively.

  • What are the most popular routes from Washington, D.C. to Chicago?

    While some choose either Washington, D.C. Dulles Intl - Chicago O'Hare Intl or Washington, D.C. Reagan-National - 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 Air China (94%), Egyptair (93%) or Ethiopian Air (80%) 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 £627. While the most popular route (Baltimore/Washington - Chicago O'Hare Intl) can be booked for £91 on average, our data indicates £670 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, March is the cheapest month in which you can book a flight from Washington, D.C. to Chicago (average of £38). Flying from Washington, D.C. to Chicago in June is currently the most expensive (average of £101). 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 7 November 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest£162Average£162FlexibilityNo 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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