Cheap flights from Washington, D.C. to Chicago from £48
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 2/3. Fares are subject to change and may not be available on all flights or dates of travel.
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
Find flight deals from Washington, D.C. to Chicago
Cheapest flights from Washington, D.C. to ChicagoExplore 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 26 October 2025.
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 26 October 2025.
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 26 October 2025.
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
Washington, D.C.Chicago
DCA - ORD
DCAORD
Washington, D.C. Reagan-National
Wed 28/1
06:15-13:10
1 stop7h 55m
Chicago O'Hare Intl
Sat 31/1
14:05-22:47
1 stop7h 42m
BaltimoreChicago
BWI - ORD
BWIORD
Baltimore/Washington
Thu 1/1
06:15-07:35
Nonstop2h 20m
Chicago O'Hare Intl
Sun 11/1
11:05-14:11
Nonstop2h 06m
Washington, D.C.Chicago
DCA - ORD
DCAORD
Washington, D.C. Reagan-National
Tue 11/11
16:55-20:52
1 stop4h 57m
Chicago O'Hare Intl
Wed 12/11
06:45-14:36
1 stop6h 51m
Washington, D.C.Chicago
DCA - ORD
DCAORD
Washington, D.C. Reagan-National
Sun 25/1
06:15-13:10
1 stop7h 55m
Chicago O'Hare Intl
Wed 28/1
14:05-22:47
1 stop7h 42m
Washington, D.C.Chicago
DCA - ORD
DCAORD
Washington, D.C. Reagan-National
Fri 14/11
16:55-20:52
1 stop4h 57m
Chicago O'Hare Intl
Tue 18/11
07:00-14:36
1 stop6h 36m
Washington, D.C.Chicago
DCA - ORD
DCAORD
Washington, D.C. Reagan-National
Fri 30/1
06:15-13:10
1 stop7h 55m
Chicago O'Hare Intl
Sun 1/2
14:05-22:47
1 stop7h 42m
Washington, D.C.Chicago
DCA - ORD
DCAORD
Washington, D.C. Reagan-National
Fri 9/1
06:15-13:10
1 stop7h 55m
Chicago O'Hare Intl
Sun 11/1
14:05-22:47
1 stop7h 42m
BaltimoreChicago
BWI - ORD
BWIORD
Baltimore/Washington
Wed 3/12
13:10-14:19
Nonstop2h 09m
Chicago O'Hare Intl
Wed 10/12
14:30-17:25
Nonstop1h 55m
BaltimoreChicago
BWI - ORD
BWIORD
Baltimore/Washington
Sat 6/12
17:18-18:26
Nonstop2h 08m
Chicago O'Hare Intl
Wed 10/12
14:30-17:25
Nonstop1h 55m
BaltimoreChicago
BWI - ORD
BWIORD
Baltimore/Washington
Sat 6/12
10:20-11:28
Nonstop2h 08m
Chicago O'Hare Intl
Tue 9/12
18:09-21:08
Nonstop1h 59m
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.
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 24 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 £99). 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 26 October 2025.
It’s optimal to fly from Washington, D.C. to Chicago in the morning. By choosing this option you can save up to 44% 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 26 October 2025.
The most flights from WAS to CHI are scheduled on a Sunday (75 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (24 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.
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Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on 26 October 2025.
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 26 October 2025.
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How does Cheapflights help users find flights from Washington, D.C. to Chicago?
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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.