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$99+ Cheap flights from Washington, D.C. (WAS) to Chicago (CHI)

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 7/18. Fares are subject to change and may not be available on all flights or dates of travel.
WAS — CHI
Jul 24 — Jul 311
Fri 7/24
Fri 7/31
1 adult, Economy
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Find cheap flights from Washington, D.C. to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

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Cheapflights Tip: The best prices from Washington, D.C. to Chicago are usually found in September or January, booked 67 days in advance, depart on a Thursday or Friday and return on a Friday

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

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 June 24, 2026.

This Kiwi.com deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/88:25 am
BWI
-
ORD
1 stop12h 28m
Frontier
Mon 8/101:50 pm
ORD
-
BWI
1 stop16h 36m
Frontier
Deal found 6/23$232
This Delta deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/96:10 pm
BWI
-
MDW
1 stop5h 00m
Delta
Tue 11/105:25 pm
MDW
-
BWI
1 stop6h 01m
Delta
Deal found 6/22$234
This Delta deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/94:39 pm
BWI
-
ORD
1 stop5h 31m
Delta
Tue 11/109:30 am
ORD
-
BWI
1 stop6h 33m
Delta
Deal found 6/22$234
This Southwest deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/183:00 pm
BWI
-
MDW
1 stop5h 30m
Southwest
Sat 7/255:00 am
MDW
-
BWI
Nonstop1h 45m
Southwest
Deal found 6/20$235
This Kiwi.com deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/286:37 pm
BWI
-
ORD
Nonstop2h 28m
Frontier
Sun 9/138:00 am
ORD
-
BWI
Nonstop2h 07m
Frontier
Deal found 6/20$235
This Southwest deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/210:55 am
BWI
-
MDW
1 stop3h 35m
Southwest
Sat 9/511:45 am
MDW
-
BWI
1 stop3h 15m
Southwest
Deal found 6/22$236
This Super.com deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1112:02 pm
BWI
-
ORD
Nonstop2h 24m
Frontier
Sun 9/138:00 am
ORD
-
BWI
Nonstop2h 07m
Frontier
Deal found 6/21$236
This Kiwi.com deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/306:28 am
BWI
-
MDW
1 stop5h 44m
Frontier
Sat 7/46:00 am
MDW
-
BWI
1 stop9h 26m
Frontier
Deal found 6/23$237
This Kiwi.com deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/19:37 pm
BWI
-
ORD
1 stop11h 16m
Frontier
Mon 8/31:50 pm
ORD
-
BWI
1 stop16h 36m
Frontier
Deal found 6/22$237
This Southwest deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/87:30 pm
BWI
-
MDW
Nonstop2h 00m
Southwest
Mon 8/1010:30 am
MDW
-
BWI
Nonstop1h 45m
Southwest
Deal found 6/19$238
This United Airlines deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/16:15 am
BWI
-
ORD
Nonstop2h 15m
United Airlines
Thu 8/68:13 pm
ORD
-
BWI
Nonstop2h 06m
United Airlines
Deal found 6/19$238
This Southwest deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/306:25 am
BWI
-
MDW
1 stop5h 20m
Southwest
Tue 7/147:35 pm
MDW
-
BWI
Nonstop1h 55m
Southwest
Deal found 6/22$239

Find 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 June 24, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$232
(Kiwi.com)

One-way from

$99
(Delta)

Popular in

June

Cheapest in

September

Average price

$354

Good round-trip deal

$299 or less

Good one-way deal

$179 or less
Provider with most accurate pricing for Washington, D.C. (WAS)-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Washington, D.C. (WAS)-Chicago (CHI) flights.
Search Deals
From Washington, D.C. (WAS) to Chicago (CHI)
Search Deals
One-way flight from Washington, D.C. (WAS) to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 14% potential increase in price ($47 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 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

 
Customize 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 2,558,603 searches. Data last updated June 24, 2026.
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 round-trip

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Mon 11/9

4:39 pm-9:10 pm

1 stop5h 31m

Chicago O'Hare Intl

Tue 11/10

9:30 am-5:03 pm

1 stop6h 33m

$234

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Sat 8/15

10:50 am-1:05 pm

1 stop3h 15m

Chicago Midway

Sat 8/22

11:45 am-4:00 pm

1 stop3h 15m

$236

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Mon 7/27

5:05 pm-8:20 pm

1 stop4h 15m

Chicago Midway

Wed 7/29

8:10 am-11:10 am

Nonstop2h 00m

$249

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Thu 8/6

1:59 pm-8:52 pm

1 stop7h 53m

Chicago O'Hare Intl

Mon 8/10

9:57 pm-4:59 pm

1 stop18h 02m

$252

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Mon 8/10

12:10 pm-3:30 pm

1 stop4h 20m

Chicago Midway

Tue 8/11

12:45 pm-5:00 pm

1 stop3h 15m

$253

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Tue 9/1

12:23 pm-4:17 pm

1 stop4h 54m

Chicago O'Hare Intl

Thu 9/3

1:50 pm-7:34 pm

1 stop4h 44m

$257

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Sat 8/1

5:29 pm-8:31 pm

1 stop4h 02m

Chicago O'Hare Intl

Sat 8/8

6:40 am-12:47 pm

1 stop5h 07m

$257

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Mon 7/27

6:00 am-10:05 am

1 stop5h 05m

Chicago Midway

Wed 7/29

6:00 am-2:01 pm

1 stop7h 01m

$257

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Tue 7/28

6:00 am-9:13 am

1 stop4h 13m

Chicago Midway

Thu 7/30

12:41 pm-6:37 pm

1 stop4h 56m

$257

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Sat 7/18

9:37 pm-7:53 am

1 stop11h 16m

Chicago O'Hare Intl

Sat 7/25

7:05 am-6:33 pm

1 stop10h 28m

$258

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/21

Showing 1-10 of 60 resultsSorted by cheapest first
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Compare providers for flights from Washington, D.C. to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Washington, D.C. to Chicago in June.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
OvagoPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy2 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy2 starsTrust Score*1 star
CheapfaremartPrice Accuracy-Trust Score*1 star
Trip.comPrice Accuracy1 starTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Washington, D.C.-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Washington, D.C.-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Washington, D.C.-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Washington, D.C.-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Washington, D.C.-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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 round-trip 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

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 $215). Flying from Washington, D.C. to Chicago in June is currently the most expensive (average of $424). 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 June 24, 2026.

Unlike in the morning, when flights are generally more expensive, you can save up to 12% on flights from Washington, D.C. to Chicago by exploring options for tickets 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 June 24, 2026.

The most flights from WAS to CHI are scheduled on a Tuesday (103 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (28 on average).

How much does it cost to fly round-trip from Washington, D.C. to Chicago?

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

To ensure you get the cheapest price possible for a flight from Washington, D.C. to Chicago, you should look to book at least 54 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

What is the cheapest day to fly from Washington, D.C. to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Washington, D.C. to Chicago. Price data was last updated on June 20, 2026.

Travelers seeking maximum savings on their Washington, D.C. to Chicago flight should consider departing on Friday at noon when fares are most often at their lowest. Thursday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

The best insider tips for Washington, D.C. to Chicago flights

AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Washington, D.C. to Chicago trip
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on ORD, MDW and IAD

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more
Emily Zemler

Emily Zemler

Expert on DCA

Emily is a freelance writer and book author based in London covering entertainment and travel. Her work has appeared in Los Angeles Times, Observer, and Conde Nast Traveler She has ventured to more than 40 countries and all seven continents, always in search of a great art museum. She has written extensively about hotels, luxury travel, and aviation.

Read more

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated June 24, 2026.
Read reviews from past customers who have flown Southwest,Delta, andUnited Airlines from Washington, D.C. to Chicago. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
7.9
Good
4,242 reviews

Entertainment

7.5

Crew

8.6

Overall

7.9

Comfort

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
Southwest
7.9
Good
4,242 reviews
Southwest
7.9
Good
4,242 reviews

Entertainment

7.5

Crew

8.6

Overall

7.9

Comfort

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
Delta
7.8
Good
8,432 reviews
Southwest
7.9
Good
4,242 reviews

Entertainment

7.5

Crew

8.6

Overall

7.9

Comfort

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
United Airlines
7.4
Good
9,881 reviews
Southwest
7.9
Good
4,242 reviews

Entertainment

7.5

Crew

8.6

Overall

7.9

Comfort

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
American Airlines
7.1
Good
11,751 reviews
Southwest
7.9
Good
4,242 reviews

Entertainment

7.5

Crew

8.6

Overall

7.9

Comfort

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
Frontier
5.6
Fair
2,867 reviews
Southwest
7.9
Good
4,242 reviews

Entertainment

7.5

Crew

8.6

Overall

7.9

Comfort

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

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?

    Airlines like Delta, Southwest, and Frontier fly from Washington, D.C. to Chicago in about 3h 15m. The time it takes to get you to your destination can typically vary by up to 4h 38m. The distance from Washington, D.C. to Chicago is about 609 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines flying from Washington, D.C. to Chicago round-trip?

    Cheapflights users have booked flights from Washington, D.C. to Chicago round-trip from $29. Other airlines that can offer you cheap pricing are Delta, from $149, and American Airlines, from $182. Frontier is 89% 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?

    One-way options have recently been found by users for as low as $53 on Frontier. Other airlines that offer cheap prices include American Airlines from $98 and Southwest from $98 one-way.

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

    The most popular route from Washington, D.C. to Chicago is Baltimore/Washington - Chicago O'Hare Intl. You may also consider Washington, D.C. Reagan-National - Chicago O'Hare Intl or Washington, D.C. Dulles Intl - Chicago O'Hare Intl.

  • What are the most reliable airlines from Washington, D.C. to Chicago?

    The top 3 most reliable airlines when flying from Washington, D.C. to Chicago are Egyptair (88%), Air China (82%) and Ethiopian Air (80%).

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

    Looking at all options, your cheapest flight can be booked for $154. While the most popular route (Baltimore/Washington - Chicago O'Hare Intl) can be booked for $143 on average, our data indicates $852 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 vacation 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 $215). Flying from Washington, D.C. to Chicago in June is currently the most expensive (average of $424). 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

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Benton Harbor
Lansing
Merrillville
Hammond
Porter

Browse thousands of different options on Cheapflights for your next trip

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Top 5 airlines flying from Washington, D.C. to Chicago

Discover the top 5 airlines 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 2,558,603 searches. Data last updated June 24, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$29Average$174FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$117Average$304FlexibilityNo cancel feeOn-time63%
DeltaCheapest$149Average$342FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$157Average$367FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$158Average$324FlexibilityNo cancel feeOn-time71%

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