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$55+ 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 12/15. Fares are subject to change and may not be available on all flights or dates of travel.
WAS — CHI
Dec 7 — Dec 141
Sun 12/7
Sun 12/14
1 adult, Economy
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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 Friday or Thursday and return on a Friday

Find 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 November 7, 2025.

This CheapOair deal was found by Cheapflights users on 11/6. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/147:25 pmBWI - MDW
Nonstop2h 06mFrontier
Mon 11/173:40 pmMDW - BWI
Nonstop1h 55mFrontier
Deal found 11/6$118
This Super.com deal was found by Cheapflights users on 11/6. 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 12/53:36 pmBWI - ORD
Nonstop2h 18mFrontier
Mon 12/86:30 pmORD - BWI
Nonstop2h 07mFrontier
Deal found 11/6$118
This Frontier deal was found by Cheapflights users on 11/4. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/215:40 amBWI - MDW
1 stop10h 00mFrontier
Sat 11/2212:25 pmMDW - BWI
Nonstop1h 56mFrontier
Deal found 11/4$121
This Priceline deal was found by Cheapflights users on 11/6. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/219:18 amBWI - ORD
1 stop9h 21mFrontier
Sun 11/238:30 amORD - BWI
Nonstop1h 59mFrontier
Deal found 11/6$121
This CheapOair deal was found by Cheapflights users on 11/6. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/2011:14 amBWI - MDW
1 stop12h 03mFrontier
Sun 11/2312:25 pmMDW - BWI
Nonstop1h 56mFrontier
Deal found 11/6$122
This Booking.com deal was found by Cheapflights users on 11/4. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/2312:24 pmBWI - ORD
1 stop6h 15mFrontier
Wed 11/264:15 pmORD - BWI
Nonstop1h 59mFrontier
Deal found 11/4$122
This Kiwi.com deal was found by Cheapflights users on 11/4. 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.
Mon 11/244:06 pmBWI - MDW
Nonstop2h 09mFrontier
Wed 11/2612:25 pmMDW - BWI
Nonstop1h 56mFrontier
Deal found 11/4$123
This Kiwi.com deal was found by Cheapflights users on 11/6. 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.
Wed 12/108:00 amBWI - ORD
1 stop7h 31mFrontier
Fri 12/124:20 pmORD - BWI
1 stop7h 12mFrontier
Deal found 11/6$123
This CheapOair deal was found by Cheapflights users on 11/6. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/411:48 amBWI - MDW
1 stop11h 24mFrontier
Sun 12/76:37 pmMDW - BWI
1 stop12h 05mFrontier
Deal found 11/6$124
This Mytrip deal was found by Cheapflights users on 11/6. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/136:15 amBWI - ORD
1 stop5h 26mFrontier
Mon 11/1712:04 pmORD - BWI
Nonstop2h 03mFrontier
Deal found 11/6$125
This Super.com deal was found by Cheapflights users on 11/6. 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 11/144:02 pmBWI - ORD
Nonstop2h 16mFrontier
Mon 11/1712:04 pmORD - BWI
Nonstop2h 03mFrontier
Deal found 11/6$126
This CheapOair deal was found by Cheapflights users on 11/4. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/2011:14 amBWI - MDW
1 stop29h 32mFrontier
Sat 11/223:55 pmMDW - BWI
1 stop17h 24mFrontier
Deal found 11/4$127

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 November 7, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$118
(Super.com)

One-way from

$55
(Priceline)

Popular in

April

Cheapest in

September

Average price

$264

Good round-trip deal

$167 or less

Good one-way deal

$103 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. 7% potential increase in price ($21 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($3 potential savings vs. average RT 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).
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 November 7, 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 - MDW

BWIMDW

Baltimore/Washington

Mon 1/12

10:25 am-11:35 am

Nonstop2h 10m

Chicago Midway

Thu 1/15

10:45 am-1:35 pm

Nonstop1h 50m

$139

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Fri 11/21

9:18 am-5:39 pm

1 stop9h 21m

Chicago O'Hare Intl

Mon 11/24

6:30 am-10:19 am

1 stop26h 49m

$144

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Sat 12/6

5:45 am-11:54 am

1 stop7h 09m

Chicago O'Hare Intl

Sat 12/13

1:24 pm-11:05 pm

1 stop8h 41m

$146

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Sun 2/1

8:15 pm-9:25 pm

Nonstop2h 10m

Chicago Midway

Tue 2/3

5:15 pm-8:10 pm

Nonstop1h 55m

$148

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Fri 12/12

1:40 pm-10:24 pm

2 stops9h 44m

Chicago O'Hare Intl

Sun 12/14

5:11 am-8:18 am

Nonstop2h 07m

$154

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Wed 11/19

9:36 pm-9:17 am

1 stop12h 41m

Chicago O'Hare Intl

Fri 11/21

12:29 pm-9:07 pm

1 stop7h 38m

$155

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Fri 1/23

1:45 pm-2:55 pm

Nonstop2h 10m

Chicago Midway

Sun 1/25

7:05 pm-9:55 pm

Nonstop1h 50m

$157

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Tue 12/23

9:37 am-10:55 am

Nonstop2h 18m

Chicago O'Hare Intl

Fri 12/26

1:40 pm-4:47 pm

Nonstop2h 07m

$159

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Wed 11/19

8:40 am-12:41 pm

1 stop5h 01m

Chicago Midway

Sun 11/23

6:05 am-5:46 pm

1 stop10h 41m

$166

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Wed 11/19

8:40 am-12:41 pm

1 stop5h 01m

Chicago Midway

Fri 11/21

6:05 am-5:46 pm

1 stop10h 41m

$167

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/4

Showing 1-10 of 60 results
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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 November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
OvagoPrice Accuracy2 starsTrust Score*2 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*2 stars
MytripPrice Accuracy3 starsTrust Score*3 stars
Kiwi.comPrice Accuracy3 starsTrust Score*3 stars
Trip.comPrice Accuracy2 starsTrust 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 Mytrip to be most consistent on Cheapflights vs. Mytrip Users can find the same prices on Washington, D.C.-Chicago flight deals on Cheapflights vs. Mytrip >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 Mytrip the most. Mytrip 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

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 round-trip flight from Washington, D.C. to Chicago. Price data was last updated on October 31, 2025.

To ensure you get the cheapest price possible for a flight from Washington, D.C. to Chicago, you should look to book at least 83 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 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 $50). Flying from Washington, D.C. to Chicago in June is currently the most expensive (average of $132). 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 November 7, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 39% on flights from Washington, D.C. to Chicago by exploring options for tickets in the evening.

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 November 2, 2025.

Travelers seeking maximum savings on their Washington, D.C. to Chicago flight should consider departing on Saturday evenings 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.

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 November 7, 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 to fly round-trip from Washington, D.C. to Chicago?

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

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your Washington, D.C. to Chicago trip
Airports
DCA

DCA offers easy Metro access with a dedicated stop on the Yellow and Blue lines, making it a convenient choice for travelers from D.C. and nearby areas.

Read more about DCAby Emily Zemler
IAD

IAD's Aerotrain connects the main terminal to concourses, but be prepared for long walks, especially to United Express gates.

Read more about IADby Ramsey Qubein
ORD

At ORD, expect long walks between terminals. Use the free shuttle train for easier navigation, especially if arriving internationally at Terminal 5.

Read more about ORDby Ramsey Qubein
MDW

MDW is closer to downtown Chicago than ORD, with the Orange Line offering a quick, affordable ride to the city center in under 30 minutes.

Read more about MDWby Ramsey Qubein
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on ORD, MDW and IAD

Ramsey Qubein

Ramsey Qubein

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 Zemler

Emily Zemler

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 November 7, 2025.
Read reviews from past customers who have flown Southwest, United Airlines, and American 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
8.0
Very good
4,240 reviews

Entertainment

7.5

Food

7.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,240 reviews
Southwest
8.0
Very good
4,240 reviews

Entertainment

7.5

Food

7.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
9,007 reviews
Southwest
8.0
Very good
4,240 reviews

Entertainment

7.5

Food

7.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
11,040 reviews
Southwest
8.0
Very good
4,240 reviews

Entertainment

7.5

Food

7.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Spirit Airlines
6.3
Okay
8,123 reviews
Southwest
8.0
Very good
4,240 reviews

Entertainment

7.5

Food

7.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Frontier
5.8
Fair
3,115 reviews
Southwest
8.0
Very good
4,240 reviews

Entertainment

7.5

Food

7.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 Southwest, Frontier, and Delta fly from Washington, D.C. to Chicago in about 2h 10m. The time it takes to get you to your destination can typically vary by up to 7h 11m. 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 $99. Other airlines that can offer you cheap pricing are American Airlines, from $168, and Southwest, from $179. Frontier is 60% 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 $70 on Southwest. Other airlines that offer cheap prices include United Airlines from $70 and Frontier from $72 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 Washington, D.C. Dulles Intl - Chicago O'Hare Intl. You may also consider Baltimore/Washington - Chicago O'Hare Intl or Washington, D.C. Reagan-National - 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 Air China (94%), Egyptair (93%) 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 $118. While the most popular route (Washington, D.C. Dulles Intl - Chicago O'Hare Intl) can be booked for $143 on average, our data indicates $940 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, March is the cheapest month in which you can book a flight from Washington, D.C. to Chicago (average of $50). Flying from Washington, D.C. to Chicago in June is currently the most expensive (average of $132). 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
Lansing
Hammond
Porter
Benton Harbor
Merrillville

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Alternative routes for Washington, D.C. to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Top 6 airlines flying from Washington, D.C. to Chicago

Discover the top 6 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 November 7, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$52Average$120FlexibilityNo cancel feeOn-time65%
FrontierCheapest$69Average$181FlexibilityNo cancel feeOn-time62%
DeltaCheapest$98Average$328FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$156Average$299FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$158Average$323FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$166Average$306FlexibilityNo cancel feeOn-time71%

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