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$69+ 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 9/28. Fares are subject to change and may not be available on all flights or dates of travel.
WAS — CHI
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheapflights Tip: The best prices from Washington, D.C. to Chicago are usually found in September or January, booked 83 days in advance, depart on a Friday or Thursday and return on a Friday

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 September 11, 2025.

Round-trip from

$107
(Cheapflightsfares)

One-way from

$69
(Priceline)

Popular in

April

Cheapest in

September

Average price

$201

Good round-trip deal

$139 or less

Good one-way deal

$87 or less
From Washington, D.C. (WAS) to Chicago (CHI)
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One-way flight from Washington, D.C. (WAS) to Chicago (CHI)
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Highest demand for flights based on searches. 7% potential increase in price ($21 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($3 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Washington, D.C. (WAS) to Chicago (CHI).
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Price to beat on a one-way flight from Washington, D.C. (WAS) to Chicago (CHI).
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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 September 11, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 9/11. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/224:06 pmBWI - MDW
Nonstop2h 09mFrontier
Sun 11/2312:25 pmMDW - BWI
Nonstop1h 56mFrontier
Deal found 9/11$107
This Priceline deal was found by Cheapflights users on 9/11. 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.
Tue 10/148:45 amBWI - MDW
1 stop5h 53mFrontier
Sat 10/1812:30 pmMDW - BWI
Nonstop1h 57mFrontier
Deal found 9/11$108
This Priceline deal was found by Cheapflights users on 9/8. 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.
Mon 9/229:59 pmBWI - ORD
Nonstop2h 21mFrontier
Thu 9/256:11 pmORD - BWI
Nonstop2h 03mFrontier
Deal found 9/8$108
This Mytrip deal was found by Cheapflights users on 9/10. 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 10/25:40 pmBWI - MDW
Nonstop2h 03mFrontier
Mon 10/65:33 pmMDW - BWI
1 stop6h 20mFrontier
Deal found 9/10$109
This Frontier deal was found by Cheapflights users on 9/8. 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.
Thu 10/29:59 pmBWI - ORD
Nonstop2h 21mFrontier
Sat 10/45:40 pmORD - BWI
1 stop5h 26mFrontier
Deal found 9/8$111
This Cheapflightsfares deal was found by Cheapflights users on 9/10. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3111:08 amBWI - MDW
1 stop7h 07mFrontier
Sun 11/25:40 amMDW - BWI
Nonstop1h 56mFrontier
Deal found 9/10$113
This Kiwi.com deal was found by Cheapflights users on 9/11. 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 9/269:59 pmBWI - ORD
Nonstop2h 21mMultiple Airlines
Sun 9/286:10 amORD - BWI
Nonstop1h 52mMultiple Airlines
Deal found 9/11$113
This Frontier deal was found by Cheapflights users on 9/10. 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.
Wed 10/18:12 amBWI - MDW
1 stop8h 46mFrontier
Mon 10/61:49 pmMDW - BWI
Nonstop2h 01mFrontier
Deal found 9/10$114
This Cheapflightsfares deal was found by Cheapflights users on 9/10. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/255:40 pmBWI - MDW
Nonstop2h 03mFrontier
Fri 9/265:15 pmMDW - BWI
1 stop6h 02mFrontier
Deal found 9/10$115
This Cheapflightsfares deal was found by Cheapflights users on 9/10. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/29:59 pmBWI - ORD
Nonstop2h 21mFrontier
Fri 10/35:50 pmORD - BWI
1 stop5h 27mFrontier
Deal found 9/10$115
This Frontier deal was found by Cheapflights users on 9/11. 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.
Wed 9/248:12 amBWI - MDW
1 stop8h 46mFrontier
Thu 9/251:49 pmMDW - BWI
Nonstop2h 01mFrontier
Deal found 9/11$116
This Frontier deal was found by Cheapflights users on 9/11. 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.
Thu 11/64:15 pmBWI - ORD
1 stop8h 56mFrontier
Fri 11/72:45 pmORD - BWI
Nonstop2h 03mFrontier
Deal found 9/11$116

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 September 11, 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

Tue 11/4

8:55 am-10:10 am

Nonstop2h 15m

Chicago Midway

Wed 12/3

6:55 pm-9:45 pm

Nonstop1h 50m

$129

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Wed 10/1

10:51 am-12:05 pm

Nonstop2h 14m

Chicago O'Hare Intl

Fri 10/3

6:15 pm-9:22 pm

Nonstop2h 07m

$133

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Wed 10/1

10:45 am-11:45 am

Nonstop2h 00m

Chicago Midway

Thu 10/2

8:05 pm-10:55 pm

Nonstop1h 50m

$133

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Sat 11/15

11:20 am-12:25 pm

Nonstop2h 05m

Chicago Midway

Sun 11/16

5:05 am-7:55 am

Nonstop1h 50m

$133

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Mon 10/6

7:30 pm-8:35 pm

Nonstop2h 05m

Chicago Midway

Tue 10/7

7:55 am-10:45 am

Nonstop1h 50m

$133

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Tue 11/11

6:15 am-7:31 am

Nonstop2h 16m

Chicago O'Hare Intl

Wed 12/10

2:30 pm-5:25 pm

Nonstop1h 55m

$139

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Wed 9/24

9:15 am-3:58 pm

1 stop7h 43m

Chicago Midway

Sat 9/27

10:51 am-6:24 pm

1 stop6h 33m

$143

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Sat 11/1

5:00 pm-6:23 pm

Nonstop2h 23m

Chicago O'Hare Intl

Tue 11/4

1:36 pm-7:35 pm

1 stop4h 59m

$143

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Thu 10/30

3:10 pm-4:10 pm

Nonstop2h 00m

Chicago Midway

Tue 11/4

8:10 am-4:05 pm

1 stop6h 55m

$143

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Sat 11/8

6:15 am-7:32 am

Nonstop2h 17m

Chicago O'Hare Intl

Sun 11/9

7:05 am-9:59 am

Nonstop1h 54m

$144

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

Showing 1-10 of 60 results
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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

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 August 29, 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, August is the cheapest month in which you can book a flight from Washington, D.C. to Chicago (average of $245). Flying from Washington, D.C. to Chicago in March is currently the most expensive (average of $321). 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 September 11, 2025.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 24% 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 September 7, 2025.

Travelers seeking maximum savings on their Washington, D.C. to Chicago flight should consider departing on Thursday evenings when fares are most often at their lowest. Sunday afternoons 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 September 11, 2025.

The most flights from WAS to CHI are scheduled on a Wednesday (85 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (35 on average).

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 September 11, 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
4,248 reviews

Crew

8.6

Food

7.0

Entertainment

7.5

Overall

8.0

Comfort

8.0

Boarding

8.1

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
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Food

7.0

Entertainment

7.5

Overall

8.0

Comfort

8.0

Boarding

8.1

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
8,937 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Food

7.0

Entertainment

7.5

Overall

8.0

Comfort

8.0

Boarding

8.1

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
10,000 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Food

7.0

Entertainment

7.5

Overall

8.0

Comfort

8.0

Boarding

8.1

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
8,023 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Food

7.0

Entertainment

7.5

Overall

8.0

Comfort

8.0

Boarding

8.1

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
3,177 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Food

7.0

Entertainment

7.5

Overall

8.0

Comfort

8.0

Boarding

8.1

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, United Airlines, and Frontier fly from Washington, D.C. to Chicago in about 2h 14m. The time it takes to get you to your destination can typically vary by up to 5h 29m. The distance from Washington, D.C. to Chicago is about 620 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 $163, and Southwest, from $178. 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 United Airlines. Other airlines that offer cheap prices include Frontier from $72 and Southwest from $75 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. Reagan-National - Chicago O'Hare Intl. You may also consider Washington, D.C. Dulles Intl - Chicago O'Hare Intl or Baltimore/Washington - 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 (92%), Air China (91%) and Ethiopian Air (74%).

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

    Looking at all options, your cheapest flight can be booked for $128. While the most popular route (Washington, D.C. Reagan-National - Chicago O'Hare Intl) can be booked for $117 on average, our data indicates $973 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, August is the cheapest month in which you can book a flight from Washington, D.C. to Chicago (average of $245). Flying from Washington, D.C. to Chicago in March is currently the most expensive (average of $321). 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
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$46Average$125FlexibilityNo cancel feeOn-time65%
FrontierCheapest$61Average$187FlexibilityNo cancel feeOn-time62%
DeltaCheapest$98Average$309FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$157Average$296FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$158Average$326FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$159Average$301FlexibilityNo cancel feeOn-time71%

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