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$76+ 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 8/25. Fares are subject to change and may not be available on all flights or dates of travel.
WAS — CHI
Aug 2 — Aug 91
Sat 8/2
Sat 8/9
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 90 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 July 28, 2025.

Round-trip from

$117
(Cheapflightsfares)

One-way from

$76
(Kiwi.com)

Popular in

April

Cheapest in

September

Average price

$266

Good round-trip deal

$151 or less

Good one-way deal

$117 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 ($19 potential increase over avg. RT price).
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Cheapest flight prices on average. 0% potential price decrease ($3 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 28, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 7/27. 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 9/125:40 pmBWI - MDW
Nonstop2h 03mFrontier
Sun 9/141:49 pmMDW - BWI
Nonstop2h 01mFrontier
Deal found 7/27$118
This Kiwi.com deal was found by Cheapflights users on 7/26. 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 8/2312:21 pmBWI - ORD
1 stop7h 46mMultiple Airlines
Mon 8/251:15 pmORD - BWI
Nonstop2h 06mMultiple Airlines
Deal found 7/26$118
This Frontier deal was found by Cheapflights users on 7/27. 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 8/225:06 pmBWI - ORD
Nonstop2h 22mFrontier
Mon 8/251:15 pmORD - BWI
Nonstop2h 06mFrontier
Deal found 7/27$122
This FlightHub deal was found by Cheapflights users on 7/27. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/79:57 amBWI - ORD
Nonstop2h 13mSpirit Airlines
Tue 9/96:30 amORD - BWI
1 stop8h 02mSpirit Airlines
Deal found 7/27$124
This American Airlines deal was found by Cheapflights users on 7/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/2610:09 pmDCA - ORD
Nonstop2h 16mAmerican Airlines
Wed 8/275:21 pmORD - DCA
Nonstop1h 55mAmerican Airlines
Deal found 7/26$157
This Southwest deal was found by Cheapflights users on 7/25. 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 9/173:15 pmDCA - MDW
Nonstop2h 10mSouthwest
Mon 9/298:30 pmMDW - DCA
Nonstop1h 55mSouthwest
Deal found 7/25$157
This Southwest deal was found by Cheapflights users on 7/27. 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.
Sun 8/176:45 amBWI - MDW
Nonstop2h 00mSouthwest
Mon 8/185:10 amMDW - BWI
Nonstop1h 45mSouthwest
Deal found 7/27$159
This Southwest deal was found by Cheapflights users on 7/26. 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 9/310:35 amBWI - ORD
Nonstop2h 15mSouthwest
Sat 9/61:30 pmORD - BWI
Nonstop2h 00mSouthwest
Deal found 7/26$161
This Cheapflightsfares deal was found by Cheapflights users on 7/26. 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.
Wed 9/39:30 amIAD - MDW
1 stop5h 31mFrontier
Sat 9/610:51 amMDW - IAD
1 stop6h 33mFrontier
Deal found 7/26$166
This Southwest deal was found by Cheapflights users on 7/26. 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 9/36:00 amDCA - ORD
1 stop7h 45mSouthwest
Sat 9/62:55 pmORD - DCA
1 stop5h 00mSouthwest
Deal found 7/26$177
This eDestinos deal was found by Cheapflights users on 7/26. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/268:18 pmIAD - ORD
1 stop21h 46mFrontier
Tue 10/288:00 amORD - IAD
1 stop14h 45mFrontier
Deal found 7/26$184
This Delta deal was found by Cheapflights users on 7/25. 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.
Tue 8/264:00 pmDCA - ORD
1 stop7h 37mDelta
Thu 8/287:05 amORD - DCA
1 stop6h 45mDelta
Deal found 7/25$197

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 July 28, 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

Fri 9/12

5:40 pm-6:43 pm

Nonstop2h 03m

Chicago Midway

Sun 9/14

1:49 pm-4:50 pm

Nonstop2h 01m

$118

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Sat 8/23

12:21 pm-7:07 pm

1 stop7h 46m

Chicago O'Hare Intl

Mon 8/25

1:15 pm-4:21 pm

Nonstop2h 06m

$118

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Fri 8/22

5:06 pm-6:28 pm

Nonstop2h 22m

Chicago O'Hare Intl

Mon 8/25

1:15 pm-4:21 pm

Nonstop2h 06m

$122

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Sun 9/7

9:57 am-11:10 am

Nonstop2h 13m

Chicago O'Hare Intl

Tue 9/9

6:30 am-3:32 pm

1 stop8h 02m

$124

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Tue 8/26

10:09 pm-11:25 pm

Nonstop2h 16m

Chicago O'Hare Intl

Wed 8/27

5:21 pm-8:16 pm

Nonstop1h 55m

$157

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Wed 9/17

3:15 pm-4:25 pm

Nonstop2h 10m

Chicago Midway

Mon 9/29

8:30 pm-11:25 pm

Nonstop1h 55m

$157

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Sun 8/17

6:45 am-7:45 am

Nonstop2h 00m

Chicago Midway

Mon 8/18

5:10 am-7:55 am

Nonstop1h 45m

$159

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Wed 9/3

10:35 am-11:50 am

Nonstop2h 15m

Chicago O'Hare Intl

Sat 9/6

1:30 pm-4:30 pm

Nonstop2h 00m

$161

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Wed 9/3

9:30 am-2:01 pm

1 stop5h 31m

Chicago Midway

Sat 9/6

10:51 am-6:24 pm

1 stop6h 33m

$166

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Wed 9/3

6:00 am-12:45 pm

1 stop7h 45m

Chicago O'Hare Intl

Sat 9/6

2:55 pm-8:55 pm

1 stop5h 00m

$177

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/26

Showing 1-10 of 51 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
Airlines
United Airlines

United's Economy Plus offers extra legroom and priority boarding, ideal for frequent business travelers.


United's Polaris Lounges in Chicago offer showers, napping areas, and dining for premium passengers.

Read more about United Airlinesby Harriet Baskas
Southwest

Southwest's Wanna Get Away fare includes two free checked bags, perfect for budget-conscious travelers.


Southwest offers free in-flight entertainment streamed to your device, enhancing the travel experience.

Read more about Southwestby Marisa Garcia
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
Harriet Baskas

Harriet Baskas

Expert on United Airlines

Harriet Baskas

Harriet Baskas

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Read more
Marisa Garcia

Marisa Garcia

Expert on Southwest

Marisa Garcia

Marisa Garcia

Marisa knows planes inside and out, spending 16 years working on aircraft in hangars at airports around the world. She is an aviation industry expert, specialized in airline interiors and regulations. Ten years ago, she pivoted to journalism. She shares her insights in leading aviation, travel, and business publications and on her site FlightChic.

Read more
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 July 25, 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 90 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 July 28, 2025.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 25% 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 July 27, 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 July 28, 2025.

The most flights from WAS to CHI are scheduled on a Monday (85 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (58 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 July 28, 2025.
Read reviews from past customers who have flown Southwest, Delta, and United 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
4,237 reviews

Overall

8.0

Comfort

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,237 reviews
Southwest
8.0
Very good
4,237 reviews

Overall

8.0

Comfort

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,971 reviews
Southwest
8.0
Very good
4,237 reviews

Overall

8.0

Comfort

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
United Airlines
7.4
Good
8,893 reviews
Southwest
8.0
Very good
4,237 reviews

Overall

8.0

Comfort

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
JetBlue
7.3
Good
2,913 reviews
Southwest
8.0
Very good
4,237 reviews

Overall

8.0

Comfort

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,237 reviews

Overall

8.0

Comfort

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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.

  • 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 $117. Other airlines that can offer you cheap pricing are Spirit Airlines, from $121, and American Airlines, from $157. Frontier is 53% 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 $76 on Spirit Airlines. Other airlines that offer cheap prices include Frontier from $77 and Southwest from $80 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 Washington, D.C. Reagan-National - 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 ANA (95%), Spirit Airlines (93%) and Royal Jordanian (88%).

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

    Looking at all options, your cheapest flight can be booked for $76. While the most popular route (Washington, D.C. Dulles Intl - Chicago O'Hare Intl) can be booked for $174 on average our data indicates $1,494 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
Valparaiso
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.
Dulles Intl to O'Hare Intl flights
Reagan-National to O'Hare Intl flights
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Reagan-National to Paducah flights

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 July 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$52Average$152FlexibilityNo cancel feeOn-time65%
FrontierCheapest$61Average$188FlexibilityNo cancel feeOn-time62%
DeltaCheapest$98Average$296FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$152Average$329FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$157Average$292FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$157Average$328FlexibilityNo cancel feeOn-time69%

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