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$90+ 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 4/27. Fares are subject to change and may not be available on all flights or dates of travel.
WAS — CHI
May 14 — May 211
Thu 5/14
Thu 5/21
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”

2. Select your favorite providers

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3. Compare prices and book

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Cheapflights Tip: The best prices from Washington, D.C. to Chicago are usually found in September or August, booked 67 days in advance, depart on a Friday or Thursday 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 April 14, 2026.

This Kiwi.com deal was found by Cheapflights users on 4/12. 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 4/2512:18 pm
BWI
-
MDW
1 stop7h 19m
Frontier
Tue 4/282:15 pm
MDW
-
BWI
1 stop9h 29m
Frontier
Deal found 4/12$199
This Expedia deal was found by Cheapflights users on 4/12. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/811:32 am
BWI
-
ORD
Nonstop2h 22m
Frontier
Sun 5/107:30 am
ORD
-
BWI
Nonstop2h 07m
Frontier
Deal found 4/12$199
This Southwest deal was found by Cheapflights users on 4/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/27:30 pm
BWI
-
MDW
Nonstop2h 10m
Southwest
Mon 5/49:25 pm
MDW
-
BWI
Nonstop1h 50m
Southwest
Deal found 4/10$200
This CheapOair deal was found by Cheapflights users on 4/10. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/157:48 pm
BWI
-
ORD
1 stop13h 34m
Spirit Airlines
Mon 5/187:33 pm
ORD
-
BWI
1 stop18h 55m
Spirit Airlines
Deal found 4/10$200
This Frontier deal was found by Cheapflights users on 4/10. 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 6/36:45 am
BWI
-
MDW
1 stop5h 24m
Frontier
Mon 6/86:00 am
MDW
-
BWI
1 stop11h 28m
Frontier
Deal found 4/10$201
This Frontier deal was found by Cheapflights users on 4/10. 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.
Fri 4/246:14 am
BWI
-
ORD
1 stop6h 18m
Frontier
Sat 4/255:50 am
ORD
-
BWI
1 stop10h 08m
Frontier
Deal found 4/10$201
This Frontier deal was found by Cheapflights users on 4/10. 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.
Mon 4/2712:27 pm
BWI
-
MDW
1 stop10h 52m
Frontier
Thu 4/306:00 am
MDW
-
BWI
1 stop10h 11m
Frontier
Deal found 4/10$202
This Kiwi.com deal was found by Cheapflights users on 4/14. 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 5/83:26 pm
BWI
-
ORD
1 stop7h 48m
Multiple Airlines
Wed 5/207:15 am
ORD
-
BWI
1 stop8h 07m
Multiple Airlines
Deal found 4/14$202
This Trip.com deal was found by Cheapflights users on 4/11. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/14:25 pm
BWI
-
MDW
1 stop7h 01m
Frontier
Mon 5/46:00 am
MDW
-
BWI
1 stop6h 48m
Frontier
Deal found 4/11$203
This Kiwi.com deal was found by Cheapflights users on 4/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/2511:46 am
BWI
-
ORD
1 stop13h 13m
Multiple Airlines
Mon 4/277:15 pm
ORD
-
BWI
2 stops15h 07m
Multiple Airlines
Deal found 4/10$203
This Southwest deal was found by Cheapflights users on 4/9. 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 5/124:50 pm
BWI
-
MDW
1 stop3h 45m
Southwest
Sat 5/166:10 am
MDW
-
BWI
Nonstop1h 50m
Southwest
Deal found 4/9$204
This Kiwi.com deal was found by Cheapflights users on 4/13. 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 5/811:32 am
BWI
-
ORD
Nonstop2h 22m
Multiple Airlines
Sat 5/231:18 pm
ORD
-
BWI
1 stop9h 11m
Multiple Airlines
Deal found 4/13$204

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 April 14, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$199
(Kiwi.com)

One-way from

$90
(Expedia)

Popular in

March

Cheapest in

September

Average price

$317

Good round-trip deal

$296 or less

Good one-way deal

$182 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. 9% potential increase in price ($29 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 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 April 14, 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
Quickest round-trip

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Wed 5/6

6:30 am-7:35 am

Nonstop2h 05m

Chicago Midway

Wed 5/27

1:00 pm-3:50 pm

Nonstop1h 50m

$200

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Tue 5/5

10:30 pm-11:44 pm

Nonstop2h 14m

Chicago O'Hare Intl

Thu 5/7

12:55 pm-3:58 pm

Nonstop2h 03m

$219

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Sat 5/9

7:30 pm-8:40 pm

Nonstop2h 10m

Chicago Midway

Sat 5/16

12:05 pm-2:55 pm

Nonstop1h 50m

$219

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Thu 6/4

6:05 am-8:45 am

1 stop3h 40m

Chicago O'Hare Intl

Tue 6/9

2:07 pm-6:59 pm

1 stop3h 52m

$228

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Sat 5/16

1:55 pm-7:14 pm

1 stop6h 19m

Chicago O'Hare Intl

Wed 5/20

8:10 am-2:59 pm

1 stop5h 49m

$228

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Thu 5/7

6:00 am-2:20 pm

1 stop9h 20m

Chicago O'Hare Intl

Tue 5/12

11:55 am-8:50 pm

1 stop7h 55m

$228

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Wed 5/27

6:00 am-8:45 am

1 stop3h 45m

Chicago O'Hare Intl

Mon 6/1

5:30 am-2:10 pm

1 stop7h 40m

$228

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Mon 5/11

6:05 am-12:50 pm

1 stop7h 45m

Chicago O'Hare Intl

Tue 5/12

11:55 am-8:50 pm

1 stop7h 55m

$228

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Wed 5/27

6:08 am-11:56 am

1 stop6h 48m

Chicago Midway

Mon 6/1

6:23 am-2:10 pm

1 stop6h 47m

$228

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Thu 6/4

2:35 pm-7:35 pm

1 stop6h 00m

Chicago Midway

Tue 6/9

11:25 am-4:10 pm

1 stop3h 45m

$228

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/9

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 April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
OvagoPrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy2 starsTrust Score*2 stars
Kiwi.comPrice Accuracy3 starsTrust Score*3 stars
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

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 April 10, 2026.

To ensure you get the cheapest price possible for a flight from Washington, D.C. to Chicago, you should look to book at least 67 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, January is the cheapest month in which you can book a flight from Washington, D.C. to Chicago (average of $57). Flying from Washington, D.C. to Chicago in June is currently the most expensive (average of $140). 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 April 14, 2026.

Unlike in the morning, when flights are generally more expensive, you can save up to 18% 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 April 11, 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.

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 April 14, 2026.

The most flights from WAS to CHI are scheduled on a Tuesday (93 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (38 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

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 April 14, 2026.
Read reviews from past customers who have flown Southwest,United Airlines, andAmerican 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
4,328 reviews

Crew

8.6

Entertainment

7.5

Overall

8.0

Boarding

8.1

Food

7.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,328 reviews
Southwest
8.0
Very good
4,328 reviews

Crew

8.6

Entertainment

7.5

Overall

8.0

Boarding

8.1

Food

7.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
United Airlines
7.4
Good
9,582 reviews
Southwest
8.0
Very good
4,328 reviews

Crew

8.6

Entertainment

7.5

Overall

8.0

Boarding

8.1

Food

7.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
American Airlines
7.1
Good
11,573 reviews
Southwest
8.0
Very good
4,328 reviews

Crew

8.6

Entertainment

7.5

Overall

8.0

Boarding

8.1

Food

7.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Spirit Airlines
6.3
Okay
8,614 reviews
Southwest
8.0
Very good
4,328 reviews

Crew

8.6

Entertainment

7.5

Overall

8.0

Boarding

8.1

Food

7.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Frontier
5.7
Fair
2,994 reviews
Southwest
8.0
Very good
4,328 reviews

Crew

8.6

Entertainment

7.5

Overall

8.0

Boarding

8.1

Food

7.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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 Delta fly from Washington, D.C. to Chicago in about 2h 05m. The time it takes to get you to your destination can typically vary by up to 1h 35m. 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 American Airlines, from $166, and Southwest, from $191. Frontier is 88% 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 $55 on Frontier. Other airlines that offer cheap prices include American Airlines from $89 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 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 CommutAir (100%), Egyptair (85%) and ANA (81%).

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

    Looking at all options, your cheapest flight can be booked for $129. While the most popular route (Washington, D.C. Dulles Intl - Chicago O'Hare Intl) can be booked for $160 on average, our data indicates $622 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, January is the cheapest month in which you can book a flight from Washington, D.C. to Chicago (average of $57). Flying from Washington, D.C. to Chicago in June is currently the most expensive (average of $140). 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
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Browse thousands of different options on Cheapflights for your next trip

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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 April 14, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$29Average$170FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$52Average$115FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$134Average$295FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$152Average$339FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$158Average$315FlexibilityNo cancel feeOn-time71%
DeltaCheapest$194Average$342FlexibilityNo cancel feeOn-timeN/A

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