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$70+ 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 1/18. Fares are subject to change and may not be available on all flights or dates of travel.
WAS — CHI
Dec 23 — Dec 301
Mon 12/23
Mon 12/30
1 adult, Economy
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The best prices from Washington, D.C. to Chicago are usually found in September or January, booked 87 days in advance, depart on a Monday or Wednesday and return on a Wednesday

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 December 18, 2024.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$110
(Kiwi.com)

One-way from

$70
(Southwest)

Popular in

March

Cheapest in

September

Average price

$269
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.
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From Washington, D.C. (WAS) to Chicago (CHI)
Search Deals
One-way flight from Washington, D.C. (WAS) to Chicago (CHI)
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High demand for flights, 4% potential price rise
Search Deals
Best time to find cheap flights, 1% potential price drop
Search Deals
Average for round-trip flights in December 2024
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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 December 18, 2024.

This Frontier deal was found by Cheapflights users on 12/16. 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.
Tue 12/315:10 pmBWI - MDW
1 stop6h 23mFrontier
Wed 1/16:25 amMDW - BWI
Nonstop1h 52mFrontier
Deal found 12/16$114
This Frontier deal was found by Cheapflights users on 12/17. 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.
Tue 12/3111:34 amIAD - MDW
1 stop11h 59mFrontier
Fri 1/32:35 pmMDW - IAD
1 stop5h 30mFrontier
Deal found 12/17$158
This American Airlines deal was found by Cheapflights users on 12/18. 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.
Wed 12/258:45 pmDCA - ORD
Nonstop2h 20mAmerican Airlines
Wed 1/88:25 pmORD - DCA
Nonstop1h 55mAmerican Airlines
Deal found 12/18$225
This Delta deal was found by Cheapflights users on 12/17. 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.
Wed 12/2512:30 pmBWI - MDW
1 stop4h 40mDelta
Wed 1/86:28 pmMDW - BWI
1 stop3h 51mDelta
Deal found 12/17$237
This Delta deal was found by Cheapflights users on 12/17. 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.
Wed 12/256:05 amBWI - ORD
1 stop4h 16mDelta
Wed 1/87:05 amORD - BWI
1 stop4h 51mDelta
Deal found 12/17$237
This Delta deal was found by Cheapflights users on 12/18. 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.
Wed 12/255:42 pmDCA - ORD
1 stop4h 35mDelta
Wed 1/86:45 amORD - DCA
1 stop4h 15mDelta
Deal found 12/18$244
This Delta deal was found by Cheapflights users on 12/18. 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.
Wed 12/256:00 amIAD - ORD
1 stop4h 21mDelta
Wed 1/85:45 amORD - IAD
1 stop6h 01mDelta
Deal found 12/18$244
This Delta deal was found by Cheapflights users on 12/18. 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.
Wed 12/2512:30 pmIAD - MDW
1 stop4h 40mDelta
Wed 1/86:00 amMDW - IAD
1 stop5h 46mDelta
Deal found 12/18$244
This Delta deal was found by Cheapflights users on 12/18. 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.
Wed 12/2512:31 pmDCA - MDW
1 stop4h 39mDelta
Wed 1/86:00 amMDW - DCA
1 stop5h 49mDelta
Deal found 12/18$244
This American Airlines deal was found by Cheapflights users on 12/18. 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.
Wed 12/259:36 amBWI - ORD
1 stop7h 33mAmerican Airlines
Wed 1/86:00 pmORD - BWI
Nonstop2h 03mAmerican Airlines
Deal found 12/18$249
This Frontier deal was found by Cheapflights users on 12/18. 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.
Tue 12/319:07 amBWI - ORD
1 stop8h 21mFrontier
Sat 1/47:25 amORD - BWI
1 stop8h 28mFrontier
Deal found 12/18$258
This Frontier deal was found by Cheapflights users on 12/17. 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 12/251:01 pmDCA - MDW
1 stop9h 31mFrontier
Wed 1/88:15 amMDW - DCA
1 stop7h 47mFrontier
Deal found 12/17$258

Find flights from Washington, D.C. to Chicago within your budget

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 December 18, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Tue 2/25

8:21 am-3:12 pm

1 stop7h 51m

Chicago Midway

Mon 3/3

12:26 pm-3:21 pm

Nonstop1h 55m

$110

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Thu 2/13

8:55 pm-8:24 am

1 stop12h 29m

Chicago O'Hare Intl

Wed 2/19

7:18 pm-7:21 am

1 stop11h 03m

$111

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Sat 3/1

11:25 am-12:45 pm

Nonstop2h 20m

Chicago O'Hare Intl

Wed 3/5

4:35 pm-7:30 pm

Nonstop1h 55m

$139

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Thu 1/9

4:34 pm-10:42 pm

1 stop7h 08m

Chicago O'Hare Intl

Tue 1/14

8:00 am-3:14 pm

1 stop6h 14m

$146

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Mon 1/6

1:01 pm-11:46 pm

1 stop11h 45m

Chicago O'Hare Intl

Fri 1/10

7:25 am-9:56 pm

1 stop13h 31m

$158

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Sun 2/9

11:34 am-10:27 pm

1 stop11h 53m

Chicago O'Hare Intl

Fri 2/14

7:18 pm-5:13 pm

1 stop20h 55m

$158

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Tue 12/31

11:34 am-10:33 pm

1 stop11h 59m

Chicago Midway

Fri 1/3

2:35 pm-9:05 pm

1 stop5h 30m

$158

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Thu 1/9

1:01 pm-12:13 am

1 stop12h 12m

Chicago Midway

Sun 1/12

7:15 am-5:02 pm

1 stop8h 47m

$158

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Sat 2/1

7:30 am-8:51 am

Nonstop2h 21m

Chicago O'Hare Intl

Sat 2/8

8:20 am-11:17 am

Nonstop1h 57m

$160

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Tue 1/7

10:35 am-11:45 am

Nonstop2h 10m

Chicago Midway

Wed 1/8

5:05 pm-7:50 pm

Nonstop1h 45m

$160

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

Showing 1-10 of 58 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 December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
CheapfaremartPrice Accuracy-Trust Score*3 stars
MytripPrice Accuracy3 starsTrust Score*3 stars
CheapOairPrice Accuracy2 starsTrust Score*2 stars
PricelinePrice 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.

Travel insights for flights from Washington, D.C. to Chicago

Get recent, data-driven insights about flights from Washington, D.C. to Chicago including ideal travel times, pricing trends, and more.

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 December 13, 2024.

To ensure you get the cheapest price possible for a flight from Washington, D.C. to Chicago, you should look to book at least 87 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, September is the cheapest month in which you can book a flight from Washington, D.C. to Chicago (average of $232). Flying from Washington, D.C. to Chicago in June is currently the most expensive (average of $308). 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 December 18, 2024.

Unlike at noon, when flights are generally more expensive, you can save up to 16% on flights from Washington, D.C. to Chicago by exploring options for tickets in the afternoon.

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 December 16, 2024.

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

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 December 18, 2024.
Read through reviews of airlines operating flights from Washington, D.C. to Chicago, such as Frontier, American Airlines and United Airlines. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,848 reviews

Overall

8.1

Boarding

8.2

Crew

8.7

Food

7.2

Comfort

8.1

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,848 reviews
Southwest
8.1
Very good
4,848 reviews

Overall

8.1

Boarding

8.2

Crew

8.7

Food

7.2

Comfort

8.1

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Alaska Airlines
8.0
Very good
9,552 reviews
Southwest
8.1
Very good
4,848 reviews

Overall

8.1

Boarding

8.2

Crew

8.7

Food

7.2

Comfort

8.1

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,604 reviews
Southwest
8.1
Very good
4,848 reviews

Overall

8.1

Boarding

8.2

Crew

8.7

Food

7.2

Comfort

8.1

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

JetBlue
7.4
Good
3,279 reviews
Southwest
8.1
Very good
4,848 reviews

Overall

8.1

Boarding

8.2

Crew

8.7

Food

7.2

Comfort

8.1

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

United Airlines
7.4
Good
9,059 reviews
Southwest
8.1
Very good
4,848 reviews

Overall

8.1

Boarding

8.2

Crew

8.7

Food

7.2

Comfort

8.1

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 $110. Other airlines that can offer you cheap pricing are Southwest, from $139, and American Airlines, from $160. Frontier is 57% 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 $71 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 ANA (89%), Ethiopian Air (89%) and Copa Airlines (87%).

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

    Looking at all options, your cheapest flight can be booked for $114. While the most popular route (Washington, D.C. Dulles Intl - Chicago O'Hare Intl) can be booked for $147 on average our data indicates $1,058 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, September is the cheapest month in which you can book a flight from Washington, D.C. to Chicago (average of $232). Flying from Washington, D.C. to Chicago in June is currently the most expensive (average of $308). 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

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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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Dulles Intl to Moline 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 December 18, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$58Average$176FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$101Average$193FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$136Average$324FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$152Average$333FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$157Average$299FlexibilityNo cancel feeOn-time63%
DeltaCheapest$175Average$283FlexibilityNo cancel feeOn-timeN/A
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