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$65+ 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 1/30. Fares are subject to change and may not be available on all flights or dates of travel.
WAS — CHI
Nov 25 — Dec 21
Mon 11/25
Mon 12/2
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 November 20, 2024.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Popular in

March

Cheapest in

September

Round-trip from

$101
(Kiwi.com)

One-way from

$65
(CheapOair)
Provider with most accurate pricing for Washington, D.C. (WAS)-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Washington, D.C. (WAS)-Chicago (CHI) flights.
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High demand for flights, 13% potential price rise
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Best time to find cheap flights, 20% potential price drop
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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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Find flight deals from Washington, D.C. to Chicago

Cheapest flights from Washington, D.C. to Chicago
Explore the most affordable flight options available from Washington, D.C. to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 20, 2024.

This Kiwi.com deal was found by Cheapflights users on 11/19. 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 12/134:33 pmBWI - MDW
Nonstop2h 04mFrontier
Thu 12/197:17 amMDW - BWI
Nonstop1h 52mFrontier
Deal found 11/19$101
This Frontier deal was found by Cheapflights users on 11/19. 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 12/179:07 amBWI - ORD
1 stop8h 26mFrontier
Wed 12/186:55 amORD - BWI
1 stop6h 42mFrontier
Deal found 11/19$108
This Trip.com deal was found by Cheapflights users on 11/19. 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 12/67:00 amDCA - ORD
1 stop18h 35mFrontier
Sun 12/87:25 amORD - DCA
1 stop27h 36mFrontier
Deal found 11/19$144
This CheapOair deal was found by Cheapflights users on 11/20. 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.
Sun 12/155:57 pmIAD - ORD
1 stop16h 57mFrontier
Wed 12/186:55 amORD - IAD
1 stop8h 33mFrontier
Deal found 11/20$148
This Frontier deal was found by Cheapflights users on 11/19. 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 12/183:25 pmIAD - MDW
1 stop6h 52mFrontier
Wed 12/258:25 amMDW - IAD
1 stop5h 00mFrontier
Deal found 11/19$148
This Trip.com deal was found by Cheapflights users on 11/19. 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.
Wed 12/47:00 amDCA - MDW
1 stop18h 13mFrontier
Sun 12/87:15 amMDW - DCA
1 stop27h 46mFrontier
Deal found 11/19$155
This Kiwi.com deal was found by Cheapflights users on 11/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/1110:10 amBWI - ORD
1 stop23h 14mMultiple Airlines
Sun 12/157:45 pmORD - BWI
1 stop11h 53mMultiple Airlines
Deal found 11/19$160
This Mytrip deal was found by Cheapflights users on 11/19. 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.
Tue 12/37:35 pmBWI - ORD
2 stops15h 57mSpirit Airlines
Tue 12/109:58 amORD - BWI
2 stops24h 17mSpirit Airlines
Deal found 11/19$166
This United Airlines deal was found by Cheapflights users on 11/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/1710:10 amBWI - ORD
Nonstop2h 12mUnited Airlines
Wed 12/185:59 pmORD - BWI
Nonstop1h 54mUnited Airlines
Deal found 11/19$169
This Southwest deal was found by Cheapflights users on 11/19. 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 12/177:55 amBWI - MDW
Nonstop2h 05mSouthwest
Wed 12/187:20 amMDW - BWI
Nonstop1h 50mSouthwest
Deal found 11/19$170
This Southwest deal was found by Cheapflights users on 11/19. 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.
Thu 12/198:10 pmBWI - ORD
Nonstop2h 20mSouthwest
Tue 1/217:00 amORD - BWI
Nonstop1h 55mSouthwest
Deal found 11/19$174
This JetBlue deal was found by Cheapflights users on 11/19. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/1111:00 amDCA - ORD
1 stop5h 53mJetBlue
Tue 12/178:51 amORD - DCA
1 stop9h 07mJetBlue
Deal found 11/19$182

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 2,629,791 searches. Data last updated November 20, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Fri 2/21

4:21 pm-5:33 pm

Nonstop2h 12m

Chicago Midway

Mon 2/24

12:26 pm-3:21 pm

Nonstop1h 55m

$100

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Tue 12/17

9:07 am-4:33 pm

1 stop8h 26m

Chicago O'Hare Intl

Wed 12/18

6:55 am-2:37 pm

1 stop6h 42m

$108

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Sat 5/10

4:15 pm-10:21 pm

1 stop7h 06m

Chicago O'Hare Intl

Tue 5/13

6:15 am-3:12 pm

1 stop7h 57m

$131

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Fri 1/10

11:32 am-7:17 pm

1 stop8h 45m

Chicago O'Hare Intl

Sun 1/12

4:11 pm-5:01 pm

1 stop23h 50m

$141

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Fri 12/6

7:00 am-12:35 am

1 stop18h 35m

Chicago O'Hare Intl

Sun 12/8

7:25 am-12:01 pm

1 stop27h 36m

$144

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Wed 12/18

3:25 pm-9:17 pm

1 stop6h 52m

Chicago Midway

Wed 12/25

8:25 am-2:25 pm

1 stop5h 00m

$148

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Tue 1/7

11:51 am-1:12 pm

Nonstop2h 21m

Chicago O'Hare Intl

Thu 1/9

6:00 pm-9:03 pm

Nonstop2h 03m

$149

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Wed 12/4

7:00 am-12:13 am

1 stop18h 13m

Chicago Midway

Sun 12/8

7:15 am-12:01 pm

1 stop27h 46m

$155

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Wed 12/11

10:10 am-8:24 am

1 stop23h 14m

Chicago O'Hare Intl

Sun 12/15

7:45 pm-8:38 am

1 stop11h 53m

$160

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Tue 12/17

10:10 am-11:22 am

Nonstop2h 12m

Chicago O'Hare Intl

Wed 12/18

5:59 pm-8:53 pm

Nonstop1h 54m

$169

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/19

Showing 1-10 of 60 results
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Compare providers for flights from Washington, D.C. to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Washington, D.C. to Chicago in November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
CheapfaremartPrice Accuracy-Trust Score*1 star
MytripPrice Accuracy3 starsTrust Score*3 stars
CheapOairPrice Accuracy2 starsTrust Score*3 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 November 15, 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 November 20, 2024.

Unlike at noon, when flights are generally more expensive, you can save up to 15% 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 November 18, 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.

Weekly flight availability from Washington, D.C. to Chicago

Explore weekly flight availability from Washington, D.C. to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated November 20, 2024.

The most flights from WAS to CHI are scheduled on a Monday (72 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (18 on average).

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 November 20, 2024.
Read through reviews of airlines operating flights from Washington, D.C. to Chicago, such as Frontier, Delta 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
5,014 reviews

Overall

8.1

Entertainment

7.7

Comfort

8.1

Food

7.2

Boarding

8.2

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Southwest
8.1
Very good
5,014 reviews
Southwest
8.1
Very good
5,014 reviews

Overall

8.1

Entertainment

7.7

Comfort

8.1

Food

7.2

Boarding

8.2

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Delta
8.0
Very good
8,756 reviews
Southwest
8.1
Very good
5,014 reviews

Overall

8.1

Entertainment

7.7

Comfort

8.1

Food

7.2

Boarding

8.2

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Alaska Airlines
8.0
Very good
9,461 reviews
Southwest
8.1
Very good
5,014 reviews

Overall

8.1

Entertainment

7.7

Comfort

8.1

Food

7.2

Boarding

8.2

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Porter Airlines
7.8
Good
288 reviews
Southwest
8.1
Very good
5,014 reviews

Overall

8.1

Entertainment

7.7

Comfort

8.1

Food

7.2

Boarding

8.2

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Air Transat
7.8
Good
389 reviews
Southwest
8.1
Very good
5,014 reviews

Overall

8.1

Entertainment

7.7

Comfort

8.1

Food

7.2

Boarding

8.2

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

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 $101. Other airlines that can offer you cheap pricing are American Airlines, from $149, and Spirit Airlines, from $166. Frontier is 61% 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 $65 on Frontier. Other airlines that offer cheap prices include Southwest from $69 and United Airlines from $69 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 Baltimore/Washington - Chicago O'Hare Intl. You may also consider Washington, D.C. Dulles Intl - 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 Egyptair (100%), ANA (93%) and Ethiopian Air (92%).

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

    Looking at all options, your cheapest flight can be booked for $88. While the most popular route (Baltimore/Washington - Chicago O'Hare Intl) can be booked for $123 on average our data indicates $906 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.
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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 2,629,791 searches. Data last updated November 20, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$58Average$175FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$101Average$193FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$137Average$323FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$153Average$333FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$157Average$280FlexibilityNo cancel feeOn-time63%
DeltaCheapest$175Average$284FlexibilityNo cancel feeOn-timeN/A
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