HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$68+ Cheap flights from District of Columbia 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 1/7. Fares are subject to change and may not be available on all flights or dates of travel.
IAD — CHI
Jan 16 — Jan 231
Fri 1/16
Fri 1/23
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from District of Columbia 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

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from District of Columbia to Chicago

Cheapest flights from District of Columbia to Chicago
Explore the most affordable flight options available from District of Columbia to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 17, 2025.

This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:05 amIAD - ORD
1 stop17h 19mFrontier
Tue 1/62:26 pmORD - IAD
1 stop25h 24mFrontier
Deal found 12/17$183
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.
Mon 12/299:58 pmIAD - ORD
1 stop12h 04mFrontier
Mon 1/59:47 amORD - IAD
1 stop10h 16mFrontier
Deal found 12/16$213
This Expedia deal was found by Cheapflights users on 12/15. 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.
Tue 12/309:58 pmIAD - MDW
1 stop25h 00mFrontier
Thu 1/16:12 amMDW - IAD
1 stop11h 04mFrontier
Deal found 12/15$213
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/305:37 pmIAD - ORD
1 stop5h 47mFrontier
Sun 1/48:09 pmORD - IAD
1 stop23h 54mFrontier
Deal found 12/16$215
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:05 amIAD - ORD
1 stop17h 19mMultiple Airlines
Tue 1/66:05 pmORD - IAD
2 stops21h 45mMultiple Airlines
Deal found 12/17$219
This American Airlines deal was found by Cheapflights users on 12/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/257:01 amDCA - ORD
Nonstop2h 25mAmerican Airlines
Thu 1/16:09 amORD - DCA
Nonstop1h 49mAmerican Airlines
Deal found 12/14$223
This United Airlines deal was found by Cheapflights users on 12/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/245:31 pmIAD - ORD
Nonstop2h 21mUnited Airlines
Wed 12/312:30 pmORD - IAD
Nonstop2h 00mUnited Airlines
Deal found 12/14$223
This Southwest deal was found by Cheapflights users on 12/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/258:45 pmDCA - MDW
Nonstop2h 10mSouthwest
Thu 1/13:30 pmMDW - DCA
Nonstop1h 45mSouthwest
Deal found 12/14$223
This American Airlines deal was found by Cheapflights users on 12/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/319:36 amDCA - ORD
Nonstop2h 14mAmerican Airlines
Wed 1/79:45 amORD - DCA
Nonstop1h 59mAmerican Airlines
Deal found 12/14$227
This Southwest deal was found by Cheapflights users on 12/15. 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 12/313:45 pmDCA - MDW
1 stop4h 50mSouthwest
Thu 1/17:30 amMDW - DCA
Nonstop1h 45mSouthwest
Deal found 12/15$233
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 12/305:37 pmIAD - ORD
1 stop5h 47mFrontier
Mon 1/59:47 amORD - IAD
1 stop10h 16mFrontier
Deal found 12/16$234
This Delta deal was found by Cheapflights users on 12/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/315:42 pmDCA - ORD
1 stop7h 20mDelta
Wed 1/76:00 amORD - DCA
1 stop5h 57mDelta
Deal found 12/14$247

Find flight deals from District of Columbia to Chicago

Keep the following information in mind while searching for District of Columbia to Chicago flight deals. Data was last updated December 17, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$146
(Kiwi.com)

One-way from

$68
(Kiwi.com)

Popular in

November

Cheapest in

September

Average price

$269

Good round-trip deal

$317 or less

Good one-way deal

$177 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 District of Columbia to Chicago (CHI)
Search Deals
One-way flight from District of Columbia to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($12 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from District of Columbia to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from District of Columbia to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from District of Columbia 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 17, 2025.
Use the filters below to find and compare flights from District of Columbia to Chicago that are best for you.

Fly from

District of Columbia

Fly to

Chicago

Route

Depart

Return

Price

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 1/29

5:37 pm-10:19 pm

1 stop5h 42m

Chicago Midway

Thu 2/5

6:20 am-4:28 pm

1 stop9h 08m

$163

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Wed 1/7

1:00 pm-5:43 pm

1 stop5h 43m

Chicago O'Hare Intl

Sat 1/10

7:45 am-5:04 pm

1 stop8h 19m

$197

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Thu 1/22

1:00 pm-5:43 pm

1 stop5h 43m

Chicago O'Hare Intl

Mon 1/26

7:45 am-4:19 pm

1 stop7h 34m

$197

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Fri 1/23

11:55 am-5:43 pm

1 stop6h 48m

Chicago O'Hare Intl

Mon 1/26

7:45 am-2:29 pm

1 stop5h 44m

$197

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Fri 1/30

1:00 pm-5:43 pm

1 stop5h 43m

Chicago O'Hare Intl

Mon 2/2

8:29 am-4:19 pm

1 stop6h 50m

$197

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Fri 3/6

6:00 am-11:49 am

1 stop6h 49m

Chicago O'Hare Intl

Mon 3/9

10:00 am-6:55 pm

1 stop7h 55m

$207

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Sat 2/14

8:15 am-9:34 am

Nonstop2h 19m

Chicago O'Hare Intl

Sat 2/14

6:20 pm-9:18 pm

Nonstop1h 58m

$223

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Wed 1/14

10:28 pm-11:39 pm

Nonstop2h 11m

Chicago O'Hare Intl

Sun 1/18

1:00 pm-4:00 pm

Nonstop2h 00m

$227

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 2/26

11:22 am-4:16 pm

1 stop5h 54m

Chicago Midway

Sun 3/1

3:00 pm-7:20 am

2 stops15h 20m

$227

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Wed 1/14

6:55 pm-8:05 pm

Nonstop2h 10m

Chicago Midway

Wed 1/21

10:15 am-1:00 pm

Nonstop1h 45m

$231

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

Showing 1-10 of 60 results
1
2
3
...
6

Best time to book a flight from District of Columbia to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from District of Columbia 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 District of Columbia to Chicago

What is the cheapest month to book a flight from District of Columbia to Chicago?

Currently, March is the cheapest month in which you can book a flight from District of Columbia to Chicago (average of $49). Flying from District of Columbia to Chicago in June is currently the most expensive (average of $133). 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 DC to CHI?

Find hourly flight availability from District of Columbia 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 17, 2025.

A simple way to save on the total cost of your ticket is to fly from District of Columbia to Chicago in the evening. If you’re flexible enough to do this you can expect to save up to 36% on your trip compared to booking a flight in the morning.

What is the cheapest day to fly from District of Columbia to Chicago?

Use this chart to determine the cheapest time to fly round-trip from District of Columbia to Chicago. Price data was last updated on December 13, 2025.

Travelers seeking maximum savings on their District of Columbia to Chicago flight should consider departing on Saturday evenings 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.

Related info for your journey

Find useful and relevant information for your journey from District of Columbia 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 District of Columbia to Chicago?

    Frontier, JetBlue, and United Airlines can get you from District of Columbia to Chicago in just under 2h 19m. Your travel time can differ by up to 3h 24m. District of Columbia and Chicago are separated by a distance of 587 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from District of Columbia to Chicago one-way?

    To fly one-way, consider booking your trip with Frontier, which is currently one of the cheapest options available, starting at $16. Spirit Airlines flights start at $45 while deals on Southwest start at $79 one-way.

  • What are the most popular routes from District of Columbia to Chicago?

    While some choose either Washington, D.C. Dulles Intl - Chicago O'Hare Intl or Washington, D.C. Dulles Intl - Chicago Midway, Washington, D.C. Reagan-National - Chicago O'Hare Intl is the most popular route from District of Columbia to Chicago.

  • What are the most reliable airlines from District of Columbia to Chicago?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from District of Columbia to Chicago on time: Egyptair (85%), Air China (84%), ANA (82%).

  • What are the cheapest flights from District of Columbia to Chicago?

    Looking for the cheapest flight from District of Columbia to Chicago? While on average our users pay $949, our data indicates the cheapest price to be $115. The most popular route (Washington, D.C. Reagan-National - Chicago O'Hare Intl), is priced around $168.

  • Can I find deals for flights from District of Columbia to Chicago that include hotel bookings?

    Yes. In addition to deals on District of Columbia to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from District of Columbia to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from District of Columbia to Chicago.

  • Can I find deals for business class flights from District of Columbia to Chicago?

    Yes. Cheapflights offers flight deals from District of Columbia 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 District of Columbia to Chicago?

    Currently, March is the cheapest month in which you can book a flight from District of Columbia to Chicago (average of $49). Flying from District of Columbia to Chicago in June is currently the most expensive (average of $133). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for District of Columbia to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
John F Kennedy Intl to O'Hare Intl flights
Dallas/Fort Worth to O'Hare Intl flights
LaGuardia to O'Hare Intl flights
Los Angeles to O'Hare Intl flights
Newark to O'Hare Intl flights
Dallas/Fort Worth to Midway flights
Atlanta to O'Hare Intl flights
Boston to O'Hare Intl flights
Seattle to O'Hare Intl flights
Denver to O'Hare Intl flights
Baltimore to O'Hare Intl flights
San Francisco to O'Hare Intl flights
Reagan-National to O'Hare Intl flights
Los Angeles to Midway flights
Philadelphia to O'Hare Intl flights
John F Kennedy Intl to Midway flights
Sky Harbor Intl to O'Hare Intl flights
Atlanta to Midway flights
Love Field to O'Hare Intl flights
LaGuardia to Midway flights
Dulles Intl to O'Hare Intl flights
Tampa to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
Ontario to O'Hare Intl flights
Austin to O'Hare Intl flights
Hobby to O'Hare Intl flights
Minneapolis to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
Charlotte to O'Hare Intl flights
Minneapolis to Midway flights
Hobby to Midway flights
Denver to Midway flights
Santa Ana to O'Hare Intl flights
San Diego to O'Hare Intl flights
Orlando to O'Hare Intl flights
Raleigh to O'Hare Intl flights
Love Field to Midway flights
Boston to Midway flights
Philadelphia to Midway flights
Miami to O'Hare Intl flights
Cleveland to O'Hare Intl flights
Dulles Intl to Midway flights
Newark to St. Louis flights
George Bush Intcntl to Midway flights
Baltimore to Midway flights
Denver to St. Louis flights
Fort Lauderdale to Midway flights
Las Vegas to O'Hare Intl flights
Hartford to O'Hare Intl flights
Detroit to O'Hare Intl flights

Top 6 airlines flying from District of Columbia to Chicago

Discover the top 6 airlines that operate flights from District of Columbia 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 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$52Average$120FlexibilityNo cancel feeOn-time65%
FrontierCheapest$58Average$176FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$150Average$294FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$158Average$321FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$168Average$309FlexibilityNo cancel feeOn-time71%
DeltaCheapest$234Average$327FlexibilityNo cancel feeOn-timeN/A

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.