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$78+ 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 2/9. Fares are subject to change and may not be available on all flights or dates of travel.
IAD — CHI
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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Cheap 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 October 30, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$141
(Kiwi.com)

One-way from

$78
(Trip.com)

Popular in

April

Cheapest in

September

Average price

$252

Good round-trip deal

$291 or less

Good one-way deal

$158 or less
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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From District of Columbia to Chicago (CHI)
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One-way flight from District of Columbia to Chicago (CHI)
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Highest demand for flights based on searches. 7% potential increase in price ($21 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($3 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Price to beat on a round-trip flight from District of Columbia to Chicago (CHI).
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Price to beat on a one-way flight from District of Columbia to Chicago (CHI).
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Find 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 October 30, 2025.

This Frontier deal was found by Cheapflights users on 10/30. 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 12/55:45 amIAD - ORD
1 stop9h 55mFrontier
Sun 12/76:11 amORD - IAD
1 stop9h 13mFrontier
Deal found 10/30$141
This Frontier deal was found by Cheapflights users on 10/30. 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 12/55:19 pmIAD - MDW
1 stop5h 53mFrontier
Sun 12/76:15 amMDW - IAD
1 stop9h 09mFrontier
Deal found 10/30$141
This Booking.com deal was found by Cheapflights users on 10/30. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/125:19 pmIAD - MDW
1 stop5h 53mFrontier
Sun 12/142:59 pmMDW - IAD
1 stop23h 06mFrontier
Deal found 10/30$142
This CheapOair deal was found by Cheapflights users on 10/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/142:00 pmDCA - ORD
1 stop11h 15mFrontier
Mon 11/176:00 amORD - DCA
1 stop14h 59mFrontier
Deal found 10/27$143
This CheapOair deal was found by Cheapflights users on 10/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/146:00 amIAD - ORD
1 stop11h 56mFrontier
Mon 11/175:05 amORD - IAD
1 stop10h 53mFrontier
Deal found 10/27$143
This Priceline deal was found by Cheapflights users on 10/29. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/145:34 pmIAD - MDW
1 stop5h 34mFrontier
Sat 11/151:37 pmMDW - IAD
1 stop9h 18mFrontier
Deal found 10/29$143
This CheapOair deal was found by Cheapflights users on 10/28. 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.
Wed 11/128:15 amDCA - MDW
1 stop28h 15mFrontier
Fri 11/1412:30 pmMDW - DCA
1 stop8h 29mFrontier
Deal found 10/28$143
This Booking.com deal was found by Cheapflights users on 10/27. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/76:00 pmDCA - ORD
1 stop7h 15mFrontier
Wed 11/126:05 pmORD - DCA
1 stop26h 54mFrontier
Deal found 10/27$144
This Booking.com deal was found by Cheapflights users on 10/29. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/55:19 pmIAD - MDW
1 stop5h 53mFrontier
Sat 12/62:59 pmMDW - IAD
1 stop19h 10mFrontier
Deal found 10/29$145
This Booking.com deal was found by Cheapflights users on 10/29. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/125:19 pmIAD - ORD
1 stop6h 05mFrontier
Sun 12/148:45 amORD - IAD
1 stop22h 46mFrontier
Deal found 10/29$146
This Kiwi.com deal was found by Cheapflights users on 10/30. 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.
Mon 11/246:46 pmIAD - ORD
1 stop6h 22mFrontier
Thu 11/276:00 amORD - IAD
1 stop10h 46mFrontier
Deal found 10/30$147
This Mytrip deal was found by Cheapflights users on 10/30. 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.
Fri 11/146:00 pmDCA - ORD
1 stop7h 15mFrontier
Tue 11/186:05 pmORD - DCA
1 stop17h 57mFrontier
Deal found 10/30$149

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 October 30, 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

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Sat 1/17

6:15 am-1:10 pm

1 stop7h 55m

Chicago O'Hare Intl

Sat 1/31

2:05 pm-10:47 pm

1 stop7h 42m

$153

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Sat 1/10

6:15 am-1:10 pm

1 stop7h 55m

Chicago O'Hare Intl

Thu 1/15

2:05 pm-10:47 pm

1 stop7h 42m

$154

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Wed 11/12

8:40 am-12:41 pm

1 stop5h 01m

Chicago Midway

Fri 11/14

1:37 pm-12:11 am

1 stop9h 34m

$167

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Mon 11/24

5:43 pm-10:50 pm

1 stop6h 07m

Chicago O'Hare Intl

Thu 11/27

8:20 am-2:59 pm

1 stop5h 39m

$181

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 11/13

6:00 am-2:33 pm

2 stops9h 33m

Chicago Midway

Mon 11/17

9:27 am-7:52 pm

1 stop9h 25m

$195

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Mon 11/10

4:55 pm-8:52 pm

1 stop4h 57m

Chicago O'Hare Intl

Sat 11/15

6:45 am-2:35 pm

1 stop6h 50m

$207

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Sat 11/8

4:55 pm-8:52 pm

1 stop4h 57m

Chicago O'Hare Intl

Wed 11/19

6:45 am-2:36 pm

1 stop6h 51m

$207

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Fri 11/14

4:55 pm-8:52 pm

1 stop4h 57m

Chicago O'Hare Intl

Mon 11/17

6:45 am-2:36 pm

1 stop6h 51m

$218

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Fri 11/14

4:55 pm-8:52 pm

1 stop4h 57m

Chicago O'Hare Intl

Tue 11/18

7:00 am-2:36 pm

1 stop6h 36m

$218

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Wed 12/17

3:30 pm-4:54 pm

Nonstop2h 24m

Chicago O'Hare Intl

Tue 12/30

11:15 am-2:17 pm

Nonstop2h 02m

$237

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

Showing 1-10 of 60 results
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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 $50). Flying from District of Columbia to Chicago in June is currently the most expensive (average of $132). 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 October 30, 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 40% on your trip compared to booking a flight at noon.

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 October 26, 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?

    JetBlue, Frontier, and United Airlines can get you from District of Columbia to Chicago in just under 2h 16m. Your travel time can differ by up to 5h 39m. 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 JetBlue, which is currently one of the cheapest options available, starting at $78. Frontier flights start at $87 while deals on United Airlines start at $110 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: Air China (97%), Egyptair (96%), Ethiopian Air (79%).

  • 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 $1,032, our data indicates the cheapest price to be $128. The most popular route (Washington, D.C. Reagan-National - Chicago O'Hare Intl), is priced around $110.

  • 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 $50). Flying from District of Columbia to Chicago in June is currently the most expensive (average of $132). 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
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Hammond
Porter
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Alternative routes for District of Columbia to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$52Average$124FlexibilityNo cancel feeOn-time65%
FrontierCheapest$68Average$182FlexibilityNo cancel feeOn-time62%
DeltaCheapest$98Average$328FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$157Average$298FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$158Average$322FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$166Average$305FlexibilityNo cancel feeOn-time71%

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