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$69+ 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 2/21. Fares are subject to change and may not be available on all flights or dates of travel.
IAD — CHI
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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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 January 29, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/2311:41 am
IAD
-
ORD
1 stop11h 58m
Frontier
Fri 2/274:42 pm
ORD
-
IAD
1 stop15h 52m
Frontier
Deal found 1/27$148
This Priceline deal was found by Cheapflights users on 1/27. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/2311:41 am
IAD
-
MDW
1 stop9h 06m
Frontier
Mon 3/26:00 am
MDW
-
IAD
1 stop9h 08m
Frontier
Deal found 1/27$148
This Frontier deal was found by Cheapflights users on 1/27. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/235:22 pm
IAD
-
ORD
1 stop6h 17m
Frontier
Mon 3/25:05 am
ORD
-
IAD
1 stop10h 03m
Frontier
Deal found 1/27$149
This Frontier deal was found by Cheapflights users on 1/28. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/2611:22 am
IAD
-
MDW
1 stop5h 54m
Frontier
Mon 3/26:00 am
MDW
-
IAD
1 stop9h 08m
Frontier
Deal found 1/28$150
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/235:22 pm
IAD
-
ORD
1 stop6h 17m
Multiple Airlines
Thu 2/267:23 pm
ORD
-
IAD
1 stop21h 44m
Multiple Airlines
Deal found 1/27$151
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/2110:29 am
IAD
-
ORD
1 stop13h 10m
Multiple Airlines
Wed 2/258:16 pm
ORD
-
IAD
2 stops19h 27m
Multiple Airlines
Deal found 1/28$152
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/235:22 pm
IAD
-
ORD
1 stop18h 29m
Frontier
Sat 2/284:42 pm
ORD
-
IAD
1 stop16h 48m
Frontier
Deal found 1/27$156
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/2611:22 am
IAD
-
MDW
1 stop5h 54m
Frontier
Thu 3/57:30 am
MDW
-
IAD
1 stop8h 13m
Frontier
Deal found 1/28$156
This Super.com deal was found by Cheapflights users on 1/27. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/2611:22 am
IAD
-
ORD
1 stop12h 17m
Frontier
Wed 3/48:30 am
ORD
-
IAD
1 stop23h 55m
Frontier
Deal found 1/27$159
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/2311:41 am
IAD
-
ORD
1 stop11h 58m
Multiple Airlines
Wed 2/257:23 pm
ORD
-
IAD
2 stops20h 20m
Multiple Airlines
Deal found 1/28$160
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/275:37 pm
IAD
-
MDW
1 stop6h 00m
Frontier
Thu 3/57:30 am
MDW
-
IAD
1 stop8h 13m
Frontier
Deal found 1/28$160
This Kiwi.com deal was found by Cheapflights users on 1/26. 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.
Thu 2/2611:22 am
IAD
-
ORD
1 stop12h 17m
Multiple Airlines
Thu 3/512:44 pm
ORD
-
IAD
1 stop17h 40m
Multiple Airlines
Deal found 1/26$161

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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$148
(Kiwi.com)

One-way from

$69
(Super.com)

Popular in

December

Cheapest in

September

Average price

$253

Good round-trip deal

$297 or less

Good one-way deal

$175 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. 7% potential increase in price ($21 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 January 2026
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 January 29, 2026.
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 2/12

5:37 pm-10:34 pm

1 stop5h 57m

Chicago Midway

Mon 2/23

6:00 am-4:08 pm

1 stop9h 08m

$193

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Thu 2/26

6:00 am-11:54 am

1 stop6h 54m

Chicago O'Hare Intl

Wed 3/4

10:00 am-5:49 pm

1 stop6h 49m

$207

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Mon 3/2

6:00 am-11:49 am

1 stop6h 49m

Chicago O'Hare Intl

Wed 3/4

10:00 am-5:49 pm

1 stop6h 49m

$207

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Sat 2/21

10:30 pm-11:43 pm

Nonstop2h 13m

Chicago O'Hare Intl

Tue 2/24

1:02 pm-4:05 pm

Nonstop2h 03m

$214

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 2/26

11:22 am-10:29 pm

1 stop12h 07m

Chicago Midway

Thu 3/5

5:16 pm-7:24 am

2 stops13h 08m

$214

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 4/30

8:09 am-8:04 am

1 stop24h 55m

Chicago Midway

Sun 5/3

9:14 am-7:27 am

1 stop21h 13m

$215

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Wed 2/25

6:00 am-8:54 am

1 stop3h 54m

Chicago Midway

Wed 3/4

6:20 pm-11:09 pm

1 stop3h 49m

$217

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 2/12

5:37 pm-10:34 pm

1 stop5h 57m

Chicago Midway

Sat 2/21

6:00 am-10:15 am

1 stop27h 15m

$220

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Mon 4/20

11:55 am-1:15 pm

Nonstop2h 20m

Chicago O'Hare Intl

Wed 4/22

6:00 am-8:56 am

Nonstop1h 56m

$221

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Wed 3/11

12:40 pm-7:20 pm

1 stop7h 40m

Chicago Midway

Mon 3/16

8:45 pm-11:30 pm

Nonstop1h 45m

$231

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

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 $55). 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 January 29, 2026.

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 26% 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 January 24, 2026.

Travelers seeking maximum savings on their District of Columbia to Chicago flight should consider departing on Saturday at noon when fares are most often at their lowest. Sunday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from District of Columbia to Chicago

Explore weekly flight availability from District of Columbia 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 January 29, 2026.

The most flights from USDC to CHI are scheduled on a Thursday (19 on average). You will have fewer flight options on Friday, which is when the least amount of flights are scheduled (11 on average).

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 13m. Your travel time can differ by up to 4h 41m. 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: Ethiopian Air (87%), Air China (86%), Egyptair (85%).

  • 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 $588, our data indicates the cheapest price to be $156. The most popular route (Washington, D.C. Reagan-National - Chicago O'Hare Intl), is priced around $197.

  • 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 $55). 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
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Hammond
Porter
Benton Harbor

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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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$41Average$115FlexibilityNo cancel feeOn-time65%
FrontierCheapest$57Average$168FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$148Average$299FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$153Average$322FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$159Average$307FlexibilityNo cancel feeOn-time71%
DeltaCheapest$194Average$327FlexibilityNo cancel feeOn-timeN/A

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