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$70+ Cheap flights from Reagan-National (DCA) 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 1/21. Fares are subject to change and may not be available on all flights or dates of travel.
DCA — CHI
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheapflights Tip: The best prices from Washington, D.C. Reagan-National to Chicago are usually found in February or May, booked 69 days in advance, depart on a Wednesday or Friday and return on a Thursday

Cheap flight deals from Reagan-National to Chicago

Cheapest flights from Reagan-National to Chicago
Explore the most affordable flight options available from Reagan-National to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 18, 2025.

This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/256:30 amDCA - ORD
Nonstop2h 18mUnited Airlines
Thu 1/19:00 amORD - DCA
Nonstop1h 58mUnited Airlines
Deal found 12/17$223
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/246:55 pmDCA - MDW
Nonstop2h 05mSouthwest
Thu 1/17:30 amMDW - DCA
Nonstop1h 45mSouthwest
Deal found 12/16$223
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/245:00 pmDCA - ORD
Nonstop2h 19mUnited Airlines
Thu 12/256:00 amORD - DCA
1 stop5h 24mUnited Airlines
Deal found 12/17$233
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/315:42 pmDCA - MDW
1 stop5h 40mDelta
Tue 1/66:45 amMDW - DCA
1 stop6h 48mDelta
Deal found 12/16$247
This Southwest 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 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 1/110:05 amMDW - DCA
Nonstop1h 55mSouthwest
Deal found 12/17$258
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/244:29 pmDCA - ORD
1 stop5h 12mAmerican Airlines
Thu 12/256:09 amORD - DCA
Nonstop1h 49mAmerican Airlines
Deal found 12/15$268
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 12/316:05 amDCA - ORD
1 stop7h 10mSouthwest
Thu 1/11:45 pmORD - DCA
1 stop7h 55mSouthwest
Deal found 12/15$283
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 12/246:00 pmDCA - ORD
Nonstop2h 17mUnited Airlines
Wed 12/317:00 amORD - DCA
Nonstop1h 59mUnited Airlines
Deal found 12/14$284
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/257:30 amDCA - ORD
Nonstop2h 22mUnited Airlines
Tue 1/67:00 amORD - DCA
Nonstop1h 58mUnited Airlines
Deal found 12/15$297
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/312:00 pmDCA - ORD
1 stop5h 46mMultiple Airlines
Sun 1/47:00 amORD - DCA
1 stop29h 01mMultiple Airlines
Deal found 12/17$302
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.
Wed 12/316:10 amDCA - ORD
1 stop7h 50mSouthwest
Sun 1/45:15 pmORD - DCA
1 stop5h 40mSouthwest
Deal found 12/14$306
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/318:00 amDCA - ORD
1 stop17h 12mFrontier
Sun 1/47:00 amORD - DCA
1 stop29h 01mFrontier
Deal found 12/17$317

Find flight deals from Reagan-National to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Reagan-National (DCA) 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, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$168
(Expedia)

One-way from

$70
(Expedia)

Popular in

December

Cheapest in

February

Average price

$379

Good round-trip deal

$317 or less

Good one-way deal

$177 or less
Provider with most accurate pricing for Washington, D.C. Reagan-National-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Washington, D.C. Reagan-National-Chicago (CHI) flights.
Search Deals
From Washington, D.C. Reagan-National to Chicago (CHI)
Search Deals
One-way flight from Washington, D.C. Reagan-National to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 15% potential increase in price ($56 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($7 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 Washington, D.C. Reagan-National to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Washington, D.C. Reagan-National to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Reagan-National 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, 2025.
Use the filters below to find and compare flights from Washington, D.C. Reagan-National Airport to Chicago that are best for you.

Fly from

Reagan-National

Fly to

Chicago

Route

Depart

Return

Price

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Thu 1/29

10:05 am-5:43 pm

1 stop8h 38m

Chicago O'Hare Intl

Tue 2/3

7:45 am-2:29 pm

1 stop5h 44m

$197

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Fri 2/6

11:55 am-5:44 pm

1 stop6h 49m

Chicago O'Hare Intl

Mon 2/9

7:45 am-4:19 pm

1 stop7h 34m

$197

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Wed 1/7

11:55 am-5:43 pm

1 stop6h 48m

Chicago O'Hare Intl

Sun 1/11

7:45 am-5:34 pm

1 stop8h 49m

$197

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 1/30

11:55 am-5:43 pm

1 stop6h 48m

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

Thu 1/8

1:00 pm-5:43 pm

1 stop5h 43m

Chicago O'Hare Intl

Mon 1/12

6:45 am-1:20 pm

1 stop5h 35m

$197

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Mon 5/11

11:30 am-7:26 pm

1 stop8h 56m

Chicago O'Hare Intl

Fri 5/15

3:15 pm-10:59 pm

1 stop6h 44m

$207

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Sat 1/17

7:00 pm-8:25 pm

Nonstop2h 25m

Chicago O'Hare Intl

Sun 1/18

6:00 am-8:59 am

Nonstop1h 59m

$223

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Tue 1/13

6:05 am-7:20 am

Nonstop2h 15m

Chicago Midway

Sun 1/18

12:10 pm-2:55 pm

Nonstop1h 45m

$227

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

Showing 1-10 of 48 results
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Compare providers for flights from Reagan-National 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 Reagan-National to Chicago in December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

*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. Reagan-National Airport-Chicago flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Washington, D.C. Reagan-National Airport-Chicago flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Washington, D.C. Reagan-National Airport-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Washington, D.C. Reagan-National Airport-Chicago flights, Cheapflights users trust eDreams the most. eDreams 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. Reagan-National Airport-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 Reagan-National to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Reagan-National 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 Washington, D.C. Reagan-National Airport to Chicago

How far ahead should I book a flight from Washington, D.C. Reagan-National Airport to Chicago?

Use this chart to determine the optimal time to book a round-trip flight from Reagan-National to Chicago. Price data was last updated on December 12, 2025.

The best time to book flights from Washington, D.C. Reagan-National Airport to Chicago is 69 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

What is the cheapest month to book a flight from Washington, D.C. Reagan-National Airport to Chicago?

Currently, November is the cheapest month in which you can book a flight from Washington, D.C. Reagan-National Airport to Chicago (average of $98). Flying from Washington, D.C. Reagan-National Airport to Chicago in December is currently the most expensive (average of $222). 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 DCA to CHI?

Find hourly flight availability from Reagan-National 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, 2025.

It’s typically best to fly out from Washington, D.C. Reagan-National Airport to Chicago in the evening. Doing so could potentially save you 16% on the flight price compared to flying in the afternoon, which is usually more expensive.

What is the cheapest day to fly from Washington, D.C. Reagan-National Airport to Chicago?

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

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

The best insider tips for Washington, D.C. Reagan-National Airport to Chicago flights

AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Washington, D.C. Reagan-National Airport to Chicago trip
Airports
DCA

Reserve parking online at DCA to ensure availability, especially during busy times. Parking Garage 1 serves Terminal 1, and Garage 2 serves Terminal 2.

Read more about DCABy Emily Zemler
ORD

Take the “L” train from ORD to avoid traffic and reach downtown Chicago efficiently.

Read more about ORDBy Ramsey Qubein
MDW

Use the Orange Line train for a quick, affordable trip from MDW to downtown Chicago in under 30 minutes.

Read more about MDWBy Ramsey Qubein
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on ORD and MDW

Ramsey Qubein

Ramsey Qubein

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more
Emily Zemler

Emily Zemler

Expert on DCA

Emily Zemler

Emily Zemler

Emily is a freelance writer and book author based in London covering entertainment and travel. Her work has appeared in Los Angeles Times, Observer, and Conde Nast Traveler She has ventured to more than 40 countries and all seven continents, always in search of a great art museum. She has written extensively about hotels, luxury travel, and aviation.

Read more

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, 2025.
Get a feel of what it's like to fly with Southwest, United Airlines, and American Airlines from Washington, D.C. Reagan-National Airport to Chicago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
7.9
Good
4,250 reviews

Entertainment

7.5

Boarding

8.1

Overall

7.9

Food

7.0

Crew

8.6

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
7.9
Good
4,250 reviews
Southwest
7.9
Good
4,250 reviews

Entertainment

7.5

Boarding

8.1

Overall

7.9

Food

7.0

Crew

8.6

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
United Airlines
7.4
Good
9,093 reviews
Southwest
7.9
Good
4,250 reviews

Entertainment

7.5

Boarding

8.1

Overall

7.9

Food

7.0

Crew

8.6

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
American Airlines
7.2
Good
11,055 reviews
Southwest
7.9
Good
4,250 reviews

Entertainment

7.5

Boarding

8.1

Overall

7.9

Food

7.0

Crew

8.6

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Frontier
5.8
Fair
3,081 reviews
Southwest
7.9
Good
4,250 reviews

Entertainment

7.5

Boarding

8.1

Overall

7.9

Food

7.0

Crew

8.6

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Related info for your journey

Find useful and relevant information for your journey from Reagan-National 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 Washington, D.C. Reagan-National Airport to Chicago?

    Departing from Washington, D.C. Reagan-National Airport to Chicago will take you 2h 15m. Airlines will cover a distance of 599 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines flying from Washington, D.C. Reagan-National Airport to Chicago round-trip?

    Flying on Frontier is currently your cheapest option to Chicago, with prices starting at $98. Additional round-trip tickets that might be worth considering are offered by American Airlines and Southwest, with the lowest prices starting at $168 and $178, respectively. Frontier is 68% 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. Reagan-National Airport to Chicago one-way?

    The cheapest airlines for a one-way flight from Washington, D.C. Reagan-National Airport to Chicago are Frontier ($16), Southwest ($88), and American Airlines ($89).

  • What are the most popular routes from Washington, D.C. Reagan-National Airport to Chicago?

    The most popular flight routes from Washington, D.C. Reagan-National Airport to Chicago are Washington, D.C. Reagan-National - Chicago O'Hare Intl, Washington, D.C. Reagan-National - Chicago Midway and Washington, D.C. Reagan-National - Chicago Greater Rockford.

  • What are the most reliable airlines from Washington, D.C. Reagan-National Airport to Chicago?

    Before booking your flight to Chicago from Washington, D.C. Reagan-National Airport, check out the most reliable airlines to get you to your destination on time: Envoy Air (87%), Royal Jordanian (78%), ANA( 77%).

  • What are the cheapest flights from Washington, D.C. Reagan-National Airport to Chicago?

    While on average a flight from Washington, D.C. Reagan-National Airport to Chicago is generally $838, our data shows the cheapest flight currently is $132. When looking at the most popular route, (Washington, D.C. Reagan-National - Chicago O'Hare Intl), you can expect to pay $173 for that flight.

  • Can I find deals for flights from Reagan-National to Chicago that include hotel bookings?

    Yes. In addition to deals on Reagan-National to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Reagan-National to Chicago?

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

  • Can I find deals for business class flights from Reagan-National to Chicago?

    Yes. Cheapflights offers flight deals from Reagan-National 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. Reagan-National Airport to Chicago?

    Currently, November is the cheapest month in which you can book a flight from Washington, D.C. Reagan-National Airport to Chicago (average of $98). Flying from Washington, D.C. Reagan-National Airport to Chicago in December is currently the most expensive (average of $222). 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 Reagan-National to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Reagan-National to O'Hare Intl flights
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Top 4 airlines flying from Reagan-National to Chicago

Discover the top 4 airlines that operate flights from Reagan-National 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, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$98Average$167FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$168Average$298FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$178Average$306FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$199Average$323FlexibilityNo cancel feeOn-time69%

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