Chicago

$86+ 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 7/4. Fares are subject to change and may not be available on all flights or dates of travel.
DCA — CHI
May 6 — May 131
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Find cheap flights from Reagan-National 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

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Cheapflights Tip: The best prices from Washington, D.C. Reagan-National to Chicago are usually found in September or February, booked 35 days in advance, depart on a Wednesday or Friday and return on a Thursday

Cheap 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 May 1, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$195
(American Airlines)

One-way from

$86
(Southwest)

Popular in

April

Cheapest in

September

Average price

$307

Good round-trip deal

$258 or less

Good one-way deal

$160 or less
Provider with most accurate pricing for Washington, D.C. Reagan-National-Chicago (CHI) flight deals.
Provider most trusted by Cheapflights users for Washington, D.C. Reagan-National-Chicago (CHI) flights.
From Washington, D.C. Reagan-National to Chicago (CHI)
One-way flight from Washington, D.C. Reagan-National to Chicago (CHI)
Highest demand for flights based on searches. 3% potential increase in price ($10 potential increase over avg. RT price).
Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
Average for round-trip flights in May 2025
Price to beat on a round-trip flight from Washington, D.C. Reagan-National to Chicago (CHI).
Price to beat on a one-way flight from Washington, D.C. Reagan-National to Chicago (CHI).

Find 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 May 1, 2025.

This Southwest deal was found by Cheapflights users on 4/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/246:50 pmDCA - MDW
1 stop4h 00mSouthwest
Sun 5/259:20 amMDW - DCA
1 stop4h 40mSouthwest
Deal found 4/29$181
This CheapOair deal was found by Cheapflights users on 4/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/117:00 amDCA - MDW
1 stop13h 08mFrontier
Thu 5/158:03 pmMDW - DCA
1 stop19h 56mFrontier
Deal found 4/29$191
This American Airlines deal was found by Cheapflights users on 4/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/512:10 pmDCA - ORD
Nonstop2h 19mAmerican Airlines
Thu 7/108:05 amORD - DCA
Nonstop1h 50mAmerican Airlines
Deal found 4/30$195
This Delta deal was found by Cheapflights users on 4/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/246:05 amDCA - ORD
1 stop6h 42mDelta
Sun 5/255:30 amORD - DCA
1 stop6h 13mDelta
Deal found 4/30$197
This Delta deal was found by Cheapflights users on 4/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/19:39 amDCA - MDW
1 stop3h 50mDelta
Thu 7/31:09 pmMDW - DCA
1 stop4h 50mDelta
Deal found 4/29$197
This JetBlue deal was found by Cheapflights users on 4/30. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/56:30 amDCA - ORD
1 stop5h 48mJetBlue
Wed 7/98:40 amORD - DCA
1 stop5h 05mJetBlue
Deal found 4/30$202
This United Airlines deal was found by Cheapflights users on 4/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/306:25 amDCA - ORD
Nonstop2h 14mUnited Airlines
Mon 6/24:00 pmORD - DCA
Nonstop2h 02mUnited Airlines
Deal found 4/30$204
This Frontier deal was found by Cheapflights users on 4/29. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/21:00 pmDCA - ORD
1 stop11h 59mFrontier
Sat 6/76:00 amORD - DCA
1 stop9h 57mFrontier
Deal found 4/29$208
This Southwest deal was found by Cheapflights users on 4/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/286:05 amDCA - ORD
2 stops11h 20mSouthwest
Sun 8/319:30 amORD - DCA
1 stop6h 45mSouthwest
Deal found 4/30$236

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 May 1, 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 - MDW

DCAMDW

Washington, D.C. Reagan-National

Sat 5/24

6:50 pm-9:50 pm

1 stop4h 00m

Chicago Midway

Sun 5/25

9:20 am-3:00 pm

1 stop4h 40m

$181

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Sun 5/11

7:00 am-7:08 pm

1 stop13h 08m

Chicago Midway

Thu 5/15

8:03 pm-4:59 pm

1 stop19h 56m

$191

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Sat 7/5

12:10 pm-1:29 pm

Nonstop2h 19m

Chicago O'Hare Intl

Thu 7/10

8:05 am-10:55 am

Nonstop1h 50m

$195

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Sat 5/24

6:00 am-9:18 am

1 stop4h 18m

Chicago O'Hare Intl

Sat 5/24

5:15 pm-10:10 pm

1 stop3h 55m

$197

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Tue 7/1

9:39 am-12:29 pm

1 stop3h 50m

Chicago Midway

Thu 7/3

1:09 pm-6:59 pm

1 stop4h 50m

$197

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Sat 7/5

6:30 am-11:18 am

1 stop5h 48m

Chicago O'Hare Intl

Wed 7/9

8:40 am-2:45 pm

1 stop5h 05m

$202

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Fri 5/30

6:25 am-7:39 am

Nonstop2h 14m

Chicago O'Hare Intl

Mon 6/2

4:00 pm-7:02 pm

Nonstop2h 02m

$204

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Mon 6/2

1:00 pm-11:59 pm

1 stop11h 59m

Chicago O'Hare Intl

Sat 6/7

6:00 am-4:57 pm

1 stop9h 57m

$208

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Thu 8/28

6:05 am-4:25 pm

2 stops11h 20m

Chicago O'Hare Intl

Sun 8/31

9:30 am-5:15 pm

1 stop6h 45m

$236

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Fri 7/4

3:00 pm-6:30 pm

1 stop4h 30m

$86

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

Showing 1-10 of 21 results
1
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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 May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy2 starsTrust Score*3 stars
MytripPrice Accuracy3 starsTrust 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. Reagan-National Airport-Chicago flights, users find the pricing of Mytrip to be most consistent on Cheapflights vs. Mytrip Users can find the same prices on Washington, D.C. Reagan-National Airport-Chicago flight deals on Cheapflights vs. Mytrip >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 Mytrip the most. Mytrip 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.

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

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your Washington, D.C. Reagan-National Airport to Chicago trip
Airlines
United Airlines

Basic Economy allows a personal item only; no carry-on bags unless exceptions apply.


Prepay checked bags 24 hours before to save on fees.

Southwest

Enjoy free snacks and non-alcoholic drinks, with alcoholic options available for purchase.


Two free checked bags are included, even oversized items like skis or golf clubs.

Airports
DCA

Reserve parking in advance at DCA to ensure a spot, as lots fill up quickly, especially during busy travel times.

Read more about DCAby Emily Zemler
ORD

For a quick city transfer, take the 'L' train from ORD to downtown Chicago, avoiding potential traffic delays.

Read more about ORDby Ramsey Qubein
MDW

Use the Orange Line 'L' train for a fast and affordable trip from MDW to downtown Chicago, taking under 30 minutes.

Read more about MDWby Ramsey Qubein
Our travel experts
Harriet Baskas

Harriet Baskas

Expert on United Airlines

Harriet Baskas

Harriet Baskas

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Read more
Marisa Garcia

Marisa Garcia

Expert on Southwest

Marisa Garcia

Marisa Garcia

Marisa knows planes inside and out, spending 16 years working on aircraft in hangars at airports around the world. She is an aviation industry expert, specialized in airline interiors and regulations. Ten years ago, she pivoted to journalism. She shares her insights in leading aviation, travel, and business publications and on her site FlightChic.

Read more
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

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 April 25, 2025.

The best time to book flights from Washington, D.C. Reagan-National Airport to Chicago is 35 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, August is the cheapest month in which you can book a flight from Washington, D.C. Reagan-National Airport to Chicago (average of $245). Flying from Washington, D.C. Reagan-National Airport to Chicago in March is currently the most expensive (average of $321). 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 May 1, 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 21% on the flight price compared to flying at noon, 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 March 30, 2025.

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

Weekly flight availability from Washington, D.C. Reagan-National Airport to Chicago

Explore weekly flight availability from Reagan-National 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 May 1, 2025.

The most flights from DCA to CHI are scheduled on a Thursday (52 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (14 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 May 1, 2025.
Read through reviews of airlines operating flights from Washington, D.C. to Chicago, such as Southwest, Delta and United Airlines. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.

Overall

8.0

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Food

7.1

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

Overall

8.0

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Food

7.1

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
8.0
Very good

Overall

8.0

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Food

7.1

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

Overall

8.0

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Food

7.1

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

Overall

8.0

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Food

7.1

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

Overall

8.0

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Food

7.1

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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

    Flying on American Airlines is currently your cheapest option to Chicago, with prices starting at $195. Additional round-trip tickets that might be worth considering are offered by Southwest and Delta, with the lowest prices starting at $195 and $197, respectively. American Airlines is 36% 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 Southwest ($86), United Airlines ($90), and American Airlines ($91).

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

  • 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: Japan Airlines (90%), Republic Airways (89%), ANA( 89%).

  • 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 $650, our data shows the cheapest flight currently is $89. When looking at the most popular route, (Washington, D.C. Reagan-National - Chicago O'Hare Intl), you can expect to pay $195 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, August is the cheapest month in which you can book a flight from Washington, D.C. Reagan-National Airport to Chicago (average of $245). Flying from Washington, D.C. Reagan-National Airport to Chicago in March is currently the most expensive (average of $321). 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 Washington, D.C. Reagan-National Airport?

Book flights to Washington, D.C. Reagan-National Airport if you plan to visit one of these locations
Merrillville
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$101Average$223FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$170Average$304FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$177Average$312FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$193Average$332FlexibilityNo cancel feeOn-time69%

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