HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$99+ 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 7/28. Fares are subject to change and may not be available on all flights or dates of travel.
DCA — CHI
Aug 1 — Aug 81
Sat 8/1
Sat 8/8
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

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

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.
Cheapflights Tip: The best prices from Washington, D.C. Reagan-National to Chicago are usually found in September or October, booked 79 days in advance, depart on a Saturday or Thursday and return on a Saturday

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 July 2, 2026.

This JetBlue deal was found by Cheapflights users on 7/1. 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.
Thu 8/2011:00 am
DCA
-
ORD
1 stop9h 27m
JetBlue
Mon 8/248:20 pm
ORD
-
DCA
1 stop10h 38m
JetBlue
Deal found 7/1$246
This American Airlines deal was found by Cheapflights users on 7/1. 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 8/18:06 pm
DCA
-
ORD
Nonstop2h 36m
American Airlines
Mon 8/35:07 am
ORD
-
DCA
1 stop4h 43m
American Airlines
Deal found 7/1$247
This Southwest deal was found by Cheapflights users on 7/1. 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 7/299:30 am
DCA
-
MDW
Nonstop1h 55m
Southwest
Mon 8/37:15 am
MDW
-
DCA
1 stop4h 15m
Southwest
Deal found 7/1$247
This JetBlue deal was found by Cheapflights users on 7/1. 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.
Wed 7/2211:00 am
DCA
-
ORD
1 stop9h 15m
JetBlue
Tue 7/2810:56 am
ORD
-
DCA
1 stop7h 02m
JetBlue
Deal found 7/1$248
This Delta deal was found by Cheapflights users on 6/29. 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.
Wed 10/146:00 am
DCA
-
MDW
1 stop4h 52m
Delta
Thu 10/156:45 pm
MDW
-
DCA
1 stop3h 24m
Delta
Deal found 6/29$248
This Kiwi.com deal was found by Cheapflights users on 6/28. 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 8/141:59 pm
DCA
-
ORD
1 stop7h 53m
Frontier
Mon 8/179:57 pm
ORD
-
DCA
1 stop23h 02m
Frontier
Deal found 6/28$249
This Southwest deal was found by Cheapflights users on 6/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/271:00 pm
DCA
-
MDW
2 stops5h 50m
Southwest
Mon 8/318:55 am
MDW
-
DCA
Nonstop1h 55m
Southwest
Deal found 6/28$249
This Frontier deal was found by Cheapflights users on 7/2. 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 9/111:59 pm
DCA
-
ORD
1 stop8h 36m
Frontier
Sun 9/1311:06 am
ORD
-
DCA
1 stop9h 52m
Frontier
Deal found 7/2$250
This Orbitz deal was found by Cheapflights users on 6/28. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/227:00 am
DCA
-
ORD
1 stop14h 52m
Frontier
Sun 7/269:57 pm
ORD
-
DCA
1 stop13h 54m
Frontier
Deal found 6/28$251
This Expedia deal was found by Cheapflights users on 6/30. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/32:20 pm
DCA
-
ORD
1 stop6h 05m
JetBlue
Wed 8/510:56 am
ORD
-
DCA
1 stop6h 04m
JetBlue
Deal found 6/30$252
This Southwest deal was found by Cheapflights users on 7/1. 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 8/156:10 am
DCA
-
MDW
Nonstop1h 55m
Southwest
Sat 8/1510:05 am
MDW
-
DCA
2 stops9h 45m
Southwest
Deal found 7/1$252
This American Airlines deal was found by Cheapflights users on 7/1. 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.
Fri 8/75:00 am
DCA
-
ORD
1 stop5h 00m
American Airlines
Tue 8/115:55 pm
ORD
-
DCA
Nonstop2h 04m
American Airlines
Deal found 7/1$253

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 July 2, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$245
(United Airlines)

One-way from

$99
(Delta)

Popular in

June

Cheapest in

September

Average price

$349

Good round-trip deal

$293 or less

Good one-way deal

$166 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. 10% potential increase in price ($38 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
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 July 2, 2026.
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

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Thu 8/20

11:00 am-7:27 pm

1 stop9h 27m

Chicago O'Hare Intl

Thu 8/27

11:01 am-7:05 pm

1 stop7h 04m

$248

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Thu 9/17

9:15 pm-10:10 pm

Nonstop1h 55m

Chicago Midway

Mon 9/21

8:10 am-2:10 pm

1 stop5h 00m

$255

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Tue 7/28

7:15 am-8:28 am

Nonstop2h 13m

Chicago O'Hare Intl

Tue 7/28

6:00 pm-9:10 pm

Nonstop2h 10m

$257

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Tue 9/1

8:10 pm-9:30 pm

Nonstop2h 20m

Chicago O'Hare Intl

Wed 9/2

2:00 pm-5:09 pm

Nonstop2h 09m

$257

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Wed 9/2

5:29 pm-8:30 pm

1 stop4h 01m

Chicago O'Hare Intl

Fri 9/4

5:20 pm-10:59 pm

1 stop4h 39m

$263

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Thu 8/20

12:15 pm-3:25 pm

1 stop4h 10m

Chicago Midway

Mon 8/24

5:30 am-1:40 pm

1 stop7h 10m

$265

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Wed 10/14

6:30 am-11:47 am

1 stop6h 17m

Chicago O'Hare Intl

Thu 10/15

2:15 pm-9:00 pm

1 stop5h 45m

$270
Quickest round-trip

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Thu 8/6

7:25 am-8:20 am

Nonstop1h 55m

Chicago Midway

Thu 8/6

2:05 pm-4:55 pm

Nonstop1h 50m

$271

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Thu 7/30

11:57 am-1:15 pm

Nonstop2h 18m

Chicago O'Hare Intl

Sat 8/1

7:00 am-9:59 am

Nonstop1h 59m

$273

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Fri 10/16

1:05 pm-2:05 pm

Nonstop2h 00m

Chicago Midway

Mon 10/19

8:50 am-11:35 am

Nonstop1h 45m

$277

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/29

Showing 1-10 of 51 resultsSorted by cheapest first
1
2
3
...
6

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 July.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Washington, D.C. Reagan-National Airport-Chicago flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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

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

Currently, January is the cheapest month in which you can book a flight from Washington, D.C. Reagan-National Airport to Chicago (average of $29). Flying from Washington, D.C. Reagan-National Airport to Chicago in June is currently the most expensive (average of $790). 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 July 2, 2026.

It’s typically best to fly out from Washington, D.C. Reagan-National Airport to Chicago at noon. Doing so could potentially save you 5% on the flight price compared to flying in the afternoon, which is usually more expensive.

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 July 2, 2026.

The most flights from DCA to CHI are scheduled on a Thursday (70 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (10 on average).

How much does it cost to fly round-trip 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?

The best time to book flights from Washington, D.C. Reagan-National Airport to Chicago is 47 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 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 June 27, 2026.

Travelers seeking maximum savings on their Washington, D.C. Reagan-National Airport to Chicago flight should consider departing on Monday at noon when fares are most often at their lowest. Sunday evenings 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
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on ORD and MDW

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 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 July 2, 2026.
Get a feel of what it's like to fly with Southwest,United Airlines, andAmerican 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
4,249 reviews

Entertainment

7.5

Crew

8.6

Food

7.0

Overall

7.9

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
Southwest
7.9
Good
4,249 reviews
Southwest
7.9
Good
4,249 reviews

Entertainment

7.5

Crew

8.6

Food

7.0

Overall

7.9

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
United Airlines
7.4
Good
9,926 reviews
Southwest
7.9
Good
4,249 reviews

Entertainment

7.5

Crew

8.6

Food

7.0

Overall

7.9

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
American Airlines
7.1
Good
11,770 reviews
Southwest
7.9
Good
4,249 reviews

Entertainment

7.5

Crew

8.6

Food

7.0

Overall

7.9

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

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 1h 55m. 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 $29. Additional round-trip tickets that might be worth considering are offered by American Airlines and Southwest, with the lowest prices starting at $182 and $213, respectively. Frontier is 91% 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 American Airlines ($98), Southwest ($98), and United Airlines ($115).

  • 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 (100%), Republic Airways (89%), Cathay Pacific( 84%).

  • 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 $1,621, our data shows the cheapest flight currently is $101. When looking at the most popular route, (Washington, D.C. Reagan-National - Chicago O'Hare Intl), you can expect to pay $177 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, January is the cheapest month in which you can book a flight from Washington, D.C. Reagan-National Airport to Chicago (average of $29). Flying from Washington, D.C. Reagan-National Airport to Chicago in June is currently the most expensive (average of $790). 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
Benton Harbor
Hammond
Lansing
Merrillville
Valparaiso
Porter

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.

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 July 2, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$29Average$130FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$182Average$344FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$213Average$356FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$223Average$384FlexibilityNo cancel feeOn-time69%

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.