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$90+ 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 2/19. Fares are subject to change and may not be available on all flights or dates of travel.
DCA — CHI
Jan 26 — Feb 21
Sun 1/26
Sun 2/2
1 adult, Economy
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The best prices from Washington, D.C. Reagan-National to Chicago are usually found in September or February, booked 33 days in advance, depart on a Saturday or Wednesday and return on a Saturday

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 January 21, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$179
(American Airlines)

One-way from

$90
(United Airlines)

Popular in

December

Cheapest in

September

Average price

$299
Provider with most accurate pricing for Washington, D.C. Reagan-National-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Washington, D.C. Reagan-National-Chicago (CHI) flights.
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From Washington, D.C. Reagan-National to Chicago (CHI)
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One-way flight from Washington, D.C. Reagan-National to Chicago (CHI)
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High demand for flights, 3% potential price rise
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Best time to find cheap flights, 1% potential price drop
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Average for round-trip flights in January 2025
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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 January 21, 2025.

This American Airlines deal was found by Cheapflights users on 1/20. 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 2/128:45 pmDCA - ORD
Nonstop2h 19mAmerican Airlines
Wed 2/191:43 pmORD - DCA
Nonstop1h 46mAmerican Airlines
Deal found 1/20$179
This eDestinos deal was found by Cheapflights users on 1/19. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/196:00 pmDCA - MDW
1 stop7h 17mFrontier
Sat 2/226:40 amMDW - DCA
1 stop14h 19mFrontier
Deal found 1/19$179
This Frontier deal was found by Cheapflights users on 1/20. 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.
Sat 3/17:00 amDCA - ORD
1 stop11h 25mFrontier
Wed 3/56:50 amORD - DCA
1 stop9h 09mFrontier
Deal found 1/20$180
This JetBlue deal was found by Cheapflights users on 1/20. 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.
Tue 4/87:00 amDCA - ORD
1 stop6h 27mJetBlue
Wed 4/99:43 amORD - DCA
1 stop6h 15mJetBlue
Deal found 1/20$183
This Southwest deal was found by Cheapflights users on 1/19. 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.
Tue 2/1811:55 amDCA - MDW
Nonstop2h 10mSouthwest
Tue 2/253:15 pmMDW - DCA
Nonstop1h 45mSouthwest
Deal found 1/19$189
This United Airlines deal was found by Cheapflights users on 1/19. 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 2/2010:35 amDCA - ORD
Nonstop2h 30mUnited Airlines
Thu 2/2711:15 amORD - DCA
Nonstop1h 54mUnited Airlines
Deal found 1/19$199
This Southwest deal was found by Cheapflights users on 1/20. 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 2/1511:10 amDCA - ORD
1 stop6h 35mSouthwest
Sat 2/227:00 amORD - DCA
1 stop7h 05mSouthwest
Deal found 1/20$208
This Delta deal was found by Cheapflights users on 1/20. 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 2/127:30 amDCA - MDW
1 stop5h 29mDelta
Wed 2/196:28 pmMDW - DCA
1 stop3h 55mDelta
Deal found 1/20$217
This Delta deal was found by Cheapflights users on 1/19. 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 2/226:00 amDCA - ORD
1 stop4h 16mDelta
Mon 2/242:59 pmORD - DCA
1 stop4h 37mDelta
Deal found 1/19$218

Find flights from Reagan-National to Chicago within your budget

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 January 21, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Tue 3/4

2:54 pm-4:15 pm

Nonstop2h 21m

Chicago O'Hare Intl

Tue 3/4

8:20 pm-11:09 pm

Nonstop1h 49m

$177

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Sat 2/22

6:05 am-7:15 am

Nonstop2h 10m

Chicago Midway

Mon 2/24

6:25 am-9:15 am

Nonstop1h 50m

$178

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Wed 2/19

6:00 pm-12:17 am

1 stop7h 17m

Chicago Midway

Sat 2/22

6:40 am-9:59 pm

1 stop14h 19m

$179

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Sat 2/22

7:00 am-5:25 pm

1 stop11h 25m

Chicago O'Hare Intl

Mon 2/24

6:50 am-12:03 pm

1 stop28h 13m

$180

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Tue 4/8

7:00 am-12:27 pm

1 stop6h 27m

Chicago O'Hare Intl

Wed 4/9

9:43 am-4:58 pm

1 stop6h 15m

$183

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Wed 4/9

12:28 pm-6:19 pm

1 stop6h 51m

Chicago O'Hare Intl

Tue 4/22

4:56 pm-10:51 pm

1 stop4h 55m

$197

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Mon 3/3

9:55 am-1:05 pm

1 stop4h 10m

Chicago Midway

Wed 3/5

2:08 pm-8:00 pm

1 stop4h 52m

$197

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Thu 2/20

10:35 am-12:05 pm

Nonstop2h 30m

Chicago O'Hare Intl

Thu 2/27

11:15 am-2:09 pm

Nonstop1h 54m

$199

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Sat 2/22

6:00 am-4:45 pm

2 stops11h 45m

Chicago O'Hare Intl

Mon 2/24

7:30 am-6:05 pm

1 stop9h 35m

$274

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Sat 2/22

8:30 am-9:51 am

Nonstop2h 21m

$90

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/20

Showing 1-10 of 18 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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 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 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.

Travel insights for flights from Reagan-National to Chicago

Get recent, data-driven insights about flights from Reagan-National to Chicago including ideal travel times, pricing trends, and more.

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 January 17, 2025.

The best time to book flights from Washington, D.C. Reagan-National Airport to Chicago is 33 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 $320). 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 January 21, 2025.

It’s typically best to fly out from Washington, D.C. Reagan-National Airport to Chicago in the morning. Doing so could potentially save you 12% 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 16, 2024.

Travelers seeking maximum savings on their Washington, D.C. Reagan-National Airport to Chicago flight should consider departing on Saturday evenings when fares are most often at their lowest. Tuesday evenings 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 January 21, 2025.

The most flights from DCA to CHI are scheduled on a Wednesday (53 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (32 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 January 21, 2025.
Read through reviews of airlines operating flights from Washington, D.C. to Chicago, such as JetBlue, United Airlines and Frontier. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,659 reviews

Overall

8.1

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Crew

8.7

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,659 reviews
Southwest
8.1
Very good
4,659 reviews

Overall

8.1

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Crew

8.7

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,521 reviews
Southwest
8.1
Very good
4,659 reviews

Overall

8.1

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Crew

8.7

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

JetBlue
7.4
Good
3,201 reviews
Southwest
8.1
Very good
4,659 reviews

Overall

8.1

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Crew

8.7

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

United Airlines
7.4
Good
8,982 reviews
Southwest
8.1
Very good
4,659 reviews

Overall

8.1

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Crew

8.7

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,659 reviews

Overall

8.1

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Crew

8.7

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 $179. Additional round-trip tickets that might be worth considering are offered by Frontier and JetBlue, with the lowest prices starting at $179 and $183, respectively. American Airlines is 42% 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 United Airlines ($90), Southwest ($90), and Frontier ($91).

  • 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: Japan Airlines (91%), Republic Airways (91%), 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 $1,049, our data shows the cheapest flight currently is $114. When looking at the most popular route, (Washington, D.C. Reagan-National - Chicago O'Hare Intl), you can expect to pay $179 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 $320). 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
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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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.
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Dulles Intl to Dubuque flights
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Top 5 airlines flying from Reagan-National to Chicago

Discover the top 5 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 January 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$101Average$219FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$159Average$327FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$162Average$309FlexibilityNo cancel feeOn-time71%
DeltaCheapest$175Average$276FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$189Average$345FlexibilityNo cancel feeOn-time69%
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