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$89+ 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 8/12. Fares are subject to change and may not be available on all flights or dates of travel.
DCA — CHI
jun. 17 — jun. 241
mar. 6/17
mar. 6/24
1 adult, Economy
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Cheapflights Tip: The best prices from Washington, D.C. Reagan-National to Chicago are usually found in September or February, booked 35 days in advance, depart on a Friday or Thursday 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 junio 12, 2025.

Round-trip from

$167
(United Airlines)

One-way from

$89
(Southwest)

Popular in

December

Cheapest in

September

Average price

$299

Good round-trip deal

$256 or less

Good one-way deal

$150 or less
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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Highest demand for flights based on searches. 8% potential increase in price ($29 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in June 2025
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Price to beat on a round-trip flight from Washington, D.C. Reagan-National to Chicago (CHI).
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Price to beat on a one-way flight from Washington, D.C. Reagan-National to Chicago (CHI).
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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 junio 12, 2025.

This Southwest deal was found by Cheapflights users on 6/11. 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.
lun. 10/276:00 amDCA - MDW
Nonstop2h 00mSouthwest
mar. 10/287:40 amMDW - DCA
1 stop4h 10mSouthwest
Deal found 6/11$163
This United Airlines deal was found by Cheapflights users on 6/11. 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.
jue. 8/146:25 amDCA - ORD
Nonstop2h 14mUnited Airlines
mar. 8/198:50 amORD - DCA
1 stop4h 32mUnited Airlines
Deal found 6/11$167
This American Airlines deal was found by Cheapflights users on 6/10. 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.
mié. 8/272:15 pmDCA - ORD
Nonstop2h 13mAmerican Airlines
dom. 8/316:06 amORD - DCA
Nonstop1h 54mAmerican Airlines
Deal found 6/10$168
This Southwest deal was found by Cheapflights users on 6/11. 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.
mié. 8/132:10 pmDCA - ORD
1 stop8h 20mSouthwest
mié. 8/203:10 pmORD - DCA
1 stop6h 50mSouthwest
Deal found 6/11$177
This Delta deal was found by Cheapflights users on 6/10. 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.
mié. 8/1310:11 amDCA - ORD
1 stop5h 08mDelta
lun. 8/185:00 pmORD - DCA
1 stop4h 59mDelta
Deal found 6/10$197
This Delta deal was found by Cheapflights users on 6/9. 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.
mar. 8/510:19 amDCA - MDW
1 stop6h 51mDelta
lun. 8/1112:43 pmMDW - DCA
1 stop7h 03mDelta
Deal found 6/9$197
This JetBlue deal was found by Cheapflights users on 6/9. 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.
dom. 9/146:25 amDCA - ORD
1 stop6h 45mJetBlue
vie. 9/191:36 pmORD - DCA
1 stop8h 20mJetBlue
Deal found 6/9$208
This Frontier deal was found by Cheapflights users on 6/10. 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.
dom. 8/241:00 pmDCA - ORD
1 stop12h 31mFrontier
jue. 8/2811:44 amORD - DCA
1 stop9h 15mFrontier
Deal found 6/10$321
This Frontier deal was found by Cheapflights users on 6/12. 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.
sáb. 6/281:00 pmDCA - MDW
1 stop8h 53mFrontier
lun. 6/3012:35 pmMDW - DCA
1 stop8h 24mFrontier
Deal found 6/12$328

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 junio 12, 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

jue. 8/14

6:25 am-7:39 am

Nonstop2h 14m

Chicago O'Hare Intl

mar. 8/19

8:50 am-2:22 pm

1 stop4h 32m

$167

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

jue. 8/14

9:00 pm-10:00 pm

Nonstop2h 00m

Chicago Midway

mar. 8/19

9:55 am-2:25 pm

1 stop3h 30m

$167

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

mié. 8/27

2:15 pm-3:28 pm

Nonstop2h 13m

Chicago O'Hare Intl

dom. 8/31

6:06 am-9:00 am

Nonstop1h 54m

$168

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

mié. 8/13

2:10 pm-9:30 pm

1 stop8h 20m

Chicago O'Hare Intl

mié. 8/20

3:10 pm-11:00 pm

1 stop6h 50m

$177

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

mié. 8/13

10:11 am-2:19 pm

1 stop5h 08m

Chicago O'Hare Intl

lun. 8/18

5:00 pm-10:59 pm

1 stop4h 59m

$197

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

mar. 8/5

9:39 am-12:29 pm

1 stop3h 50m

Chicago Midway

mar. 8/5

6:20 pm-10:59 pm

1 stop3h 39m

$197

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

vie. 7/11

10:30 am-3:32 pm

1 stop6h 02m

Chicago O'Hare Intl

mar. 7/15

8:40 am-3:03 pm

1 stop5h 23m

$272

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

dom. 8/24

1:00 pm-12:31 am

1 stop12h 31m

Chicago O'Hare Intl

jue. 8/28

11:44 am-9:59 pm

1 stop9h 15m

$321

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

sáb. 6/28

1:00 pm-8:53 pm

1 stop8h 53m

Chicago Midway

lun. 6/30

12:35 pm-9:59 pm

1 stop8h 24m

$328

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

mar. 8/12

6:00 am-12:45 pm

1 stop7h 45m

$89

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

Showing 1-10 of 19 results
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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.

Read more about United Airlinesby Harriet Baskas
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.

Read more about Southwestby Marisa Garcia
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
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 June 9, 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 junio 12, 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 17% 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 June 8, 2025.

Travelers seeking maximum savings on their Washington, D.C. Reagan-National Airport to Chicago flight should consider departing on Tuesday 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 junio 12, 2025.

The most flights from DCA to CHI are scheduled on a Thursday (57 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (17 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 junio 12, 2025.
Read through reviews of airlines operating flights from Washington, D.C. to Chicago, such as Alaska Airlines, Southwest and Delta. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.1

Overall

8.0

Boarding

8.1

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.1

Overall

8.0

Boarding

8.1

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,287 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.1

Overall

8.0

Boarding

8.1

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,950 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.1

Overall

8.0

Boarding

8.1

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,790 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.1

Overall

8.0

Boarding

8.1

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
JetBlue
7.3
Good
2,925 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.1

Overall

8.0

Boarding

8.1

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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 United Airlines is currently your cheapest option to Chicago, with prices starting at $167. Additional round-trip tickets that might be worth considering are offered by Southwest and American Airlines, with the lowest prices starting at $167 and $168, respectively. United Airlines is 43% 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 ($89), United Airlines ($90), and American Airlines ($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 (86%), ANA (85%), United Airlines( 79%).

  • 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 $1,073, our data shows the cheapest flight currently is $113. When looking at the most popular route, (Washington, D.C. Reagan-National - Chicago O'Hare Intl), you can expect to pay $157 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
Lansing
Benton Harbor
Porter
Hammond
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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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 junio 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$101Average$220FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$162Average$295FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$177Average$305FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$190Average$331FlexibilityNo cancel feeOn-time69%

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