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

Flying on JetBlue is currently your cheapest option to Chicago, with prices starting at $202. Additional round-trip tickets that might be worth considering are offered by American Airlines and United Airlines, with the lowest prices starting at $209 and $217, respectively. JetBlue is 31% 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 JetBlue ($102), United Airlines ($109), and Southwest ($109).

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.

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).

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 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 $1,441, our data shows the cheapest flight currently is $93. When looking at the most popular route, (Washington, D.C. Reagan-National - Chicago O'Hare Intl), you can expect to pay $203 for that flight.

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: SkyWest Airlines (100%), Japan Airlines (81%), ANA( 76%).

What are the most popular airlines that fly from Washington, D.C. Reagan-National Airport to Chicago?

Consider American Airlines, Frontier or United Airlines when booking your flight. These represent the most popular airlines when flying from Washington, D.C. Reagan-National Airport to Chicago.

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

Saturday flights are found to be more expensive to fly from Washington, D.C. Reagan-National Airport to Chicago. This shouldn’t discourage you from searching, as you can still find great deals by being flexible with your options. Use our search form to find deals on tickets to Chicago.

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

September can be a great time to fly to Chicago from Washington, D.C. Reagan-National Airport with a flight ticket averaging about $250. Cheapflights users have found deals in the month of September for as cheap as $70. The most expensive prices can be found in the month of April.

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.

$102+ Flights from Washington, D.C. Reagan-National Airport to Chicago

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Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

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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.

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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

Round-trip from	$202 (lastminute.com)
One-way from	$102 (JetBlue)
Popular in	December
Cheapest in	September
Average price	$299
Good round-trip deal	$220 or less
Good one-way deal	$155 or less

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. 9% potential increase in price ($29 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).

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Average for round-trip flights in July 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 July 31, 2025.

Tue 8/266:30 amDCA - ORD

1 stop5h 48mJetBlue

Wed 9/39:42 amORD - DCA

1 stop7h 18mJetBlue

Deal found 7/31

$203

Sat 8/237:00 amDCA - ORD

Nonstop2h 22mAmerican Airlines

Sat 8/2310:15 amORD - DCA

1 stop4h 44mAmerican Airlines

Deal found 7/30

$209

Tue 8/2612:00 pmDCA - ORD

Nonstop2h 13mUnited Airlines

Tue 9/27:00 amORD - DCA

Nonstop1h 58mUnited Airlines

Deal found 7/29

$217

Sat 8/308:25 amDCA - MDW

Nonstop2h 00mSouthwest

Sat 9/612:45 pmMDW - DCA

Nonstop1h 55mSouthwest

Deal found 7/31

$217

Sat 9/61:00 pmDCA - ORD

1 stop9h 28mFrontier

Wed 9/107:20 amORD - DCA

1 stop13h 39mFrontier

Deal found 7/30

$218

Sat 8/3012:29 pmDCA - ORD

1 stop8h 54mDelta

Tue 9/912:59 pmORD - DCA

1 stop5h 00mDelta

Deal found 7/28

$227

Sat 8/161:00 pmDCA - MDW

1 stop8h 54mFrontier

Mon 8/1812:35 pmMDW - DCA

1 stop27h 24mFrontier

Deal found 7/29

$228

Wed 8/276:00 amDCA - MDW

1 stop3h 35mDelta

Sat 8/304:25 pmMDW - DCA

1 stop5h 21mDelta

Deal found 7/31

$237

Tue 8/266:55 amDCA - ORD

2 stops6h 50mSouthwest

Tue 8/263:10 pmORD - DCA

1 stop6h 50mSouthwest

Deal found 7/31

$242

Best flights from Reagan-National to Chicago
Discover carefully curated flight deals from Reagan-National to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 31, 2025.

Tue 8/266:30 amDCA - ORD

1 stop5h 48mJetBlue

Wed 9/39:42 amORD - DCA

1 stop7h 18mJetBlue

Deal found 7/31

$203

Sat 8/237:00 amDCA - ORD

Nonstop2h 22mAmerican Airlines

Sat 8/2310:15 amORD - DCA

1 stop4h 44mAmerican Airlines

Deal found 7/30

$209

Tue 8/2612:00 pmDCA - ORD

Nonstop2h 13mUnited Airlines

Tue 9/27:00 amORD - DCA

Nonstop1h 58mUnited Airlines

Deal found 7/29

$217

Sat 8/308:25 amDCA - MDW

Nonstop2h 00mSouthwest

Sat 9/612:45 pmMDW - DCA

Nonstop1h 55mSouthwest

Deal found 7/31

$217

Sat 9/61:00 pmDCA - ORD

1 stop9h 28mFrontier

Sat 9/138:25 amORD - DCA

1 stop12h 34mFrontier

Deal found 7/28

$218

Sat 8/3012:29 pmDCA - ORD

1 stop8h 54mDelta

Tue 9/912:59 pmORD - DCA

1 stop5h 00mDelta

Deal found 7/28

$227

Sat 8/161:00 pmDCA - MDW

1 stop8h 54mFrontier

Mon 8/1812:35 pmMDW - DCA

1 stop27h 24mFrontier

Deal found 7/29

$228

Wed 8/276:00 amDCA - MDW

1 stop3h 35mDelta

Sat 8/304:25 pmMDW - DCA

1 stop5h 21mDelta

Deal found 7/31

$237

Tue 8/266:55 amDCA - ORD

2 stops6h 50mSouthwest

Tue 8/263:10 pmORD - DCA

1 stop6h 50mSouthwest

Deal found 7/31

$242

Last-minute flights from Reagan-National to Chicago
Discover last-minute flight deals from Reagan-National to Chicago. Data last updated July 31, 2025 and is based on user searches.

Tue 8/57:00 amDCA - ORD

Nonstop2h 27mAmerican Airlines

Wed 9/31:37 pmORD - DCA

Nonstop1h 52mAmerican Airlines

Deal found 7/30

$374

Tue 8/59:39 amDCA - MDW

1 stop3h 50mDelta

Wed 9/36:17 pmMDW - DCA

1 stop3h 42mDelta

Deal found 7/30

$429

Tue 8/56:05 amDCA - MDW

Nonstop1h 55mSouthwest

Fri 9/52:45 pmMDW - DCA

Nonstop1h 50mSouthwest

Deal found 7/30

$435

Tue 8/51:40 pmDCA - ORD

1 stop5h 19mDelta

Fri 9/511:15 amORD - DCA

1 stop5h 05mDelta

Deal found 7/31

$455

Fri 8/811:45 amDCA - ORD

2 stops10h 45mSouthwest

Tue 8/193:10 pmORD - DCA

1 stop6h 50mSouthwest

Deal found 7/29

$451

Sat 8/97:00 pmDCA - ORD

2 stops13h 42mUnited Airlines

Sun 8/1010:00 amORD - DCA

Nonstop1h 58mUnited Airlines

Deal found 7/31

$463

Sun 8/107:00 amDCA - ORD

1 stop18h 32mFrontier

Sun 8/175:40 amORD - DCA

1 stop29h 24mFrontier

Deal found 7/29

$238

Sun 8/107:00 amDCA - MDW

1 stop29h 41mFrontier

Thu 8/142:44 pmMDW - DCA

1 stop30h 13mFrontier

Deal found 7/29

$238

Tue 8/121:00 pmDCA - ORD

1 stop12h 32mFrontier

Wed 8/137:00 amORD - DCA

1 stop13h 57mFrontier

Deal found 7/29

$218

Sat 8/161:00 pmDCA - MDW

1 stop8h 54mFrontier

Mon 8/1812:35 pmMDW - DCA

1 stop27h 24mFrontier

Deal found 7/29

$228

Sat 8/2312:30 pmDCA - ORD

1 stop5h 52mAmerican Airlines

Sat 8/237:15 pmORD - DCA

Nonstop2h 00mAmerican Airlines

Deal found 7/29

$209

Tue 8/266:30 amDCA - ORD

1 stop5h 48mJetBlue

Wed 9/39:42 amORD - DCA

1 stop7h 18mJetBlue

Deal found 7/31

$203

One-way flights from Reagan-National to Chicago
Search for one-way flight options from Reagan-National to Chicago. Find affordable one-way fares based on user searches. Data last updated July 31, 2025.

Tue 8/266:30 amDCA - ORD

1 stop5h 48mJetBlue

Deal found 7/30

$102

Wed 8/272:00 pmDCA - ORD

Nonstop2h 13mUnited Airlines

Deal found 7/30

$109

Tue 8/2611:55 amDCA - MDW

Nonstop1h 55mSouthwest

Deal found 7/29

$109

Wed 9/31:00 pmDCA - ORD

1 stop9h 42mFrontier

Deal found 7/30

$110

Tue 8/263:50 pmDCA - ORD

Nonstop2h 21mAmerican Airlines

Deal found 7/29

$111

Sat 10/116:00 pmDCA - MDW

1 stop29h 38mFrontier

Deal found 7/30

$116

Tue 8/266:00 amDCA - MDW

1 stop4h 36mDelta

Deal found 7/29

$119

Tue 8/2610:45 amDCA - ORD

2 stops11h 45mSouthwest

Deal found 7/29

$124

Mon 9/16:00 amDCA - ORD

1 stop5h 20mDelta

Deal found 7/31

$136

Cheapflights Fare Finder

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

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Tue 8/26

6:30 am-11:18 am

1 stop5h 48m

Chicago O'Hare Intl

Wed 9/3

9:42 am-6:00 pm

1 stop7h 18m

$203

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Sat 8/23

7:00 am-8:22 am

Nonstop2h 22m

Chicago O'Hare Intl

Sat 8/23

10:15 am-3:59 pm

1 stop4h 44m

$209

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Tue 8/26

12:00 pm-1:13 pm

Nonstop2h 13m

Chicago O'Hare Intl

Tue 9/2

7:00 am-9:58 am

Nonstop1h 58m

$217

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Sat 8/30

8:25 am-9:25 am

Nonstop2h 00m

Chicago Midway

Sat 9/6

12:45 pm-3:40 pm

Nonstop1h 55m

$217

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Sat 9/6

1:00 pm-9:28 pm

1 stop9h 28m

Chicago O'Hare Intl

Sat 9/13

8:25 am-9:59 pm

1 stop12h 34m

$218

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Sat 8/30

12:29 pm-8:23 pm

1 stop8h 54m

Chicago O'Hare Intl

Tue 9/9

12:59 pm-6:59 pm

1 stop5h 00m

$227

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Sat 8/16

1:00 pm-8:54 pm

1 stop8h 54m

Chicago Midway

Mon 8/18

12:35 pm-4:59 pm

1 stop27h 24m

$228

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Wed 8/27

6:00 am-8:35 am

1 stop3h 35m

Chicago Midway

Sat 8/30

4:25 pm-10:46 pm

1 stop5h 21m

$237

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Tue 8/26

6:55 am-12:45 pm

2 stops6h 50m

Chicago O'Hare Intl

Tue 8/26

3:10 pm-11:00 pm

1 stop6h 50m

$242

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Tue 8/26

6:30 am-11:18 am

1 stop5h 48m

$102

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

Showing 1-10 of 18 results

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

Cheapflights partnered with top experts to bring you the best recommendations for your Washington, D.C. Reagan-National Airport to Chicago trip

Airlines

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

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

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.

ORD

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

MDW

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

Our travel experts

Marisa Garcia

Expert on Southwest

Harriet Baskas

Expert on United Airlines

Ramsey Qubein

Expert on ORD and MDW

Emily Zemler

Expert on DCA

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?

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?

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 20% 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?

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

The most flights from DCA to CHI are scheduled on a Thursday (55 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (16 on average).

Reviews of airlines servicing Chicago

Get a feel of what it's like to fly with Southwest, Delta, and United 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

8.0

Very good

4,246 reviews

Reviews

1 / 20

8.0

Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

Southwest

8.0

Very good

4,246 reviews

Southwest

8.0

Very good

4,246 reviews

Reviews

1 / 20

8.0

Excellent

Gina,Jul 2025

LAS - DEN

Delta

8.0

Very good

7,981 reviews

Southwest

8.0

Very good

4,246 reviews

Reviews

1 / 20

8.0

Excellent

Gina,Jul 2025

LAS - DEN

United Airlines

7.4

Good

8,900 reviews

Southwest

8.0

Very good

4,246 reviews

Reviews

1 / 20

8.0

Excellent

Gina,Jul 2025

LAS - DEN

JetBlue

7.3

Good

2,914 reviews

Southwest

8.0

Very good

4,246 reviews

Reviews

1 / 20

8.0

Excellent

Gina,Jul 2025

LAS - DEN

American Airlines

7.2

Good

10,000 reviews

Southwest

8.0

Very good

4,246 reviews

Reviews

1 / 20

8.0

Excellent

Gina,Jul 2025

LAS - DEN

Related info for your journey

What are the cheapest airlines flying from Washington, D.C. Reagan-National Airport to Chicago round-trip?
Flying on JetBlue is currently your cheapest option to Chicago, with prices starting at $202. Additional round-trip tickets that might be worth considering are offered by American Airlines and United Airlines, with the lowest prices starting at $209 and $217, respectively. JetBlue is 31% 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 JetBlue ($102), United Airlines ($109), and Southwest ($109).
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: SkyWest Airlines (100%), Japan Airlines (81%), ANA( 76%).
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 $1,441, our data shows the cheapest flight currently is $93. When looking at the most popular route, (Washington, D.C. Reagan-National - Chicago O'Hare Intl), you can expect to pay $203 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

Merrillville

Lansing

Hammond

Benton Harbor

Porter

Valparaiso

Chesterton

Browse thousands of different options on Cheapflights for your next trip

Top 4 airlines flying from Reagan-National to Chicago

Airline	Cheapest	Average	Flexibility	On-time
Frontier	Cheapest$99	Average$213	FlexibilityNo cancel fee	On-time62%
American Airlines	Cheapest$157	Average$295	FlexibilityNo cancel fee	On-time71%
Southwest	Cheapest$173	Average$298	FlexibilityNo cancel fee	On-time63%
United Airlines	Cheapest$187	Average$333	FlexibilityNo cancel fee	On-time69%

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$102+ 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 8/26. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Reagan-National to Chicago with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

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

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Good round-trip deal

Good one-way deal

Find flight deals from Reagan-National to Chicago

Cheapest flights from Reagan-National to ChicagoExplore 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 31, 2025.

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 31, 2025.

Cheapflights Fare Finder

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

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

Cheapflights partnered with top experts to bring you the best recommendations for your Washington, D.C. Reagan-National Airport to Chicago trip

Airlines

Southwest

United Airlines

Airports

DCA

ORD

MDW

Our travel experts

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.

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 July 25, 2025.

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

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 31, 2025.

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 July 27, 2025.

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

Reviews of airlines servicing Chicago

Get a feel of what it's like to fly with Southwest, Delta, and United 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.

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?

What are the cheapest airlines to fly from Washington, D.C. Reagan-National Airport to Chicago one-way?

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?

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

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

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

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

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

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Alternative routes for Reagan-National to Chicago

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Top 4 airlines flying from Reagan-National to Chicago

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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 31, 2025.