DCA - CHI

$79 Find Cheap Flights from Reagan Washington National Airport to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Reagan-National to Chicago departing on 5/2. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Washington, D.C. to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Washington, D.C. to Chicago, as well as popular online travel agencies
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Cheap Flight Deals from Reagan-National to Chicago (DCA-CHI)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Reagan-National to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent round-trip flight deals from Reagan-National to Chicago

KAYAK's recommended round-trip deals from the most popular airlines that fly from Reagan-National to Chicago.
Discover the best prices for you by selecting your travel dates on KAYAK.
Choose your dates
Frontier Logo
7:00 am - 7:08 pmDCA-MDW
13h 08m1 stop
Frontier Logo
8:03 pm - 9:59 pmMDW-DCA
24h 56m1 stop
$160Frontier
Find Deal
Thu, May 1 - Sun, May 4
United Airlines Logo
6:00 pm - 7:17 pmDCA-ORD
2h 17mnonstop
United Airlines Logo
12:45 pm - 3:41 pmORD-DCA
1h 56mnonstop
$161United Airlines
Find Deal
Tue, May 13 - Wed, May 14
Southwest Logo
8:55 pm - 9:55 pmDCA-MDW
2h 00mnonstop
Southwest Logo
9:40 am - 12:30 pmMDW-DCA
1h 50mnonstop
$161Southwest
Find Deal
Tue, Apr 29 - Wed, Apr 30
Southwest Logo
1:10 pm - 3:20 pmDCA-MDW
3h 10m1 stop
Southwest Logo
12:25 pm - 3:15 pmMDW-DCA
1h 50mnonstop
$167Southwest
Find Deal
Tue, May 13 - Wed, May 14
American Airlines Logo
6:00 am - 7:20 amDCA-ORD
2h 20mnonstop
American Airlines Logo
11:37 am - 2:24 pmORD-DCA
1h 47mnonstop
$170American Airlines
Find Deal
Wed, May 7 - Thu, May 29
American Airlines Logo
6:59 am - 8:26 amDCA-ORD
2h 27mnonstop
American Airlines Logo
6:00 am - 8:54 amORD-DCA
1h 54mnonstop
$196American Airlines
Find Deal
Thu, May 8 - Sun, May 11
Delta Logo
6:00 am - 10:03 amDCA-ORD
5h 03m1 stop
Delta Logo
1:45 pm - 6:59 pmORD-DCA
4h 14m1 stop
$197Delta
Find Deal
Wed, May 7 - Wed, May 14
Delta Logo
6:00 am - 8:40 amDCA-MDW
3h 40m1 stop
Delta Logo
5:59 pm - 11:10 pmMDW-DCA
4h 11m1 stop
$197Delta
Find Deal
Wed, Apr 23 - Tue, Apr 29
JetBlue Logo
6:15 am - 12:13 pmDCA-ORD
6h 58m1 stop
JetBlue Logo
8:50 am - 6:00 pmORD-DCA
8h 10m1 stop
$203JetBlue
Find Deal
Sat, May 3 - Mon, May 5
JetBlue Logo
6:15 am - 12:13 pmDCA-ORD
6h 58m1 stop
JetBlue Logo
4:03 pm - 10:58 pmORD-DCA
5h 55m1 stop
$267JetBlue
Find Deal
Thu, May 1 - Thu, May 8

Expert advice for your flight from Reagan-National to Chicago

 
Snippets provided in this section are AI-generated based on a summarization of KAYAK-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.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airlines
American Airlines

American's Main Cabin Extra offers early boarding and complimentary alcoholic drinks.


American's Basic Economy includes carry-on but no free checked bags or seat selection.

United Airlines

United's Economy Plus offers up to 6 inches more legroom than standard economy seats.


United's Priority Boarding puts you in Zone 2, avoiding gate-checking carry-ons.

Southwest

Southwest offers two free checked bags, saving on baggage fees.


Southwest's EarlyBird Check-In improves boarding position, avoiding middle seats.

Read more about Southwestby Blane Bachelor
Airports
DCA

DCA's metro access makes it easy to reach from downtown D.C. in under 30 minutes, ideal for business travelers.

Read more about DCAby Ramsey Qubein
ORD

Take the CTA Blue Line from ORD to downtown Chicago in about 45 minutes, avoiding traffic delays.

Read more about ORDby Stefanie Waldek
Our travel experts
Harriet Baskas

Harriet Baskas

Expert on American 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
Stefanie Waldek

Stefanie Waldek

Expert on United Airlines and ORD

Stefanie Waldek

Stefanie Waldek

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Read more
Blane Bachelor

Blane Bachelor

Expert on Southwest

Blane Bachelor

Blane Bachelor

Blane Bachelor is a journalist and editor specializing in travel and aviation who writes regularly for top global outlets. Born and raised in Florida, Blane has worked and lived in four countries, including the Netherlands, where she’s currently based with her family. Her favorite way to get to know a new destination is by running or riding a bike around town – or hearing a spooky ghost story about local history. She will always choose the window seat.

Read more
Ramsey Qubein

Ramsey Qubein

Expert on DCA

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

KAYAK's insights & trends for Reagan-National to Chicago flights

Get data-powered insights and trends into flights from Reagan-National to Chicago to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Washington, D.C. Reagan-National Airport to Chicago flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Washington, D.C. Reagan-National Airport to Chicago.
Our data shows that the cheapest route for a return flight from Washington, D.C. Reagan-National Airport to Chicago cost $177 and was between Washington, D.C. Reagan-National Airport (DCA) and Chicago Midway Airport (MDW). On average, the best prices are found if you fly this route. The average price for a return flight for this route is $177.

What’s the cheapest day of the week to fly from Reagan Washington National Airport to Chicago?

The average price of all round-trip flights from Washington, D.C. Reagan-National Airport to Chicago clicked on KAYAK for each day over the last 12 months.
For Reagan Washington National Airport to Chicago, Wednesday is the cheapest day to fly on average and Sunday is the most expensive. Flying from Chicago back to Reagan Washington National Airport, the best deals are generally found on Thursday, with Sunday being the most expensive.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Washington, D.C. Reagan-National Airport to Chicago, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.
The cheapest month for flights from Washington, D.C. Reagan-National Airport to Chicago is September, where tickets cost $263 (return) on average. On the other hand, the most expensive months are December and June, where the average cost of round-trip tickets is $353 and $336 respectively.

Can I save money by flying with a layover from Washington, D.C. Reagan-National Airport to Chicago?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.
Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $587 on average.

How far in advance should I book a flight from Washington, D.C. Reagan-National Airport to Chicago?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Washington, D.C. Reagan-National Airport to Chicago, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.
To get a below average price on the flight from Washington, D.C. Reagan-National Airport to Chicago, you should book around 4 weeks before departure. For the absolute cheapest price, our data suggests you should book 16 weeks before departure.

Good to know

Low season

February

High season

August

Cheapest flight

$79
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly and prices are also 5% lower on average.
Flight from Reagan Washington National Airport to Chicago Midway Airport

When to book flights from Reagan-National to Chicago

Are your dates flexible? Find out the best times to travel from Reagan-National to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Reagan Washington National Airport to Chicago flights

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

    In the last 3 days, the lowest price for a flight from Washington, D.C. Reagan-National Airport to Chicago was $79 for a one-way ticket and $160 for a round-trip.

  • Do I need a passport to fly between Reagan Washington National Airport and Chicago?

    A passport is not required to fly from Reagan Washington National Airport to Chicago.

  • Which airports will I be using when flying from Reagan Washington National Airport to Chicago?

    Reagan Washington National Airport is served by only 1 airport and there are 2 airports in Chicago. You will leave Reagan Washington National Airport from Washington, D.C. Reagan-National and you will be arriving in Chicago at one of these airports: Chicago Midway or Chicago O'Hare Intl.

  • Which airlines offer Wi-Fi service onboard planes from Reagan Washington National Airport to Chicago?

    American Airlines, Alaska Airlines, and Hawaiian Airlines offer inflight Wi-Fi service on the Reagan Washington National Airport to Chicago flight route.

  • Which aircraft models fly most regularly from Reagan Washington National Airport to Chicago?

    The Boeing 737-800 is the aircraft model that flies most regularly on the Reagan Washington National Airport to Chicago flight route.

  • Which airline alliances offer flights from Reagan Washington National Airport to Chicago?

    oneworld, and Star Alliance are the airline alliances operating flights between Reagan Washington National Airport and Chicago, with oneworld being the most commonly used for this route.

  • On which days can I fly direct from Reagan Washington National Airport to Chicago?

    There are nonstop flights from Reagan Washington National Airport to Chicago on a daily basis.

  • Which is the best airline for flights from Washington, D.C. to Chicago, Southwest or Delta?

    The two airlines most popular with KAYAK users for flights from Washington, D.C. to Chicago are Southwest and Delta. With an average price for the route of $274 and an overall rating of 8.0, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $267 and an overall rating of 8.0.

  • How does KAYAK find such low prices on flights from Reagan Washington National Airport to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Reagan Washington National Airport to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Reagan Washington National Airport to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Reagan Washington National Airport is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Reagan Washington National Airport to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Reagan Washington National Airport with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Reagan Washington National Airport to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Reagan Washington National Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

KAYAK’s top tips for finding a cheap flight from Washington, D.C. Reagan-National Airport to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $169 or less one-way and $244 or less round-trip.

Prefer to fly direct from Reagan Washington National Airport to Chicago?

Find which airlines fly direct from Washington, D.C. Reagan-National Airport to Chicago, which days they fly and book direct flights.

Direct departures

Washington, D.C. Reagan-National to Chicago

Monday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Tuesday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Wednesday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Thursday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Friday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Saturday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Sunday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

See more direct flights

Direct returns

Chicago to Washington, D.C. Reagan-National

Monday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Tuesday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Wednesday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Thursday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Friday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Saturday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Sunday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

See more direct flights
See more direct flights

Top 5 airlines serving from Reagan-National to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Washington, D.C. to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Reagan-National to Chicago? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4274 reviews
7.6Entertainment
8.6Crew
8.0Comfort
8.2Boarding
7.1Food
Airline reviews

Boarding process, crew were good. But the seats were so uncomfortable that was all I could focus on. I literally had to sit forward so that all 3 of us could fit in row. I will try to avoid Southwest in the future for any flights over 60 minutes.

6.0 GoodCarolynn, Mar 2025KOA - SMF
Read more Southwest reviews

Boarding process, crew were good. But the seats were so uncomfortable that was all I could focus on. I literally had to sit forward so that all 3 of us could fit in row. I will try to avoid Southwest in the future for any flights over 60 minutes.

1.5 hour delay, poor service, no compassion from the crew. Terrible experience

Great flight, 47 passengers on a 180 seat plane. Stewardess was pleasant and cheerful.

Short flight with plenty of open seats. Drinks and snacks were still provided even on such a short flight. <1 hr

I liked the crew member who gave flight instructions on "in case of a problem:. The seats are so small that only a young teenager could sit in middle seat.

Great experience flying Southwest. The crew was really kind and helpful, and very friendly with our toddler.

Very good. Sad to learn Southwest is going start to charge for bags

Our flight was diverted from being a non-stop to getting within 150 miles and requiring another plane. We heard 4 or 5 different versions from SW as to why we had to stop, then wait for a replacement plane. Five hour delay, weather did not come up as a single excuse.... communication was not clear and well explained. No one really took charge!

My flight to Chicago left and landed early. My return flight left two minutes late and arrived 2 minutes late. My seat selections were ideal! There were no snacks going to Chicago and no snacks on the return trip. There are no charging outlets on board.

WiFi on the flight was not working. Thus, entertainment options were limited.

A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.

Simply outstanding. Their new lounge for Delta One customers is a cut above the rest.

The Dekta Rep that checked us in was great. She's very personable, pleasant, and can tell she enjoys her job.

The plane was old with small storage areas that had problems closing/latching and not enough storage for everyone, and worn, damaged seats. Service was great but feel a little unsafe on such well used planes.

Terrible and im avoiding them in the future. My initial flight was delayed causing me to rebook my flight and when speaking with the representative to rebook I explained this is the second time my flights were delayed and they did nothing to help me. I wasn't booked to comfort plus or given a voucher or anything. I was almost late for my meeting that I needed to attend on Monday because of the games delta played delaying my flights even more and putting me in the very back of the plane next to an extremely intoxicated passenger

Flights on time. .Ride was as comfortable as can be expected in steerage. Luggage arrived at destination. Attendants were fairly friendly.

Great staff. Wifi is terrible. Signing up for skylines is a painstaking process. Had to call customer service just to get my flight itinerary and confirmation sent to me. Consistent delays. A well staffed company that is run so poorly. Upper management needs to be renewed.

The WiFi didn't seem as fast as it normally is

Thank you for not flipping the plane on the run way. You guys get a 5 star rating for the flight!!!

The crew was wonderful and attentive. The seats near exit row were restrictive. Offer healthy snacks please

Overall poor for me I paid extra for seats with leg room and my regional flights exit row seats have less leg room then the others that's money that could have been saved and on my final flight home the flights air was not operating it was unbearably hot in the cabin I will be contacting United and filing a DOT complaint

There's just no way to sit fully upright and comfortably in these seats. There needs to be 2 more inches of room, and that's not something that only one person on the flight needs - the whole flight needs 2 more inches of room. If that means you sell 6 less seats, so be it. It's too close for anyone. Forcing people to pay for "premium" economy just to get "barely enough space to breathe" isn't really an answer to that.

The crew were very nice. The Chocolate is good and v there’s no entertainment. Thanks

The crew were very nice. I would have appreciated a pillow for comfort. I had a special meal that was sloppy, but the salad was great. Thanks

The plane was in Moline all night. Consequently, we assumed an on time departure at 8:15am. Unfortunately, and as is the normal case with United in Moline, we departed 2.5 hours late. When the crew came, it was discovered that there was very little heat in the plane. Seems this should have been checked hours before the crew arrived. Then when we boarded and the plane was to be de-iced, the United de-icing truck was not working! We awaited the American Airlines truck. All of this caused us to miss our connection in Chicago. My suggestion is never take United Airlines flight from Moline. We have been disappointed 80% of the time and have vowed to not take United again from Moline.

Flight was delayed two hours. No snacks and no tv screens. My bag got stuck in Chicago

The aircrew was solid, the flight was chill, I had no issues. The gate agent was not the best. I was trying to use a military bag upgrade to move my bag from under the seat to the overhead bins and he told me there’s no overhead bins on the plane, argued with me why booking put a military member in basic economy (I don’t really understand this) and made it an issue to even try to help me stating I’d have to call reservations to get a bag upgrade. When every other agent with United can add it at the gate, this man couldn’t be bothered.

They canceled our flight and left us stranded to figure it out

Never nice, United Express partners always do an amazing job.

Everything was very good. Was able to change a make run flight leaving on direct earlier in the app -seamless!!! Well done

The plane was late and then sat on the runway for almost 45 minutes before taking off.

Wonderful as usual except for other guests that were unruly and not kept in check by the Crew.

The flight was initially delayed, then cancelled. American Airlines says the cancellation was weather related, though the actual weather was not bad in both Washington and Providence and between. There were very few cancellations that day. In fact, AA2120 from Washington, DC to Boston flew with a minor delay at about the same time. So, the weather somehow affected only this particular flight AA5230. The next available flight was the following morning. The American Airlines refused to reimburse accommodation (hotel at DCA)

Fine. On time, cabin service was fine, bag arrived. All good. Flying into DCA so did not collide with any helicopters, which is also good. Horrid incident that could have and should have been prevented.

Crew professional. Easy bag drop off. On time. Good entertainment.

Good experience but the snacks are not gluten free, so I cannot eat them.

Standard. No different than a discount carrier on a short trip.

Everything was great. Boarding, early departure, early arrival, and deplaning were smooth. Smooth flight.

I blame kayak for my last trip to dca. Kayak cancelled my direct flight and put on a one stop flight and made lost whole day from my vacation and had not even refunded my ticket.

Per usual, flight status, staff courtesy and professionalism were excellent

Cancelled and declined to find alternatives Earlier flight is 2 days later Sent the cancellation notification very late, wish I knew earlier would have stayed to watch the Miami open final game Very disappointing service

The worst flight of my life. Never will I fly frontier again

Landing in terminal 2, but my luggage is terminal 3. We (and others) were looking for it in terminal 1. We probably missed the crew broadcast, but the communication could have been clearer for non native (or elderly) passengers.

I chose the seats when booked the flight and paid for them. However after checking in I found we were assigned different seats!

Bag should not be so much money. This is how Frontier takes advantage of customers

The plane was comfortable. The time to board was way too slow and very unorganized! The crew was not as friendly as normally. The was not a single time that they offered water nor anything!!!

They switched my flight to Spirit, Never using Kayak again,

i was denied boarding, even though i had an assigned seat, checked in on line and was at airport early. Then they refused to fully refund the the fair and replacement fair because they claimed it was "no show/denied boarding". I will never fly this airline again

I was not permitted on my flight and had to purchase another flight ticket to Las Vegas.

This was a full flight and I was in Zone 1, however upon boarding, several other zones went in ahead of me, leaving no overhead cabin space near my seat. This created a challenging disembarkment process.

Everything you need to know for your flight from Reagan-National to Chicago

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