DCA - CHI

$58 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 3/4. 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.
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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 Washington National Airport 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 Washington National Airport 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

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Reagan-National to Chicago.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
6:00 pm - 12:44 amDCA-ORD
7h 44m1 stop
6:50 am - 4:59 pmORD-DCA
9h 09m1 stop
$110Frontier
Find Deal
Mon, Mar 3 - Wed, Mar 5
1:03 pm - 12:17 amDCA-MDW
12h 14m1 stop
7:05 am - 4:59 pmMDW-DCA
8h 54m1 stop
$110Frontier
Find Deal
Sat, Mar 1 - Tue, Mar 4
11:50 am - 1:00 pmDCA-MDW
2h 10mnonstop
3:15 pm - 6:00 pmMDW-DCA
1h 45mnonstop
$172Southwest
Find Deal
Wed, Mar 5 - Wed, Mar 5
7:44 am - 9:05 amDCA-ORD
2h 21mnonstop
2:00 pm - 4:54 pmORD-DCA
1h 54mnonstop
$177United Airlines
Find Deal
Mon, Mar 3 - Wed, Mar 5
11:55 am - 1:05 pmDCA-MDW
2h 10mnonstop
6:25 am - 9:15 amMDW-DCA
1h 50mnonstop
$177Southwest
Find Deal
Thu, Feb 20 - Mon, Feb 24
7:44 am - 9:05 amDCA-ORD
2h 21mnonstop
10:15 am - 1:17 pmORD-DCA
2h 02mnonstop
$178United Airlines
Find Deal
Sat, Feb 22 - Tue, Feb 25
11:59 am - 1:14 pmDCA-ORD
2h 15mnonstop
6:06 am - 8:55 amORD-DCA
1h 49mnonstop
$198American Airlines
Find Deal
Fri, Feb 21 - Sat, Feb 22
10:30 am - 1:18 pmDCA-ORD
3h 48m1 stop
5:10 pm - 10:50 pmORD-DCA
4h 40m1 stop
$207Delta
Find Deal
Sat, Feb 22 - Mon, Feb 24
2:35 pm - 7:55 pmDCA-ORD
6h 20m1 stop
2:35 pm - 9:00 pmORD-DCA
5h 25m1 stop
$216Delta
Find Deal
Sat, Mar 1 - Mon, Mar 3
2:30 pm - 6:44 pmDCA-ORD
5h 14m1 stop
8:14 am - 11:00 amORD-DCA
1h 46mnonstop
$224American Airlines
Find Deal
Sat, Feb 15 - Tue, Feb 18

Flights from Reagan-National to Chicago - Travel Insights & Trends

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 $203 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 $203.

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 Monday 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 May, where the average cost of round-trip tickets is $353 and $344 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.
No, with an average price for the route of $651, prices are generally cheapest when you fly direct.

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 26 weeks before departure.

Good to know

Low season

January

High season

August

Cheapest flight

$58
Best time to beat the crowds with an average 5% drop in price.
Most popular time to fly and prices are also 7% lower on average.
Flight from Reagan Washington National Airport to Chicago O'Hare 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 $58 for a one-way ticket and $110 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 Delta 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 $269 and an overall rating of 8.1, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $318 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 $193 or less one-way and $265 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

ANA, Air New Zealand, Alaska Airlines, +9 more

ANA, Air New Zealand, +10 more

Tuesday

ANA, Air New Zealand, Alaska Airlines, +8 more

ANA, Air New Zealand, +9 more

Wednesday

ANA, Air New Zealand, Alaska Airlines, +9 more

ANA, Air New Zealand, +10 more

Thursday

ANA, Air New Zealand, Alaska Airlines, +8 more

ANA, Air New Zealand, +9 more

Friday

ANA, Air New Zealand, Alaska Airlines, +9 more

ANA, Air New Zealand, +10 more

Saturday

ANA, Air New Zealand, Alaska Airlines, +9 more

ANA, Air New Zealand, +10 more

Sunday

ANA, Air New Zealand, Alaska Airlines, +9 more

ANA, Air New Zealand, +10 more

See more direct flights

Direct returns

Chicago to Washington, D.C. Reagan-National

Monday

ANA, Air New Zealand, Alaska Airlines, +9 more

ANA, Air New Zealand, +10 more

Tuesday

ANA, Air New Zealand, Alaska Airlines, +8 more

ANA, Air New Zealand, +9 more

Wednesday

ANA, Air New Zealand, Alaska Airlines, +9 more

ANA, Air New Zealand, +10 more

Thursday

ANA, Air New Zealand, Alaska Airlines, +9 more

ANA, Air New Zealand, +10 more

Friday

ANA, Air New Zealand, Alaska Airlines, +9 more

ANA, Air New Zealand, +10 more

Saturday

ANA, Air New Zealand, Alaska Airlines, +9 more

ANA, Air New Zealand, +10 more

Sunday

ANA, Air New Zealand, Alaska Airlines, +9 more

ANA, Air New Zealand, +10 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.
8.1
SouthwestOverall score based on 4587 reviews
8.7Crew
7.1Food
7.7Entertainment
8.2Boarding
8.1Comfort
Airline reviews

Gate agents were informative and friendly… flight attendants were as well. Had a fun time chatting about their legacy AirTran experiences as a former fan of the airline that Southwest acquired.

10.0 ExcellentAnonymous, Jan 2025ATL - LGA
Read more Southwest reviews

Gate agents were informative and friendly… flight attendants were as well. Had a fun time chatting about their legacy AirTran experiences as a former fan of the airline that Southwest acquired.

Flight was awfully bumpy and landing was a bit jolting. I was in the restroom when snacks and drinks were served and was not asked if i wanted any. I had to ask for water finally.

Wi Fi was horrible kept cutting out the whole time and too expensive

I really like open seating. I hate that I've heard this is going away. This is one of the unique things that makes Southwest my goto choice.

Boarding was a little late, but made up for it. It was quick to taxi to the runway, since it's a smallish airport.

Excellent! Only question is how we check in at exactly 24 hours in advance and end up at the end of the B boarding group

Multiple delays and gate changes. Arrived at final destination 6 hours late. All rental cars had been taken.

Employees were kind and funny, as always! Flight was late but no announcements were made for people with tight connections to help them transition quickly. No service due to turbulence.

It was 2 hours 45 minutes late, for no apparently clear reason.

I like that it was on time and the staff was friendly.

Great service. Great staff. Boarding was a little slow, but I think there was a service dog slowing things down.

Flight left early and arrived early. the whole trip was excellent.

Seats were really tight and the seat belts did not give enough slack.

I like in St George and prefer to fly out of CDC than SGU. Hopefully, they will continue the flights out of Cedar

Broken jer bridge. Poor communication about it. Lost 2 of 4 luggage pieces

Overall, it was okay. Seat was a little cramped. Would’ve liked more substantial snacks or opportunity to buy some.

Newer plane, relatively easy boarding, not a full flight and was told that we could not be moved up because of weight and balance issues. Otherwise, a very good experience.

Other then mechanical/ computer problem and 3.5 hours flight delay the flight was great. I guess that what happened when you fly an old airplane now a day.

I was with one of the last zones to board. It was kind of annoying to finally get called to board and my whole section was already on the plane. Clearly they boarded with previous zones. So by the time I got on board, there were no spaces for my luggage above my head. I had to put my luggage 4+ rows behind me, which meant that I had to wait even longer to get off the plane, since I had to wait for those rows to clear the aisle before I could retrieve my luggage and exit the plane. This also held up the plane cleaners, as they couldn't service my row until I cleared it, so they were all standing there waiting for me, while I'm standing there waiting for the other passengers to clear the aisle. Anyways, I wasn't in a rush this time, so I just waited, but I could see that being a problem in the future. Now, I could have checked my luggage, of course, but coincidentally, a friend of mine on the same flight got their luggage damaged (wheel completely knocked off) and was told by the Baggage Attendant in the airport that Delta doesn't "cover wheel damage" on luggage. This was disappointing to hear. I'm glad I didn't check mine through. If it were my luggage, I'd be highly frustrated to hear that. It makes me not want to check my luggage in the future.

The dear was very limited in space. I could put my water bottle in seat basket. Also, there was no inflight entertainment in the delta app?

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

Being stick waiting for gate at ORD cause me to almost miss my connecting flight…being deaf United made no no effort to keep me updated as I couldn’t hear the PA

First, to be fair, the flight was on time and the trip through the air was relatively smooth. But the flight was full, and they were checking carryons. As this process went on, the crew got increasingly rude and overbearing. During the drink service, a young girl (maybe 9) who had gotten up to use the lavatory got stuck behind the cart. At some point, she started feeling fearful and overwhelmed. Passengers noticed this and asked the crew to let her return to her seat. They refused. Then she started crying, and they still refused to move the cart forward to let her sit. The poor girl was trying to be brave and compose herself. The crew handled the situation terribly and with zero grace or decency. That episode, to me, encapsulates AA’s attitude toward its passengers. Disgraceful. The plane itself was cramped and miserable, as usual. There was zero inflight media or entertainment, other than the lane and borderline inappropriate jokes the steward made during the safety briefing. Then, of course, it took the better part of an hour for the checked bags to show up at the carousel. AA is no better than the el cheapo airlines these days and a far, far cry from its former self.

Customer service for American Airlines first class is at an all time low.

Seating was horrible. Small seats. Access to flight information and extras very iser unfriendly. Kept losing internet after paying for it. Staff in madison was as unprofessional and unhelpful.

Very mediocre greeting as we boarded, and the lead flight attendant accent was almost unrecognizable. He joked around a lot, while trying to give the safety demonstration, but did not succeed. My wife’s row was completely missed for beverages and the lead flight attendant didn’t even know that our row was Main cabin and able to have beverages at no charge. We are platinum, 2,000,000 miles on American Airlines and this was not a stellar crew.

Delayed due to no crew. On a major holiday travel day.

Other than being delayed 5.5 hours and having to get a hotel because I missed my connecting flight, it was an okay flight. No in-flight Wi-Fi or entertainment.

No overhead space so all carryons were checked. No internet.

Check bag location is full of rude employees who are unwilling to assist with issues after talking to AA on the phone and relaying messages. The boarding was good. While on the flight it got really hot. Asked flight attendant if there’s a way to drop the temp and make it more comfortable as we are flying from DC to Miami so flying from cold to hot weather. No changes made. Stayed hot and uncomfortable on the plane. When asked again about the AC being down the flight attendant said no the WiFi was down but not the AC. I mentioned it was still hot. No changes.

It was nice being on a flight that had working wifi. The boarding was quick - why don’t all airlines have small boarding groups window to aisle? Makes so much sense!!! I was disappointed to be the first person stopped to have to gate check my carryon. Especially when there was plenty of overhead space at the back! But I get it…keeps it moving. Crew was nice.

The flight from Buffalo to Chicago was on an older and smaller plane. Seating was tight. Looking closely at the interior of the aircraft there were definitely signs of aging and wear.

Very easy with the app to board and staff skills

After waiting several minutes to be acknowledged by 3 employees on their phones, was told we had missed our flight because the doors were closed at that literal moment. Had they given any actual service or help while we were standing there we would have been on with time to spare. More than 10 people were turned away in this fashion claiming there was no way they could let us on the plane, even though it was still sitting connected to the terminal. After the desk agents let us know they didn't care about the situation we were forced to pay more than twice the price of our original tickets as no credits were given for the price of the "missed" flight. And the icing on the cake was after being treated poorly, fleeced for another few hundred dollars for new tickets? We waited on the next plane for 25 minutes passed the "doors closed" time, letting almost an extra dozen passengers on board. You're company has lazy, disinterested employees and your lack of any real help will ensure this was the first and last time we fly Frontier. Awful.

My experience with the phoenix airport was terrible, the personnel lay the ticket counter charged me for a carry on that fit in the carry on size box, and the two women I spoke with were terribly rude and not willing to help.,,, there was one lady “candy” on the flight crew that was amazing and is the only reason I stayed on the flight at all, because the other stewards helping people to get seated on the plane were terrible

I loked walking out on the tarmac to board and no first class. I didn't like that they have no snacks or onboard wifi to bide your time.

The plane was clean, the crew was friendly and helpful. It’s a low cost airline so there was no food, drinks or in flight entertainment but we didn’t expect any of these things. In the room for improvement department, they should install USB ports in seats to charge mobile devices.

The seats were extremely hard and uncomfortable, even for a budget airline.

The seats were extremely hard and uncomfortable. It was disappointing even for a budget airline.

Charging $74 for one checked bag is outrageous. I will never fly Frontier again.

Boarding was very well executed. Got my bag right away.

I was surprised that all baggage, including carry on, were charged. Each additional bag went up in cost. Really disappointed in the additional costs.

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

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