$54 Find Cheap Flights from Chicago Midway Airport to District of Columbia

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to District of Columbia departing on 2/6. 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
0 bags

Search hundreds of travel sites at once for deals on flights to District of Columbia

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to District of Columbia, 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 Chicago to District of Columbia, as well as popular online travel agencies
In the last 7 days travelers have searched 41,299,237 times on KAYAK, and here is why:

Save 23% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Bundle and saveSave money when you bundle your flight + hotel.

Best District of Columbia Flight Deals from Midway

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Washington, D.C.
Baltimorenonstop$71

Good to know

Low season

March

High season

October

Cheapest flight

$54
Best time to beat the crowds but there is an average 79% increase in price.
Most popular time to fly and prices are also 49% lower on average.
Flight from Chicago Midway Airport to Reagan Washington National Airport

FAQs - booking District of Columbia flights

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to District of Columbia?

    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 Chicago Midway Airport to District of Columbia.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport to District of Columbia?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago Midway Airport to District of Columbia 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 Chicago Midway Airport to District of Columbia?

    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 from Chicago Midway Airport to District of Columbia with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway Airport to District of Columbia?

    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 from Chicago Midway Airport to District of Columbia up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding cheap flights to District of Columbia

  • Looking for a cheap flight? 25% of our users found tickets from Chicago Midway Airport to the following destinations at these prices or less: Washington, D.C. $115 one-way - $230 round-trip
  • High season is considered to be February, March and April. The cheapest month to fly from Chicago is April.
  • Morning departure is around 6% more expensive than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

Top 3 airlines serving from Midway to District of Columbia

 
See real verified KAYAK customer reviews for airlines flying from Chicago to District of Columbia. 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 Midway to District of Columbia? 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 4821 reviews
8.1Comfort
8.7Crew
7.2Food
8.2Boarding
7.7Entertainment
Airline reviews

I recently flew Southwest from San Jose to Honolulu. I was very impressed with the flight crew, especially the flight attendant in charge of the front of the plane. She came through the aisle at least five times for drinks and water, and two times for snacks. I have not seen such service since I flew first class. Also, for the first time, they gave us the correct baggage claim number, and the luggage came out quickly. I can't wait for Southwest to have assigned seating! I absolutely hate the Cattle Call boarding procedure and the mad dash to get seats and overhead bins. However, the boarding was efficient.

10.0 ExcellentWilliam Drew, Dec 2024SJC - HNL
Read more Southwest reviews

I recently flew Southwest from San Jose to Honolulu. I was very impressed with the flight crew, especially the flight attendant in charge of the front of the plane. She came through the aisle at least five times for drinks and water, and two times for snacks. I have not seen such service since I flew first class. Also, for the first time, they gave us the correct baggage claim number, and the luggage came out quickly. I can't wait for Southwest to have assigned seating! I absolutely hate the Cattle Call boarding procedure and the mad dash to get seats and overhead bins. However, the boarding was efficient.

Crew was great flight was great baggage claim was a failure. It took over 1 hour for bags to arrive. Poor communication poor effort when I spoke to the supervisor about the delay

Much better than the.last. flight on SW on Thanksgiving day

Fine, but how to board on SW versus othrr airlines, is just lame. Goood staff though and all was solid otherwise.

The movies using Southwest WiFi kept pausing and I had to restart multiple times.

It went well. Plane wasn't full. Will be great when assigned seating is in place

Everything was great except the food. The pretzels are really crappy.

For the first time in a long time we had a flawless experience with Southwest. Both flights were early and no mechanical errors at all. We were shocked and pleasantly surprised 😮.

It was fine. For some reason the flight was much longer than usual. It may have been explained, but I had noise cancelling earbuds on and missed a couple of announcements. The crew was fine, but there was a flight attendant who kept telling dumb jokes, occasionally one I found distasteful. This was my second time with him, but luckily it was a late flight so he didn't do as many. But I heard all of today's jokes twice, which was two times too many. Good takeout and landing.

One of the crew performed a hilarious skit to accompany the standard instructions. Passengers enjoyed it so much they applauded at the end!

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?

Typically I give delta excellent reviews. Our flight was delayed 2hrs, I was one of the fortunate ones who were able to get to my connecting flight. Also, annoying that on the connecting flight boarding personnel make me put away a small bag into my carryon. It small enough to put in back pocket seat, why hold me and the line up to just push it into my carryon.

Everything was great. Great service, excellent communication, and early arrival

Delta flight attendants poorly managed the boarding process and overhead storage. My bag was checked last minute and no claim ticket was provided. My bag is now lost. Complete incompetence by all flight crew involved.

Inexpensive, got an exit row aisle aeat with no middle passenger, bought a great breakfast sandwich, flight comfortable & arrived ahead of schedule.

Customer service at the gate in the flight was exceptional. On time. Aircraft and seat was decent. Thanks Delta. 💗

It was terrible, if they ran flights on time it would make a big difference.

Great flight. On-time, comfortable, clean aircraft, and offered snacks pre-flight to plan for a potentially turbulent route. I wish there was Wi-Fi an all Delta Aircrafts but for a short flight this is not much of a problem.

Delta seems to be improving in many areas, except they are super bad with the food available. Bring back normal food service on long flights.

Delayed each time on a round trip with no significant weather interference. Updates to flight times came after the fact. 30 min behind in boarding and board and phone still show an on time departure. Some mysterious extra 300 miles that came so surprising they had to fuel while we were already on board?

A lady asked to stop the flight after the tunnel pulled away and we began to depart a flight that was already hours late. The attendance respectfully stopped the the plane and had the tunnel return. After the tunnel returned the passenger claimed to have changed her mind . The tunnel was then put in reverse and the passenger remained on the plane .. They should have sent the sick passenger off the plane like initially replaced. They existed a couple off the plane prior to that situation.. So.. all and all.. it was a long and flight.. .

terrible cascading delays and unhelpful customer service. uncomfortable plane. crew was great, however!

I ended up paying $70+ dollars to for a carryon because the website is confusing and misleading. I now realize I did not need to pay that. I request a refund. I will pay extra to other airlines and not fly Frontier again.

With frontier you get what you pay for. The flight was two hours late. It’s a tight fit for the number of people they bring but you get to where you’re going cheap. Sometimes that’s more important than a nifty drink and cool TV..

Charges unexpected. For seat that didnt recline. Please reverse extra seat and carryon charge. Bad business that is a bait and switch.

Although we received an email from Kayak AND the airline, turns out we were not on Frontier’s manifest for the flight. We had to purchase tickets at the gate. Not sure where this transaction fell apart, but it did. We are now disputing the charges for the SLC to PDX flight originally booked through Kayak.

We had an awful experience getting our bags checked in. Frontier’s check in on the app manipulated us into buying the business package because that was the only option available for a checked bag which included two checked bags per person which we did not need. Upon arriving to the airport, we stood in line for what seemed like forever at the baggage check in and there was no one available at the counter. We were first in line and we were afraid we were going to miss our flight due to the baggage attendant being late. After realizing there were a lot of other people waiting at the baggage check in and no one available. I reached out to Frontier and could not get any customer service so I had to call the airport to page the baggage attendant to send someone to the counter to check in our bags before we were able to go through security , I finally spoke to the attendant at the counter and explained to her that we had to pay for two checked bags person a total of six bags when we only had a total of three bags between three people she said to reach out to Frontier and they would issue a refund for the three bags that we paid for and did not need. I reached out to Frontier which I was not able to reach anybody by phone so I had to go through their automated chat feature, which sent me around in circles until I finally reached a representative to assist me. I explained to them what happened and they explained that they were not able to assist me. I continued to push the issue with them as this was very frustrating and they finally put in a customer service ticket where we were issued a flight credit and we were so disappointed because after this experience, we NEVER want to fly Frontier again, and we do not want a credit that we will not use. Frontier charged us almost $500 for us to check three bags which is absolutely absurd! The customer service agents were not able to offer anything else other than a flight credit and I do not feel like my frustrations were truly heard , we will never use Frontier Airlines again ! Truly Theft by Manipulation! They should be ashamed!

I couldn’t check in because the app didn’t work. It took 3 Frontier employees at the counter to get me checked in. Flight left 3 hours after departure time

One crew member was rude about our bags. Be nice about it. We don’t fly a lot. And the fact that you have to pay for a carry on is ridiculous

Book cheap flights from Chicago to District of Columbia

Recent round-trip flight deals

 
These are the cheapest round-trip flights from Chicago to District of Columbia found on KAYAK in the last 72 hours.
1/9Thu
1 stopFrontier
8h 47mMDW-DCA
1/13Mon
1 stopFrontier
12h 12mDCA-MDW
$108
3/5Wed
1 stopFrontier
5h 27mMDW-IAD
3/11Tue
1 stopFrontier
6h 44mIAD-MDW
$112
2/6Thu
1 stopFrontier
13h 44mMDW-DCA
2/10Mon
1 stopFrontier
12h 16mDCA-MDW
$118
1/13Mon
nonstopSouthwest
1h 50mMDW-DCA
1/16Thu
nonstopSouthwest
2h 15mDCA-MDW
$191
1/17Fri
nonstopSouthwest
1h 50mMDW-DCA
1/20Mon
nonstopSouthwest
2h 15mDCA-MDW
$192
1/28Tue
nonstopSouthwest
1h 50mMDW-DCA
1/29Wed
1 stopSouthwest
13h 25mDCA-MDW
$200
1/10Fri
nonstopSouthwest
1h 50mMDW-DCA
1/14Tue
1 stopSouthwest
5h 05mDCA-MDW
$201
1/14Tue
1 stopDelta
4h 26mMDW-DCA
1/16Thu
1 stopDelta
3h 54mDCA-MDW
$210
1/23Thu
1 stopDelta
4h 57mMDW-IAD
1/25Sat
1 stopDelta
3h 54mIAD-MDW
$210
2/2Sun
1 stopDelta
4h 42mMDW-DCA
2/5Wed
1 stopDelta
6h 08mDCA-MDW
$229

Search by stops

Search by airline

Search by price

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Chicago to District of Columbia found on KAYAK in the last 72 hours.
2/6Thu
1 stopFrontier
8h 44mMDW-DCA
$54
2/25Tue
1 stopFrontier
7h 25mMDW-IAD
$54
2/23Sun
1 stopAllegiant Air
13h 35mMDW-IAD
$93
1/26Sun
nonstopSouthwest
1h 50mMDW-DCA
$96
2/27Thu
1 stopAllegiant Air
13h 57mMDW-IAD
$102
1/25Sat
1 stopDelta
5h 49mMDW-DCA
$105
1/9Thu
1 stopDelta
4h 40mMDW-IAD
$105
2/17Mon
nonstopSouthwest
1h 45mMDW-DCA
$115
2/2Sun
3 stops
25h 05mMDW-IAD
$182
1/30Thu
3 stops
25h 05mMDW-IAD
$200

Search by stops

Search by airline

Search by price

Last minute flights from Midway to District of Columbia

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Chicago to District of Columbia that are departing in the next 10 days.
12/23Mon
multi-stopFrontier
7h 34mMDW-IAD
1/6Mon
multi-stopFrontier
22h 05mIAD-MDW
$308
12/25Wed
multi-stopDelta
4h 11mMDW-IAD
1/2Thu
multi-stopDelta
6h 01mIAD-MDW
$333
12/25Wed
multi-stopFrontier
5h 00mMDW-IAD
12/30Mon
multi-stopFrontier
7h 32mIAD-MDW
$338
12/23Mon
multi-stopFrontier
7h 34mMDW-IAD
12/30Mon
multi-stopFrontier
7h 32mIAD-MDW
$378
12/25Wed
nonstopSouthwest
1h 45mMDW-DCA
12/29Sun
nonstopSouthwest
2h 10mDCA-MDW
$425
12/23Mon
multi-stopFrontier
7h 34mMDW-IAD
12/25Wed
multi-stopFrontier
6h 52mIAD-MDW
$428
12/25Wed
nonstopSouthwest
1h 45mMDW-DCA
12/29Sun
multi-stopSouthwest
4h 45mDCA-MDW
$434
12/25Wed
multi-stopDelta
6h 07mMDW-DCA
12/29Sun
multi-stopDelta
3h 50mDCA-MDW
$443
12/22Sun
nonstopSouthwest
1h 50mMDW-DCA
1/3Fri
nonstopSouthwest
2h 10mDCA-MDW
$505
12/22Sun
nonstopSouthwest
1h 45mMDW-DCA
1/3Fri
multi-stopSouthwest
4h 30mDCA-MDW
$514

Search by stops

Search by airline

Search by price

Everything you need to know for your flight from Midway to District of Columbia

Information on your arrival and departure airports

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.