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Find cheap flights from Chicago Midway Airport to Maryland from $48

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 Maryland departing on 6/19. 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
Sat 6/15
Sat 6/22

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Best Maryland Flight Deals

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

Washington, D.C.
Baltimorenonstop$58

Good to know

Low season

April

High season

June

Cheapest flight

$48
Best time to beat the crowds with an average 76% drop in price.
Most popular time to fly and prices are also 29% lower on average.
Flight from Chicago Midway Airport to Philadelphia

FAQs - booking Maryland flights

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

    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 Maryland.

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

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

    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 Maryland with an airline and back to Chicago Midway Airport 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 Maryland?

    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 Maryland from Chicago Midway Airport 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 Maryland

  • Looking for a cheap flight? 25% of our users found tickets from Chicago Midway Airport to the following destinations at these prices or less: Baltimore $44 one-way - $68 round-trip; Philadelphia $47 one-way - $78 round-trip
  • Morning departure is around 9% cheaper 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 Maryland

 
Need help choosing which airline to fly with from Midway to Maryland? 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
DeltaOverall score based on 10673 reviews
7.4Food
8.6Crew
7.9Comfort
8.2Boarding
8.0Entertainment
Airline reviews

5-hour delay due to storms in Tanoa and airspace restricted by Miami traffic controllers.

6.0 GoodGary, May 2024MSP - TPA
Read more about Delta reviews

5-hour delay due to storms in Tanoa and airspace restricted by Miami traffic controllers.

A regional sized plane was used for a cross country flight with no overhead bin space. I had to "pink check" my laptop and my medications. I was NOT pleased!!!!

Absolutely nothing flight was cancelled and delayed for 2 days. Barely a heads up I want a full refund

The plane from SNA wouldn’t start after 5 tries. The team gave me an option of flying direct from LAX and giving me a Lyft ride there! Perfect!

Best airline! Always friendly and welcoming. Skyclub was great and loved the fast free wifi on board. I also love that you can pre-order your meal on the app!

Atlanta boarding crew at gate were filled with arrogance and were disrespectful. In flight crew showed indifference to the needs of passengers. This is about the flight from ATL to BDL.

Boarding was somewhat chaotic. Unable to evaluate crew or food/drink because captain kept them seated due to turbulence. Have no idea if entertainment was offered.

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

Very frustrated with boarding gate crew. She announced the plane was small and they would be limiting us to one item to carry on. Not a problem for me as I understand the tiny planes have limited space!! Not the case here! It was a rather large plane and had plenty of room for bags! So because I don’t want to be one of “those people” who ignores the request to check a carry on I did so asking if I would be able to pick it up at the bottom of the ramp on arrival in Knoxville to which she responded “yes”! Then I watched as every other passenger held onto their 2 items and boarded!! Then when we arrived in Knoxville our 2 carry ons had been put with all the other luggage and we had to go to baggage pick up and wait for all the big checked bags to come off the carousel! So she lied!! Frustrating. Next time I won’t be so nice!

It was a good experience except when boarding a female flight attendant did not go out of her way to assist my teenage daughters in finding space for their carry-ons after their compartments were full.

Horrible, first flight delayed. They switched my connecting flight while I was en route and even though I was originally supposed to be on the flight going back home to boston, refused to let me board and told me I would have to wait for next flight that was 14 hours later. Ended up renting a car and driving 6.5 hours back home. Still getting messages about flight and it is now showing that the other flight they put me on is now canceled and I would have to wait 24 hours for the next one. I will never book with spirit again

They seemingly have no respect for their customers, on any level. Avoid flying spirit, they will bump you to another flight without thinking twice so they can sell your seat, no joke.

One hour late taking off. Concerning, very hard landing. Uncomfortable seats with no recline. Extremely slow baggage claim. Very professional, knowledgeable flight attendants. Brand new, very clean plane.

The flight attendants were very personable, extremely friendly, and had a very good feeling of the energy around them not to mention they’re very funny and engaging. What made up for the discomfort of the seats and the fact that the plane sat for a long time on the Turmac. Not sure if the pilot was new, but the landing was very rough sort of like I was at a magic mountain theme park ride that was built in 1959

Flight was delayed 2+ hours missed a concert because of it…

I liked that bag check was rather quick and efficient. The airplane chairs on the first leg of the trip were hard and uncomfortable. Also, the cabin temperature was too cold. The lady giving seat assignments took entirely too long. She said she would call me back to the desk in 5 minutes, and she never called me back.

Seats could use more padding. Kind of hard on the tush.

The Spirit travel experience was exceptional during the peak holiday season. The flight was on time and the service was exceptional.

Turbulence Lady at ticket counter who “took care of me was completely horrible and super disrespectful And staff on plane looked like they hate their job

Amazed that Spirit can even get planes in the air, would never use again.

Check in online was easy. Seats aren’t very comfortable

Fecal matter in seat back pocket. Presumably from a kids diaper.

Worst airline to travel with. They treat you like a prisoner in a jailhouse barking out orders and threats. Nickle and dime you to the same price or higher than a respectable airline like one of the big 3 . Might as well fly with standard airlines

Well I mean u get what u pay for so 🤷‍♂️

Over an hour delay in departure but I was notified beforehand. Another delay on tarmac upon arrival at LGA. We ended up departing the plane almost 2 hours later than expected

I fly Frontier because it’s affordable. I understand that the seats are tight and not the most comfortable…but that’s part of it. The problem with this flight was that there was a group of travelers directly behind me at the back of the plane who were ridiculously loud and obnoxious the entire flight. I’m pretty sure they were drunk and I could periodically smell an odd odor that I believe was one of them using a smokeless vape pen. The stewards had to remind them to keep quiet during the pre-flight instruction, but that was it. They never said another thing to them for the rest of the flight. It was a miserable.

I checked a bag because it was $5 less than carry on. They managed to lose my bag on a 2.5 hr direct flight! Frontier has no airport staff at baggage claim to help. As soon as I got home around 11 pm I tried to use their online system to file the claim for lost bag - system wouldn't take the # on my baggage claim ticket - said it was not the correct number. Also said that I had not checked a bag, which wasn't true - even my online boarding pass showed that I had checked a bag. Wasted about an hour on that process with no luck. Tried again in the morning - same thing. So tried online chat with Frontier bot - waited 35-40" twice to be connected to a baggage agent and it never happened. Eventually drove to PDX after work and waited 2 hrs for the Frontier ticket agents to arrive prior to the next Frontier flight out of PDX and FINALLY got some help from one of them, to take me to lost luggage area where I was able to retrive my bag. Probably took 4-5 hrs. of my time and endless frustration to get my bag. This was my first -- and LAST -- experience flying Frontier Airlines. Check-in was also extremely difficult and time consuming. The flight itself (and staff) were fine but everything else about the experience was a total disaster! The fact that Frontier literally has NO WAY to connect to a human voice for customer service (in this case for lost luggage) is the WORST!!!!!

Frontier is a crappy airline nothing about it is honest

I didn't get to do this flight l, hard to review

Not good 😐 Over priced baggage fees Small hard seats No wifi or entertainment options 😕

Book cheap flights from Chicago to Maryland

Recent round-trip flight deals

6/1Sat
nonstopFrontier
2h 01mMDW-PHL
6/4Tue
nonstopFrontier
2h 21mPHL-MDW
$55
5/29Wed
nonstopFrontier
2h 03mMDW-PHL
6/4Tue
nonstopFrontier
2h 21mPHL-MDW
$58
6/1Sat
1 stopDelta
4h 17mMDW-PHL
6/5Wed
1 stopDelta
4h 06mPHL-MDW
$176
7/12Fri
1 stopDelta
4h 35mMDW-BWI
7/20Sat
1 stopDelta
3h 38mBWI-MDW
$176
5/28Tue
1 stopSouthwest
11h 15mMDW-DCA
8/10Sat
nonstopSouthwest
2h 00mDCA-MDW
$309
5/28Tue
2 stopsSouthwest
12h 50mMDW-DCA
8/10Sat
nonstopSouthwest
2h 05mDCA-MDW
$314
7/14Sun
1 stop
7h 22mMDW-IAD
7/18Thu
2 stops
27h 43mIAD-MDW
$444
5/28Tue
1 stopPorter Airlines
6h 52mMDW-IAD
5/30Thu
1 stopPorter Airlines
9h 37mIAD-MDW
$497
6/13Thu
1 stop
7h 02mMDW-IAD
6/15Sat
3 stops
21h 27mIAD-MDW
$540
7/8Mon
1 stopPorter Airlines
6h 52mMDW-IAD
7/13Sat
1 stopPorter Airlines
5h 12mIAD-MDW
$547

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Recent one-way flight deals

6/19Wed
nonstopFrontier
2h 01mMDW-PHL
$48
6/19Wed
nonstopFrontier
2h 01mMDW-PHL
$49
6/15Sat
nonstopFrontier
1h 48mMDW-BWI
$49
7/15Mon
1 stopDelta
5h 57mMDW-PHL
$88
6/17Mon
1 stopDelta
4h 37mMDW-BWI
$88
6/10Mon
1 stopSouthwest
4h 55mMDW-PHL
$138
6/10Mon
1 stopSouthwest
9h 10mMDW-PHL
$144
6/7Fri
2 stops
9h 31mMDW-BWI
$154
6/3Mon
2 stops
20h 25mMDW-BWI
$168
6/12Wed
2 stopsSpirit Airlines
15h 48mMDW-BWI
$274

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Last minute flights from Midway to Maryland

Last minute flight, train and bus deals

5/21Tue
nonstopFrontier
2h 03mMDW-PHL
5/25Sat
nonstopFrontier
2h 16mPHL-MDW
$91
5/17Fri
nonstopFrontier
2h 00mMDW-PHL
5/25Sat
nonstopFrontier
2h 16mPHL-MDW
$108
5/21Tue
nonstopFrontier
2h 03mMDW-PHL
5/22Wed
nonstopFrontier
2h 13mPHL-MDW
$114
5/20Mon
nonstopFrontier
2h 02mMDW-PHL
5/26Sun
nonstopFrontier
2h 16mPHL-MDW
$120
5/18Sat
multi-stopDelta
4h 17mMDW-PHL
5/23Thu
multi-stopDelta
4h 06mPHL-MDW
$289
5/21Tue
multi-stopDelta
6h 40mMDW-BWI
5/22Wed
multi-stopDelta
3h 28mBWI-MDW
$307
5/20Mon
nonstopSouthwest
2h 00mMDW-PHL
5/23Thu
multi-stopSouthwest
10h 25mPHL-MDW
$385
5/20Mon
nonstopSouthwest
2h 00mMDW-PHL
5/23Thu
multi-stopSouthwest
14h 50mPHL-MDW
$443
5/17Fri
multi-stop
21h 38mMDW-BWI
5/19Sun
multi-stop
13h 43mBWI-MDW
$612
5/17Fri
multi-stop
31h 16mMDW-BWI
5/19Sun
multi-stop
13h 43mBWI-MDW
$668

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Chicago Midway Airport - Maryland Flights

Departure:

Chicago Midway Airport (MDW)United States

Return flight deals:

Maryland - Chicago Midway Airport

Cabin classes:

$27