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Find cheap flights from Chicago Midway Airport to Maryland from $37

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 7/10. 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
Tue 7/9
Tue 7/16

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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

$37
Best time to beat the crowds with an average 75% drop in price.
Most popular time to fly and prices are also 25% 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 $31 one-way - $75 round-trip; Philadelphia $39 one-way - $78 round-trip
  • Morning departure is around 12% 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 10295 reviews
8.0Entertainment
7.4Food
8.2Boarding
7.9Comfort
8.6Crew
Airline reviews

3 hours late and all they have is was a $12 meal voucher. That’s not even enough to cover fast food.

2.0 MediocreCraig, Jun 2024CVG - LGA
Read more about Delta reviews

3 hours late and all they have is was a $12 meal voucher. That’s not even enough to cover fast food.

Among the poorest flights I’ve had with Delta in a while. Entertainment system failed completely on a 7.5 hr flight. Crew seemed distracted and not the normal friendly crew. Flight overbooked it seemed… very crowded.

If I can, I always fly Delta. I’ve found their service to always be reliable and pleasant.

You could have not cancelled the flight (AA, which I will be flying from now on) left for BOS despite the fictitious weather issues (that no one in my Boston family could see). You could have rebooked my direct flight to another direct flight instead of sending me though JFK, the worst US airport after O’Hara You could have rebooked me on a Main Cabin seat (like the one I paid for in my original ticket instead of putting me a the last row on JFK->BOS leg, pocketing the difference in ticket price But I do not really care whether you will ever do that in a future because in a future neither I nor anyone from my company (unless they pay out of pocket) nor an of my clients and partners (if they heed my advice) will ever be caught dead on any of Delta flights

Really bad baggage handling. Had my Rimowa bag badly damaged at the latches.

It was pretty good I was worried with the short Layover that I might not catch my connection but the gate was there

It was good until there was a 3 hour delay because there was not any pilots to fly the plane.

There was plenty of overhead room but half of the passengers were told they had to check their carryon bags. My partner and I checked in as early as possible and our seats were split across the aisle.

Friendly flight attendants. Comfort plus seats were very comfortable and had lots of leg room. 10A and 10 B.

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

Flight was canceled less than 6 hours before takeoff, rebooked on a flight that was twice as long and left earlier so we couldn’t make it, when using text support option took over 2 hours to speak with someone.

The plane was not on time for boarding or departure or arrivals.

Flight expected to leave at 6:40 pm ended leaving at 8:00 am the following day. I slept in a cold airport. Never again Spirit for me…

This was the return leg of my journey with Spirit Airlines. Despite its reputation, I found no issues as it got me from point A to B safely and without delay, especially with no mechanical delays, which is fantastic in my book! The staff, from ground crew to cabin crew, were all pleasant and hassle-free. The flight was smooth from takeoff to landing. I have absolutely no complaints about this no-frills airline!

I got a one-way, last-minute nonstop flight from PDX to BWI for only $125. Yes, I got nicked $79 more for a checked suitcase and $89 more for the BIG SEAT option, but it was worth it, even with $4.50 for coffee and $10 for a snack (the latter no different than any other airline). The grand total was still less flying on any other airline.

It was the worst ever, i will be filing a lawsuit to get a refund. Our flight was delayed 4 hours so we would miss our connecting flight, we were not rebooked to our destination the same day, we were not offered any options to get home on the same day despite being clear that we absolutely cannot get stranded at night due to family, we were forced to book our own flights on a different airline to get home, and spririt is refusing a refund because our flight wasn't cancelled, only delayed. oh yeah, and they lost our luggage on the first part of the trip and you cannot get a hold of customer service when anything goes wrong, on hold for 30+ minutes. and their app breaks so you can't use that either.

My flight was cancelled!!! I had to spend 200.00 on another flight!!

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.

8 hr delay. had to buy another ticket with another airline

Four and a half hour delay in total. What frustrates me most is the poor communication and disorganization.

I appreciated the upgrade to free cary-on bag and seat selection at no charge

FRONTIER SUCKS! The agent downstairs tricked me into booking, just to get to the gate. At the gate, they told me they couldn't help. I then called Customer Service. They and the gate attendants kept blaming each other. Neither side was willing to help the customer.

The agent at check-in was strident, unwelcoming, and condescending to customers ahead of me.

Flight was delay 9hrs and nothing was provided at airport, had to go and get a room to sleep in, paid for Uber back and fort with no offers until we landed back home a 1hr later for a $75 voucher for a future flight.

Didn't like anything..entire crew was very rude to everyone on the flight. Plane old and the trays fall down on you the while time you're flying. Charged more for a carry on bag than for the plane ticket itself. Did make it from point a to point b, but worth the extra money to fly with another airline

9 hours of delay!! Was not able to check my luggage that I paid for!!!

It was delayed 9 hours for operational reasons, despite the plane arriving to the airport on time.

I am very disappointed with Frontier Airlines. They cancelled our flight because they couldn't find a crew member, and then didn't get us to our connecting flight. We had to cancel our whole vacation. We were promised flight and hotel vouchers, but they never sent them.

Book cheap flights from Chicago to Maryland

Recent round-trip flight deals

8/7Wed
nonstopFrontier
2h 01mMDW-PHL
8/14Wed
nonstopFrontier
2h 13mPHL-MDW
$48
8/24Sat
nonstopFrontier
1h 51mMDW-BWI
8/28Wed
nonstopFrontier
1h 59mBWI-MDW
$48
8/7Wed
nonstopFrontier
2h 01mMDW-PHL
8/14Wed
nonstopFrontier
2h 13mPHL-MDW
$50
8/24Sat
nonstopFrontier
1h 51mMDW-BWI
8/28Wed
nonstopFrontier
1h 59mBWI-MDW
$51
8/13Tue
nonstopFrontier
2h 13mMDW-PHL
8/14Wed
nonstopFrontier
2h 13mPHL-MDW
$52
7/20Sat
1 stopDelta
4h 27mMDW-PHL
7/23Tue
1 stopDelta
5h 06mPHL-MDW
$186
6/29Sat
1 stopDelta
4h 37mMDW-BWI
7/11Thu
1 stopDelta
3h 38mBWI-MDW
$186
7/10Wed
1 stopSouthwest
10h 30mMDW-DCA
7/11Thu
1 stopSouthwest
10h 05mDCA-MDW
$200
7/1Mon
3 stops
22h 17mMDW-IAD
7/7Sun
1 stop
16h 37mIAD-MDW
$540
7/1Mon
1 stopPorter Airlines
17h 22mMDW-IAD
7/7Sun
1 stopPorter Airlines
16h 37mIAD-MDW
$619

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Recent one-way flight deals

7/10Wed
nonstopFrontier
2h 01mMDW-PHL
$37
6/26Wed
nonstopFrontier
1h 48mMDW-BWI
$37
6/15Sat
1 stopDelta
4h 24mMDW-PHL
$88
8/17Sat
1 stopDelta
4h 35mMDW-BWI
$88
6/17Mon
2 stops
17h 46mMDW-PHL
$152
6/14Fri
2 stops
9h 36mMDW-BWI
$152
6/20Thu
1 stopAllegiant Air
6h 27mMDW-IAD
$179
6/20Thu
2 stopsAllegiant Air
10h 14mMDW-BWI
$246
6/21Fri
1 stopPorter Airlines
7h 02mMDW-IAD
$257
7/21Sun
1 stopPorter Airlines
7h 22mMDW-IAD
$267

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Last minute flights from Midway to Maryland

Last minute flight, train and bus deals

6/12Wed
nonstopFrontier
2h 01mMDW-PHL
6/18Tue
nonstopFrontier
2h 12mPHL-MDW
$88
6/11Tue
nonstopFrontier
2h 02mMDW-PHL
6/18Tue
nonstopFrontier
2h 12mPHL-MDW
$90
6/12Wed
nonstopFrontier
2h 01mMDW-PHL
6/17Mon
nonstopFrontier
2h 11mPHL-MDW
$106
6/14Fri
nonstopFrontier
2h 01mMDW-PHL
6/18Tue
nonstopFrontier
2h 12mPHL-MDW
$108
6/13Thu
multi-stopDelta
6h 00mMDW-PHL
6/16Sun
multi-stopDelta
3h 48mPHL-MDW
$245
6/14Fri
multi-stopDelta
7h 52mMDW-PHL
6/16Sun
multi-stopDelta
3h 48mPHL-MDW
$270
6/14Fri
multi-stop
9h 36mMDW-BWI
6/16Sun
multi-stop
22h 33mBWI-MDW
$510
6/14Fri
multi-stop
9h 36mMDW-BWI
6/17Mon
multi-stop
11h 58mBWI-MDW
$597
6/14Fri
multi-stopWestJet
28h 59mMDW-DCA
6/21Fri
multi-stopWestJet
32h 30mDCA-MDW
$1,094
6/12Wed
multi-stopWestJet
24h 58mMDW-BWI
6/17Mon
multi-stopWestJet
21h 38mBWI-MDW
$1,849

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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:

$37