$67 Find Cheap Flights from Chicago Midway Airport to Maryland

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 2/22. 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
1 adult, Economy, 0 bags

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

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Maryland, 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 Maryland, as well as popular online travel agencies
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Flight Deals

Book Cheap Midway to Maryland Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to Maryland 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.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to Maryland

Wed, Dec 24 - Wed, Dec 31
Frontier Logo
6:12 am - 12:29 amMDW-BWI
17h 17m1 stop
Frontier Logo
5:30 am - 10:12 pmBWI-MDW
17h 42m1 stop
$133Frontier
Find Deal
Wed, Dec 24 - Wed, Dec 31
Southwest Logo
6:40 am - 9:30 amMDW-BWI
1h 50mnonstop
Southwest Logo
8:00 pm - 9:05 pmBWI-MDW
2h 05mnonstop
$139Southwest
Find Deal
Wed, Dec 24 - Wed, Dec 31
Southwest Logo
6:40 am - 9:30 amMDW-BWI
1h 50mnonstop
Southwest Logo
11:20 am - 2:05 pmBWI-MDW
3h 45m1 stop
$145Southwest
Find Deal
Fri, Jan 9 - Mon, Jan 12
Frontier Logo
4:31 pm - 8:57 amMDW-PHL
15h 26m1 stop
Frontier Logo
3:56 pm - 11:09 pmPHL-MDW
8h 13m1 stop
$146Frontier
Find Deal
Fri, Jan 9 - Tue, Jan 13
Southwest Logo
9:50 am - 12:40 pmMDW-BWI
1h 50mnonstop
Southwest Logo
5:50 pm - 7:00 pmBWI-MDW
2h 10mnonstop
$148Southwest
Find Deal
Wed, Jan 7 - Tue, Jan 13
Frontier Logo
5:10 pm - 12:29 amMDW-BWI
6h 19m1 stop
Frontier Logo
6:05 am - 10:34 amBWI-MDW
5h 29m1 stop
$155Frontier
Find Deal
Fri, Jan 9 - Tue, Jan 13
Multiple Airlines Logo
4:31 pm - 11:17 amMDW-BWI
17h 46m1 stop
Multiple Airlines Logo
6:05 am - 10:34 amBWI-MDW
5h 29m1 stop
$156Multiple Airlines
Find Deal
Fri, Jan 9 - Sun, Jan 11
Southwest Logo
5:15 pm - 8:10 pmMDW-BWI
1h 55mnonstop
Southwest Logo
4:25 pm - 5:35 pmBWI-MDW
2h 10mnonstop
$157Southwest
Find Deal
Wed, Jan 14 - Tue, Jan 20
Multiple Airlines Logo
11:39 am - 11:47 pmMDW-BWI
11h 08m2 stops
Multiple Airlines Logo
7:10 am - 12:05 pmBWI-MDW
5h 55m1 stop
$158Multiple Airlines
Find Deal
Fri, Jan 9 - Mon, Jan 12
Delta Logo
6:45 am - 1:23 pmMDW-PHL
5h 38m1 stop
Delta Logo
4:59 pm - 10:07 pmPHL-MDW
6h 08m1 stop
$177Delta
Find Deal
Booking Insights

KAYAK's insights & trends for Midway to Maryland flights

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

What is the cheapest Chicago Midway Airport to Maryland flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Maryland from Chicago Midway Airport found in the last 72 hours was to Baltimore, at $93 round-trip. The most popular route is from Chicago Midway Airport (MDW) to Baltimore (BWI), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $93.

What is the cheapest month to fly from Chicago Midway Airport to Maryland?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago Midway Airport to Maryland, 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 Chicago Midway Airport to Maryland is September, when tickets cost $154 (return) on average. On the other hand, the most expensive months are March and June, when the average cost of round-trip tickets is $268 and $263 respectively.

What’s the cheapest day of the week to fly from Chicago Midway Airport to Maryland?

The average price of all round-trip flights from Chicago Midway Airport to Maryland clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from Chicago Midway Airport to Maryland, look for departures on Thursdays and avoid leaving on a Thursday, as it's usually the priciest day. When flying back from Maryland, Tuesday is the cheapest day to fly and Wednesday is the most expensive.

Good to know

Low seasonJanuary
Cheapest flight$67
Best time to beat the crowds but there is an average 10% increase in price.
Most popular time to fly and prices are also 4% 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 from Chicago Midway Airport to Maryland 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 from Chicago Midway Airport to Maryland 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 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 from Chicago Midway Airport to Maryland up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Maryland?

    The cheapest time of day to fly to Maryland is generally in the evening, when round-trip flights cost $283 on average. Morning departures are around 4% more expensive than evening flights, on average. The most expensive time of day to fly to Maryland is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $306.

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 $75 one-way - $208 round-trip; Philadelphia $88 one-way - $161 round-trip

Reviews of the top airlines flying from Midway to Maryland

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Maryland. 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 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
SouthwestOverall score based on 4254 reviews
7.0Food
8.6Crew
7.5Entertainment
8.1Boarding
8.0Comfort
Airline reviews

No delays and arrived to destination 30 min early. Staff was super friendly.

10.0 ExcellentIlevba, Nov 2025DCA - DAL
Read more Southwest reviews

No delays and arrived to destination 30 min early. Staff was super friendly.

San Diego airport is brand new, spacious, airy and very smooth checkin at SW baggage drop.

Crew could have been friendlier, maybe I'm spoiled by SW crews. In flight wifi was good. Would be nice to have more food offerings on a 4 plus hour flight

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

Great flight. Outstanding Service. Southwest was able to put us on a direct flight to Denver when the connection could have been affected by a later arrival to Baltimore. The direct flight was less expensive that the flight with the connection in Baltimore.

After being assaulted by a flight attendant I was then brushed off as oh well because he long braids didn’t mean to whip me in the eye. I have filed complaints and will see. But like any other issue I’ve had with kayak involved it’s been trash. Last time I’ll be using your app

AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.

The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.

If we are going to have to pay for luggage, make it easier to do. Put something on the app during check-in so I don't need to do it at the kiosk. I've done it twice recently and I ended up having to pay at the desk because something went wrong at the kiosk in Tampa.

Delayed. Text notifications were slow. Not much information o what was happening. Boarding was slow and confusing. Wasn’t even offered water other flight. Had to ask. No entertainment at all. Felt like.a Greyhound bus.

When I wanted to check in 3 hours prior to boarding time, the employees mentioned “a little over an hour delay” so I waited for an hour then I went to go look for food in the terminal and most people from that flight were in the same area looking for food. Finally I decided after food to check to see if it’s anytime closer and now it’s 2 mins until boarding closes?! What are you kidding me? I didn’t receive anything via sms about boarding now nor via email or on the intercom. I luckily made it through, barely, and then there’s no room for my carry on mind you I’m in the very first row so I had to place my purse in one further row back and my carry on sections down. Not sure who pays for better seats to get your stuff placed all over the plane but that was the worst experience I’ve ever had flying with anyone.

Better than expected. Staff were friendly and nice on both flights.

There was no one at the counter to assist with our check in. The app didn’t work, so I arrived at the airport with time to check in and I couldn’t because no employees were there. When I finally got someone on the phone, it was inside the 60min rule and they said I could no longer check in and they could sell me another ticket. We had to scramble and pay an additional $800 for tickets and THEN AFTER (about 60 min from my original convo with customer service and 10min after original departure time) I had boarded my new flight, there was email saying my original flight from Frontier was delayed and leaving 2hr 50min later, but I STILL wouldn’t have been able to check in. Which means customer service should have been able to see it and let me check in because I was well within my check in time. When I call Frontier, they hang up on me. So their app didn’t work and they employees left and they take zero responsibility or assistance with their “customer service”

Terrible. Flight cancelled with no reasoning and no flights to rebook. Employees were useless and did nothing to help. Did not even know where to retrieve luggage from the cancelled flight. Flyers beware.

No fault of Frontier staff: plane was very late, reached Orlando at 1 am, took a while to get luggage. Weather, gov financial shutdown impact on TSA, air controllers seemed to have multiple flights backed up. Frontier staff seemed to cope as gracefully as possible. It did reassure me that I and my new hip could adapt to travel challenges. Food/entertainment were irrelevant to my trip.

Terrible. The canceled my entire flight when I requested a refund for a trip frontier canceled trip one way.

Boarding was on time and plane departed as scheduled. There are obviously no amenities (food, drink, entertainment) on Frontier, but there also didn't seem to be any issues with luggage space either.

Inbound plane was on time and flight departed on time with no issues while boarding.

I knew going into this that Frontier, being a low cost carrier, would be pretty bare bones and charge for most extras but this was made up for by the fact that the airplane was a reasonably new Airbus, every employee was great and best of all, Everett Washington is an amazing airport - thanks Frontier for flying there!!!

Everything you need to know for your flight from Midway to Maryland

Information on your arrival and departure airports