$66 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 9/11. 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

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

Cheap Flights from Midway to Maryland

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Washington, D.C.
Baltimorenonstop$100
Washington, D.C.
Baltimorenonstop$100

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

Fri, Sep 5 - Mon, Sep 8
Frontier Logo
1:49 pm - 4:50 pmMDW-BWI
2h 01mnonstop
Frontier Logo
5:40 pm - 6:43 pmBWI-MDW
2h 03mnonstop
$100Frontier
Find Deal
Thu, Oct 30 - Mon, Nov 3
Frontier Logo
3:40 pm - 6:35 pmMDW-BWI
1h 55mnonstop
Frontier Logo
7:25 pm - 8:31 pmBWI-MDW
2h 06mnonstop
$102Frontier
Find Deal
Fri, Oct 31 - Mon, Nov 3
Frontier Logo
3:40 pm - 6:35 pmMDW-BWI
1h 55mnonstop
Frontier Logo
7:25 pm - 8:31 pmBWI-MDW
2h 06mnonstop
$103Frontier
Find Deal
Thu, Sep 4 - Mon, Sep 8
Frontier Logo
1:49 pm - 4:50 pmMDW-BWI
2h 01mnonstop
Frontier Logo
5:40 pm - 6:43 pmBWI-MDW
2h 03mnonstop
$104Frontier
Find Deal
Sat, Sep 27 - Sat, Oct 4
Southwest Logo
7:00 am - 9:50 amMDW-BWI
1h 50mnonstop
Southwest Logo
7:55 pm - 8:55 pmBWI-MDW
2h 00mnonstop
$139Southwest
Find Deal
Tue, Sep 23 - Wed, Sep 24
Southwest Logo
7:00 am - 9:55 amMDW-PHL
1h 55mnonstop
Southwest Logo
3:20 pm - 4:25 pmPHL-MDW
2h 05mnonstop
$139Southwest
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Wed, Oct 1 - Mon, Oct 6
 Logo
9:00 am - 10:29 pmMDW-PHL
12h 29m2 stops
 Logo
6:00 am - 7:11 amPHL-MDW
2h 11mnonstop
Sun, Sep 28 - Tue, Sep 30
 Logo
8:06 am - 11:07 amMDW-PHL
2h 01mnonstop
 Logo
5:00 am - 3:58 pmPHL-MDW
11h 58m2 stops
Tue, Sep 16 - Sat, Sep 20
Delta Logo
6:15 pm - 10:57 pmMDW-DCA
3h 42m1 stop
Delta Logo
6:10 am - 1:03 pmDCA-MDW
7h 53m1 stop
$217Delta
Find Deal
Thu, Oct 2 - Sun, Oct 5
Delta Logo
9:35 am - 4:35 pmMDW-DCA
6h 00m1 stop
Delta Logo
6:00 am - 8:40 amDCA-MDW
3h 40m1 stop
$258Delta
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 $99 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 $99.

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 October, when tickets cost $168 (return) on average. On the other hand, the most expensive months are November and December, when the average cost of round-trip tickets is $326 and $275 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$66
Best time to beat the crowds with an average 20% drop in price.
Most popular time to fly and prices are also 7% lower on average.
Flight from Chicago Midway Airport to Baltimore

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 at night, when round-trip flights cost $266 on average. Morning departures are around 2% 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 $319.

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 $83 one-way - $141 round-trip; Philadelphia $110 one-way - $159 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 4246 reviews
7.0Food
8.1Boarding
8.6Crew
7.5Entertainment
8.0Comfort
Airline reviews

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

6.0 GoodDavid, Aug 2025MCO - DEN
Read more Southwest reviews

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

Southwest's seats are the least comfortable I have ever sat in.

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.

Southwest like most American domestic airlines, is a mediocre airline. But it is among the cheapest. Oh well.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

Other than a bit of a delay, everything was good. Again, the boarding process and picking seats is the only thing I don't enjoy.

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.

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

The quality of Southwest Airlines continues to degrade each time I fly with them. If it were not for the free luggage, I would probably choose another airline. Their prices are a little bit competitive, but way too high for the quality of the service. Southwest is not unique in this way. Domestic flight in the United States of America has continued to be a lower and lower quality product. Very sad when you compare the quality of domestic airlines to that of many international airlines around the world.

Great for the price. No wifi or entertainment, but gate agents and crew were fantastic and we boarded quickly and left on time.

sluggish boarding and arrival procedures, fake nice flight attendants, and lots of delays.

Disaster. They lied every step of the way. We ended up being delayed due to crew and then allegedly abandoned the flight because of a curfew at LGA. No rebooking to LGA at any reasonable time. No hotel. No meal vouchers. Had to sleep in the airport and fly to Newark instead. Will never fly Frontier again.

What I expected, nickeled and dined and a frontier flight attendant loudly complained about her job and lack of communication as she headed to the gate on her cell phone. Not professional.

As every law enforcement agency I could imagine surrounded the plane and we didn’t disembark for 2 hours and then had to stick around for another hour to go get our personal belongings after leaving them behind and being bused away from the plane, it was scary and inconvenient. We were given no information as to why this was happening. Lack of communication with passengers was disappointing.

After boarding and un-boarding twice over 6+hours, the flight was canceled.

Severe turbulence. Captain never came on to reassure passengers after things settled down.

My first flight was delayed 5 hours. The 2nd flight was canceled til the next day and the never even tried to compensate for it. Worse I was delayed again on the flight the rebooked me on.

Boarding in Orlando was not good. Giant mob at the gate, should have been lines.

Decent clean onboard experience. Okay discount airline experience. Unfortunately, any customer service interactions are difficult and unhelpful. There is no service. Also, a premium seat only gets you premium boarding if you line up first. Once they start general boarding you must go to the back of the line. Not very premium

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

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