$50 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 11/16. 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

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

Thu, Oct 23 - Sat, Oct 25
Frontier Logo
12:30 pm - 3:27 pmMDW-BWI
1h 57mnonstop
Frontier Logo
4:12 pm - 5:13 pmBWI-MDW
2h 01mnonstop
$87Frontier
Find Deal
Thu, Oct 23 - Sat, Oct 25
Frontier Logo
12:30 pm - 3:27 pmMDW-BWI
1h 57mnonstop
Frontier Logo
4:12 pm - 5:13 pmBWI-MDW
2h 01mnonstop
$88Frontier
Find Deal
Thu, Oct 30 - Fri, Oct 31
Frontier Logo
3:40 pm - 6:35 pmMDW-BWI
1h 55mnonstop
Frontier Logo
7:25 pm - 8:31 pmBWI-MDW
2h 06mnonstop
$89Frontier
Find Deal
Thu, Oct 30 - Thu, Nov 6
Frontier Logo
3:40 pm - 6:35 pmMDW-BWI
1h 55mnonstop
Frontier Logo
7:25 pm - 8:31 pmBWI-MDW
2h 06mnonstop
$90Frontier
Find Deal
Wed, Dec 17 - Tue, Jan 6
Southwest Logo
6:55 pm - 9:45 pmMDW-BWI
1h 50mnonstop
Southwest Logo
5:50 pm - 7:00 pmBWI-MDW
2h 10mnonstop
$139Southwest
Find Deal
Wed, Jan 14 - Sat, Jan 17
Southwest Logo
5:30 pm - 8:20 pmMDW-PHL
1h 50mnonstop
Southwest Logo
4:15 pm - 5:30 pmPHL-MDW
2h 15mnonstop
$139Southwest
Find Deal
Wed, Nov 12 - Sun, Nov 16
Multiple Airlines Logo
2:06 pm - 9:13 pmMDW-PHL
30h 07m2 stops
Multiple Airlines Logo
6:15 am - 7:30 amPHL-MDW
2h 15mnonstop
$155Multiple Airlines
Find Deal
Thu, Oct 30 - Mon, Nov 3
Multiple Airlines Logo
9:15 am - 12:19 pmMDW-PHL
2h 04mnonstop
Multiple Airlines Logo
9:32 pm - 11:38 amPHL-MDW
15h 06m2 stops
$156Multiple Airlines
Find Deal
Wed, Dec 24 - Wed, Dec 31
Delta Logo
9:50 am - 4:42 pmMDW-DCA
5h 52m1 stop
Delta Logo
6:00 am - 11:06 amDCA-MDW
6h 06m1 stop
$229Delta
Find Deal
Fri, Oct 31 - Tue, Nov 4
Delta Logo
4:23 pm - 11:41 pmMDW-DCA
6h 18m1 stop
Delta Logo
6:20 pm - 10:14 pmDCA-MDW
4h 54m1 stop
$243Delta
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 $98 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 $98.

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 December and March, when the average cost of round-trip tickets is $275 and $268 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$50
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly and prices are also 28% 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 in the evening, when round-trip flights cost $273 on average. Morning departures are around 7% 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 $297.

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 $86 one-way - $149 round-trip; Washington, D.C. $149 one-way - $265 round-trip; Philadelphia $89 one-way - $136 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 4236 reviews
8.0Comfort
7.5Entertainment
8.1Boarding
7.0Food
8.6Crew
Airline reviews

mandatory demand customer to check their carry on because not enough people check bags.

6.0 GoodHung, Oct 2025PHX - ABQ
Read more Southwest reviews

mandatory demand customer to check their carry on because not enough people check bags.

Connecting flight is on time and boarding was a breeze!

Excellent. Would encourage Southwest to keep current boarding procedures with free style seating. Makes for a fantastic experience

As always, the entire Southwest experience was perfect. Purchasing the tickets on the Southwest web site was effortless, departure and arrival gates were spotless and comfortable, plane was clean and comfortable, crew was excellent and flight was on time. Wheelchair service in Las Vegas at departure was somewhat chaotic and disjointed, but I am not sure if that was Southwest problem, airport problem or combination.

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.

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

WiFi did not work. For as outrageous as these flights cost, when they’re advertised with certain services/ features they should be in working order

Too many extra fees, uncomfortable, little leg room. Will not recommend this airline.

Everyone seemed to be in zone 1 for boarding. Maybe break it up a little. Otherwise, smooth flight.

Frontier is the Walmart of airlines. Frontier has removed adjustability and comfort from their seats to make the flight lighter and save gas. This makes it impossible to sleep on their flights. Their customer service is abysmal. Once, I bought a drink on the plane, and they swiped my credit card on the plane to pay for it. Then I got three weeks of daily notices from my bank telling me they tried to charge the wrong card number over and over again. I tried to call them, but they removed the ability to actually talk to someone that can resolve such a problem from their company to cut corners. The only way to talk to someone in person is to go to the check-in counter at the airport (40 minutes drive from my house). Eventually their system gave up on trying to charge the card, after 21 days of repeated tries. They don't pad their prices even a little to handle customer service issues like missed flights. They also have a blanket policy preventing helping you reschedule a missed flight if their system says you "cancelled" your own flight online. This is a major problem because their website is broken on mobile devices, the only web browser you have at the airport when their gate staff tell you that you have to reschedule your own missed flight online because they can't help you. I tried to reschedule my flight on my android device and instead, their website crashed and "cancelled" my missed flight. When I got to the counter, the agent argued with me for 5 minutes insisting that I intentionally cancelled my own flight (implying I had to buy another flight). She missed the point: the problem was that I could not buy another flight because their website is broken. I left to avoid more conflict with the "customer service" agent. I tried to redress my issue with their only other "customer service" chanel available: the contact form on their website. The response I got was more of the same: you cancelled your own flight, according to our website / computer records, therefore we won't help you. I was trying to explain the problem with their broken website that cost me hundreds of dollars by crashing / malfunctioning and resulting in a cancelled flight, but they only had deaf ears for this problem. Worst customer service I have ever experienced. I will never buy another Frontier flight again, because it is a risky, painful move that I will likely regret often.

I think Frontier was very good at communication. Their app worked very well. Loading was great and the flight was nice and easy.

This airline sucks. They offer low rates then charge you for everything, the app does not work well, the seats are the most uncomfortable. Maintenance issues on the flight, and you still have to sit through their credit card commercials. People are nice enough but does not make up for overall poor experience.

Seats were new and comfortable. Staff was fine. Missed my connection due to weather -which wasn’t their fault- but got no help at all. Gate staff sent me to customer service, which was and stayed unstaffed. Sign with QR code directed me to call or chat. Chat was useless. Call was returned after an hour. No itinerary offered by Frontier could get me home in less than 30 hours. Rebooked with another airline and got a partial refund that came to about 10 percent of what I paid to get home.

Finally a Frontier on time and efficient. I've had problems before with your airline, but this time everything went fine.

The experience was good. No frills but I got there safe and sound and on time.

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.

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

Information on your arrival and departure airports

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