$79 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 4/25. 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

ג', אפר' 14 - ג', אפר' 21
Frontier Logo
2:15 pm - 12:44 am
MDW
-
BWI
9h 29m
1 stop
Frontier Logo
12:17 pm - 10:14 pm
BWI
-
MDW
10h 57m
1 stop
$126Frontier
ה', אפר' 30 - ג', מאי 5
Frontier Logo
6:00 am - 12:44 am
MDW
-
BWI
17h 44m
1 stop
Frontier Logo
9:07 am - 10:19 pm
BWI
-
MDW
14h 12m
1 stop
$128Frontier
ג', מאי 5 - ד', מאי 6
Frontier Logo
6:00 am - 4:59 pm
MDW
-
BWI
9h 59m
1 stop
Frontier Logo
9:07 am - 7:31 pm
BWI
-
MDW
11h 24m
1 stop
$130Frontier
ג', מאי 5 - ב', מאי 11
Frontier Logo
6:00 am - 12:49 am
MDW
-
BWI
17h 49m
1 stop
Frontier Logo
7:34 pm - 10:19 pm
BWI
-
MDW
27h 45m
1 stop
$131Frontier
ה', אפר' 23 - א', אפר' 26
Southwest Logo
3:25 pm - 6:25 pm
MDW
-
PHL
2h 00mnonstop
Southwest Logo
7:05 pm - 8:25 pm
PHL
-
MDW
2h 20mnonstop
$177Southwest
ש', אפר' 11 - ש', אפר' 18
Delta Logo
1:10 pm - 5:47 pm
MDW
-
DCA
3h 37m
1 stop
Delta Logo
9:35 am - 12:43 pm
DCA
-
MDW
4h 08m
1 stop
$181Delta
ו', אפר' 24 - ש', אפר' 25
Delta Logo
9:27 am - 4:36 pm
MDW
-
DCA
6h 09m
1 stop
Delta Logo
6:00 am - 8:47 am
DCA
-
MDW
3h 47m
1 stop
$188Delta
ד', אפר' 1 - ד', אפר' 1
Southwest Logo
11:30 am - 2:15 pm
MDW
-
DCA
1h 45mnonstop
Southwest Logo
9:15 pm - 10:20 pm
DCA
-
MDW
2h 05mnonstop
$197Southwest
ג', מרץ 24 - ד', מרץ 25
Southwest Logo
5:30 am - 8:25 am
MDW
-
DCA
1h 55mnonstop
Southwest Logo
9:05 am - 10:15 am
DCA
-
MDW
2h 10mnonstop
$209Southwest
ה', אפר' 9 - ש', אפר' 11
Southwest Logo
5:00 pm - 7:55 pm
MDW
-
DCA
1h 55mnonstop
Southwest Logo
6:40 am - 7:45 am
DCA
-
MDW
2h 05mnonstop
$215Southwest
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 $243 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 $243.

Good to know

Low seasonSeptember
Cheapest flight$79
Best time to beat the crowds with an average 39% drop in price.
Most popular time to fly with an average 21% increase in price.
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 $286 on average. Morning departures are around 6% 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.

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 4301 reviews
7.5Entertainment
8.0Comfort
7.0Food
8.1Boarding
8.6Crew
Airline reviews

Flight boarded late after announcing on time boarding. Flight arrived only a little late despite late departure. Had trouble connecting to WiFi

4.0 OkayEmma, Mar 2026
LAX - PHX
Read more Southwest reviews

Flight boarded late after announcing on time boarding. Flight arrived only a little late despite late departure. Had trouble connecting to WiFi

Mediocre. Boarding is now unpleasant. The employees, once friendly and nice, are now regularly speaking sternly to passengers, badgering them to do things right so they can take off on time and gate check bags because they don't have enough overhead bin space. The pretzel snack was crushed flat and broken into even smaller pieces, which happens frequently lately. Drink service was suspended before they reached my row.

The last 3 flights between BWI and BDL canceled the beverage service mid- way. Just say up front that the fight is too short. Thanks!

I was assigned seat 7E, yet my boarding was Group 5, which caused me to have to put my luggage in the back of the plance above `19 or 20 aisle, as passengers who had boarded earlier took the overhead bins in the front. SW needs to monitor bin space and ensure that bin space above the seat are aligned to those sitting near their seats. Also the seating assignments needs to align with group number. Maybe board those last first and so on? Having said the ALL the passengers on the plane were gracious enough to allow me and other passengers in this dilema to retrieve our luggage and helped us along the way. I always love the flight staff, as always their fantastic and I can't rave about them enough!

WIFI was great. My selection for seating is an aisle, but during my trip, I never had an aisle seat. If we can get that corrected, I will be thrilled.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

Departure was delayed more than 1/2 hour while we waited for luggage (only) transfer from another flight/plane. Once approved for takeoff, the flight was excellent.

Never went on board this flight. Kayak uses Underpricer (which is a scam business) as it's "customer service provider". This customer service is a classic bait and switch "service". I Got caught in the UnderPricer Bait and switch scam. 14 hours on the phone with people from India with heavy accents and upselling me to useless products. The original sell was a flight on spirit. Then they contact me later, an say after they have my money that the flight is no good as is is only one seat for a party of two. I am still in dispute to get my money back. Went to Spirit direct and had a beautiful vacation. I should never have used Kayak and their rip off artists UnderPricer.

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.

Gate not determined until I got to the airport - hard to plan the trip to the airport.

Our flight was canceled. I will never use Kayak nor Frontier for travel again. The entire experience was a headache.

Frontier.. nickel and dime add-ons. Flight late, on time, late again, last minute gate change, arrival gate required a shuttle to the terminal. They sure keep you guessing.. if you like a little chaos and airport anxiety, this is the airline for you!

This is my second time flying with Frontier. My current experience was very favorable. The staff from the gate to the plane was friendly, warm and professional. The food options lacked in my opinion. This area needs some attention in my opinion.

There was no food and no entertainment, so I'm not sure why these are even in the survey, as my understanding is frontier does not ever offer food without a few, not even a snack, and there are no screens so unless the flight safety talk is our entertainment why ask how we liked it?. One of the flight attendants say in the back of the plane as people filed in to their seats, yelling orders about where to put baggage and telling people to hurry up. It was the least professional experience I've ever had on a flight.

Very well recently! Frontier is improving and less harrassing customer on luggages! Positive!

Good for a budget airline! It was easy to get on, staff was really nice. Can’t say anything about the food or entertainment because it wasn’t available, which is fine.

I am writing to express my disappointment with my recent Frontier Airlines flight. I was charged $99 at the gate because my bag was said to be too large, yet once onboard there was no available overhead bin space, and I was required to place the bag under the seat in front of me anyway. This made the charge feel unnecessary and unfair. Additionally, before the flight even took off, I was asked to move from the seat I paid for into a middle seat so another passenger and her cat could have my seat to themselves. I was not offered compensation or an explanation for being moved from a paid seat. Between the unexpected bag fee and being forced to give up my seat, this experience fell well below acceptable customer service standards. I would appreciate a review of this situation and appropriate compensation.

It was costly and difficult to check in. $85 to take a small suitcase with me, carry on or checked and $75 on the return trip, Plus $25 if I didn't check my self in check in $25, because I couldn't do it on the kiosk. Small very uncomfortable seats, waited on the runway for near an hour each way. It was my worst flight to date.

It was ok. It was expensive to check 2 bags ($75.00 per bag), and then it took a long time to wait for shuttle to take us from one terminal to the terminal where the plane was taking off at LAX. And all of this for a flight where we had to pay for any food or drink that was not water.

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

Information on your arrival and departure airports