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$59+ Cheap flights from Midway (MDW) to Maryland

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/9. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — BWI
oct. 16 — oct. 231
jue. 10/16
jue. 10/23
1 adult, Economy
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Cheap flight deals from Midway to Maryland

Keep the following information in mind while searching for Midway to Maryland flight deals. Data was last updated septiembre 16, 2025.

Round-trip from

$92
(Kiwi.com)

One-way from

$59
(Frontier)

Popular in

January

Cheapest in

August

Average price

$212

Good round-trip deal

$111 or less

Good one-way deal

$89 or less
From Chicago Midway to Maryland
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One-way flight from Chicago Midway to Maryland
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Highest demand for flights based on searches. 5% potential increase in price ($13 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($3 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Chicago Midway to Maryland.
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Price to beat on a one-way flight from Chicago Midway to Maryland.
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Find flight deals from Midway to Maryland

Cheapest flights from Midway to Maryland
Explore the most affordable flight options available from Midway to Maryland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on septiembre 16, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/2312:30 pmMDW - BWI
Nonstop1h 57mFrontier
sáb. 10/254:12 pmBWI - MDW
Nonstop2h 01mFrontier
Deal found 9/15$92
This Gotogate deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 10/1812:30 pmMDW - BWI
Nonstop1h 57mFrontier
lun. 10/207:54 pmBWI - MDW
Nonstop2h 06mFrontier
Deal found 9/15$94
This Booking.com deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 11/73:47 pmMDW - BWI
Nonstop1h 55mFrontier
dom. 11/99:21 amBWI - MDW
Nonstop2h 05mFrontier
Deal found 9/13$96
This Cheapflightsfares deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/1612:30 pmMDW - BWI
Nonstop1h 57mFrontier
lun. 10/207:54 pmBWI - MDW
Nonstop2h 06mFrontier
Deal found 9/15$101
This CheapOair deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 11/73:47 pmMDW - BWI
Nonstop1h 55mFrontier
lun. 11/107:25 pmBWI - MDW
Nonstop2h 06mFrontier
Deal found 9/14$102
This Gotogate deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/63:40 pmMDW - BWI
Nonstop1h 55mFrontier
dom. 11/99:21 amBWI - MDW
Nonstop2h 05mFrontier
Deal found 9/16$103
This Frontier deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/174:12 pmMDW - BWI
Nonstop1h 56mFrontier
sáb. 10/184:37 pmBWI - MDW
1 stop7h 10mFrontier
Deal found 9/13$104
This Frontier deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/104:12 pmMDW - BWI
Nonstop1h 56mFrontier
sáb. 10/114:12 pmBWI - MDW
Nonstop2h 01mFrontier
Deal found 9/14$112
This Trip.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 10/218:05 amMDW - PHL
1 stop7h 30mFrontier
dom. 10/266:10 amPHL - MDW
Nonstop2h 15mFrontier
Deal found 9/15$120
This Priceline deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 11/712:14 pmMDW - PHL
Nonstop2h 00mFrontier
dom. 11/97:00 amPHL - MDW
Nonstop2h 13mFrontier
Deal found 9/16$121
This Priceline deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/3010:12 amMDW - PHL
1 stop7h 18mFrontier
dom. 11/25:15 amPHL - MDW
Nonstop2h 15mFrontier
Deal found 9/15$122
This Priceline deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/38:15 amMDW - PHL
Nonstop2h 01mFrontier
dom. 10/56:00 amPHL - MDW
Nonstop2h 11mFrontier
Deal found 9/14$123

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Maryland that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated septiembre 16, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Maryland that are best for you.

Fly from

Midway

Fly to

Maryland

Route

Depart

Return

Price

ChicagoBaltimore

MDW - BWI

MDWBWI

Chicago Midway

jue. 10/30

3:40 pm-6:35 pm

Nonstop1h 55m

Baltimore/Washington

lun. 11/3

7:25 pm-8:31 pm

Nonstop2h 06m

$117

ChicagoBaltimore

MDW - BWI

MDWBWI

Chicago Midway

vie. 10/31

3:40 pm-6:35 pm

Nonstop1h 55m

Baltimore/Washington

dom. 11/2

8:21 pm-8:32 am

1 stop13h 11m

$123

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

mar. 10/14

6:45 am-9:40 am

Nonstop1h 55m

Philadelphia

sáb. 10/18

12:05 pm-1:10 pm

Nonstop2h 05m

$139

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

sáb. 10/25

5:35 pm-8:30 pm

Nonstop1h 55m

Philadelphia

mar. 10/28

5:25 am-6:30 am

Nonstop2h 05m

$139

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

sáb. 11/1

12:50 pm-3:40 pm

Nonstop1h 50m

Philadelphia

mar. 11/11

6:00 am-7:15 am

Nonstop2h 15m

$139

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

sáb. 10/18

5:35 pm-8:30 pm

Nonstop1h 55m

Philadelphia

mar. 10/21

6:05 pm-7:10 pm

Nonstop2h 05m

$139

ChicagoBaltimore

MDW - BWI

MDWBWI

Chicago Midway

mié. 12/10

6:55 pm-9:45 pm

Nonstop1h 50m

Baltimore/Washington

sáb. 12/13

3:15 pm-4:20 pm

Nonstop2h 05m

$139

ChicagoBaltimore

MDW - BWI

MDWBWI

Chicago Midway

mar. 10/14

5:35 am-8:20 am

Nonstop1h 45m

Baltimore/Washington

mar. 10/21

10:55 am-12:00 pm

Nonstop2h 05m

$139

ChicagoBaltimore

MDW - BWI

MDWBWI

Chicago Midway

mié. 10/15

7:40 pm-10:30 pm

Nonstop1h 50m

Baltimore/Washington

mié. 10/22

1:25 pm-2:25 pm

Nonstop2h 00m

$139

ChicagoBaltimore

MDW - BWI

MDWBWI

Chicago Midway

vie. 10/10

4:12 pm-7:08 pm

Nonstop1h 56m

Baltimore/Washington

lun. 10/13

12:30 pm-11:46 pm

1 stop12h 16m

$142

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/13

Showing 1-10 of 60 results
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Best time to book a flight from Midway to Maryland

Have a flexible travel schedule? Discover the best time to fly to Maryland from Midway with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago Midway Airport to Maryland

What is the cheapest month to book a flight from Chicago Midway Airport to Maryland?

Currently, August is the cheapest month in which you can book a flight from Chicago Midway Airport to Maryland (average of $241). Flying from Chicago Midway Airport to Maryland in March is currently the most expensive (average of $290). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from MDW to MD?

Find hourly flight availability from Midway to Maryland. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated septiembre 16, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago Midway Airport to Maryland as you normally would.

Reviews of airlines servicing Maryland

Get insights into the airlines that provide service to Maryland. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Maryland. Reviews last updated septiembre 16, 2025.
Read through reviews of airlines operating flights from Chicago Midway Airport to Maryland, such as Southwest and Frontier. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Overall

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Overall

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Frontier
5.8
Fair
3,174 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Overall

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

Find useful and relevant information for your journey from Midway to Maryland. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Chicago Midway Airport to Maryland?

    Frontier, Southwest, and Delta can get you from Chicago Midway Airport to Maryland in just under 1h 55m. Your travel time can differ by up to 3h 30m. Airlines will cover a distance of 609 mi. This flight may include one or multiple stops.

  • What are the most popular routes from Chicago Midway Airport to Maryland?

    While some choose either Chicago Midway - Washington, D.C. Dulles Intl or Chicago Midway - Philadelphia, Chicago Midway - Baltimore/Washington is the most popular route from Chicago Midway Airport to Maryland.

  • What are the cheapest flights from Chicago Midway Airport to Maryland?

    On average you can expect to pay $149 for a flight from Chicago Midway Airport to Maryland. The cheapest flight overall is $54 while the most popular route, (Chicago Midway - Baltimore/Washington) is currently priced at $102.

  • Can I find deals for flights from Midway to Maryland that include hotel bookings?

    Yes. In addition to deals on Midway to Maryland flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Maryland?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Maryland.

  • Can I find deals for business class flights from Midway to Maryland?

    Yes. Cheapflights offers flight deals from Midway to Maryland by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago Midway Airport to Maryland?

    Currently, August is the cheapest month in which you can book a flight from Chicago Midway Airport to Maryland (average of $241). Flying from Chicago Midway Airport to Maryland in March is currently the most expensive (average of $290). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for Midway to Maryland

See prices for flight routes from nearby airports that may be better suited for you.
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Top 2 airlines flying from Midway to Maryland

Discover the top 2 airlines that operate flights from Midway to Maryland. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated septiembre 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$79Average$173FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$159Average$286FlexibilityNo cancel feeOn-time63%

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