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$60+ 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 3/10. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — BWI
Mar 14 — Mar 211
Sat 3/14
Sat 3/21
1 adult, Economy
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Cheap 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 February 12, 2026.

This Kiwi.com deal was found by Cheapflights users on 2/9. 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.
Wed 3/116:05 am
MDW
-
BWI
1 stop7h 19m
Frontier
Wed 3/183:19 pm
BWI
-
MDW
1 stop8h 00m
Frontier
Deal found 2/9$125
This Priceline deal was found by Cheapflights users on 2/10. 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.
Tue 3/37:30 am
MDW
-
PHL
1 stop8h 42m
Frontier
Wed 3/411:40 am
PHL
-
MDW
1 stop8h 27m
Frontier
Deal found 2/10$128
This Kiwi.com deal was found by Cheapflights users on 2/10. 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.
Tue 3/176:00 am
MDW
-
BWI
1 stop7h 24m
Frontier
Wed 3/183:19 pm
BWI
-
MDW
1 stop8h 00m
Frontier
Deal found 2/10$128
This Kiwi.com deal was found by Cheapflights users on 2/10. 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.
Tue 3/37:30 am
MDW
-
BWI
1 stop8h 43m
Frontier
Wed 3/113:19 pm
BWI
-
MDW
1 stop8h 00m
Frontier
Deal found 2/10$130
This Kiwi.com deal was found by Cheapflights users on 2/10. 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.
Wed 2/257:00 am
MDW
-
BWI
1 stop9h 47m
Frontier
Mon 3/26:00 am
BWI
-
MDW
1 stop17h 29m
Frontier
Deal found 2/10$131
This Kiwi.com deal was found by Cheapflights users on 2/10. 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.
Thu 2/265:16 pm
MDW
-
BWI
1 stop6h 15m
Frontier
Tue 3/36:00 am
BWI
-
MDW
1 stop14h 07m
Frontier
Deal found 2/10$132
This Kiwi.com deal was found by Cheapflights users on 2/12. 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.
Tue 2/246:10 am
MDW
-
BWI
1 stop10h 03m
Frontier
Sat 2/286:15 am
BWI
-
MDW
1 stop16h 24m
Frontier
Deal found 2/12$133
This Kiwi.com deal was found by Cheapflights users on 2/10. 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.
Thu 2/265:16 pm
MDW
-
BWI
1 stop6h 15m
Frontier
Sat 3/74:53 pm
BWI
-
MDW
1 stop6h 31m
Frontier
Deal found 2/10$134
This Kiwi.com deal was found by Cheapflights users on 2/9. 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.
Wed 3/47:15 am
MDW
-
BWI
1 stop9h 32m
Frontier
Sat 3/74:53 pm
BWI
-
MDW
1 stop6h 31m
Frontier
Deal found 2/9$136
This Kiwi.com deal was found by Cheapflights users on 2/9. 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.
Thu 3/126:05 am
MDW
-
BWI
1 stop7h 19m
Frontier
Sat 3/144:47 pm
BWI
-
MDW
1 stop6h 22m
Frontier
Deal found 2/9$140
This Kiwi.com deal was found by Cheapflights users on 2/10. 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.
Fri 3/62:41 pm
MDW
-
BWI
1 stop24h 17m
Frontier
Wed 3/183:19 pm
BWI
-
MDW
1 stop8h 00m
Frontier
Deal found 2/10$143
This Frontier deal was found by Cheapflights users on 2/11. 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.
Mon 3/22:19 pm
MDW
-
PHL
1 stop9h 42m
Frontier
Wed 3/411:40 am
PHL
-
MDW
1 stop8h 27m
Frontier
Deal found 2/11$144

Find flight deals from Midway to Maryland

Keep the following information in mind while searching for Midway to Maryland flight deals. Data was last updated February 12, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$125
(Kiwi.com)

One-way from

$60
(Kiwi.com)

Popular in

November

Cheapest in

August

Average price

$279

Good round-trip deal

$253 or less

Good one-way deal

$148 or less
Provider with most accurate pricing for Chicago (CHI)-Washington, D.C. (WAS) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Washington, D.C. (WAS) flights.
Search Deals
From Chicago Midway to Maryland
Search Deals
One-way flight from Chicago Midway to Maryland
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($24 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals
Price to beat on a round-trip flight from Chicago Midway to Maryland.
Search Deals
Price to beat on a one-way flight from Chicago Midway to Maryland.
Search Deals

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 February 12, 2026.
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

Wed 3/18

6:05 am-2:24 pm

1 stop7h 19m

Baltimore/Washington

Mon 3/23

3:19 pm-7:47 pm

1 stop5h 28m

$155

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Wed 4/15

2:20 pm-12:36 am

1 stop9h 16m

Washington, D.C. Dulles Intl

Thu 4/16

9:51 am-7:31 pm

1 stop10h 40m

$160

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Thu 4/16

2:20 pm-12:36 am

1 stop9h 16m

Washington, D.C. Dulles Intl

Sat 4/18

10:51 am-7:31 pm

1 stop9h 40m

$160

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Thu 3/12

2:41 pm-12:31 am

1 stop8h 50m

Washington, D.C. Dulles Intl

Thu 3/19

6:30 am-7:47 pm

1 stop14h 17m

$172

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Fri 4/17

2:20 pm-12:36 am

1 stop9h 16m

Washington, D.C. Dulles Intl

Tue 4/21

6:20 am-10:19 pm

1 stop16h 59m

$178

ChicagoBaltimore

MDW - BWI

MDWBWI

Chicago Midway

Thu 3/5

7:30 am-4:58 pm

1 stop8h 28m

Baltimore/Washington

Wed 3/11

3:19 pm-10:19 pm

1 stop8h 00m

$179

ChicagoBaltimore

MDW - BWI

MDWBWI

Chicago Midway

Thu 2/26

7:30 am-8:54 pm

1 stop12h 24m

Baltimore/Washington

Fri 2/27

6:08 pm-10:37 pm

1 stop5h 29m

$181

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Thu 2/19

9:05 am-4:43 pm

1 stop6h 38m

Washington, D.C. Dulles Intl

Mon 2/23

5:22 pm-10:29 pm

1 stop6h 07m

$181

ChicagoBaltimore

MDW - BWI

MDWBWI

Chicago Midway

Sat 4/18

6:38 pm-10:57 pm

1 stop3h 19m

Baltimore/Washington

Fri 4/24

6:00 am-9:56 am

1 stop4h 56m

$187

ChicagoBaltimore

MDW - BWI

MDWBWI

Chicago Midway

Wed 2/25

5:15 pm-8:10 pm

Nonstop1h 55m

Baltimore/Washington

Wed 3/4

7:45 am-9:05 am

Nonstop2h 20m

$194

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/9

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, March is the cheapest month in which you can book a flight from Chicago Midway Airport to Maryland (average of $87). Flying from Chicago Midway Airport to Maryland in January is currently the most expensive (average of $219). 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 February 12, 2026.

It’s optimal to fly from Chicago Midway Airport to Maryland at noon. By choosing this option you can save up to 38% on the cost of your flight, compared to a flight in the evening.

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

Use this chart to determine the cheapest time to fly round-trip from Midway to Maryland. Price data was last updated on February 7, 2026.

Travelers seeking maximum savings on their Chicago Midway Airport to Maryland flight should consider departing on Monday at noon when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

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 February 12, 2026.
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
4,280 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,280 reviews
Southwest
8.0
Very good
4,280 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Frontier
5.7
Fair
3,052 reviews
Southwest
8.0
Very good
4,280 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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, Delta, and Southwest can get you from Chicago Midway Airport to Maryland in just under 1h 55m. Your travel time can differ by up to 5h 24m. 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 - Philadelphia or Chicago Midway - Baltimore/Washington, Chicago Midway - Washington, D.C. Dulles Intl 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 $266 for a flight from Chicago Midway Airport to Maryland. The cheapest flight overall is $114 while the most popular route, (Chicago Midway - Washington, D.C. Dulles Intl) is currently priced at $160.

  • 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, March is the cheapest month in which you can book a flight from Chicago Midway Airport to Maryland (average of $87). Flying from Chicago Midway Airport to Maryland in January is currently the most expensive (average of $219). 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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Midway to Fort Myers flights
Midway to Newark flights

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 February 12, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$90Average$173FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$159Average$293FlexibilityNo cancel feeOn-time63%

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