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$70+ Cheap flights from Maryland to Midway (MDW)

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 10/15. Fares are subject to change and may not be available on all flights or dates of travel.
BWI — MDW
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
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Cheap flight deals from Maryland to Midway

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

Round-trip from

$108
(Frontier)

One-way from

$70
(Southwest)

Popular in

April

Cheapest in

September

Average price

$217

Good round-trip deal

$139 or less

Good one-way deal

$84 or less
From Maryland to Chicago Midway
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One-way flight from Maryland to Chicago Midway
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Highest demand for flights based on searches. 8% potential increase in price ($21 potential increase over avg. RT price).
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Cheapest flight prices on average. 0% 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 Maryland to Chicago Midway.
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Price to beat on a one-way flight from Maryland to Chicago Midway.
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Find flight deals from Maryland to Midway

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

This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/295:40 pmBWI - MDW
Nonstop2h 03mFrontier
Mon 10/61:49 pmMDW - BWI
Nonstop2h 01mFrontier
Deal found 9/15$108
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/289:27 pmBWI - MDW
1 stop10h 56mFrontier
Mon 9/291:49 pmMDW - BWI
Nonstop2h 01mFrontier
Deal found 9/15$110
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.
Fri 10/249:48 pmPHL - MDW
Nonstop2h 15mFrontier
Sun 10/268:25 amMDW - PHL
Nonstop2h 02mFrontier
Deal found 9/16$113
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.
Sat 10/184:12 pmBWI - MDW
Nonstop2h 01mFrontier
Thu 10/239:26 pmMDW - BWI
1 stop9h 12mFrontier
Deal found 9/14$113
This Flightnetwork 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/311:19 pmPHL - MDW
Nonstop2h 14mFrontier
Fri 11/712:14 pmMDW - PHL
Nonstop2h 00mFrontier
Deal found 9/16$114
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.
Sat 10/114:12 pmBWI - MDW
Nonstop2h 01mFrontier
Sat 11/156:15 amMDW - BWI
1 stop8h 20mFrontier
Deal found 9/14$114
This Gotogate 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/254:12 pmBWI - MDW
Nonstop2h 01mFrontier
Mon 10/275:28 pmMDW - BWI
1 stop15h 52mFrontier
Deal found 9/14$115
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/184:12 pmBWI - MDW
Nonstop2h 01mFrontier
Mon 10/205:28 pmMDW - BWI
1 stop15h 52mFrontier
Deal found 9/16$116
This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/78:45 amBWI - MDW
1 stop5h 53mFrontier
Thu 10/912:30 pmMDW - BWI
Nonstop1h 57mFrontier
Deal found 9/13$119
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.
Thu 10/301:19 pmPHL - MDW
Nonstop2h 14mFrontier
Sun 11/28:32 amMDW - PHL
Nonstop2h 02mFrontier
Deal found 9/15$120
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/77:30 pmBWI - MDW
Nonstop2h 06mFrontier
Sun 11/95:40 amMDW - BWI
Nonstop1h 56mFrontier
Deal found 9/14$120
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/126:10 amPHL - MDW
Nonstop2h 15mFrontier
Sun 10/268:25 amMDW - PHL
Nonstop2h 02mFrontier
Deal found 9/16$121

Cheapflights Fare Finder

 
Customize your flight search to find flights from Maryland to Midway 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 September 16, 2025.
Use the filters below to find and compare flights from Maryland to Chicago Midway Airport that are best for you.

Fly from

Maryland

Fly to

Midway

Route

Depart

Return

Price

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Sat 11/1

5:10 pm-6:15 pm

Nonstop2h 05m

Chicago Midway

Tue 11/4

11:05 am-2:00 pm

Nonstop1h 55m

$139

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Wed 1/14

5:45 pm-7:00 pm

Nonstop2h 15m

Chicago Midway

Wed 1/21

2:15 pm-5:05 pm

Nonstop1h 50m

$139

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Sat 10/25

7:55 pm-8:55 pm

Nonstop2h 00m

Chicago Midway

Tue 10/28

5:55 pm-8:45 pm

Nonstop1h 50m

$139

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Mon 9/29

1:55 pm-11:20 pm

1 stop10h 25m

Chicago Midway

Mon 10/6

8:19 am-6:24 pm

1 stop9h 05m

$144

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Fri 9/26

7:14 pm-9:51 am

1 stop15h 37m

Chicago Midway

Mon 9/29

6:21 am-8:09 pm

1 stop12h 48m

$144

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Wed 10/15

5:25 am-6:30 am

Nonstop2h 05m

Chicago Midway

Thu 10/16

9:15 pm-12:10 am

Nonstop1h 55m

$158

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Sat 10/25

7:55 pm-8:55 pm

Nonstop2h 00m

Chicago Midway

Mon 10/27

9:30 am-12:20 pm

Nonstop1h 50m

$158

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Fri 11/14

9:55 pm-11:00 pm

Nonstop2h 05m

Chicago Midway

Sat 11/15

8:40 am-11:30 am

Nonstop1h 50m

$158

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Wed 10/8

5:25 am-6:30 am

Nonstop2h 05m

Chicago Midway

Sat 10/11

5:35 pm-8:30 pm

Nonstop1h 55m

$159

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Sat 11/1

8:36 pm-10:12 am

1 stop14h 36m

Chicago Midway

Mon 11/3

1:37 pm-12:11 am

1 stop9h 34m

$160

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

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

Have a flexible travel schedule? Discover the best time to fly to Midway from Maryland 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 Maryland to Chicago Midway Airport

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

Currently, April is the cheapest month in which you can book a flight from Maryland to Chicago Midway Airport (average of $160). Flying from Maryland to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 MD to MDW?

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

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

Related info for your journey

Find useful and relevant information for your journey from Maryland to Midway. 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 Maryland to Chicago Midway Airport?

    Departing from Maryland to Chicago Midway Airport will take you 2h 05m. There are 666 mi between Maryland and Chicago Midway Airport. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Maryland to Chicago Midway Airport one-way?

    The cheapest airlines for a one-way flight from Maryland to Chicago Midway Airport are Southwest ($70), Frontier ($78), and Delta ($99).

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

    The most popular flight routes from Maryland to Chicago Midway Airport are Baltimore/Washington - Chicago Midway, Washington, D.C. Dulles Intl - Chicago Midway and Philadelphia - Chicago Midway.

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

    On average you can expect to pay $152 for a flight from Maryland to Chicago Midway Airport. The cheapest flight overall is $36 while the most popular route, (Baltimore/Washington - Chicago Midway) is currently priced at $82.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Maryland to Midway 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 Maryland to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Maryland to Chicago Midway Airport (average of $160). Flying from Maryland to Chicago Midway Airport in November is currently the most expensive (average of $249). 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

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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Alternative routes for Maryland to Midway

See prices for flight routes from nearby airports that may be better suited for you.
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Miami to O'Hare Intl flights
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Fort Lauderdale to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
San Jose to O'Hare Intl flights
Minneapolis to Midway flights
San Diego to O'Hare Intl flights
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Orlando to O'Hare Intl flights

Top 3 airlines flying from Maryland to Midway

Discover the top 3 airlines that operate flights from Maryland to Midway. 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 September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$62Average$163FlexibilityNo cancel feeOn-time62%
DeltaCheapest$98Average$328FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$163Average$294FlexibilityNo cancel feeOn-time63%

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