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$72+ 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 9/1. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — BWI
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
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 July 31, 2025.

Round-trip from

$113
(Gotogate)

One-way from

$72
(Frontier)

Popular in

January

Cheapest in

August

Average price

$229

Good round-trip deal

$140 or less

Good one-way deal

$107 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. 4% potential increase in price ($10 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 July 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 July 31, 2025.

This Gotogate deal was found by Cheapflights users on 7/29. 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.
Thu 8/2812:20 pmMDW - BWI
Nonstop1h 56mFrontier
Sun 8/312:42 pmBWI - MDW
Nonstop2h 04mFrontier
Deal found 7/29$113
This Kiwi.com deal was found by Cheapflights users on 7/30. 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 10/168:15 amMDW - PHL
Nonstop2h 02mFrontier
Sun 10/196:05 amPHL - MDW
Nonstop2h 15mFrontier
Deal found 7/30$142
This Southwest deal was found by Cheapflights users on 7/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/108:35 amMDW - BWI
Nonstop1h 55mSouthwest
Sat 9/1310:10 amBWI - MDW
Nonstop2h 00mSouthwest
Deal found 7/29$161
This Southwest deal was found by Cheapflights users on 7/31. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/106:30 amMDW - PHL
Nonstop1h 55mSouthwest
Sat 10/186:00 amPHL - MDW
Nonstop2h 05mSouthwest
Deal found 7/31$177
This Booking.com deal was found by Cheapflights users on 7/29. 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.
Sat 8/26:20 amMDW - IAD
1 stop7h 52mFrontier
Tue 8/56:10 amIAD - MDW
1 stop5h 30mFrontier
Deal found 7/29$177
This Delta deal was found by Cheapflights users on 7/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/304:25 pmMDW - PHL
1 stop4h 55mDelta
Sun 8/316:00 amPHL - MDW
1 stop6h 34mDelta
Deal found 7/31$197
This Southwest deal was found by Cheapflights users on 7/31. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/215:30 amMDW - DCA
Nonstop1h 50mSouthwest
Mon 8/256:55 pmDCA - MDW
Nonstop2h 00mSouthwest
Deal found 7/31$217
This Frontier deal was found by Cheapflights users on 7/30. 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.
Fri 8/1512:35 pmMDW - DCA
1 stop8h 22mFrontier
Sat 8/161:00 pmDCA - MDW
1 stop8h 54mFrontier
Deal found 7/30$228
This Delta deal was found by Cheapflights users on 7/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/236:17 pmMDW - DCA
1 stop3h 42mDelta
Tue 8/264:00 pmDCA - MDW
1 stop6h 44mDelta
Deal found 7/30$237
This Delta deal was found by Cheapflights users on 7/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/276:00 amMDW - IAD
1 stop7h 31mDelta
Wed 9/37:22 amIAD - MDW
1 stop7h 14mDelta
Deal found 7/30$237
This Mytrip deal was found by Cheapflights users on 7/30. 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.
Thu 8/1410:53 amMDW - IAD
2 stops24h 39mAllegiant Air
Mon 8/181:22 pmIAD - MDW
1 stop5h 55mAllegiant Air
Deal found 7/30$296

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 July 31, 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

Thu 8/28

12:20 pm-3:16 pm

Nonstop1h 56m

Baltimore/Washington

Sun 8/31

2:42 pm-3:46 pm

Nonstop2h 04m

$113

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Thu 10/16

8:15 am-11:17 am

Nonstop2h 02m

Philadelphia

Sun 10/19

6:05 am-7:20 am

Nonstop2h 15m

$142

ChicagoBaltimore

MDW - BWI

MDWBWI

Chicago Midway

Wed 9/10

8:35 am-11:30 am

Nonstop1h 55m

Baltimore/Washington

Sat 9/13

10:10 am-11:10 am

Nonstop2h 00m

$161

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Fri 10/10

6:30 am-9:25 am

Nonstop1h 55m

Philadelphia

Sat 10/18

6:00 am-7:05 am

Nonstop2h 05m

$177

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Sat 9/13

10:51 am-6:24 pm

1 stop6h 33m

Washington, D.C. Dulles Intl

Sat 9/20

7:14 pm-9:18 am

1 stop15h 04m

$177

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Sat 8/30

4:25 pm-10:20 pm

1 stop4h 55m

Philadelphia

Sun 8/31

6:00 am-11:34 am

1 stop6h 34m

$197

ChicagoWashington, D.C.

MDW - DCA

MDWDCA

Chicago Midway

Thu 8/21

5:30 am-8:20 am

Nonstop1h 50m

Washington, D.C. Reagan-National

Mon 8/25

6:55 pm-7:55 pm

Nonstop2h 00m

$217

ChicagoWashington, D.C.

MDW - DCA

MDWDCA

Chicago Midway

Fri 8/15

12:35 pm-9:57 pm

1 stop8h 22m

Washington, D.C. Reagan-National

Sat 8/16

1:00 pm-8:54 pm

1 stop8h 54m

$228

ChicagoWashington, D.C.

MDW - DCA

MDWDCA

Chicago Midway

Sat 8/23

6:17 pm-10:59 pm

1 stop3h 42m

Washington, D.C. Reagan-National

Tue 8/26

4:00 pm-9:44 pm

1 stop6h 44m

$237

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Wed 8/27

6:00 am-2:31 pm

1 stop7h 31m

Washington, D.C. Dulles Intl

Wed 9/3

7:22 am-1:36 pm

1 stop7h 14m

$237

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/31

Showing 1-10 of 24 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 July 31, 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 July 31, 2025.
Read through reviews of airlines operating flights from Chicago Midway Airport to Maryland, such as Southwest, Delta, and Allegiant Air. 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
4,246 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,981 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Allegiant Air
7.2
Good
702 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Frontier
5.9
Fair
3,239 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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.

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

    $72 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on Southwest and Allegiant Air, with prices starting from $81 and $87, respectively.

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

    While some choose either Chicago Midway - Baltimore/Washington or Chicago Midway - Philadelphia, 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 $167 for a flight from Chicago Midway Airport to Maryland. The cheapest flight overall is $66 while the most popular route, (Chicago Midway - Washington, D.C. Dulles Intl) is currently priced at $178.

  • 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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O'Hare Intl to Charleston flights
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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 July 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$74Average$191FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$159Average$283FlexibilityNo cancel feeOn-time63%

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