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Midway

$73+ 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 10/23. Fares are subject to change and may not be available on all flights or dates of travel.
BWI — MDW
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
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 July 31, 2025.

Round-trip from

$117
(Cheapflightsfares)

One-way from

$73
(Kiwi.com)

Popular in

April

Cheapest in

September

Average price

$266

Good round-trip deal

$151 or less

Good one-way deal

$117 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. 7% potential increase in price ($19 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 July 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 July 31, 2025.

This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/125:40 pmBWI - MDW
Nonstop2h 03mFrontier
Sun 9/141:49 pmMDW - BWI
Nonstop2h 01mFrontier
Deal found 7/29$117
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/146:10 pmPHL - MDW
1 stop5h 48mFrontier
Fri 10/178:15 amMDW - PHL
Nonstop2h 02mFrontier
Deal found 7/29$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 9/31:25 pmBWI - MDW
Nonstop1h 55mSouthwest
Sat 9/67:00 amMDW - BWI
Nonstop1h 50mSouthwest
Deal found 7/29$161
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/181:22 pmIAD - MDW
1 stop5h 55mAllegiant Air
Fri 8/229:32 amMDW - IAD
1 stop4h 51mAllegiant Air
Deal found 7/29$174
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.
Sat 9/137:14 pmIAD - MDW
1 stop15h 04mFrontier
Sat 9/2010:51 amMDW - IAD
1 stop6h 33mFrontier
Deal found 7/30$177
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/296:10 pmPHL - MDW
Nonstop2h 05mSouthwest
Sun 9/78:50 amMDW - PHL
Nonstop2h 00mSouthwest
Deal found 7/30$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.
Fri 9/265:15 pmPHL - MDW
1 stop5h 21mDelta
Tue 9/3012:43 pmMDW - PHL
1 stop6h 10mDelta
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.
Sat 8/308:25 amDCA - MDW
Nonstop2h 00mSouthwest
Sat 9/612:45 pmMDW - DCA
Nonstop1h 55mSouthwest
Deal found 7/31$217
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/305:25 pmIAD - MDW
1 stop4h 47mDelta
Tue 9/29:30 amMDW - IAD
1 stop12h 56mDelta
Deal found 7/29$227
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/161:00 pmDCA - MDW
1 stop8h 54mFrontier
Mon 8/1812:35 pmMDW - DCA
1 stop27h 24mFrontier
Deal found 7/29$228
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.
Wed 8/276:00 amDCA - MDW
1 stop3h 35mDelta
Sat 8/304:25 pmMDW - DCA
1 stop5h 21mDelta
Deal found 7/31$237

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 July 31, 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

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Fri 9/12

5:40 pm-6:43 pm

Nonstop2h 03m

Chicago Midway

Sun 9/14

1:49 pm-4:50 pm

Nonstop2h 01m

$117

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Tue 10/14

6:10 pm-10:58 pm

1 stop5h 48m

Chicago Midway

Fri 10/17

8:15 am-11:17 am

Nonstop2h 02m

$142

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Wed 9/3

1:25 pm-2:20 pm

Nonstop1h 55m

Chicago Midway

Sat 9/6

7:00 am-9:50 am

Nonstop1h 50m

$161

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Mon 8/18

1:22 pm-6:17 pm

1 stop5h 55m

Chicago Midway

Fri 8/22

9:32 am-3:23 pm

1 stop4h 51m

$174

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Fri 8/29

6:10 pm-7:15 pm

Nonstop2h 05m

Chicago Midway

Sun 9/7

8:50 am-11:50 am

Nonstop2h 00m

$177

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Sat 9/13

7:14 pm-9:18 am

1 stop15h 04m

Chicago Midway

Sat 9/20

10:51 am-6:24 pm

1 stop6h 33m

$177

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Fri 9/26

5:15 pm-9:36 pm

1 stop5h 21m

Chicago Midway

Sat 10/4

4:25 pm-10:12 pm

1 stop4h 47m

$197

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Sat 8/30

8:25 am-9:25 am

Nonstop2h 00m

Chicago Midway

Sat 9/6

12:45 pm-3:40 pm

Nonstop1h 55m

$217

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Sat 8/30

5:25 pm-9:12 pm

1 stop4h 47m

Chicago Midway

Tue 9/2

9:30 am-11:26 pm

1 stop12h 56m

$227

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Sat 8/16

1:00 pm-8:54 pm

1 stop8h 54m

Chicago Midway

Mon 8/18

12:35 pm-4:59 pm

1 stop27h 24m

$228

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

Showing 1-10 of 25 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 July 31, 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.

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated July 31, 2025.
Read reviews from past customers who have flown Southwest, Delta, and Allegiant Air from Maryland to Chicago Midway Airport. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Food

7.0

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

Overall

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Food

7.0

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

Overall

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Food

7.0

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

Overall

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Food

7.0

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

Overall

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Food

7.0

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 Maryland to Midway. 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 Maryland to Chicago Midway Airport one-way?

    The cheapest airlines for a one-way flight from Maryland to Chicago Midway Airport are Frontier ($73), Southwest ($81), 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 Washington, D.C. Dulles Intl - Chicago Midway, Baltimore/Washington - Chicago Midway and Philadelphia - Chicago Midway.

  • What are the most reliable airlines from Maryland to Chicago Midway Airport?

    Consider United Airlines (100%), Southwest (71%) or Frontier (52%) when booking your flight. These represent the most reliable airlines when flying from Maryland to Chicago Midway Airport.

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

    On average you can expect to pay $174 for a flight from Maryland to Chicago Midway Airport. The cheapest flight overall is $67 while the most popular route, (Washington, D.C. Dulles Intl - Chicago Midway) is currently priced at $178.

  • 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
Valparaiso
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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Dallas/Fort Worth to Midway flights
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Los Angeles to Midway flights
San Francisco to Midway flights
Tampa to O'Hare Intl flights
Boston to Midway flights
Las Vegas to O'Hare Intl flights
Love Field to Midway flights
Reagan-National to Midway 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 July 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$61Average$156FlexibilityNo cancel feeOn-time62%
DeltaCheapest$98Average$328FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$161Average$297FlexibilityNo cancel feeOn-time63%

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