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Midway

$80+ 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 6/3. Fares are subject to change and may not be available on all flights or dates of travel.
BWI — MDW
May 6 — May 131
Tue 5/6
Tue 5/13
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 May 1, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$146
(Kiwi.com)

One-way from

$80
(Southwest)

Popular in

April

Cheapest in

September

Average price

$275

Good round-trip deal

$197 or less

Good one-way deal

$104 or less
Provider with most accurate pricing for Washington, D.C. (WAS)-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Washington, D.C. (WAS)-Chicago (CHI) flights.
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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. 6% potential increase in price ($18 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 May 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 May 1, 2025.

This Kiwi.com deal was found by Cheapflights users on 4/30. 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.
Fri 7/184:31 pmBWI - MDW
Nonstop2h 04mFrontier
Mon 7/2112:50 pmMDW - BWI
Nonstop1h 56mFrontier
Deal found 4/30$146
This Southwest deal was found by Cheapflights users on 4/29. 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.
Sat 5/245:00 pmBWI - MDW
Nonstop2h 00mSouthwest
Sat 5/319:30 amMDW - BWI
1 stop3h 10mSouthwest
Deal found 4/29$165
This Cheapflightsfares deal was found by Cheapflights users on 4/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/306:39 pmPHL - MDW
Nonstop2h 16mFrontier
Tue 6/34:54 pmMDW - PHL
1 stop6h 05mFrontier
Deal found 4/30$176
This Southwest deal was found by Cheapflights users on 4/30. 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.
Tue 7/155:55 amPHL - MDW
Nonstop2h 05mSouthwest
Tue 7/228:30 pmMDW - PHL
Nonstop1h 55mSouthwest
Deal found 4/30$177
This Southwest deal was found by Cheapflights users on 4/29. 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.
Sat 5/246:50 pmDCA - MDW
1 stop4h 00mSouthwest
Sun 5/259:20 amMDW - DCA
1 stop4h 40mSouthwest
Deal found 4/29$181
This Frontier deal was found by Cheapflights users on 4/30. 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.
Thu 5/153:32 pmIAD - MDW
1 stop9h 07mFrontier
Wed 5/286:40 amMDW - IAD
1 stop8h 34mFrontier
Deal found 4/30$190
This CheapOair deal was found by Cheapflights users on 4/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/117:00 amDCA - MDW
1 stop13h 08mFrontier
Thu 5/158:03 pmMDW - DCA
1 stop19h 56mFrontier
Deal found 4/29$191
This Delta deal was found by Cheapflights users on 4/30. 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 5/243:37 pmIAD - MDW
1 stop6h 36mDelta
Sun 5/256:00 amMDW - IAD
1 stop4h 41mDelta
Deal found 4/30$197
This Delta deal was found by Cheapflights users on 4/29. 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.
Tue 7/14:05 pmPHL - MDW
1 stop6h 40mDelta
Fri 7/46:20 pmMDW - PHL
1 stop3h 50mDelta
Deal found 4/29$197
This Delta deal was found by Cheapflights users on 4/30. 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.
Fri 5/306:00 amBWI - MDW
1 stop3h 40mDelta
Mon 6/26:31 pmMDW - BWI
1 stop5h 17mDelta
Deal found 4/30$197
This Delta deal was found by Cheapflights users on 4/29. 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.
Tue 7/19:39 amDCA - MDW
1 stop3h 50mDelta
Thu 7/31:09 pmMDW - DCA
1 stop4h 50mDelta
Deal found 4/29$197
This Mytrip deal was found by Cheapflights users on 4/30. 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.
Sun 6/153:58 pmIAD - MDW
1 stop16h 17mAllegiant Air
Sun 6/2211:45 amMDW - IAD
2 stops25h 38mAllegiant Air
Deal found 4/30$290

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 May 1, 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 7/18

4:31 pm-5:35 pm

Nonstop2h 04m

Chicago Midway

Mon 7/21

12:50 pm-3:46 pm

Nonstop1h 56m

$146

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Sat 5/24

5:00 pm-6:00 pm

Nonstop2h 00m

Chicago Midway

Sat 5/31

9:30 am-1:40 pm

1 stop3h 10m

$165

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Fri 5/30

6:39 pm-7:55 pm

Nonstop2h 16m

Chicago Midway

Tue 6/3

4:54 pm-11:59 pm

1 stop6h 05m

$176

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Tue 7/15

5:55 am-7:00 am

Nonstop2h 05m

Chicago Midway

Tue 7/22

8:30 pm-11:25 pm

Nonstop1h 55m

$177

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Sat 5/24

6:50 pm-9:50 pm

1 stop4h 00m

Chicago Midway

Sun 5/25

9:20 am-3:00 pm

1 stop4h 40m

$181

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 5/15

3:32 pm-11:39 pm

1 stop9h 07m

Chicago Midway

Wed 5/28

6:40 am-4:14 pm

1 stop8h 34m

$190

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Sun 5/11

7:00 am-7:08 pm

1 stop13h 08m

Chicago Midway

Thu 5/15

8:03 pm-4:59 pm

1 stop19h 56m

$191

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Sat 5/24

3:37 pm-9:13 pm

1 stop6h 36m

Chicago Midway

Sun 5/25

6:00 am-11:41 am

1 stop4h 41m

$197

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Tue 7/1

4:05 pm-9:45 pm

1 stop6h 40m

Chicago Midway

Fri 7/4

6:20 pm-11:10 pm

1 stop3h 50m

$197

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Fri 5/30

6:00 am-8:40 am

1 stop3h 40m

Chicago Midway

Mon 6/2

6:31 pm-12:48 am

1 stop5h 17m

$197

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

Showing 1-10 of 29 results
1
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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 May 1, 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.

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 May 1, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta and Allegiant Air from Maryland to Chicago to help guide your decision. 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
4,294 reviews

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.2

Entertainment

7.6

Food

7.1

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,294 reviews
Southwest
8.0
Very good
4,294 reviews

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.2

Entertainment

7.6

Food

7.1

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,934 reviews
Southwest
8.0
Very good
4,294 reviews

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.2

Entertainment

7.6

Food

7.1

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Allegiant Air
7.3
Good
734 reviews
Southwest
8.0
Very good
4,294 reviews

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.2

Entertainment

7.6

Food

7.1

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Frontier
6.0
Okay
3,287 reviews
Southwest
8.0
Very good
4,294 reviews

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.2

Entertainment

7.6

Food

7.1

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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 Southwest ($80), Frontier ($83), and Allegiant Air ($90).

  • 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 Washington, D.C. Reagan-National - Chicago Midway.

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

    On average you can expect to pay $214 for a flight from Maryland to Chicago Midway Airport. The cheapest flight overall is $49 while the most popular route, (Washington, D.C. Dulles Intl - Chicago Midway) is currently priced at $197.

  • 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 Maryland?

Book flights to Maryland if you plan to visit one of these locations
Merrillville
Hammond
Benton Harbor
Porter
Lansing
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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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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$58Average$151FlexibilityNo cancel feeOn-time62%
DeltaCheapest$98Average$296FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$179Average$302FlexibilityNo cancel feeOn-time63%

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