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Midway

$66+ 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 3/2. Fares are subject to change and may not be available on all flights or dates of travel.
BWI — MDW
Feb 21 — Feb 281
Sat 2/21
Sat 2/28
1 adult, Economy
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Cheap 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 January 22, 2026.

This Expedia deal was found by Cheapflights users on 1/20. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/2411:40 am
PHL
-
MDW
1 stop8h 27m
Frontier
Sat 2/286:25 am
MDW
-
PHL
1 stop10h 46m
Frontier
Deal found 1/20$128
This CheapOair deal was found by Cheapflights users on 1/19. 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.
Wed 2/258:25 pm
BWI
-
MDW
1 stop19h 01m
Frontier
Sat 2/286:25 am
MDW
-
BWI
1 stop10h 22m
Frontier
Deal found 1/19$129
This Kiwi.com deal was found by Cheapflights users on 1/20. 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 2/175:54 pm
BWI
-
MDW
1 stop26h 13m
Frontier
Tue 2/246:10 am
MDW
-
BWI
1 stop10h 03m
Frontier
Deal found 1/20$132
This Kiwi.com deal was found by Cheapflights users on 1/19. 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.
Mon 2/235:30 am
PHL
-
MDW
1 stop15h 17m
Frontier
Wed 2/257:00 am
MDW
-
PHL
1 stop9h 12m
Frontier
Deal found 1/19$133
This Southwest deal was found by Cheapflights users on 1/20. 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 2/2812:10 pm
BWI
-
MDW
Nonstop2h 10m
Southwest
Sat 2/286:15 pm
MDW
-
BWI
Nonstop1h 50m
Southwest
Deal found 1/20$139
This Frontier deal was found by Cheapflights users on 1/22. 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.
Wed 2/1111:40 am
PHL
-
MDW
1 stop8h 27m
Frontier
Wed 2/187:00 am
MDW
-
PHL
1 stop9h 32m
Frontier
Deal found 1/22$144
This CheapOair deal was found by Cheapflights users on 1/20. 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.
Mon 3/26:08 pm
BWI
-
MDW
1 stop5h 21m
Frontier
Wed 3/47:15 am
MDW
-
BWI
1 stop9h 32m
Frontier
Deal found 1/20$144
This Kiwi.com deal was found by Cheapflights users on 1/19. 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 2/256:00 am
BWI
-
MDW
1 stop14h 07m
Frontier
Mon 3/22:19 pm
MDW
-
BWI
1 stop9h 12m
Frontier
Deal found 1/19$145
This Kiwi.com deal was found by Cheapflights users on 1/20. 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 2/2712:28 pm
PHL
-
MDW
1 stop7h 10m
Frontier
Mon 3/22:19 pm
MDW
-
PHL
1 stop9h 42m
Frontier
Deal found 1/20$146
This Trip.com deal was found by Cheapflights users on 1/22. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/1812:21 pm
PHL
-
MDW
1 stop26h 35m
Frontier
Tue 2/246:10 am
MDW
-
PHL
1 stop10h 02m
Frontier
Deal found 1/22$147
This Southwest deal was found by Cheapflights users on 1/20. 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 2/187:45 am
BWI
-
MDW
Nonstop2h 20m
Southwest
Thu 2/196:50 am
MDW
-
BWI
Nonstop1h 55m
Southwest
Deal found 1/20$149
This Booking.com deal was found by Cheapflights users on 1/20. 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 2/2812:28 pm
PHL
-
MDW
1 stop10h 11m
Frontier
Wed 3/47:15 am
MDW
-
PHL
1 stop8h 57m
Frontier
Deal found 1/20$156

Find flight deals from Maryland to Midway

Keep the following information in mind while searching for Maryland to Midway flight deals. Data was last updated January 22, 2026.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$128
(Expedia)

One-way from

$66
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$247

Good round-trip deal

$231 or less

Good one-way deal

$125 or less
Provider with most accurate pricing for Washington, D.C. (WAS)-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Washington, D.C. (WAS)-Chicago (CHI) flights.
Search Deals
From Maryland to Chicago Midway
Search Deals
One-way flight from Maryland to Chicago Midway
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($19 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals
Price to beat on a round-trip flight from Maryland to Chicago Midway.
Search Deals
Price to beat on a one-way flight from Maryland to Chicago Midway.
Search Deals

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 January 22, 2026.
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

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Sat 2/21

10:29 am-9:33 pm

1 stop12h 04m

Chicago Midway

Mon 2/23

6:00 am-4:08 pm

1 stop9h 08m

$160

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Tue 2/24

6:00 am-9:54 am

1 stop4h 54m

Chicago Midway

Mon 3/2

6:20 pm-10:53 pm

1 stop3h 33m

$177

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Fri 2/20

9:35 pm-10:45 pm

Nonstop2h 10m

Chicago Midway

Sun 2/22

7:25 am-10:20 am

Nonstop1h 55m

$177

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Thu 2/19

7:40 am-9:00 am

Nonstop2h 20m

Chicago Midway

Thu 2/26

9:20 pm-12:05 am

Nonstop1h 45m

$179

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Sat 2/14

6:00 am-8:54 am

1 stop3h 54m

Chicago Midway

Tue 2/17

6:20 pm-10:53 pm

1 stop3h 33m

$179

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Thu 2/19

7:40 am-9:00 am

Nonstop2h 20m

Chicago Midway

Sat 2/28

6:15 pm-9:05 pm

Nonstop1h 50m

$179

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Fri 2/27

6:25 am-11:35 am

1 stop6h 10m

Chicago Midway

Mon 3/2

7:05 pm-9:55 pm

Nonstop1h 50m

$179

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Tue 3/3

11:45 am-5:37 pm

1 stop6h 52m

Chicago Midway

Thu 3/5

9:34 am-4:38 pm

1 stop6h 04m

$187

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Sun 3/1

6:00 am-9:54 am

1 stop4h 54m

Chicago Midway

Wed 3/4

6:20 pm-10:53 pm

1 stop3h 33m

$187

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Tue 2/17

7:40 am-9:00 am

Nonstop2h 20m

Chicago Midway

Fri 2/20

4:55 pm-7:45 pm

Nonstop1h 50m

$187

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/22

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, March is the cheapest month in which you can book a flight from Maryland to Chicago Midway Airport (average of $53). Flying from Maryland to Chicago Midway Airport in December is currently the most expensive (average of $156). 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 January 22, 2026.

It’s optimal to fly from Maryland to Chicago Midway Airport in the afternoon. By choosing this option you can save up to 45% on the cost of your flight, compared to a flight in the morning.

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

Use this chart to determine the cheapest time to fly round-trip from Maryland to Midway. Price data was last updated on January 17, 2026.

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

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 10m. There are 609 mi between Maryland and Chicago Midway Airport. This flight may include one or multiple stops.

  • 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 cheapest flights from Maryland to Chicago Midway Airport?

    On average you can expect to pay $278 for a flight from Maryland to Chicago Midway Airport. The cheapest flight overall is $69 while the most popular route, (Washington, D.C. Dulles Intl - Chicago Midway) is currently priced at $144.

  • 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, March is the cheapest month in which you can book a flight from Maryland to Chicago Midway Airport (average of $53). Flying from Maryland to Chicago Midway Airport in December is currently the most expensive (average of $156). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

Browse thousands of different options on Cheapflights for your next trip

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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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Austin to O'Hare Intl flights
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Los Angeles to Midway flights
Dulles Intl to Midway flights
Orlando to O'Hare Intl flights
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Minneapolis to O'Hare Intl flights
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Atlanta to Midway flights
San Diego to O'Hare Intl flights
Hartford to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
Philadelphia to Midway flights
LaGuardia to Midway flights
Minneapolis to Midway flights
Miami to O'Hare Intl flights
Cleveland to O'Hare Intl flights
George Bush Intcntl to Midway flights
Detroit to O'Hare Intl flights
Tampa to O'Hare Intl flights
Reagan-National to Midway flights
Sacramento to O'Hare Intl flights
Portland to O'Hare Intl flights
Kansas City to O'Hare Intl flights
San Antonio to O'Hare Intl flights
San Francisco to Midway flights

Top 2 airlines flying from Maryland to Midway

Discover the top 2 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 January 22, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$62Average$160FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$158Average$293FlexibilityNo cancel feeOn-time63%

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