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$67+ 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 4/1. Fares are subject to change and may not be available on all flights or dates of travel.
BWI — MDW
Jan 28 — Feb 41
Tue 1/28
Tue 2/4
1 adult, Economy
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Cheap flight deals from Maryland to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Maryland (USMD) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 23, 2025.

Round-trip from

$122
(FlightHub)

One-way from

$67
(Kiwi.com)

Good round-trip deal

$166 or less

Good one-way deal

$150 or less
From Maryland to Chicago Midway
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One-way flight from Maryland to Chicago Midway
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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 January 23, 2025.

This FlightHub deal was found by Cheapflights users on 1/23. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/2712:17 pmBWI - MDW
1 stop10h 12mFrontier
Sat 3/14:48 pmMDW - BWI
1 stop6h 22mFrontier
Deal found 1/23$122
This FlightHub deal was found by Cheapflights users on 1/21. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/102:02 pmPHL - MDW
1 stop9h 58mFrontier
Thu 3/138:44 pmMDW - PHL
1 stop32h 21mFrontier
Deal found 1/21$124
This Southwest deal was found by Cheapflights users on 1/23. 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 3/15:10 pmBWI - MDW
Nonstop2h 10mSouthwest
Mon 3/36:10 pmMDW - BWI
Nonstop1h 50mSouthwest
Deal found 1/23$158
This CheapOair deal was found by Cheapflights users on 1/23. 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.
Thu 5/89:14 amIAD - MDW
1 stop14h 26mFrontier
Sun 5/114:00 pmMDW - IAD
1 stop15h 24mFrontier
Deal found 1/23$170
This eDestinos deal was found by Cheapflights users on 1/23. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/156:00 pmDCA - MDW
1 stop7h 17mFrontier
Wed 3/196:40 amMDW - DCA
1 stop9h 19mFrontier
Deal found 1/23$173
This Southwest deal was found by Cheapflights users on 1/23. 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 2/132:45 pmDCA - MDW
Nonstop2h 05mSouthwest
Tue 2/183:15 pmMDW - DCA
Nonstop1h 45mSouthwest
Deal found 1/23$177
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/166:35 pmPHL - MDW
Nonstop2h 10mSouthwest
Mon 4/215:50 amMDW - PHL
Nonstop1h 55mSouthwest
Deal found 1/22$187
This Delta deal was found by Cheapflights users on 1/23. 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.
Thu 2/206:05 amIAD - MDW
1 stop7h 37mDelta
Mon 2/246:28 pmMDW - IAD
1 stop3h 45mDelta
Deal found 1/23$197
This Delta deal was found by Cheapflights users on 1/23. 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 2/286:00 amBWI - MDW
1 stop3h 51mDelta
Mon 3/36:28 pmMDW - BWI
1 stop3h 40mDelta
Deal found 1/23$197
This KAYAK 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/186:00 amPHL - MDW
1 stop7h 42mDelta
Thu 2/209:33 amMDW - PHL
1 stop5h 32mDelta
Deal found 1/22$214
This Delta deal was found by Cheapflights users on 1/23. 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 3/16:00 amDCA - MDW
1 stop3h 51mDelta
Mon 3/36:28 pmMDW - DCA
1 stop3h 55mDelta
Deal found 1/23$217
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/312:40 pmIAD - MDW
2 stops22h 01mMultiple Airlines
Mon 7/78:03 amMDW - IAD
3 stops12h 06mMultiple Airlines
Deal found 1/22$584

Find flights from Maryland to Midway within your budget

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 23, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Mon 3/3

9:33 am-9:14 pm

1 stop12h 41m

Chicago Midway

Tue 3/4

8:30 am-4:10 pm

1 stop6h 40m

$122

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Wed 4/9

8:11 pm-3:29 pm

1 stop20h 18m

Chicago Midway

Wed 4/16

12:46 pm-7:32 am

1 stop17h 46m

$127

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Sat 3/1

8:30 pm-9:40 pm

Nonstop2h 10m

Chicago Midway

Mon 3/3

6:10 pm-9:00 pm

Nonstop1h 50m

$158

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 5/8

9:14 am-10:40 pm

1 stop14h 26m

Chicago Midway

Sun 5/11

4:00 pm-8:24 am

1 stop15h 24m

$170

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Sat 3/15

6:00 pm-12:17 am

1 stop7h 17m

Chicago Midway

Wed 3/19

6:40 am-4:59 pm

1 stop9h 19m

$173

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Thu 2/13

2:45 pm-3:50 pm

Nonstop2h 05m

Chicago Midway

Tue 2/18

3:15 pm-6:00 pm

Nonstop1h 45m

$177

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 3/13

6:00 am-8:45 am

1 stop3h 45m

Chicago Midway

Tue 3/18

6:42 pm-11:00 pm

1 stop3h 18m

$197

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Wed 4/16

5:02 pm-10:29 pm

1 stop6h 27m

Chicago Midway

Tue 4/22

5:59 pm-11:01 pm

1 stop4h 02m

$197

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Sat 3/1

6:00 am-8:51 am

1 stop3h 51m

Chicago Midway

Mon 3/3

6:28 pm-11:08 pm

1 stop3h 40m

$197

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Thu 2/13

5:15 am-6:35 am

Nonstop2h 20m

Chicago Midway

Thu 2/13

8:35 am-4:45 pm

1 stop7h 10m

$201

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/23

Showing 1-10 of 26 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.

Travel insights for flights from Maryland to Midway

Get recent, data-driven insights about flights from Maryland to Midway including ideal travel times, pricing trends, and more.

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 January 23, 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.

Weekly flight availability from Maryland to Chicago Midway Airport

Explore weekly flight availability from Maryland to Midway. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated January 23, 2025.

The most flights from USMD to MDW are scheduled on a Monday (11 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (1 on average).

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 January 23, 2025.
Peruse reviews from past customers who have flown with Frontier, Delta and Southwest 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
8.1
Very good
4,647 reviews

Entertainment

7.7

Comfort

8.1

Food

7.2

Boarding

8.2

Crew

8.7

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,647 reviews
Southwest
8.1
Very good
4,647 reviews

Entertainment

7.7

Comfort

8.1

Food

7.2

Boarding

8.2

Crew

8.7

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,508 reviews
Southwest
8.1
Very good
4,647 reviews

Entertainment

7.7

Comfort

8.1

Food

7.2

Boarding

8.2

Crew

8.7

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Frontier
6.1
Okay
3,440 reviews
Southwest
8.1
Very good
4,647 reviews

Entertainment

7.7

Comfort

8.1

Food

7.2

Boarding

8.2

Crew

8.7

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 ($67), Southwest ($89), 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. Reagan-National - Chicago Midway and Philadelphia - Chicago Midway.

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

    On average you can expect to pay $218 for a flight from Maryland to Chicago Midway Airport. The cheapest flight overall is $59 while the most popular route, (Baltimore/Washington - Chicago Midway) is currently priced at $74.

  • 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
New Buffalo
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 4 airlines flying from Maryland to Midway

Discover the top 4 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 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$58Average$146FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$149Average$329FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$165Average$294FlexibilityNo cancel feeOn-time63%
DeltaCheapest$176Average$296FlexibilityNo cancel feeOn-timeN/A
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