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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 5/9. Fares are subject to change and may not be available on all flights or dates of travel.
BWI — MDW
Apr 6 — Apr 131
Sun 4/6
Sun 4/13
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 April 1, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$131
(Cheapflightsfares)

One-way from

$66
(Kiwi.com)

Popular in

March

Cheapest in

September

Average price

$246

Good round-trip deal

$182 or less

Good one-way deal

$85 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. 0% potential increase in price ($1 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 1, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 3/30. 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.
Mon 4/2810:00 amBWI - MDW
Nonstop2h 06mFrontier
Mon 5/56:15 amMDW - BWI
Nonstop1h 58mFrontier
Deal found 3/30$131
This Southwest deal was found by Cheapflights users on 3/31. 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.
Wed 4/306:45 pmBWI - MDW
Nonstop2h 05mSouthwest
Wed 5/77:35 pmMDW - BWI
Nonstop1h 50mSouthwest
Deal found 3/31$158
This Frontier deal was found by Cheapflights users on 3/31. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/236:39 pmPHL - MDW
Nonstop2h 16mFrontier
Mon 5/268:55 pmMDW - PHL
Nonstop2h 04mFrontier
Deal found 3/31$167
This Southwest deal was found by Cheapflights users on 3/31. 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.
Wed 4/306:35 pmPHL - MDW
Nonstop2h 10mSouthwest
Wed 5/75:30 amMDW - PHL
1 stop7h 10mSouthwest
Deal found 3/31$169
This Frontier deal was found by Cheapflights users on 3/31. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/85:54 pmIAD - MDW
1 stop6h 30mFrontier
Sun 5/118:30 amMDW - IAD
1 stop4h 53mFrontier
Deal found 3/31$178
This Southwest deal was found by Cheapflights users on 3/31. 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 5/246:45 pmDCA - MDW
Nonstop2h 00mSouthwest
Wed 5/285:25 pmMDW - DCA
Nonstop1h 55mSouthwest
Deal found 3/31$179
This CheapOair deal was found by Cheapflights users on 3/31. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/156:00 pmDCA - MDW
1 stop7h 21mFrontier
Wed 4/166:45 amMDW - DCA
1 stop28h 19mFrontier
Deal found 3/31$180
This Delta deal was found by Cheapflights users on 3/31. 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 4/236:00 amIAD - MDW
1 stop3h 40mDelta
Tue 4/296:04 amMDW - IAD
1 stop4h 19mDelta
Deal found 3/31$197
This Delta deal was found by Cheapflights users on 3/31. 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 4/236:00 amBWI - MDW
1 stop3h 40mDelta
Wed 4/305:59 pmMDW - BWI
1 stop4h 23mDelta
Deal found 3/31$197
This Delta deal was found by Cheapflights users on 3/31. 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 4/239:41 amDCA - MDW
1 stop3h 54mDelta
Tue 4/295:59 pmMDW - DCA
1 stop4h 11mDelta
Deal found 3/31$197
This Delta deal was found by Cheapflights users on 3/31. 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.
Tue 4/2211:31 amPHL - MDW
1 stop6h 48mDelta
Sat 5/36:45 pmMDW - PHL
1 stop5h 04mDelta
Deal found 3/31$208
This Mytrip deal was found by Cheapflights users on 4/1. 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 8/73:53 pmIAD - MDW
1 stop16h 20mAllegiant Air
Sun 8/1011:37 amMDW - IAD
2 stops25h 46mAllegiant Air
Deal found 4/1$322

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 April 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

Mon 4/28

10:00 am-11:06 am

Nonstop2h 06m

Chicago Midway

Mon 5/5

6:15 am-9:13 am

Nonstop1h 58m

$131

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Wed 4/30

6:45 pm-7:50 pm

Nonstop2h 05m

Chicago Midway

Wed 5/7

7:35 pm-10:25 pm

Nonstop1h 50m

$158

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Fri 5/23

6:39 pm-7:55 pm

Nonstop2h 16m

Chicago Midway

Fri 5/30

8:55 pm-11:59 pm

Nonstop2h 04m

$167

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Wed 4/30

6:35 pm-7:45 pm

Nonstop2h 10m

Chicago Midway

Wed 5/7

5:30 am-1:40 pm

1 stop7h 10m

$169

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Sat 5/24

6:45 pm-7:45 pm

Nonstop2h 00m

Chicago Midway

Wed 5/28

5:25 pm-8:20 pm

Nonstop1h 55m

$179

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Tue 4/15

7:22 pm-9:33 pm

1 stop27h 11m

Chicago Midway

Fri 4/18

7:05 am-2:35 pm

1 stop6h 30m

$180

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Tue 4/15

6:00 pm-12:21 am

1 stop7h 21m

Chicago Midway

Wed 4/16

6:45 am-12:04 pm

1 stop28h 19m

$180

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Wed 4/23

6:00 am-8:40 am

1 stop3h 40m

Chicago Midway

Tue 4/29

6:04 am-11:23 am

1 stop4h 19m

$197

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Wed 4/23

6:00 am-8:40 am

1 stop3h 40m

Chicago Midway

Wed 4/30

5:59 pm-11:22 pm

1 stop4h 23m

$197

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Wed 4/23

9:41 am-12:35 pm

1 stop3h 54m

Chicago Midway

Tue 4/29

5:59 pm-11:10 pm

1 stop4h 11m

$197

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/31

Showing 1-10 of 28 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 April 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 April 1, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta and Avelo Airlines 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
4,275 reviews

Crew

8.6

Comfort

8.0

Food

7.1

Boarding

8.2

Overall

8.0

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.0
Very good
4,275 reviews
Southwest
8.0
Very good
4,275 reviews

Crew

8.6

Comfort

8.0

Food

7.1

Boarding

8.2

Overall

8.0

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,899 reviews
Southwest
8.0
Very good
4,275 reviews

Crew

8.6

Comfort

8.0

Food

7.1

Boarding

8.2

Overall

8.0

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Avelo Airlines
7.5
Good
Southwest
8.0
Very good
4,275 reviews

Crew

8.6

Comfort

8.0

Food

7.1

Boarding

8.2

Overall

8.0

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Allegiant Air
7.3
Good
731 reviews
Southwest
8.0
Very good
4,275 reviews

Crew

8.6

Comfort

8.0

Food

7.1

Boarding

8.2

Overall

8.0

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Frontier
6.0
Okay
3,277 reviews
Southwest
8.0
Very good
4,275 reviews

Crew

8.6

Comfort

8.0

Food

7.1

Boarding

8.2

Overall

8.0

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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 ($66), Southwest ($80), and Delta ($100).

  • 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, Philadelphia - 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 $192 for a flight from Maryland to Chicago Midway Airport. The cheapest flight overall is $36 while the most popular route, (Washington, D.C. Dulles Intl - Chicago Midway) is currently priced at $158.

  • 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 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 April 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$58Average$148FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$171Average$304FlexibilityNo cancel feeOn-time63%
DeltaCheapest$176Average$296FlexibilityNo cancel feeOn-timeN/A

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