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$63+ Cheap flights from Midway (MDW) to Maryland

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 1/7. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — BWI
Jan 23 — Jan 301
Fri 1/23
Fri 1/30
1 adult, Economy
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Cheap flight deals from Midway to Maryland

Cheapest flights from Midway to Maryland
Explore the most affordable flight options available from Midway to Maryland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 24, 2025.

This Delta deal was found by Cheapflights users on 12/24. 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 12/316:08 pmMDW - PHL
1 stop4h 09mDelta
Thu 1/16:00 amPHL - MDW
1 stop3h 49mDelta
Deal found 12/24$177
This Delta deal was found by Cheapflights users on 12/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:08 pmMDW - BWI
1 stop4h 23mDelta
Thu 1/16:00 amBWI - MDW
1 stop3h 49mDelta
Deal found 12/22$177
This Southwest deal was found by Cheapflights users on 12/24. 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 12/3111:05 amMDW - PHL
Nonstop1h 55mSouthwest
Thu 1/111:40 amPHL - MDW
Nonstop2h 10mSouthwest
Deal found 12/24$209
This Frontier deal was found by Cheapflights users on 12/22. 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.
Thu 12/256:33 pmMDW - BWI
1 stop5h 01mFrontier
Wed 1/711:45 amBWI - MDW
1 stop11h 32mFrontier
Deal found 12/22$213
This Frontier deal was found by Cheapflights users on 12/22. 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.
Thu 12/256:33 pmMDW - BWI
1 stop5h 01mFrontier
Tue 1/611:45 amBWI - MDW
1 stop11h 32mFrontier
Deal found 12/22$214
This Expedia deal was found by Cheapflights users on 12/23. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/306:14 amMDW - IAD
1 stop9h 23mFrontier
Mon 1/124:22 pmIAD - MDW
1 stop6h 55mFrontier
Deal found 12/23$232
This Expedia deal was found by Cheapflights users on 12/22. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/312:16 pmMDW - PHL
1 stop8h 27mFrontier
Mon 1/51:38 pmPHL - MDW
1 stop9h 34mFrontier
Deal found 12/22$234
This Frontier deal was found by Cheapflights users on 12/22. 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.
Thu 12/256:33 pmMDW - BWI
1 stop5h 01mFrontier
Mon 1/511:55 amBWI - MDW
1 stop11h 17mFrontier
Deal found 12/22$234
This Delta deal was found by Cheapflights users on 12/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:08 pmMDW - DCA
1 stop3h 42mDelta
Thu 1/16:00 amDCA - MDW
1 stop3h 49mDelta
Deal found 12/22$243
This Frontier deal was found by Cheapflights users on 12/21. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/256:33 pmMDW - BWI
1 stop5h 01mFrontier
Sun 1/115:45 amBWI - MDW
1 stop6h 46mFrontier
Deal found 12/21$248
This Southwest deal was found by Cheapflights users on 12/22. 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 12/3110:00 amMDW - BWI
1 stop6h 05mSouthwest
Thu 1/18:00 pmBWI - MDW
Nonstop2h 05mSouthwest
Deal found 12/22$254
This Southwest deal was found by Cheapflights users on 12/23. 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.
Wed 12/318:10 pmMDW - DCA
Nonstop1h 45mSouthwest
Thu 1/16:00 amDCA - MDW
Nonstop2h 05mSouthwest
Deal found 12/23$258

Find flight deals from Midway to Maryland

Keep the following information in mind while searching for Midway to Maryland flight deals. Data was last updated December 24, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$128
(Expedia)

One-way from

$63
(Kiwi.com)

Popular in

November

Cheapest in

August

Average price

$237

Good round-trip deal

$235 or less

Good one-way deal

$129 or less
Provider with most accurate pricing for Chicago (CHI)-Washington, D.C. (WAS) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Washington, D.C. (WAS) flights.
Search Deals
From Chicago Midway to Maryland
Search Deals
One-way flight from Chicago Midway to Maryland
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($28 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Chicago Midway to Maryland.
Search Deals
Price to beat on a one-way flight from Chicago Midway to Maryland.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Maryland 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 December 24, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Maryland that are best for you.

Fly from

Midway

Fly to

Maryland

Route

Depart

Return

Price

ChicagoBaltimore

MDW - BWI

MDWBWI

Chicago Midway

Sat 2/21

5:15 am-8:10 am

Nonstop1h 55m

Baltimore/Washington

Mon 2/23

7:40 am-9:00 am

Nonstop2h 20m

$139

ChicagoBaltimore

MDW - BWI

MDWBWI

Chicago Midway

Sat 1/17

12:15 pm-3:00 pm

Nonstop1h 45m

Baltimore/Washington

Sun 1/18

1:45 pm-2:55 pm

Nonstop2h 10m

$139

ChicagoBaltimore

MDW - BWI

MDWBWI

Chicago Midway

Thu 1/15

7:10 pm-10:00 pm

Nonstop1h 50m

Baltimore/Washington

Sun 1/18

10:25 am-11:35 am

Nonstop2h 10m

$149

ChicagoBaltimore

MDW - BWI

MDWBWI

Chicago Midway

Fri 2/6

1:25 pm-4:10 pm

Nonstop1h 45m

Baltimore/Washington

Mon 2/9

4:25 pm-5:35 pm

Nonstop2h 10m

$158

ChicagoBaltimore

MDW - BWI

MDWBWI

Chicago Midway

Fri 2/20

4:55 pm-7:45 pm

Nonstop1h 50m

Baltimore/Washington

Sat 2/21

6:20 am-7:40 am

Nonstop2h 20m

$158

ChicagoBaltimore

MDW - BWI

MDWBWI

Chicago Midway

Thu 1/29

5:01 pm-12:36 am

1 stop6h 35m

Baltimore/Washington

Mon 2/2

6:00 am-11:45 am

1 stop6h 45m

$162

ChicagoBaltimore

MDW - BWI

MDWBWI

Chicago Midway

Thu 1/8

12:41 pm-12:29 am

1 stop10h 48m

Baltimore/Washington

Sat 1/10

1:45 pm-10:27 pm

1 stop9h 42m

$162

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Thu 1/22

6:20 am-4:28 pm

1 stop9h 08m

Washington, D.C. Dulles Intl

Mon 1/26

5:33 pm-10:19 pm

1 stop5h 46m

$162

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Thu 1/29

6:20 am-4:28 pm

1 stop9h 08m

Washington, D.C. Dulles Intl

Mon 2/2

1:31 pm-7:58 pm

1 stop7h 27m

$163

ChicagoBaltimore

MDW - BWI

MDWBWI

Chicago Midway

Thu 1/29

1:15 pm-4:00 pm

Nonstop1h 45m

Baltimore/Washington

Sun 2/1

7:40 am-9:00 am

Nonstop2h 20m

$169

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/22

Showing 1-10 of 60 results
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Best time to book a flight from Midway to Maryland

Have a flexible travel schedule? Discover the best time to fly to Maryland from Midway 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 Chicago Midway Airport to Maryland

What is the cheapest month to book a flight from Chicago Midway Airport to Maryland?

Currently, February is the cheapest month in which you can book a flight from Chicago Midway Airport to Maryland (average of $64). Flying from Chicago Midway Airport to Maryland in January is currently the most expensive (average of $204). 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 MDW to MD?

Find hourly flight availability from Midway to Maryland. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 24, 2025.

It’s optimal to fly from Chicago Midway Airport to Maryland at noon. By choosing this option you can save up to 48% on the cost of your flight, compared to a flight in the morning.

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

Use this chart to determine the cheapest time to fly round-trip from Midway to Maryland. Price data was last updated on December 20, 2025.

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

Reviews of airlines servicing Maryland

Get insights into the airlines that provide service to Maryland. 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 Maryland. Reviews last updated December 24, 2025.
Read through reviews of airlines operating flights from Chicago Midway Airport to Maryland, such as Southwest and Frontier. 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
4,255 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,255 reviews
Southwest
8.0
Very good
4,255 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Frontier
5.8
Fair
3,073 reviews
Southwest
8.0
Very good
4,255 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Related info for your journey

Find useful and relevant information for your journey from Midway to Maryland. 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 Chicago Midway Airport to Maryland?

    Southwest, Frontier, and Delta can get you from Chicago Midway Airport to Maryland in just under 1h 55m. Your travel time can differ by up to 7h 13m. Airlines will cover a distance of 609 mi. This flight may include one or multiple stops.

  • What are the most popular routes from Chicago Midway Airport to Maryland?

    While some choose either Chicago Midway - Washington, D.C. Dulles Intl or Chicago Midway - Philadelphia, Chicago Midway - Baltimore/Washington is the most popular route from Chicago Midway Airport to Maryland.

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

    On average you can expect to pay $261 for a flight from Chicago Midway Airport to Maryland. The cheapest flight overall is $40 while the most popular route, (Chicago Midway - Baltimore/Washington) is currently priced at $139.

  • Can I find deals for flights from Midway to Maryland that include hotel bookings?

    Yes. In addition to deals on Midway to Maryland flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Maryland?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Maryland.

  • Can I find deals for business class flights from Midway to Maryland?

    Yes. Cheapflights offers flight deals from Midway to Maryland 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 Chicago Midway Airport to Maryland?

    Currently, February is the cheapest month in which you can book a flight from Chicago Midway Airport to Maryland (average of $64). Flying from Chicago Midway Airport to Maryland in January is currently the most expensive (average of $204). 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

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Alternative routes for Midway to Maryland

See prices for flight routes from nearby airports that may be better suited for you.
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Top 2 airlines flying from Midway to Maryland

Discover the top 2 airlines that operate flights from Midway to Maryland. 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 December 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$90Average$171FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$159Average$296FlexibilityNo cancel feeOn-time63%

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