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$64+ 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 2/5. Fares are subject to change and may not be available on all flights or dates of travel.
BWI — MDW
Jan 7 — Jan 141
Wed 1/7
Wed 1/14
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 December 8, 2025.

This Frontier deal was found by Cheapflights users on 12/7. 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 12/301:46 pmPHL - MDW
1 stop9h 12mFrontier
Thu 1/812:41 pmMDW - PHL
1 stop11h 10mFrontier
Deal found 12/7$162
This CheapOair deal was found by Cheapflights users on 12/6. 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 12/308:17 amBWI - MDW
1 stop14h 41mFrontier
Thu 1/812:41 pmMDW - BWI
1 stop10h 48mFrontier
Deal found 12/6$163
This Kiwi.com deal was found by Cheapflights users on 12/5. 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.
Sun 12/2110:00 pmPHL - MDW
1 stop24h 58mFrontier
Thu 1/812:41 pmMDW - PHL
1 stop11h 10mFrontier
Deal found 12/5$176
This Delta deal was found by Cheapflights users on 12/7. 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 12/2511:40 amPHL - MDW
1 stop6h 39mDelta
Wed 12/316:08 pmMDW - PHL
1 stop4h 09mDelta
Deal found 12/7$177
This Delta deal was found by Cheapflights users on 12/7. 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 12/256:00 amBWI - MDW
1 stop3h 49mDelta
Wed 12/316:08 pmMDW - BWI
1 stop4h 23mDelta
Deal found 12/7$177
This Expedia deal was found by Cheapflights users on 12/8. 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.
Mon 12/158:37 amBWI - MDW
1 stop14h 21mFrontier
Wed 12/172:49 pmMDW - BWI
1 stop8h 35mFrontier
Deal found 12/8$183
This CheapOair deal was found by Cheapflights users on 12/6. 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 12/158:37 amBWI - MDW
1 stop14h 21mFrontier
Tue 12/162:49 pmMDW - BWI
1 stop8h 35mFrontier
Deal found 12/6$184
This Priceline deal was found by Cheapflights users on 12/7. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/301:46 pmPHL - MDW
1 stop9h 12mFrontier
Thu 1/13:10 pmMDW - PHL
1 stop8h 30mFrontier
Deal found 12/7$187
This CheapOair deal was found by Cheapflights users on 12/7. 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 12/148:36 pmPHL - MDW
1 stop15h 32mFrontier
Thu 1/812:41 pmMDW - PHL
1 stop11h 10mFrontier
Deal found 12/7$188
This CheapOair deal was found by Cheapflights users on 12/6. 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 12/149:43 pmBWI - MDW
1 stop25h 15mFrontier
Wed 12/172:49 pmMDW - BWI
1 stop8h 35mFrontier
Deal found 12/6$188
This Kiwi.com deal was found by Cheapflights users on 12/7. 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 12/159:11 pmBWI - MDW
2 stops36h 35mFrontier
Thu 12/186:12 amMDW - BWI
1 stop17h 22mFrontier
Deal found 12/7$199
This Kiwi.com deal was found by Cheapflights users on 12/6. 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.
Sun 12/149:20 pmIAD - MDW
2 stops15h 00mFrontier
Wed 12/172:49 pmMDW - IAD
1 stop19h 49mFrontier
Deal found 12/6$205

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 December 8, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$106
(Kiwi.com)

One-way from

$64
(Priceline)

Popular in

November

Cheapest in

September

Average price

$269

Good round-trip deal

$187 or less

Good one-way deal

$112 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. 4% potential increase in price ($12 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 December 2025
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.
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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 December 8, 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

Tue 1/6

5:50 pm-7:00 pm

Nonstop2h 10m

Chicago Midway

Tue 1/13

9:50 am-12:40 pm

Nonstop1h 50m

$139

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Sat 2/7

10:15 am-11:25 am

Nonstop2h 10m

Chicago Midway

Sat 2/7

5:40 pm-8:30 pm

Nonstop1h 50m

$139

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Tue 2/10

1:45 pm-2:55 pm

Nonstop2h 10m

Chicago Midway

Sun 2/15

7:05 pm-9:55 pm

Nonstop1h 50m

$158

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Fri 1/16

6:20 pm-7:35 pm

Nonstop2h 15m

Chicago Midway

Sun 1/18

6:10 am-11:30 am

1 stop4h 20m

$168

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Wed 1/7

5:42 pm-10:17 pm

1 stop5h 35m

Chicago Midway

Fri 1/9

4:31 pm-9:08 am

1 stop15h 37m

$169

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Thu 2/5

7:40 am-9:00 am

Nonstop2h 20m

Chicago Midway

Fri 2/6

7:05 pm-9:55 pm

Nonstop1h 50m

$169

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Fri 2/6

5:33 pm-8:43 am

1 stop16h 10m

Chicago Midway

Thu 2/12

6:00 am-4:32 pm

1 stop9h 32m

$173

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Thu 12/25

6:00 am-8:49 am

1 stop3h 49m

Chicago Midway

Wed 12/31

6:08 pm-11:31 pm

1 stop4h 23m

$177

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Thu 1/22

12:15 pm-1:30 pm

Nonstop2h 15m

Chicago Midway

Thu 1/29

5:30 pm-8:20 pm

Nonstop1h 50m

$177

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Thu 1/8

12:15 pm-1:30 pm

Nonstop2h 15m

Chicago Midway

Mon 1/12

5:30 pm-8:20 pm

Nonstop1h 50m

$177

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/6

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 $49). Flying from Maryland to Chicago Midway Airport in January is currently the most expensive (average of $139). 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 December 8, 2025.

It’s optimal to fly from Maryland to Chicago Midway Airport in the afternoon. By choosing this option you can save up to 44% 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 December 6, 2025.

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

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 December 8, 2025.

The most flights from USMD to MDW are scheduled on a Friday (14 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (4 on average).

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 $232 for a flight from Maryland to Chicago Midway Airport. The cheapest flight overall is $29 while the most popular route, (Washington, D.C. Dulles Intl - Chicago Midway) is currently priced at $164.

  • 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 $49). Flying from Maryland to Chicago Midway Airport in January is currently the most expensive (average of $139). 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

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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 December 8, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$64Average$160FlexibilityNo cancel feeOn-time62%
DeltaCheapest$98Average$328FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$159Average$295FlexibilityNo cancel feeOn-time63%

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