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Midway

$97+ 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 5/27. Fares are subject to change and may not be available on all flights or dates of travel.
BWI — MDW
jun. 18 — jun. 251
jue. 6/18
jue. 6/25
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 mayo 19, 2026.

This Super.com deal was found by Cheapflights users on 5/15. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 6/304:35 pm
PHL
-
MDW
1 stop6h 36m
Frontier
mar. 7/76:00 am
MDW
-
PHL
1 stop5h 22m
Frontier
Deal found 5/15$216
This Frontier deal was found by Cheapflights users on 5/18. 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.
mié. 7/16:30 am
PHL
-
MDW
1 stop5h 39m
Frontier
mar. 7/76:00 am
MDW
-
PHL
1 stop5h 22m
Frontier
Deal found 5/18$218
This Trip.com deal was found by Cheapflights users on 5/17. 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.
mar. 7/144:30 pm
PHL
-
MDW
1 stop6h 38m
Frontier
mié. 7/156:00 am
MDW
-
PHL
1 stop5h 22m
Frontier
Deal found 5/17$220
This Super.com deal was found by Cheapflights users on 5/15. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 7/254:30 pm
PHL
-
MDW
1 stop6h 38m
Frontier
lun. 7/276:00 am
MDW
-
PHL
1 stop5h 22m
Frontier
Deal found 5/15$221
This Trip.com deal was found by Cheapflights users on 5/14. 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.
mar. 7/76:30 am
PHL
-
MDW
1 stop5h 37m
Frontier
mié. 7/86:00 am
MDW
-
PHL
1 stop5h 22m
Frontier
Deal found 5/14$222
This Frontier deal was found by Cheapflights users on 5/17. 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.
mar. 7/76:30 am
PHL
-
MDW
1 stop5h 37m
Frontier
jue. 7/1612:11 pm
MDW
-
PHL
1 stop6h 09m
Frontier
Deal found 5/17$223
This Frontier deal was found by Cheapflights users on 5/14. 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.
lun. 6/226:28 am
BWI
-
MDW
1 stop5h 41m
Frontier
mié. 6/2412:04 pm
MDW
-
BWI
1 stop5h 28m
Frontier
Deal found 5/14$224
This Super.com deal was found by Cheapflights users on 5/14. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 6/106:25 am
PHL
-
MDW
1 stop5h 44m
Frontier
jue. 6/1112:27 pm
MDW
-
PHL
1 stop5h 50m
Frontier
Deal found 5/14$225
This Kiwi.com deal was found by Cheapflights users on 5/14. 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.
sáb. 6/610:10 am
BWI
-
MDW
2 stops12h 52m
Frontier
mié. 6/106:00 am
MDW
-
BWI
1 stop9h 22m
Frontier
Deal found 5/14$225
This Kiwi.com deal was found by Cheapflights users on 5/18. 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.
vie. 5/298:52 am
BWI
-
MDW
1 stop14h 10m
Frontier
sáb. 6/206:00 am
MDW
-
BWI
1 stop9h 26m
Frontier
Deal found 5/18$226
This Priceline deal was found by Cheapflights users on 5/17. 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.
jue. 9/36:35 am
BWI
-
MDW
1 stop5h 37m
Frontier
sáb. 9/127:25 am
MDW
-
BWI
1 stop7h 47m
Frontier
Deal found 5/17$227
This Expedia deal was found by Cheapflights users on 5/18. 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.
jue. 7/94:30 pm
PHL
-
MDW
1 stop6h 38m
Frontier
lun. 7/136:00 am
MDW
-
PHL
1 stop5h 22m
Frontier
Deal found 5/18$228

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 mayo 19, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$216
(Super.com)

One-way from

$97
(Trip.com)

Popular in

March

Cheapest in

September

Average price

$313

Good round-trip deal

$309 or less

Good one-way deal

$184 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. 6% potential increase in price ($20 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 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 mayo 19, 2026.
Use the filters below to find and compare flights from Maryland to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

mié. 10/21

4:35 pm-7:25 pm

1 stop3h 50m

Chicago Midway

sáb. 10/24

10:30 am-2:35 pm

1 stop3h 05m

$244

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

vie. 6/19

9:00 pm-10:00 pm

Nonstop2h 00m

Chicago Midway

mar. 6/23

8:55 pm-11:45 pm

Nonstop1h 50m

$253

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

mié. 7/22

4:25 pm-5:30 pm

Nonstop2h 05m

Chicago Midway

lun. 7/27

7:45 am-3:00 pm

1 stop6h 15m

$257

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

vie. 6/26

8:55 pm-10:00 pm

Nonstop2h 05m

Chicago Midway

mar. 6/30

7:50 am-12:00 pm

1 stop3h 10m

$259
Quickest round-trip

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

dom. 5/24

9:55 am-10:55 am

Nonstop2h 00m

Chicago Midway

jue. 6/4

11:15 am-2:00 pm

Nonstop1h 45m

$264

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

mar. 6/16

12:37 pm-4:16 pm

1 stop4h 39m

Chicago Midway

jue. 6/18

11:05 am-4:47 pm

1 stop4h 42m

$267

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

mié. 7/22

6:00 am-9:08 am

1 stop4h 08m

Chicago Midway

sáb. 7/25

1:18 pm-6:59 pm

1 stop4h 41m

$267

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

jue. 7/2

6:00 am-9:40 am

1 stop4h 40m

Chicago Midway

mar. 7/7

3:55 pm-10:50 pm

1 stop5h 55m

$267

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

jue. 10/8

8:55 pm-10:00 pm

Nonstop2h 05m

Chicago Midway

lun. 10/12

5:10 am-7:55 am

Nonstop1h 45m

$269

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

mié. 7/1

11:05 am-6:31 pm

1 stop8h 26m

Chicago Midway

mié. 7/8

5:10 pm-12:41 am

1 stop6h 31m

$276

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/18

Showing 1-10 of 60 resultsSorted by cheapest first
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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, June is the cheapest month in which you can book a flight from Maryland to Chicago Midway Airport (average of $46). Flying from Maryland to Chicago Midway Airport in April is currently the most expensive (average of $222). 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 mayo 19, 2026.

It’s optimal to fly from Maryland to Chicago Midway Airport in the afternoon. By choosing this option you can save up to 41% on the cost of your flight, compared to a flight in the morning.

How much does it cost to fly round-trip from Maryland to Chicago Midway Airport?

How far ahead should I book a flight from Maryland to Chicago Midway Airport?

The price you pay for your flight from Maryland to Chicago Midway Airport may vary depending on when you book. For the best chance of a lower fare, look to book 40 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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 May 16, 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. Sunday evenings 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 3h 50m. 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, Philadelphia - Chicago Midway and Baltimore/Washington - Chicago Midway.

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

    On average you can expect to pay $320 for a flight from Maryland to Chicago Midway Airport. The cheapest flight overall is $118 while the most popular route, (Washington, D.C. Dulles Intl - Chicago Midway) is currently priced at $190.

  • 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, June is the cheapest month in which you can book a flight from Maryland to Chicago Midway Airport (average of $46). Flying from Maryland to Chicago Midway Airport in April is currently the most expensive (average of $222). 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
Benton Harbor
Lansing
Merrillville
Hammond
Porter

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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 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 mayo 19, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$90Average$166FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$158Average$308FlexibilityNo cancel feeOn-time63%

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