$91+ Cheap flights from Midway (MDW) to Maryland
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/11. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — BWI
Nov 29 — Dec 61
Round-trip
1 adult, Economy
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Find cheap flights from Midway to Maryland with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Cheapest flights from Midway to MarylandExplore 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 October 30, 2026.
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 October 30, 2026.
This CheapOair deal was found by Cheapflights users on 10/28. 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 12/812:28 pm -
1 stop9h 13m
Tue 12/156:00 am -
1 stop6h 33m
Deal found 10/28![Frontier logo]()
$173
This Cheapflightsfares deal was found by Cheapflights users on 10/27. 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.
Tue 12/226:52 am -
1 stop10h 39m
Tue 1/512:00 pm -
1 stop5h 26m
Deal found 10/27![Frontier logo]()
$180
This Cheapflightsfares deal was found by Cheapflights users on 10/28. 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.
Tue 12/1512:28 pm -
1 stop9h 13m
Sun 1/176:30 pm -
1 stop6h 16m
Deal found 10/28![Frontier logo]()
$182
This Cheapflightsfares deal was found by Cheapflights users on 10/29. 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.
Thu 12/35:02 pm -
1 stop5h 06m
Mon 12/76:00 am -
1 stop11h 06m
Deal found 10/29![Frontier logo]()
$184
This Mytrip deal was found by Cheapflights users on 10/26. 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.
Mon 12/75:02 pm -
1 stop15h 05m
Tue 12/88:41 pm -
1 stop15h 52m
Deal found 10/26![Frontier logo]()
$185
This Cheapflightsfares deal was found by Cheapflights users on 10/28. 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 12/76:11 pm -
1 stop14h 10m
Wed 12/96:00 am -
1 stop6h 33m
Deal found 10/28![Frontier logo]()
$190
This Kiwi.com deal was found by Cheapflights users on 10/25. 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.
Wed 11/186:08 am -
1 stop9h 06m
Thu 11/1910:00 am -
1 stop8h 47m
Deal found 10/25![Frontier logo]()
$191
This Travelocity deal was found by Cheapflights users on 10/28. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/512:28 pm -
1 stop9h 13m
Thu 12/106:27 am -
1 stop14h 15m
Deal found 10/28![Frontier logo]()
$192
This Travelocity deal was found by Cheapflights users on 10/27. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/512:28 pm -
1 stop9h 13m
Sun 12/66:00 am -
1 stop11h 06m
Deal found 10/27![Frontier logo]()
$193
This CheapOair deal was found by Cheapflights users on 10/26. 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 11/248:42 pm -
1 stop21h 32m
Tue 12/16:00 am -
1 stop6h 33m
Deal found 10/26![Frontier logo]()
$194
This Kiwi.com deal was found by Cheapflights users on 10/26. 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.
Wed 12/912:28 pm -
1 stop9h 13m
Fri 12/116:41 pm -
1 stop17h 52m
Deal found 10/26![Frontier logo]()
$195
Best flights from Midway to MarylandDiscover carefully curated flight deals from Midway to Maryland that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 30, 2026.
Discover carefully curated flight deals from Midway to Maryland that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 30, 2026.
This Southwest deal was found by Cheapflights users on 10/25. 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 11/188:50 am -
Nonstop1h 50m
Thu 11/198:15 pm -
Nonstop2h 15m
Deal found 10/25![Southwest logo]()
$259
This Southwest deal was found by Cheapflights users on 10/25. 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 12/36:15 pm -
Nonstop1h 55m
Mon 12/77:55 am -
Nonstop2h 05m
Deal found 10/25![Southwest logo]()
$259
This Southwest deal was found by Cheapflights users on 10/26. 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.
Tue 11/247:10 am -
Nonstop1h 50m
Tue 12/14:45 pm -
1 stop3h 55m
Deal found 10/26![Southwest logo]()
$268
This Southwest deal was found by Cheapflights users on 10/29. 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 11/261:45 pm -
Nonstop1h 50m
Thu 12/38:15 pm -
Nonstop2h 15m
Deal found 10/29![Southwest logo]()
$269
This Southwest deal was found by Cheapflights users on 10/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/245:45 am -
Nonstop2h 00m
Fri 1/17:55 am -
Nonstop2h 05m
Deal found 10/30![Southwest logo]()
$277
This Southwest deal was found by Cheapflights users on 10/29. 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 12/51:25 pm -
Nonstop1h 45m
Sun 12/62:55 pm -
Nonstop2h 05m
Deal found 10/29![Southwest logo]()
$278
This Southwest deal was found by Cheapflights users on 10/28. 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 12/178:25 pm -
Nonstop1h 55m
Mon 12/2810:05 pm -
Nonstop2h 10m
Deal found 10/28![Southwest logo]()
$288
This Southwest deal was found by Cheapflights users on 10/28. 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.
Fri 1/151:00 pm -
Nonstop1h 50m
Mon 1/187:40 am -
Nonstop2h 10m
Deal found 10/28![Southwest logo]()
$291
This Southwest deal was found by Cheapflights users on 10/27. 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.
Fri 11/206:30 pm -
1 stop3h 55m
Sat 11/217:10 pm -
Nonstop2h 05m
Deal found 10/27![Southwest logo]()
$294
This Southwest deal was found by Cheapflights users on 10/26. 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.
Tue 12/228:50 am -
Nonstop1h 50m
Tue 12/2910:05 pm -
Nonstop2h 10m
Deal found 10/26![Southwest logo]()
$317
Last-minute flights from Midway to MarylandDiscover last-minute flight deals from Midway to Maryland. Data last updated October 30, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Maryland. Data last updated October 30, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 10/26. 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.
Tue 11/106:42 pm -
1 stop14h 04m
Wed 11/118:41 pm -
1 stop22h 06m
Deal found 10/26![Frontier logo]()
$204
This Kiwi.com deal was found by Cheapflights users on 10/26. 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 11/166:08 am -
2 stops13h 56m
Wed 11/1810:41 am -
1 stop8h 06m
Deal found 10/26![Frontier logo]()
$217
This Cheapflightsfares deal was found by Cheapflights users on 10/28. 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.
Tue 11/176:08 am -
1 stop9h 06m
Sat 11/2110:07 am -
1 stop10h 40m
Deal found 10/28![Frontier logo]()
$198
This Cheapflightsfares deal was found by Cheapflights users on 10/28. 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.
Thu 11/196:08 am -
1 stop9h 36m
Sat 11/2110:07 am -
1 stop10h 40m
Deal found 10/28![Frontier logo]()
$208
This Cheapflightsfares deal was found by Cheapflights users on 10/28. 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.
Sat 11/218:42 pm -
1 stop11h 25m
Tue 11/241:00 pm -
1 stop7h 47m
Deal found 10/28![Frontier logo]()
$218
This CheapOair deal was found by Cheapflights users on 10/26. 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 11/248:42 pm -
1 stop21h 32m
Tue 12/16:00 am -
1 stop6h 33m
Deal found 10/26![Frontier logo]()
$194
This Frontier deal was found by Cheapflights users on 10/29. 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 11/249:09 am -
1 stop7h 36m
Sat 12/56:00 am -
1 stop6h 33m
Deal found 10/29![Frontier logo]()
$200
This Trip.com deal was found by Cheapflights users on 10/28. 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.
Wed 11/259:07 am -
1 stop7h 38m
Wed 12/26:00 am -
1 stop6h 33m
Deal found 10/28![Frontier logo]()
$191
This Expedia deal was found by Cheapflights users on 10/26. 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 11/258:42 pm -
1 stop21h 32m
Fri 12/46:25 am -
1 stop10h 42m
Deal found 10/26![Frontier logo]()
$212
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Thu 11/261:16 pm -
1 stop10h 26m
Wed 12/26:00 am -
1 stop6h 33m
Deal found 10/29![Frontier logo]()
$209
This Frontier deal was found by Cheapflights users on 10/29. 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 11/261:16 pm -
1 stop10h 26m
Sat 12/56:00 am -
1 stop6h 33m
Deal found 10/29![Frontier logo]()
$210
One-way flights from Midway to MarylandSearch for one-way flight options from Midway to Maryland. Find affordable one-way fares based on user searches. Data last updated October 30, 2026.
Search for one-way flight options from Midway to Maryland. Find affordable one-way fares based on user searches. Data last updated October 30, 2026.
This Trip.com deal was found by Cheapflights users on 10/27. 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.
Mon 1/115:21 pm -
1 stop23h 14m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Frontier logo]()
$91
This Trip.com deal was found by Cheapflights users on 10/30. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/115:02 pm -
1 stop14h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/30![Frontier logo]()
$92
This Kiwi.com deal was found by Cheapflights users on 10/28. 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.
Fri 12/45:02 pm -
1 stop23h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Frontier logo]()
$96
This Expedia deal was found by Cheapflights users on 10/29. 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.
Thu 1/211:18 pm -
1 stop10h 16m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![Frontier logo]()
$97
This Southwest deal was found by Cheapflights users on 10/29. 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 12/54:25 pm -
Nonstop1h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![Southwest logo]()
$100
This Mytrip deal was found by Cheapflights users on 10/27. 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.
Sat 12/510:40 am -
2 stops11h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Frontier logo]()
$101
This CheapOair deal was found by Cheapflights users on 10/29. 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 11/249:09 am -
1 stop7h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![Frontier logo]()
$102
This Cheapflightsfares deal was found by Cheapflights users on 10/28. 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.
Tue 12/226:52 am -
1 stop10h 39m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Frontier logo]()
$104
This Cheapflightsfares deal was found by Cheapflights users on 10/28. 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.
Thu 12/176:52 am -
1 stop10h 39m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Frontier logo]()
$106
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 October 30, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $173 (CheapOair) |
One-way from | $91 (Trip.com) |
Popular in | June |
Cheapest in | January |
Average price | $314 |
Good round-trip deal | $361 or less |
Good one-way deal | $213 or less |
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 7,457,451 searches. Data last updated October 30, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Maryland that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoBaltimore
MDW Chicago Midway - BWI Baltimore/Washington
MDWBWI
Chicago Midway
Sat 12/5
8:00 am-12:55 pm
1 stop3h 55m
Baltimore/Washington
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$105
ChicagoBaltimore
MDW Chicago Midway - BWI Baltimore/Washington
MDWBWI
Chicago Midway
Tue 11/24
8:42 pm-7:14 pm
1 stop21h 32m
Baltimore/Washington
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$126
Quickest round-trip
ChicagoBaltimore
MDW Chicago Midway - BWI Baltimore/Washington
MDWBWI
Chicago Midway
Mon 11/23
5:05 am-7:55 am
Nonstop1h 50m
Baltimore/Washington
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$130
ChicagoBaltimore
MDW Chicago Midway - BWI Baltimore/Washington
MDWBWI
Chicago Midway
Thu 11/19
6:00 am-9:00 am
Nonstop2h 00m
Baltimore/Washington
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$130
ChicagoBaltimore
MDW Chicago Midway - BWI Baltimore/Washington
MDWBWI
Chicago Midway
Thu 11/26
1:45 pm-4:35 pm
Nonstop1h 50m
Baltimore/Washington
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$130
ChicagoBaltimore
MDW Chicago Midway - BWI Baltimore/Washington
MDWBWI
Chicago Midway
Wed 11/25
9:05 pm-11:55 pm
Nonstop1h 50m
Baltimore/Washington
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$139
ChicagoBaltimore
MDW Chicago Midway - BWI Baltimore/Washington
MDWBWI
Chicago Midway
Thu 1/21
5:40 pm-8:35 pm
Nonstop1h 55m
Baltimore/Washington
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$146
ChicagoBaltimore
MDW Chicago Midway - BWI Baltimore/Washington
MDWBWI
Chicago Midway
Tue 11/24
7:10 am-10:00 am
Nonstop1h 50m
Baltimore/Washington
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$150
ChicagoBaltimore
MDW Chicago Midway - BWI Baltimore/Washington
MDWBWI
Chicago Midway
Wed 12/23
4:05 pm-6:55 pm
Nonstop1h 50m
Baltimore/Washington
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$159
ChicagoBaltimore
MDW Chicago Midway - BWI Baltimore/Washington
MDWBWI
Chicago Midway
Sat 12/26
8:55 pm-11:45 pm
Nonstop1h 50m
Baltimore/Washington
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$176
Showing 1-10 of 20 resultsSorted by cheapest first
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.
MDW-BWI
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
MDW-USMD
MDW-BWI
What is the cheapest month to book a flight from Chicago Midway Airport to Maryland?
Currently, November is the cheapest month in which you can book a flight from Chicago Midway Airport to Maryland (average of $196). Flying from Chicago Midway Airport to Maryland in March is currently the most expensive (average of $578). 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 October 30, 2026.
It’s optimal to fly from Chicago Midway Airport to Maryland in the evening. By choosing this option you can save up to 7% on the cost of your flight, compared to a flight at noon.
How much does it cost to fly round-trip from Chicago Midway Airport to Maryland?
Airfare is typical for this route at the moment.
Chicago Midway Airport to Maryland flights typically cost between $149 and $372 in December.The cheapest round-trip price found within the last 5 days was $173 on Frontier (Dec 8-Dec 15).
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 October 24, 2026.
Travelers seeking maximum savings on their Chicago Midway Airport to Maryland flight should consider departing on Saturday afternoons when fares are most often at their lowest. Sunday 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 October 30, 2026.
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.
Crew
8.6
Comfort
8.0
Boarding
8.1
Entertainment
7.4
Overall
7.9
Food
7.0
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Crew
8.6
Comfort
8.0
Boarding
8.1
Entertainment
7.4
Overall
7.9
Food
7.0
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Crew
8.6
Comfort
8.0
Boarding
8.1
Entertainment
7.4
Overall
7.9
Food
7.0
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
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Top 2 airlines flying from Midway to Maryland
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| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$149 | Average$271 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$191 | Average$351 | FlexibilityNo cancel fee | On-time63% |