$102+ Cheap flights from Maryland to Midway (MDW)
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 11/18. Fares are subject to change and may not be available on all flights or dates of travel.
BWI — MDW
Dec 1 — Dec 81
Round-trip
1 adult, Economy
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Find cheap flights from Maryland to Midway with Cheapflights
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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 Maryland to MidwayExplore 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 November 1, 2026.
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 November 1, 2026.
This CheapOair deal was found by Cheapflights users on 11/1. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/36:23 am -
1 stop10h 44m
Sat 12/512:28 pm -
1 stop9h 13m
Deal found 11/1![Frontier logo]()
$197
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/36:23 am -
1 stop10h 44m
Tue 12/812:28 pm -
1 stop9h 13m
Deal found 10/28![Frontier logo]()
$198
This Southwest deal was found by Cheapflights users on 11/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/28:15 pm -
Nonstop2h 15m
Wed 12/912:50 pm -
Nonstop1h 40m
Deal found 11/1![Southwest logo]()
$199
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 12/126:00 am -
1 stop6h 33m
Tue 12/1512:28 pm -
1 stop9h 13m
Deal found 10/28![Frontier logo]()
$200
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 11/2110:07 am -
1 stop10h 40m
Thu 11/261:16 pm -
1 stop10h 26m
Deal found 10/28![Frontier logo]()
$201
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.
Thu 11/266:15 am -
1 stop7h 06m
Tue 12/112:33 pm -
1 stop8h 50m
Deal found 10/29![Frontier logo]()
$203
This Mytrip deal was found by Cheapflights users on 11/1. 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 12/36:23 am -
1 stop10h 44m
Fri 12/45:02 pm -
1 stop14h 40m
Deal found 11/1![Frontier logo]()
$204
This Southwest deal was found by Cheapflights users on 10/31. 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 12/24:55 pm -
1 stop3h 50m
Sat 12/54:25 pm -
Nonstop1h 50m
Deal found 10/31![Southwest logo]()
$205
This Mytrip deal was found by Cheapflights users on 10/31. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/56:00 am -
1 stop6h 33m
Mon 12/75:02 pm -
1 stop15h 05m
Deal found 10/31![Frontier logo]()
$206
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/36:23 am -
1 stop10h 44m
Mon 12/75:02 pm -
1 stop15h 05m
Deal found 10/28![Frontier logo]()
$207
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.
Wed 11/1810:41 am -
1 stop8h 06m
Thu 11/196:08 am -
1 stop9h 36m
Deal found 10/27![Frontier logo]()
$208
This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/96:00 am -
1 stop6h 33m
Sat 12/1210:40 am -
2 stops11h 01m
Deal found 10/27![Frontier logo]()
$209
Best flights from Maryland to MidwayDiscover carefully curated flight deals from Maryland to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated November 1, 2026.
Discover carefully curated flight deals from Maryland to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated November 1, 2026.
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.
Tue 12/18:15 pm -
Nonstop2h 15m
Fri 12/46:00 am -
Nonstop2h 00m
Deal found 10/28![Southwest logo]()
$239
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/112:18 pm -
1 stop6h 43m
Fri 12/46:41 pm -
1 stop3h 54m
Deal found 10/28![Delta logo]()
$259
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.
Wed 12/27:55 am -
Nonstop2h 05m
Fri 12/46:00 am -
Nonstop2h 00m
Deal found 10/28![Southwest logo]()
$239
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 12/318:15 pm -
Nonstop2h 15m
Tue 1/51:15 pm -
1 stop3h 10m
Deal found 10/29![Southwest logo]()
$270
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.
Fri 1/159:55 pm -
Nonstop2h 05m
Mon 1/188:50 pm -
Nonstop1h 50m
Deal found 10/30![Southwest logo]()
$277
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.
Fri 1/157:10 pm -
Nonstop2h 05m
Tue 1/191:40 pm -
Nonstop1h 50m
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.
Sun 12/1310:00 pm -
Nonstop2h 10m
Tue 12/156:15 pm -
Nonstop1h 55m
Deal found 10/29![Southwest logo]()
$278
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.
Sun 12/62:55 pm -
Nonstop2h 05m
Wed 12/91:15 pm -
1 stop3h 20m
Deal found 10/27![Southwest logo]()
$284
This Southwest deal was found by Cheapflights users on 10/31. 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 12/94:50 pm -
2 stops5h 45m
Sun 12/137:50 am -
1 stop3h 15m
Deal found 10/31![Southwest logo]()
$306
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 11/267:50 am -
Nonstop2h 05m
Thu 11/2611:35 am -
Nonstop1h 45m
Deal found 10/30![Southwest logo]()
$318
This Southwest deal was found by Cheapflights users on 10/31. 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.
Fri 12/48:15 pm -
Nonstop2h 15m
Sun 12/67:50 am -
1 stop3h 30m
Deal found 10/31![Southwest logo]()
$324
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.
Tue 12/14:55 pm -
1 stop3h 50m
Sun 12/67:30 am -
Nonstop1h 50m
Deal found 10/30![Southwest logo]()
$324
Last-minute flights from Maryland to MidwayDiscover last-minute flight deals from Maryland to Midway. Data last updated November 1, 2026 and is based on user searches.
Discover last-minute flight deals from Maryland to Midway. Data last updated November 1, 2026 and is based on user searches.
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.
Thu 11/128:41 pm -
1 stop22h 06m
Mon 11/166:42 pm -
1 stop14h 04m
Deal found 10/28![Frontier logo]()
$212
This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/168:41 pm -
1 stop22h 06m
Tue 12/112:33 pm -
1 stop19h 15m
Deal found 10/27![Frontier logo]()
$216
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1710:41 am -
1 stop8h 06m
Sat 11/218:28 am -
1 stop8h 17m
Deal found 10/27![Frontier logo]()
$200
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.
Wed 11/1810:41 am -
1 stop8h 06m
Thu 11/196:08 am -
1 stop9h 36m
Deal found 10/27![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 11/2110:07 am -
1 stop10h 40m
Thu 11/261:16 pm -
1 stop10h 26m
Deal found 10/28![Frontier logo]()
$201
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.
Sat 11/2110:07 am -
1 stop10h 40m
Mon 11/238:42 pm -
1 stop11h 25m
Deal found 10/29![Frontier logo]()
$210
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.
Sat 11/216:15 am -
1 stop8h 30m
Sat 11/218:42 pm -
1 stop11h 25m
Deal found 10/27![Frontier logo]()
$218
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/236:40 am -
1 stop14h 07m
Tue 12/112:33 pm -
1 stop8h 50m
Deal found 10/30![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.
Wed 11/2510:07 am -
1 stop10h 40m
Wed 12/212:28 pm -
1 stop8h 55m
Deal found 10/28![Frontier logo]()
$220
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.
Thu 11/266:15 am -
1 stop7h 06m
Tue 12/112:33 pm -
1 stop8h 50m
Deal found 10/29![Frontier logo]()
$203
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/266:15 am -
1 stop7h 06m
Thu 12/35:02 pm -
1 stop5h 06m
Deal found 10/29![Frontier logo]()
$213
One-way flights from Maryland to MidwaySearch for one-way flight options from Maryland to Midway. Find affordable one-way fares based on user searches. Data last updated November 1, 2026.
Search for one-way flight options from Maryland to Midway. Find affordable one-way fares based on user searches. Data last updated November 1, 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.
Wed 11/1810:41 am -
1 stop8h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Frontier logo]()
$102
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/2110:07 am -
1 stop10h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/30![Frontier logo]()
$104
This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/249:59 pm -
1 stop22h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Frontier logo]()
$105
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/221:51 pm -
1 stop11h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/30![Frontier logo]()
$106
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 11/266:15 am -
1 stop7h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![Frontier logo]()
$108
This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/110:35 am -
2 stops23h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Frontier logo]()
$111
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/236:40 pm -
1 stop14h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Frontier logo]()
$113
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.
Thu 11/199:52 pm -
1 stop22h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Frontier logo]()
$114
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.
Wed 12/24:50 pm -
2 stops5h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Southwest logo]()
$115
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 November 1, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $195 (Cheapflightsfares) |
One-way from | $102 (Trip.com) |
Popular in | October |
Cheapest in | January |
Average price | $318 |
Good round-trip deal | $356 or less |
Good one-way deal | $188 or less |
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 7,457,451 searches. Data last updated November 1, 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
Cheapest round-trip
BaltimoreChicago
BWI Baltimore/Washington - MDW Chicago Midway
BWIMDW
Baltimore/Washington
Sat 1/16
2:15 pm-3:25 pm
Nonstop2h 10m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$106
Quickest round-trip
BaltimoreChicago
BWI Baltimore/Washington - MDW Chicago Midway
BWIMDW
Baltimore/Washington
Thu 11/26
1:30 pm-2:35 pm
Nonstop2h 05m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$130
BaltimoreChicago
BWI Baltimore/Washington - MDW Chicago Midway
BWIMDW
Baltimore/Washington
Mon 11/23
7:35 am-8:40 am
Nonstop2h 05m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$130
BaltimoreChicago
BWI Baltimore/Washington - MDW Chicago Midway
BWIMDW
Baltimore/Washington
Thu 12/24
8:15 pm-9:30 pm
Nonstop2h 15m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$139
BaltimoreChicago
BWI Baltimore/Washington - MDW Chicago Midway
BWIMDW
Baltimore/Washington
Fri 12/18
10:05 pm-11:15 pm
Nonstop2h 10m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$139
BaltimoreChicago
BWI Baltimore/Washington - MDW Chicago Midway
BWIMDW
Baltimore/Washington
Mon 12/7
7:55 am-9:00 am
Nonstop2h 05m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$139
BaltimoreChicago
BWI Baltimore/Washington - MDW Chicago Midway
BWIMDW
Baltimore/Washington
Sat 11/21
7:10 pm-12:25 am
2 stops6h 15m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$145
BaltimoreChicago
BWI Baltimore/Washington - MDW Chicago Midway
BWIMDW
Baltimore/Washington
Fri 12/18
6:00 am-9:37 am
1 stop4h 37m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$149
BaltimoreChicago
BWI Baltimore/Washington - MDW Chicago Midway
BWIMDW
Baltimore/Washington
Fri 1/1
10:45 am-2:30 pm
1 stop4h 45m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$149
BaltimoreChicago
BWI Baltimore/Washington - MDW Chicago Midway
BWIMDW
Baltimore/Washington
Wed 11/25
10:05 pm-11:15 pm
Nonstop2h 10m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$150
Showing 1-10 of 22 resultsSorted by cheapest first
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.
BWI-MDW
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
USMD-MDW
BWI-MDW
What is the cheapest month to book a flight from Maryland to Chicago Midway Airport?
Currently, February is the cheapest month in which you can book a flight from Maryland to Chicago Midway Airport (average of $279). Flying from Maryland to Chicago Midway Airport in May is currently the most expensive (average of $407). 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 November 1, 2026.
It’s optimal to fly from Maryland to Chicago Midway Airport in the evening. By choosing this option you can save up to 10% 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?
Airfare is typical for this route at the moment.
Maryland to Chicago Midway Airport flights typically cost between $170 and $358 in January.The cheapest round-trip price found within the last 5 days was $195 on Frontier (Jan 29-Feb 1).
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 11 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 October 31, 2026.
Travelers seeking maximum savings on their Maryland to Chicago Midway Airport flight should consider departing on Saturday afternoons when fares are most often at their lowest. Sunday afternoons 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.
Traveling to a place near Chicago Midway Airport?
Book flights to Chicago Midway Airport if you plan to visit one of these locationsBenton Harbor
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter
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| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$113 | Average$279 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$198 | Average$375 | FlexibilityNo cancel fee | On-time63% |