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Cheap flights from Maryland to Chicago from $77

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Maryland to Chicago departing on 3/24. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Maryland to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
12:20 pm - 6:37 pm
BWI
-
MDW
7h 17m
1 stop
Frontier Logo
2:20 pm - 12:49 am
MDW
-
BWI
9h 29m
1 stop
$126Frontier
Sat, May 2 - Sat, May 9
Frontier Logo
12:17 pm - 7:31 pm
BWI
-
MDW
8h 14m
1 stop
Frontier Logo
6:00 am - 5:15 pm
MDW
-
BWI
10h 15m
1 stop
$128Frontier
Wed, Apr 22 - Thu, Apr 30
Frontier Logo
8:57 am - 7:31 pm
BWI
-
MDW
11h 34m
1 stop
Frontier Logo
7:34 pm - 8:02 am
MDW
-
BWI
11h 28m
1 stop
$134Frontier
Thu, Apr 16 - Sat, Apr 18
Frontier Logo
9:10 pm - 8:04 am
BWI
-
MDW
11h 54m
1 stop
Frontier Logo
2:15 pm - 12:44 am
MDW
-
BWI
9h 29m
1 stop
$137Frontier
Sun, Apr 26 - Thu, Apr 30
Southwest Logo
6:05 am - 7:10 am
BWI
-
MDW
2h 05mnonstop
Southwest Logo
5:25 pm - 8:15 pm
MDW
-
BWI
1h 50mnonstop
$161Southwest
Thu, May 7 - Sat, May 9
Southwest Logo
11:10 am - 12:20 pm
PHL
-
MDW
2h 10mnonstop
Southwest Logo
3:25 pm - 6:25 pm
MDW
-
PHL
2h 00mnonstop
$163Southwest
Thu, Apr 16 - Mon, Apr 20
Multiple Airlines Logo
11:58 am - 7:31 pm
PHL
-
MDW
8h 33m
1 stop
Multiple Airlines Logo
6:00 am - 11:56 pm
MDW
-
PHL
16h 56m
1 stop
$174Multiple Airlines
Thu, Apr 16 - Sun, Apr 19
Delta Logo
6:00 am - 8:47 am
IAD
-
MDW
3h 47m
1 stop
Delta Logo
6:38 pm - 11:03 pm
MDW
-
IAD
3h 25m
1 stop
$188Delta
Mon, Apr 13 - Fri, Apr 17
Delta Logo
12:29 pm - 5:54 pm
DCA
-
MDW
6h 25m
1 stop
Delta Logo
6:34 pm - 10:51 pm
MDW
-
DCA
3h 17m
1 stop
$188Delta
Wed, Apr 8 - Fri, Apr 10
Multiple Airlines Logo
10:25 pm - 1:00 pm
IAD
-
MDW
15h 35m
2 stops
Multiple Airlines Logo
2:15 pm - 12:36 am
MDW
-
IAD
9h 21m
1 stop
$197Multiple Airlines
Mon, Apr 13 - Wed, Apr 15

Southwest flights from Maryland to Chicago Midway Airport

Our best Southwest deals on Maryland to Chicago Midway Airport flight tickets
Southwest
Apr 8
BWI6:30 amBaltimore/Washington
2h 05m
MDW7:35 amChicago Midway
Apr 11
MDW6:10 amChicago Midway
1h 50m
BWI9:00 amBaltimore/Washington
$161
Southwest
Apr 16
PHL11:10 amPhiladelphia
2h 10m
MDW12:20 pmChicago Midway
Apr 20
MDW3:25 pmChicago Midway
2h 00m
PHL6:25 pmPhiladelphia
$163
Southwest
Apr 8
PHL5:45 pmPhiladelphia
2h 10m
MDW6:55 pmChicago Midway
Apr 18
MDW7:40 amChicago Midway
1h 55m
PHL10:35 amPhiladelphia
$169

Frontier flights from Maryland to Chicago Midway Airport

Our best Frontier deals on Maryland to Chicago Midway Airport flight tickets
Frontier
May 4
BWI2:43 pmBaltimore/Washington
5h 48m
1 stop
MDW7:31 pmChicago Midway
May 6
MDW2:20 pmChicago Midway
9h 29m
1 stop
BWI12:49 amBaltimore/Washington
$126
Frontier
Apr 22
BWI12:17 pmBaltimore/Washington
8h 14m
1 stop
MDW7:31 pmChicago Midway
Apr 30
MDW6:00 amChicago Midway
10h 15m
1 stop
BWI5:15 pmBaltimore/Washington
$128
Frontier
Apr 16
BWI8:57 amBaltimore/Washington
11h 34m
1 stop
MDW7:31 pmChicago Midway
Apr 18
MDW7:34 pmChicago Midway
11h 28m
1 stop
BWI8:02 amBaltimore/Washington
$134

momondo Fare Finder

 
Customize your flight search to find flights from Maryland to Chicago Midway Airport 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, momondo users made 832,500 searches. Data last updated February 25, 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

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Sat 5/2

12:20 pm-6:37 pm

1 stop7h 17m

Chicago Midway

Sat 5/9

2:20 pm-12:49 am

1 stop9h 29m

$126

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Wed 4/22

12:17 pm-7:31 pm

1 stop8h 14m

Chicago Midway

Thu 4/30

6:00 am-5:15 pm

1 stop10h 15m

$128

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Thu 4/16

8:57 am-7:31 pm

1 stop11h 34m

Chicago Midway

Sat 4/18

7:34 pm-8:02 am

1 stop11h 28m

$134

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Sun 4/26

9:10 pm-8:04 am

1 stop11h 54m

Chicago Midway

Thu 4/30

2:15 pm-12:44 am

1 stop9h 29m

$137

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Thu 5/7

6:05 am-7:10 am

Nonstop2h 05m

Chicago Midway

Sat 5/9

5:25 pm-8:15 pm

Nonstop1h 50m

$161

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Thu 4/16

11:10 am-12:20 pm

Nonstop2h 10m

Chicago Midway

Mon 4/20

3:25 pm-6:25 pm

Nonstop2h 00m

$163

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Thu 4/16

11:58 am-7:31 pm

1 stop8h 33m

Chicago Midway

Sun 4/19

6:00 am-11:56 pm

1 stop16h 56m

$174

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Mon 4/13

6:00 am-8:47 am

1 stop3h 47m

Chicago Midway

Fri 4/17

6:38 pm-11:03 pm

1 stop3h 25m

$188

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Wed 4/8

12:29 pm-5:54 pm

1 stop6h 25m

Chicago Midway

Fri 4/10

6:34 pm-10:51 pm

1 stop3h 17m

$188

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Mon 4/13

10:25 pm-1:00 pm

2 stops15h 35m

Chicago Midway

Wed 4/15

2:15 pm-12:36 am

1 stop9h 21m

$197

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Maryland to Chicago Midway Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Chicago Midway Airport?

The month of August is, on average, the cheapest month to fly to Chicago Midway Airport from Maryland, with most prices found around $202. If you are unable to visit Chicago Midway Airport during the month of August, then departing from Maryland during the month September is also very affordable. Most momondo users find prices during this month for around $228.

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Wednesday is the cheapest day to fly to Chicago Midway Airport from Maryland. The lowest ticket price found for a Wednesday departure recently was $318. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Sunday is the most expensive day to depart from Maryland because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $378.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from Maryland in the evening is the least expensive time of day to depart. momondo users have found prices as low as $309 when looking at flights departing in the evening. Try not to purchase tickets in the morning because they tend to be around $356. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Maryland to Chicago Midway flight route?

Fly from Baltimore/Washington to Chicago Midway for the best Maryland - Chicago Midway flight prices

What cabin class options are available on Maryland to Chicago Midway flights?

There is only 1 cabin class available to choose from on Maryland to Chicago Midway flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Cheap Maryland to Chicago Midway Airport flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Maryland to Chicago Midway Airport

Best Price Found

$173

Fastest flight time

1h 55m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Maryland in the past 72 hours is $173. The best round-trip flight deal from Maryland to Chicago Midway Airport found on momondo in the last 72 hours is $253.
The fastest flight from Maryland to Chicago Midway Airport takes 1h 55m
Direct flights go from Maryland to Chicago Midway Airport every day.
Search flight deals

  • When did momondo last update prices for flights from Maryland to Chicago Midway Airport?

    Prices for flights from Maryland to Chicago Midway Airport were last updated today.

  • How many operators does momondo search for flights from Maryland to Chicago Midway Airport?

  • How old do you have to be to fly from Maryland to Chicago Midway Airport?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Maryland to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The travel and health documents required for your trip to Chicago Midway Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago Midway Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular plane model from Maryland to Chicago Midway Airport?

Best airlines flying from Maryland to Chicago Midway Airport

Compare and see reviews for airlines that fly from Maryland to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $70Free CancellationRating
5.7
3,041 reviews
Search Frontier flights
SouthwestPriceFrom $159Free CancellationRating
8.0
4,299 reviews
Search Southwest flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Munster
Crown Point
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Maryland to Chicago?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Maryland.

Can I find flights from Maryland to Chicago with flexible booking policies on momondo?

momondo does allow users to show only those flights to Chicago from Maryland which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Maryland to Chicago?

Once you have performed a search for Maryland to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Maryland to Chicago right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Maryland and alert you when they change.

An easier way to manage your Chicago Midway Airport trip

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