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Cheap flights from Maryland to Chicago from $90

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 5/17. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
6:30 am - 11:09 am
PHL
-
MDW
5h 39m
1 stop
Frontier Logo
12:04 pm - 10:29 pm
MDW
-
PHL
9h 25m
1 stop
$185Frontier
Wed, Jun 3 - Wed, Jun 10
Frontier Logo
4:35 pm - 10:02 pm
PHL
-
MDW
6h 27m
1 stop
Frontier Logo
6:00 am - 12:25 pm
MDW
-
PHL
5h 25m
1 stop
$187Frontier
Sat, May 30 - Sun, Jun 7
Multiple Airlines Logo
12:00 pm - 10:02 pm
PHL
-
MDW
11h 02m
2 stops
Multiple Airlines Logo
4:52 pm - 6:40 pm
MDW
-
PHL
24h 48m
1 stop
$188Multiple Airlines
Tue, May 5 - Mon, May 11
Frontier Logo
4:35 pm - 10:02 pm
PHL
-
MDW
6h 27m
1 stop
Frontier Logo
6:00 am - 12:25 pm
MDW
-
PHL
5h 25m
1 stop
$190Frontier
Fri, May 29 - Sat, May 30
Frontier Logo
12:47 pm - 7:41 am
PHL
-
MDW
19h 54m
1 stop
Frontier Logo
8:41 am - 8:59 am
MDW
-
PHL
23h 18m
1 stop
$191Frontier
Sat, May 2 - Mon, May 4
Multiple Airlines Logo
1:08 pm - 10:14 pm
PHL
-
MDW
10h 06m
2 stops
Multiple Airlines Logo
2:15 pm - 9:57 pm
MDW
-
PHL
6h 42m
1 stop
$197Multiple Airlines
Tue, Apr 28 - Thu, Apr 30
Southwest Logo
9:15 pm - 10:20 pm
BWI
-
MDW
2h 05mnonstop
Southwest Logo
5:00 pm - 7:50 pm
MDW
-
BWI
1h 50mnonstop
$208Southwest
Mon, May 11 - Wed, May 13
Southwest Logo
2:40 pm - 9:45 pm
DCA
-
MDW
8h 05m
2 stops
Southwest Logo
5:00 pm - 7:55 pm
MDW
-
DCA
1h 55mnonstop
$223Southwest
Tue, May 5 - Thu, May 7
Delta Logo
6:00 pm - 10:28 pm
DCA
-
MDW
5h 28m
1 stop
Delta Logo
1:24 pm - 6:59 pm
MDW
-
DCA
4h 35m
1 stop
$226Delta
Wed, Apr 29 - Wed, May 6
Delta Logo
5:33 pm - 9:09 pm
IAD
-
MDW
4h 36m
1 stop
Delta Logo
6:36 pm - 10:56 pm
MDW
-
IAD
3h 20m
1 stop
$228Delta
Mon, May 11 - Tue, May 12

Southwest flights from Maryland to Chicago Midway Airport

Our best Southwest deals on Maryland to Chicago Midway Airport flight tickets
Southwest
May 11
BWI9:15 pmBaltimore/Washington
2h 05m
MDW10:20 pmChicago Midway
May 13
MDW5:00 pmChicago Midway
1h 50m
BWI7:50 pmBaltimore/Washington
$208
Southwest
May 11
BWI7:10 pmBaltimore/Washington
2h 10m
MDW8:20 pmChicago Midway
May 13
MDW7:50 amChicago Midway
3h 10m
1 stop
BWI12:00 pmBaltimore/Washington
$214
Southwest
May 12
BWI6:30 amBaltimore/Washington
2h 05m
MDW7:35 amChicago Midway
May 14
MDW7:45 amChicago Midway
4h 00m
1 stop
BWI12:45 pmBaltimore/Washington
$218

Frontier flights from Maryland to Chicago Midway Airport

Our best Frontier deals on Maryland to Chicago Midway Airport flight tickets
Frontier
Jun 3
PHL6:30 amPhiladelphia
5h 39m
1 stop
MDW11:09 amChicago Midway
Jun 10
MDW12:04 pmChicago Midway
9h 25m
1 stop
PHL10:29 pmPhiladelphia
$185
Frontier
May 30
PHL4:35 pmPhiladelphia
6h 27m
1 stop
MDW10:02 pmChicago Midway
Jun 7
MDW6:00 amChicago Midway
5h 25m
1 stop
PHL12:25 pmPhiladelphia
$187
Frontier
May 29
PHL4:35 pmPhiladelphia
6h 27m
1 stop
MDW10:02 pmChicago Midway
May 30
MDW6:00 amChicago Midway
5h 25m
1 stop
PHL12:25 pmPhiladelphia
$190

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 April 18, 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

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Wed 6/3

6:30 am-11:09 am

1 stop5h 39m

Chicago Midway

Wed 6/10

12:04 pm-10:29 pm

1 stop9h 25m

$185

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Sat 5/30

4:35 pm-10:02 pm

1 stop6h 27m

Chicago Midway

Sun 6/7

6:00 am-12:25 pm

1 stop5h 25m

$187

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Tue 5/5

12:00 pm-10:02 pm

2 stops11h 02m

Chicago Midway

Mon 5/11

4:52 pm-6:40 pm

1 stop24h 48m

$188

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Fri 5/29

4:35 pm-10:02 pm

1 stop6h 27m

Chicago Midway

Sat 5/30

6:00 am-12:25 pm

1 stop5h 25m

$190

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Sat 5/2

12:47 pm-7:41 am

1 stop19h 54m

Chicago Midway

Mon 5/4

8:41 am-8:59 am

1 stop23h 18m

$191

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Tue 4/28

1:08 pm-10:14 pm

2 stops10h 06m

Chicago Midway

Thu 4/30

2:15 pm-9:57 pm

1 stop6h 42m

$197
Quickest round-trip

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Mon 5/11

9:15 pm-10:20 pm

Nonstop2h 05m

Chicago Midway

Wed 5/13

5:00 pm-7:50 pm

Nonstop1h 50m

$208

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Tue 5/5

2:40 pm-9:45 pm

2 stops8h 05m

Chicago Midway

Thu 5/7

5:00 pm-7:55 pm

Nonstop1h 55m

$223

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Wed 4/29

6:00 pm-10:28 pm

1 stop5h 28m

Chicago Midway

Wed 5/6

1:24 pm-6:59 pm

1 stop4h 35m

$226

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Mon 5/11

5:33 pm-9:09 pm

1 stop4h 36m

Chicago Midway

Tue 5/12

6:36 pm-10:56 pm

1 stop3h 20m

$228

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 $207. 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, Saturday is the cheapest day to fly to Chicago Midway Airport from Maryland. The lowest ticket price found for a Saturday departure recently was $328. 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 $384.

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

Flying to Chicago Midway Airport from Maryland at noon is the least expensive time of day to depart. momondo users have found prices as low as $321 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $364. 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

$203

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 $203. The best round-trip flight deal from Maryland to Chicago Midway Airport found on momondo in the last 72 hours is $296.
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

Frequently asked questions about flying from Maryland to Chicago Midway Airport

  • 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 $95Free CancellationRating
5.7
2,987 reviews
Search Frontier flights
SouthwestPriceFrom $158Free CancellationRating
8.0
4,330 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
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
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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