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Cheap flights from Chicago Midway Airport to Maryland from $67

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Maryland departing on 10/6. 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 Chicago Midway Airport to Maryland

Cheap round-trip flights

Frontier Logo
1:49 pm - 4:50 pmMDW-BWI
2h 01mnonstop
Frontier Logo
5:40 pm - 6:43 pmBWI-MDW
2h 03mnonstop
$95Frontier
Find Deal
Thu, Oct 2 - Mon, Oct 6
Frontier Logo
1:49 pm - 4:50 pmMDW-BWI
2h 01mnonstop
Frontier Logo
5:40 pm - 6:43 pmBWI-MDW
2h 03mnonstop
$96Frontier
Find Deal
Fri, Sep 12 - Mon, Sep 15
Frontier Logo
1:49 pm - 4:50 pmMDW-BWI
2h 01mnonstop
Frontier Logo
5:40 pm - 6:43 pmBWI-MDW
2h 03mnonstop
$97Frontier
Find Deal
Fri, Sep 19 - Sun, Sep 21
Frontier Logo
1:49 pm - 4:50 pmMDW-BWI
2h 01mnonstop
Frontier Logo
5:40 pm - 6:43 pmBWI-MDW
2h 03mnonstop
$98Frontier
Find Deal
Thu, Sep 18 - Sun, Sep 21
Logo
2:32 pm - 10:26 amMDW-BWI
18h 54m1 stop
Logo
5:40 pm - 6:43 pmBWI-MDW
2h 03mnonstop
$147
Find Deal
Tue, Sep 9 - Thu, Sep 11
Southwest Logo
6:30 am - 9:25 amMDW-PHL
1h 55mnonstop
Southwest Logo
10:15 am - 11:25 amPHL-MDW
2h 10mnonstop
$158Southwest
Find Deal
Fri, Oct 17 - Tue, Oct 28
Logo
8:15 am - 11:16 amMDW-PHL
2h 01mnonstop
Logo
5:00 am - 3:58 pmPHL-MDW
11h 58m2 stops
$173
Find Deal
Fri, Sep 12 - Wed, Sep 17
Southwest Logo
12:50 pm - 3:40 pmMDW-PHL
1h 50mnonstop
Southwest Logo
5:25 am - 6:30 amPHL-MDW
2h 05mnonstop
$178Southwest
Find Deal
Sat, Oct 11 - Tue, Oct 14
Delta Logo
6:00 am - 11:31 amMDW-DCA
4h 31m1 stop
Delta Logo
6:00 am - 8:40 amDCA-MDW
3h 40m1 stop
$231Delta
Find Deal
Tue, Oct 7 - Tue, Oct 14
Delta Logo
11:00 am - 5:20 pmMDW-DCA
5h 20m1 stop
Delta Logo
6:00 am - 8:40 amDCA-MDW
3h 40m1 stop
$234Delta
Find Deal
Sat, Sep 20 - Tue, Sep 23

Frontier flights from Chicago Midway Airport to Maryland

Our best Frontier deals on Chicago Midway Airport to Maryland flight tickets
Frontier
Oct 2
MDW1:49 pmChicago Midway
2h 01m
BWI4:50 pmBaltimore/Washington
Oct 6
BWI5:40 pmBaltimore/Washington
2h 03m
MDW6:43 pmChicago Midway
$95
Find similar
Frontier
Sep 12
MDW1:49 pmChicago Midway
2h 01m
BWI4:50 pmBaltimore/Washington
Sep 15
BWI5:40 pmBaltimore/Washington
2h 03m
MDW6:43 pmChicago Midway
$96
Find similar
Frontier
Sep 19
MDW1:49 pmChicago Midway
2h 01m
BWI4:50 pmBaltimore/Washington
Sep 21
BWI5:40 pmBaltimore/Washington
2h 03m
MDW6:43 pmChicago Midway
$97
Find similar

Southwest flights from Chicago Midway Airport to Maryland

Our best Southwest deals on Chicago Midway Airport to Maryland flight tickets
Southwest
Oct 17
MDW6:30 amChicago Midway
1h 55m
PHL9:25 amPhiladelphia
Oct 28
PHL10:15 amPhiladelphia
2h 10m
MDW11:25 amChicago Midway
$158
Find similar
Southwest
Oct 11
MDW12:50 pmChicago Midway
1h 50m
PHL3:40 pmPhiladelphia
Oct 14
PHL5:25 amPhiladelphia
2h 05m
MDW6:30 amChicago Midway
$178
Find similar
Southwest
Oct 23
MDW6:10 amChicago Midway
1h 45m
DCA8:55 amWashington, D.C. Reagan-National
Oct 28
DCA9:05 amWashington, D.C. Reagan-National
2h 10m
MDW10:15 amChicago Midway
$214
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport 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, momondo users made 832,500 searches. Data last updated August 28, 2025.
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

Price

ChicagoBaltimore

MDW - BWI

MDWBWI

Chicago Midway

Thu 10/2

1:49 pm-4:50 pm

Nonstop2h 01m

Baltimore/Washington

Mon 10/6

5:40 pm-6:43 pm

Nonstop2h 03m

$95

ChicagoBaltimore

MDW - BWI

MDWBWI

Chicago Midway

Fri 9/12

1:49 pm-4:50 pm

Nonstop2h 01m

Baltimore/Washington

Mon 9/15

5:40 pm-6:43 pm

Nonstop2h 03m

$96

ChicagoBaltimore

MDW - BWI

MDWBWI

Chicago Midway

Fri 9/19

1:49 pm-4:50 pm

Nonstop2h 01m

Baltimore/Washington

Sun 9/21

5:40 pm-6:43 pm

Nonstop2h 03m

$97

ChicagoBaltimore

MDW - BWI

MDWBWI

Chicago Midway

Thu 9/18

1:49 pm-4:50 pm

Nonstop2h 01m

Baltimore/Washington

Sun 9/21

5:40 pm-6:43 pm

Nonstop2h 03m

$98

ChicagoBaltimore

MDW - BWI

MDWBWI

Chicago Midway

Tue 9/9

2:32 pm-10:26 am

1 stop18h 54m

Baltimore/Washington

Thu 9/11

5:40 pm-6:43 pm

Nonstop2h 03m

$147

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Fri 10/17

6:30 am-9:25 am

Nonstop1h 55m

Philadelphia

Tue 10/28

10:15 am-11:25 am

Nonstop2h 10m

$158

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Fri 9/12

8:15 am-11:16 am

Nonstop2h 01m

Philadelphia

Wed 9/17

5:00 am-3:58 pm

2 stops11h 58m

$173

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Sat 10/11

12:50 pm-3:40 pm

Nonstop1h 50m

Philadelphia

Tue 10/14

5:25 am-6:30 am

Nonstop2h 05m

$178

ChicagoWashington, D.C.

MDW - DCA

MDWDCA

Chicago Midway

Tue 10/7

6:00 am-11:31 am

1 stop4h 31m

Washington, D.C. Reagan-National

Tue 10/14

6:00 am-8:40 am

1 stop3h 40m

$231

ChicagoWashington, D.C.

MDW - DCA

MDWDCA

Chicago Midway

Sat 9/20

11:00 am-5:20 pm

1 stop5h 20m

Washington, D.C. Reagan-National

Tue 9/23

6:00 am-8:40 am

1 stop3h 40m

$234

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 Maryland from

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

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 Maryland?

The cheapest month to fly to Maryland from Chicago Midway Airport is in October. Flight prices, which tend to average around $139, are often lower during this time because this is during the off-season. If you don’t want to visit Maryland in October, then you should wait until September to fly from Chicago Midway Airport, when ticket prices are also cheap, with an average price of $189.

What is the cheapest day to depart on your flight to Maryland?

The cheapest day to depart from Chicago Midway Airport to Maryland is on a Wednesday. Travelers who choose to depart for Maryland on a Wednesday will often find tickets for as low as $244. The most expensive day to fly to Maryland is Monday, with ticket prices averaging around $374.

What is the cheapest time of day to depart on your flight to Maryland?

Our most recent data shows that the best time of day to fly to Maryland is in the evening. Flights from Chicago Midway Airport to Maryland during this time can be as low as $267. In contrast, the most expensive time of day to depart to Maryland is at noon when prices are around $319.

What is the cheapest Chicago Midway to Maryland flight route?

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

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

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

Cheap Chicago Midway Airport to Maryland flight deals and tips

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

Best Price Found

$82

Fastest flight time

1h 40m

Direct flights

Every day

Airports in Maryland

3 airports
The best one-way flight to Maryland from Chicago Midway Airport in the past 72 hours is $82. The best round-trip flight deal from Chicago Midway Airport to Maryland found on momondo in the last 72 hours is $131.
The fastest flight from Chicago Midway Airport to Maryland takes 1h 40m
Direct flights go from Chicago Midway Airport to Maryland every day.
There are 3 airports near Maryland: Washington, D.C. Reagan-National (DCA), Baltimore/Washington (BWI), Philadelphia (PHL)
Search flight deals

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

    Prices for flights from Chicago Midway Airport to Maryland are refreshed on a daily basis.

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

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

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago Midway Airport to Maryland.

  • What documentation or ID do you need to fly to Maryland?

    The travel and health documents required for your trip to Maryland 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 Maryland. 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 Chicago Midway Airport to Maryland?

Best airlines flying from Chicago Midway Airport to Maryland

Compare and see reviews for airlines that fly from Chicago Midway Airport to Maryland with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $78Free CancellationRating
5.8
3,204 reviews
Search Frontier flights
SouthwestPriceFrom $159Free CancellationRating
8.0
4,242 reviews
Search Southwest flights

Why use momondo?

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

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Chicago to Maryland for you.

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

Yes. All flights to Maryland from Chicago on momondo can be compared and filtered by various policies on offer, including flexible booking.

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

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Maryland from Chicago.

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

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

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