What is the cheapest airline that flies from Chicago Midway to Maryland?

Southwest, Frontier, and Delta are the most popular carriers operating from Chicago Midway to Maryland

How many flights depart from Chicago Midway Airport to Maryland on average per week?

100 flights are operational weekly from Chicago Midway Airport to Maryland as of April 2026. The most popular departure day for this route is Mon, with 21% of flights per week taking off on this day.

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?

As of April 2026, there are 2 operators available to choose from 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.

$93 Cheap Flights from Chicago Midway Airport to Maryland in 2026

Q: How many flights depart from Chicago Midway Airport to Maryland on average per day?

As of April 2026, there are 14 flights per day flying from Chicago Midway Airport to Maryland. The most common time of day flights depart is 12:00PM, with 55% of flights taking off in the afternoon.

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Find the cheapest flights from Chicago Midway Airport to Maryland

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

6:49 pm - 8:51 pm

MDW

BWI

25h 02m

1 stop

12:17 pm - 7:31 pm

BWI

MDW

8h 14m

1 stop

$147Frontier

Fri, Apr 24 - Tue, Apr 28

6:10 am - 4:54 pm

MDW

BWI

9h 44m

1 stop

4:25 pm - 6:37 pm

BWI

MDW

27h 12m

1 stop

$153Frontier

Tue, Apr 28 - Fri, May 1

6:00 am - 5:00 pm

MDW

BWI

10h 00m

1 stop

12:17 pm - 7:31 pm

BWI

MDW

8h 14m

1 stop

$155Frontier

Mon, Apr 27 - Tue, Apr 28

6:00 am - 5:11 pm

MDW

BWI

10h 11m

1 stop

5:53 pm - 10:14 pm

BWI

MDW

5h 21m

1 stop

$160Frontier

Thu, Apr 30 - Sat, May 2

2:15 pm - 12:44 am

MDW

BWI

9h 29m

1 stop

12:17 pm - 10:14 pm

BWI

MDW

10h 57m

1 stop

$161Frontier

Wed, Apr 15 - Wed, Apr 22

7:00 am - 9:50 am

MDW

BWI

1h 50mnonstop

6:30 am - 7:35 am

BWI

MDW

2h 05mnonstop

$177Southwest

Tue, Apr 28 - Tue, May 5

2:15 pm - 9:57 pm

MDW

PHL

6h 42m

1 stop

7:24 pm - 2:12 pm

PHL

MDW

19h 48m

2 stops

$185Multiple Airlines

Thu, Apr 30 - Mon, May 4

1:55 pm - 6:40 pm

MDW

DCA

3h 45m

1 stop

6:40 am - 7:45 am

DCA

MDW

2h 05mnonstop

$214Southwest

Wed, Apr 22 - Sat, Apr 25

9:15 am - 3:05 pm

MDW

DCA

4h 50m

1 stop

9:55 am - 10:55 am

DCA

MDW

2h 00mnonstop

$218Southwest

Sat, May 2 - Tue, May 5

1:55 pm - 6:40 pm

MDW

DCA

3h 45m

1 stop

12:15 pm - 2:45 pm

DCA

MDW

3h 30m

1 stop

$219Southwest

Wed, Apr 22 - Sat, Apr 25

Frontier flights from Chicago Midway Airport to Maryland

Our best Frontier deals on Chicago Midway Airport to Maryland flight tickets

Frontier

Apr 24

MDW6:49 pmChicago Midway

25h 02m

1 stop

BWI8:51 pmBaltimore/Washington

Apr 28

BWI12:17 pmBaltimore/Washington

8h 14m

1 stop

MDW7:31 pmChicago Midway

$147

Frontier

Apr 28

MDW6:10 amChicago Midway

9h 44m

1 stop

BWI4:54 pmBaltimore/Washington

May 1

BWI4:25 pmBaltimore/Washington

27h 12m

1 stop

MDW6:37 pmChicago Midway

$153

Frontier

Apr 27

MDW6:00 amChicago Midway

10h 00m

1 stop

BWI5:00 pmBaltimore/Washington

Apr 28

BWI12:17 pmBaltimore/Washington

8h 14m

1 stop

MDW7:31 pmChicago Midway

$155

Southwest flights from Chicago Midway Airport to Maryland

Our best Southwest deals on Chicago Midway Airport to Maryland flight tickets

Southwest

Apr 28

MDW7:00 amChicago Midway

1h 50m

BWI9:50 amBaltimore/Washington

May 5

BWI6:30 amBaltimore/Washington

2h 05m

MDW7:35 amChicago Midway

$177

Southwest

Apr 28

MDW12:50 pmChicago Midway

3h 30m

1 stop

BWI5:20 pmBaltimore/Washington

May 5

BWI6:30 amBaltimore/Washington

2h 05m

MDW7:35 amChicago Midway

$183

Southwest

Apr 29

MDW12:45 pmChicago Midway

3h 55m

1 stop

BWI5:40 pmBaltimore/Washington

May 6

BWI1:20 pmBaltimore/Washington

3h 30m

1 stop

MDW3:50 pmChicago Midway

$188

momondo Fare Finder

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

Cheapest round-trip

ChicagoBaltimore

MDW - BWI

MDWBWI

Chicago Midway

Fri 4/24

6:49 pm-8:51 pm

1 stop25h 02m

Baltimore/Washington

Tue 4/28

12:17 pm-7:31 pm

1 stop8h 14m

$147

ChicagoBaltimore

MDW - BWI

MDWBWI

Chicago Midway

Tue 4/28

6:10 am-4:54 pm

1 stop9h 44m

Baltimore/Washington

Fri 5/1

4:25 pm-6:37 pm

1 stop27h 12m

$153

ChicagoBaltimore

MDW - BWI

MDWBWI

Chicago Midway

Mon 4/27

6:00 am-5:00 pm

1 stop10h 00m

Baltimore/Washington

Tue 4/28

12:17 pm-7:31 pm

1 stop8h 14m

$155

ChicagoBaltimore

MDW - BWI

MDWBWI

Chicago Midway

Thu 4/30

6:00 am-5:11 pm

1 stop10h 11m

Baltimore/Washington

Sat 5/2

5:53 pm-10:14 pm

1 stop5h 21m

$160

ChicagoBaltimore

MDW - BWI

MDWBWI

Chicago Midway

Wed 4/15

2:15 pm-12:44 am

1 stop9h 29m

Baltimore/Washington

Wed 4/22

12:17 pm-10:14 pm

1 stop10h 57m

$161

Quickest round-trip

ChicagoBaltimore

MDW - BWI

MDWBWI

Chicago Midway

Tue 4/28

7:00 am-9:50 am

Nonstop1h 50m

Baltimore/Washington

Tue 5/5

6:30 am-7:35 am

Nonstop2h 05m

$177

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Thu 4/30

2:15 pm-9:57 pm

1 stop6h 42m

Philadelphia

Mon 5/4

7:24 pm-2:12 pm

2 stops19h 48m

$185

ChicagoWashington, D.C.

MDW - DCA

MDWDCA

Chicago Midway

Wed 4/22

1:55 pm-6:40 pm

1 stop3h 45m

Washington, D.C. Reagan-National

Sat 4/25

6:40 am-7:45 am

Nonstop2h 05m

$214

ChicagoWashington, D.C.

MDW - DCA

MDWDCA

Chicago Midway

Sat 5/2

9:15 am-3:05 pm

1 stop4h 50m

Washington, D.C. Reagan-National

Tue 5/5

9:55 am-10:55 am

Nonstop2h 00m

$218

ChicagoWashington, D.C.

MDW - DCA

MDWDCA

Chicago Midway

Wed 4/22

1:55 pm-6:40 pm

1 stop3h 45m

Washington, D.C. Reagan-National

Sat 4/25

12:15 pm-2:45 pm

1 stop3h 30m

$219

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

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

Prices

Airlines

Other information

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 $268. The most expensive day to fly to Maryland is Monday, with ticket prices averaging around $391.

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 afternoon. Flights from Chicago Midway Airport to Maryland during this time can be as low as $299. In contrast, the most expensive time of day to depart to Maryland is in the evening when prices are around $317.

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.

Can stopping save me money on Chicago Midway Airport to Maryland flights?

You could potentially save up to 27% on your flight if you consider stops on a Chicago Midway Airport to Maryland flight.

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	$191
Fastest flight time	1h 45m
Direct flights	Every day
Airports in Maryland	112 airports

The best one-way flight to Maryland from Chicago Midway Airport in the past 72 hours is $191. The best round-trip flight deal from Chicago Midway Airport to Maryland found on momondo in the last 72 hours is $331.

The fastest flight from Chicago Midway Airport to Maryland takes 1h 45m

Direct flights go from Chicago Midway Airport to Maryland every day.

There are 112 airports in Maryland. From Chicago Midway Airport there are direct flights to Washington, D.C. Reagan-National (DCA), Baltimore/Washington (BWI), Philadelphia (PHL).

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Frequently asked questions about flying from Chicago Midway Airport to Maryland

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?
As of April 2026, there are 2 operators available to choose from 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?
Based on momondo bookings for flights between Chicago Midway Airport and Maryland, the leading plane model is Boeing 737 MAX 8, making up 15.18% of the total bookings. Other popular models include Boeing 737-800 Passenger/BBJ2 (winglets) with 12.13%, Boeing 737-900 with 9.84%, and Embraer 175 with 8.31%.

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
Frontier	PriceFrom $95	Free Cancellation	Rating 5.7 3,004 reviews		Search Frontier flights
Southwest	PriceFrom $159	Free Cancellation	Rating 8.0 4,337 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.