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

43 flights are operational weekly from Chicago Midway Airport to Maryland as of June 2026. The most popular departure day for this route is Mon, with 53% of flights per week taking off on this day.

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

Delta and Southwest are the most popular carriers operating from Chicago Midway 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 June 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.

$90 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 June 2026, there are 6 flights per day flying from Chicago Midway Airport to Maryland. The most common time of day flights depart is 12:00PM, with 63% of flights taking off in the afternoon.

1 adult

0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

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.

9:30 am - 12:25 pm

MDW

PHL

1h 55mnonstop

10:45 am - 11:55 am

PHL

MDW

2h 10mnonstop

$213Southwest

Mon, Aug 17 - Tue, Aug 25

2:55 pm - 5:55 pm

MDW

PHL

2h 00mnonstop

6:40 pm - 10:20 pm

PHL

MDW

4h 40m

1 stop

$223Southwest

Mon, Aug 17 - Tue, Aug 25

8:05 am - 1:30 pm

MDW

PHL

4h 25m

1 stop

7:15 am - 3:50 pm

PHL

MDW

9h 35m

2 stops

$226Southwest

Sat, Sep 19 - Wed, Sep 23

12:35 pm - 4:40 pm

MDW

BWI

3h 05m

1 stop

8:00 pm - 9:00 pm

BWI

MDW

2h 00mnonstop

$227Southwest

Wed, Aug 12 - Mon, Aug 17

2:55 pm - 5:55 pm

MDW

PHL

2h 00mnonstop

6:00 am - 4:00 pm

PHL

MDW

11h 00m

2 stops

$228Southwest

Mon, Aug 17 - Tue, Aug 25

6:05 am - 1:05 pm

MDW

BWI

6h 00m

1 stop

6:15 am - 9:17 am

BWI

MDW

4h 02m

1 stop

$231Delta

Wed, Aug 12 - Mon, Aug 17

6:42 pm - 10:59 pm

MDW

DCA

3h 17m

1 stop

6:10 am - 9:17 am

DCA

MDW

4h 07m

1 stop

$238Delta

Sat, Aug 8 - Sat, Aug 15

2:48 pm - 2:26 pm

MDW

IAD

22h 38m

1 stop

8:33 pm - 10:03 pm

IAD

MDW

26h 30m

1 stop

$239Multiple Airlines

Thu, Jul 16 - Tue, Jul 21

6:00 am - 4:00 pm

MDW

IAD

9h 00m

1 stop

11:24 am - 10:11 pm

IAD

MDW

11h 47m

1 stop

$244Frontier

Sat, Jun 27 - Tue, Jun 30

6:00 am - 4:52 pm

MDW

IAD

9h 52m

1 stop

11:24 am - 10:11 pm

IAD

MDW

11h 47m

1 stop

$249Frontier

Thu, Jun 25 - Tue, Jun 30

Delta flights from Chicago Midway Airport to Maryland

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

Delta

Aug 12

MDW6:05 amChicago Midway

6h 00m

1 stop

BWI1:05 pmBaltimore/Washington

Aug 17

BWI6:15 amBaltimore/Washington

4h 02m

1 stop

MDW9:17 amChicago Midway

$231

Delta

Aug 8

MDW6:42 pmChicago Midway

3h 44m

1 stop

IAD11:26 pmWashington, D.C. Dulles Intl

Aug 15

IAD6:10 amWashington, D.C. Dulles Intl

4h 07m

1 stop

MDW9:17 amChicago Midway

$238

Delta

Aug 11

MDW6:42 pmChicago Midway

3h 44m

1 stop

IAD11:26 pmWashington, D.C. Dulles Intl

Aug 13

IAD12:30 pmWashington, D.C. Dulles Intl

4h 45m

1 stop

MDW4:15 pmChicago Midway

$241

Frontier flights from Chicago Midway Airport to Maryland

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

Frontier

Jun 27

MDW6:00 amChicago Midway

9h 00m

1 stop

IAD4:00 pmWashington, D.C. Dulles Intl

Jun 30

IAD11:24 amWashington, D.C. Dulles Intl

11h 47m

1 stop

MDW10:11 pmChicago Midway

$244

Frontier

Jun 25

MDW6:00 amChicago Midway

9h 52m

1 stop

IAD4:52 pmWashington, D.C. Dulles Intl

Jun 30

IAD11:24 amWashington, D.C. Dulles Intl

11h 47m

1 stop

MDW10:11 pmChicago Midway

$249

Frontier

Jun 26

MDW6:00 amChicago Midway

10h 31m

1 stop

IAD5:31 pmWashington, D.C. Dulles Intl

Jul 1

IAD11:17 amWashington, D.C. Dulles Intl

11h 54m

1 stop

MDW10:11 pmChicago Midway

$250

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

Quickest round-trip

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Mon 8/17

9:30 am-12:25 pm

Nonstop1h 55m

Philadelphia

Tue 8/25

10:45 am-11:55 am

Nonstop2h 10m

$213

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Mon 8/17

2:55 pm-5:55 pm

Nonstop2h 00m

Philadelphia

Tue 8/25

6:40 pm-10:20 pm

1 stop4h 40m

$223

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Sat 9/19

8:05 am-1:30 pm

1 stop4h 25m

Philadelphia

Wed 9/23

7:15 am-3:50 pm

2 stops9h 35m

$226

ChicagoBaltimore

MDW - BWI

MDWBWI

Chicago Midway

Wed 8/12

12:35 pm-4:40 pm

1 stop3h 05m

Baltimore/Washington

Mon 8/17

8:00 pm-9:00 pm

Nonstop2h 00m

$227

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Mon 8/17

2:55 pm-5:55 pm

Nonstop2h 00m

Philadelphia

Tue 8/25

6:00 am-4:00 pm

2 stops11h 00m

$228

ChicagoBaltimore

MDW - BWI

MDWBWI

Chicago Midway

Wed 8/12

6:05 am-1:05 pm

1 stop6h 00m

Baltimore/Washington

Mon 8/17

6:15 am-9:17 am

1 stop4h 02m

$231

ChicagoWashington, D.C.

MDW - DCA

MDWDCA

Chicago Midway

Sat 8/8

6:42 pm-10:59 pm

1 stop3h 17m

Washington, D.C. Reagan-National

Sat 8/15

6:10 am-9:17 am

1 stop4h 07m

$238

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Thu 7/16

2:48 pm-2:26 pm

1 stop22h 38m

Washington, D.C. Dulles Intl

Tue 7/21

8:33 pm-10:03 pm

1 stop26h 30m

$239

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Sat 6/27

6:00 am-4:00 pm

1 stop9h 00m

Washington, D.C. Dulles Intl

Tue 6/30

11:24 am-10:11 pm

1 stop11h 47m

$244

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Thu 6/25

6:00 am-4:52 pm

1 stop9h 52m

Washington, D.C. Dulles Intl

Tue 6/30

11:24 am-10:11 pm

1 stop11h 47m

$249

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 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 $59, 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 $73.

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 $278. The most expensive day to fly to Maryland is Monday, with ticket prices averaging around $422.

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 at noon. Flights from Chicago Midway Airport to Maryland during this time can be as low as $308. In contrast, the most expensive time of day to depart to Maryland is in the evening when prices are around $329.

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 Airport to Maryland flights?

There is only 1 cabin class available to choose from on Chicago Midway Airport 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 12% 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	$158
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 $158. The best round-trip flight deal from Chicago Midway Airport to Maryland found on momondo in the last 72 hours is $306.

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).

Search flight deals

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 June 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 16.69% of the total bookings. Other popular models include Boeing 737-800 Passenger/BBJ2 (winglets) with 11.96%, Boeing 737-800 with 10.35%, and Boeing 737-900 with 10.35%.

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 $90	Free Cancellation	Rating 5.6 2,923 reviews		Search Frontier flights
Southwest	PriceFrom $167	Free Cancellation	Rating 8.0 4,256 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.