How long does it take to fly to Chicago Midway Airport?

On average, it takes 2h 09m to fly from Maryland to Chicago Midway Airport if you fly out of Baltimore (the most popular airport in Maryland) and into Chicago O'Hare Intl Airport (the most popular airport in Chicago Midway Airport). If you’re flying out of Salisbury and into Chicago O'Hare Intl Airport, then the flight time is around 4h 35m.

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

As of September 2025, there are 123 flights per week flying from Maryland to Chicago Midway Airport. The most common day of the week flights depart is Mon, with 21% of flights taking off on this day.

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

The number of flights available between Maryland and Chicago Midway Airport is 17 per day as of September 2025. The most frequent departure time is 10:00AM, with 45% of daily flights leaving in the afternoon.

What airlines fly to Chicago Midway Airport?

Southwest, Frontier and Delta are the top three most popular airlines that fly to Chicago Midway Airport from Maryland according to our data. Southwest is the first choice among our users, with 53% of people opting to fly with this airline when traveling to Chicago Midway Airport. Keep in mind that there are 3 different airlines that fly to Chicago Midway Airport on a routine basis, so you have a few additional options to choose from.

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

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

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?

The number of operators available for flights from Maryland to Chicago Midway Airport is 4 as of September 2025.

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.

$59 Cheap Flights from Maryland to Chicago Midway Airport in 2025/26

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Find the cheapest flights from Maryland to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

7:54 pm - 9:00 pmBWI-MDW

2h 06mnonstop

3:40 pm - 6:35 pmMDW-BWI

1h 55mnonstop

$106Frontier

Find Deal

Fri, Oct 24 - Fri, Oct 31

7:25 pm - 8:31 pmBWI-MDW

2h 06mnonstop

9:32 am - 8:16 pmMDW-BWI

9h 44m1 stop

$107Frontier

Find Deal

Thu, Oct 30 - Fri, Oct 31

7:54 pm - 9:00 pmBWI-MDW

2h 06mnonstop

12:30 pm - 3:27 pmMDW-BWI

1h 57mnonstop

$108Frontier

Find Deal

Mon, Oct 20 - Thu, Oct 23

7:30 pm - 8:36 pmBWI-MDW

2h 06mnonstop

3:40 pm - 6:35 pmMDW-BWI

1h 55mnonstop

$109Frontier

Find Deal

Fri, Nov 7 - Fri, Nov 14

5:40 pm - 6:43 pmBWI-MDW

2h 03mnonstop

1:49 pm - 4:50 pmMDW-BWI

2h 01mnonstop

$110Frontier

Find Deal

Sun, Oct 5 - Mon, Oct 6

7:30 pm - 8:36 pmBWI-MDW

2h 06mnonstop

5:40 am - 8:36 amMDW-BWI

1h 56mnonstop

$111Frontier

Find Deal

Fri, Nov 7 - Sun, Nov 9

6:05 pm - 7:10 pmPHL-MDW

2h 05mnonstop

12:50 pm - 3:40 pmMDW-PHL

1h 50mnonstop

$139Southwest

Find Deal

Tue, Oct 28 - Sat, Nov 1

3:00 pm - 6:46 pmIAD-MDW

4h 46m1 stop

8:00 am - 10:19 pmMDW-IAD

13h 19m1 stop

$188Multiple Airlines

Find Deal

Mon, Nov 24 - Wed, Dec 3

6:00 am - 7:00 amDCA-MDW

2h 00mnonstop

12:25 pm - 3:15 pmMDW-DCA

1h 50mnonstop

$257Southwest

Find Deal

Sat, Oct 18 - Sat, Oct 18

6:10 am - 10:30 amDCA-MDW

5h 20m1 stop

6:23 pm - 10:59 pmMDW-DCA

3h 36m1 stop

$277Delta

Find Deal

Sat, Oct 18 - Sat, Oct 18

Frontier flights from Maryland to Chicago Midway Airport

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

Frontier

Oct 24

BWI7:54 pmBaltimore/Washington

2h 06m

MDW9:00 pmChicago Midway

Oct 31

MDW3:40 pmChicago Midway

1h 55m

BWI6:35 pmBaltimore/Washington

$106

Find similar

Frontier

Oct 30

BWI7:25 pmBaltimore/Washington

2h 06m

MDW8:31 pmChicago Midway

Oct 31

MDW9:32 amChicago Midway

9h 44m

1 stop

BWI8:16 pmBaltimore/Washington

$107

Find similar

Frontier

Oct 20

BWI7:54 pmBaltimore/Washington

2h 06m

MDW9:00 pmChicago Midway

Oct 23

MDW12:30 pmChicago Midway

1h 57m

BWI3:27 pmBaltimore/Washington

$108

Find similar

Southwest flights from Maryland to Chicago Midway Airport

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

Southwest

Oct 28

PHL6:05 pmPhiladelphia

2h 05m

MDW7:10 pmChicago Midway

Nov 1

MDW12:50 pmChicago Midway

1h 50m

PHL3:40 pmPhiladelphia

$139

Find similar

Southwest

Oct 18

DCA6:00 amWashington, D.C. Reagan-National

2h 00m

MDW7:00 amChicago Midway

Oct 18

MDW12:25 pmChicago Midway

1h 50m

DCA3:15 pmWashington, D.C. Reagan-National

$257

Find similar

Southwest

Oct 20

DCA3:10 pmWashington, D.C. Reagan-National

2h 00m

MDW4:10 pmChicago Midway

Oct 22

MDW12:20 pmChicago Midway

1h 50m

DCA3:10 pmWashington, D.C. Reagan-National

$261

Find similar

momondo Fare Finder

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

Fri 10/24

7:54 pm-9:00 pm

Nonstop2h 06m

Chicago Midway

Fri 10/31

3:40 pm-6:35 pm

Nonstop1h 55m

$106

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Thu 10/30

7:25 pm-8:31 pm

Nonstop2h 06m

Chicago Midway

Fri 10/31

9:32 am-8:16 pm

1 stop9h 44m

$107

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Mon 10/20

7:54 pm-9:00 pm

Nonstop2h 06m

Chicago Midway

Thu 10/23

12:30 pm-3:27 pm

Nonstop1h 57m

$108

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Fri 11/7

7:30 pm-8:36 pm

Nonstop2h 06m

Chicago Midway

Fri 11/14

3:40 pm-6:35 pm

Nonstop1h 55m

$109

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Sun 10/5

5:40 pm-6:43 pm

Nonstop2h 03m

Chicago Midway

Mon 10/6

1:49 pm-4:50 pm

Nonstop2h 01m

$110

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Fri 11/7

7:30 pm-8:36 pm

Nonstop2h 06m

Chicago Midway

Sun 11/9

5:40 am-8:36 am

Nonstop1h 56m

$111

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Tue 10/28

6:05 pm-7:10 pm

Nonstop2h 05m

Chicago Midway

Sat 11/1

12:50 pm-3:40 pm

Nonstop1h 50m

$139

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Mon 11/24

3:00 pm-6:46 pm

1 stop4h 46m

Chicago Midway

Wed 12/3

8:00 am-10:19 pm

1 stop13h 19m

$188

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Sat 10/18

6:00 am-7:00 am

Nonstop2h 00m

Chicago Midway

Sat 10/18

12:25 pm-3:15 pm

Nonstop1h 50m

$257

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Sat 10/18

6:10 am-10:30 am

1 stop5h 20m

Chicago Midway

Sat 10/18

6:23 pm-10:59 pm

1 stop3h 36m

$277

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 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

Prices

Airlines

Other information

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

The month of February is, on average, the cheapest month to fly to Chicago Midway Airport from Maryland, with most prices found around $184. If you are unable to visit Chicago Midway Airport during the month of February, then departing from Maryland during the month August is also very affordable. Most momondo users find prices during this month for around $202.

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 $313. 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, Monday 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 $382.

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 $311 when looking at flights departing in the evening. Try not to purchase tickets in the morning because they tend to be around $353. 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	$73
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 $73. The best round-trip flight deal from Maryland to Chicago Midway Airport found on momondo in the last 72 hours is $139.

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?
The number of operators available for flights from Maryland to Chicago Midway Airport is 4 as of September 2025.
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?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Maryland to Chicago Midway Airport is Boeing 737 MAX 8 (13.46% of total bookings). The next most popular plane models are Airbus A320neo (12.74%), Boeing 737-800 Passenger/BBJ2 (winglets) (11.90%), and Boeing 737-900 (9.19%).

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
Frontier	PriceFrom $67	Free Cancellation	Rating 5.8 3,163 reviews	Search Frontier flights
Delta	PriceFrom $98	Free Cancellation	Rating 7.9 7,973 reviews	Search Delta flights
Southwest	PriceFrom $162	Free Cancellation	Rating 8.0 4,244 reviews	Search Southwest flights

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Hammond

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Saint Joseph

Portage

Lansing

Schererville

Valparaiso

Crown Point

Munster

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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Cheap flights from Maryland to Chicago from $59

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 10/20. 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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Filter for what you want

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Find the cheapest flights from Maryland to Chicago

Cheap round-trip flights

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Frontier flights from Maryland to Chicago Midway Airport

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

Southwest flights from Maryland to Chicago Midway Airport

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

momondo Fare Finder

Use the filters below to find and compare flights from Maryland to Chicago Midway Airport that are best for you.

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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?

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

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

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.

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

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

What airlines fly to Chicago Midway Airport?

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

The number of flights available between Maryland and Chicago Midway Airport is 17 per day as of September 2025. The most frequent departure time is 10:00AM, with 45% of daily flights leaving in the afternoon.

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

As of September 2025, there are 123 flights per week flying from Maryland to Chicago Midway Airport. The most common day of the week flights depart is Mon, with 21% of flights taking off on this day.

How long does it take to fly to Chicago Midway Airport?

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

Fastest flight time

Direct flights

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

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?

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

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

Traveling to a place near Chicago?

Why use momondo?

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

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

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

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

An easier way to manage your Chicago Midway Airport trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to Chicago

Popular cities in the United States

Popular flights according to clicks in the last 7 days on momondo