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

On average, it takes 2h 12m 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 7h 15m.

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 2026. The most frequent departure time is 4:00PM, with 59% of daily flights leaving in the afternoon.

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

As of September 2026, there are 120 flights per week flying from Maryland to Chicago Midway Airport. The most common day of the week flights depart is Wed, with 21% of flights taking off on this day.

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

Frontier, Southwest, and Delta 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 3 as of September 2026.

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.

$95 Cheap Flights from Maryland to Chicago Midway Airport in 2026

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Maryland to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

7:40 am - 11:47 pmIAD Washington, D.C. Dulles Intl-MDW Chicago Midway

17h 07m1 stop Atlanta Hartsfield-Jackson

7:25 am - 5:12 pmMDW Chicago Midway-IAD Washington, D.C. Dulles Intl

8h 47m1 stop Atlanta Hartsfield-Jackson

$178Frontier

Thu, Oct 29 - Sat, Oct 31

7:50 am - 5:46 pmIAD Washington, D.C. Dulles Intl-MDW Chicago Midway

10h 56m1 stop Atlanta Hartsfield-Jackson

6:25 am - 5:18 pmMDW Chicago Midway-IAD Washington, D.C. Dulles Intl

9h 53m1 stop Atlanta Hartsfield-Jackson

$180Frontier

Tue, Sep 29 - Wed, Sep 30

7:50 am - 5:51 pmIAD Washington, D.C. Dulles Intl-MDW Chicago Midway

11h 01m1 stop Atlanta Hartsfield-Jackson

6:25 am - 5:18 pmMDW Chicago Midway-IAD Washington, D.C. Dulles Intl

9h 53m1 stop Atlanta Hartsfield-Jackson

$181Frontier

Wed, Sep 30 - Fri, Oct 2

6:25 pm - 7:35 pmPHL Philadelphia-MDW Chicago Midway

2h 10mnonstop

12:10 pm - 3:05 pmMDW Chicago Midway-PHL Philadelphia

1h 55mnonstop

$237Southwest

Mon, Nov 2 - Sat, Nov 7

6:20 pm - 7:35 pmPHL Philadelphia-MDW Chicago Midway

2h 15mnonstop

3:50 pm - 6:45 pmMDW Chicago Midway-PHL Philadelphia

1h 55mnonstop

$237Southwest

Tue, Nov 10 - Thu, Nov 12

7:55 am - 9:00 amPHL Philadelphia-MDW Chicago Midway

2h 05mnonstop

6:55 pm - 9:55 pmMDW Chicago Midway-PHL Philadelphia

2h 00mnonstop

$237Southwest

Sat, Oct 17 - Mon, Oct 19

6:10 am - 9:32 amPHL Philadelphia-MDW Chicago Midway

4h 22m1 stop Detroit Metropolitan Wayne County

9:29 am - 4:44 pmMDW Chicago Midway-PHL Philadelphia

6h 15m1 stop Detroit Metropolitan Wayne County

$257Delta

Mon, Oct 12 - Sat, Oct 17

10:35 am - 4:17 pmPHL Philadelphia-MDW Chicago Midway

6h 42m1 stop Atlanta Hartsfield-Jackson

6:00 am - 2:57 pmMDW Chicago Midway-PHL Philadelphia

7h 57m1 stop Atlanta Hartsfield-Jackson

$257Delta

Tue, Dec 8 - Thu, Dec 31

6:00 am - 12:17 pmPHL Philadelphia-MDW Chicago Midway

7h 17m1 stop Dallas/Fort Worth

1:26 pm - 6:41 pmMDW Chicago Midway-PHL Philadelphia

4h 15m1 stop Knoxville McGhee Tyson

$320Multiple Airlines

Sun, Oct 11 - Mon, Oct 12

7:55 pm - 11:43 pmPHL Philadelphia-MDW Chicago Midway

28h 48m2 stops Tampa St. Petersburg Atlanta Hartsfield-Jackson

6:40 pm - 7:21 amMDW Chicago Midway-PHL Philadelphia

11h 41m1 stop Atlanta Hartsfield-Jackson

$322Multiple Airlines

Fri, Oct 16 - Sun, Oct 18

Cheap last minute flights

Enter your travel dates to find the best prices.

7:50 am - 5:46 pmIAD Washington, D.C. Dulles Intl-MDW Chicago Midway

10h 56m1 stop Atlanta Hartsfield-Jackson

6:25 am - 5:18 pmMDW Chicago Midway-IAD Washington, D.C. Dulles Intl

9h 53m1 stop Atlanta Hartsfield-Jackson

$260Frontier

Thu, Sep 17 - Wed, Sep 23

7:50 am - 5:51 pmIAD Washington, D.C. Dulles Intl-MDW Chicago Midway

11h 01m1 stop Atlanta Hartsfield-Jackson

6:25 am - 5:18 pmMDW Chicago Midway-IAD Washington, D.C. Dulles Intl

9h 53m1 stop Atlanta Hartsfield-Jackson

$260Frontier

Wed, Sep 16 - Tue, Sep 22

7:50 am - 5:51 pmIAD Washington, D.C. Dulles Intl-MDW Chicago Midway

11h 01m1 stop Atlanta Hartsfield-Jackson

6:25 am - 5:18 pmMDW Chicago Midway-IAD Washington, D.C. Dulles Intl

9h 53m1 stop Atlanta Hartsfield-Jackson

$260Frontier

Wed, Sep 16 - Wed, Sep 23

12:40 pm - 5:51 pmPHL Philadelphia-MDW Chicago Midway

6h 11m1 stop Atlanta Hartsfield-Jackson

6:25 am - 6:14 pmMDW Chicago Midway-PHL Philadelphia

10h 49m1 stop Atlanta Hartsfield-Jackson

$261Frontier

Wed, Sep 16 - Wed, Sep 23

1:45 pm - 2:50 pmPHL Philadelphia-MDW Chicago Midway

2h 05mnonstop

5:55 pm - 9:00 pmMDW Chicago Midway-PHL Philadelphia

2h 05mnonstop

$375Southwest

Tue, Sep 15 - Tue, Sep 15

3:40 pm - 4:45 pmPHL Philadelphia-MDW Chicago Midway

2h 05mnonstop

1:00 pm - 4:00 pmMDW Chicago Midway-PHL Philadelphia

2h 00mnonstop

$375Southwest

Sat, Sep 12 - Wed, Sep 16

1:45 pm - 2:50 pmPHL Philadelphia-MDW Chicago Midway

2h 05mnonstop

11:25 am - 2:20 pmMDW Chicago Midway-PHL Philadelphia

1h 55mnonstop

$375Southwest

Tue, Sep 15 - Tue, Sep 22

5:10 pm - 10:44 pmBWI Baltimore/Washington-MDW Chicago Midway

6h 34m1 stop Atlanta Hartsfield-Jackson

9:29 am - 4:55 pmMDW Chicago Midway-BWI Baltimore/Washington

6h 26m1 stop Detroit Metropolitan Wayne County

$460Delta

Sat, Sep 12 - Fri, Sep 18

6:35 pm - 10:44 pmBWI Baltimore/Washington-MDW Chicago Midway

5h 09m1 stop Atlanta Hartsfield-Jackson

1:00 pm - 7:23 pmMDW Chicago Midway-BWI Baltimore/Washington

5h 23m1 stop Atlanta Hartsfield-Jackson

$479Delta

Mon, Sep 14 - Tue, Sep 15

6:10 am - 9:07 amBWI Baltimore/Washington-MDW Chicago Midway

3h 57m1 stop Detroit Metropolitan Wayne County

6:40 pm - 11:01 pmMDW Chicago Midway-BWI Baltimore/Washington

3h 21m1 stop Detroit Metropolitan Wayne County

$480Delta

Sat, Sep 12 - Sun, Sep 13

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Southwest flights from Maryland to Chicago Midway Airport

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

Southwest

Oct 24

PHL10:15 amPhiladelphia

2h 10m

MDW11:25 amChicago Midway

Oct 27

MDW7:45 amChicago Midway

1h 55m

PHL10:40 amPhiladelphia

$237

Southwest

Oct 2

PHL7:10 pmPhiladelphia

2h 05m

MDW8:15 pmChicago Midway

Oct 5

MDW4:40 pmChicago Midway

1h 55m

PHL7:35 pmPhiladelphia

$246

Southwest

Oct 24

PHL10:15 amPhiladelphia

2h 10m

MDW11:25 amChicago Midway

Oct 27

MDW9:40 amChicago Midway

4h 45m

1 stop

PHL3:25 pmPhiladelphia

$247

Frontier flights from Maryland to Chicago Midway Airport

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

Frontier

Oct 29

IAD7:40 amWashington, D.C. Dulles Intl

17h 07m

1 stop

MDW11:47 pmChicago Midway

Oct 31

MDW7:25 amChicago Midway

8h 47m

1 stop

IAD5:12 pmWashington, D.C. Dulles Intl

$178

Frontier

Sep 29

IAD7:50 amWashington, D.C. Dulles Intl

10h 56m

1 stop

MDW5:46 pmChicago Midway

Sep 30

MDW6:25 amChicago Midway

9h 53m

1 stop

IAD5:18 pmWashington, D.C. Dulles Intl

$180

Frontier

Oct 3

IAD7:50 amWashington, D.C. Dulles Intl

11h 01m

1 stop

MDW5:51 pmChicago Midway

Oct 10

MDW6:21 amChicago Midway

9h 52m

1 stop

IAD5:13 pmWashington, D.C. Dulles Intl

$181

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

Cheapest round-trip

Washington, D.C.Chicago

IAD Washington, D.C. Dulles Intl - MDW Chicago Midway

IADMDW

Washington, D.C. Dulles Intl

Thu 10/29

7:40 am-11:47 pm

1 stop17h 07m

Chicago Midway

Sat 10/31

7:25 am-5:12 pm

1 stop8h 47m

$178

Washington, D.C.Chicago

IAD Washington, D.C. Dulles Intl - MDW Chicago Midway

IADMDW

Washington, D.C. Dulles Intl

Tue 9/29

7:50 am-5:46 pm

1 stop10h 56m

Chicago Midway

Wed 9/30

6:25 am-5:18 pm

1 stop9h 53m

$180

Washington, D.C.Chicago

IAD Washington, D.C. Dulles Intl - MDW Chicago Midway

IADMDW

Washington, D.C. Dulles Intl

Wed 9/30

7:50 am-5:51 pm

1 stop11h 01m

Chicago Midway

Fri 10/2

6:25 am-5:18 pm

1 stop9h 53m

$181

Quickest round-trip

PhiladelphiaChicago

PHL Philadelphia - MDW Chicago Midway

PHLMDW

Philadelphia

Mon 11/2

6:25 pm-7:35 pm

Nonstop2h 10m

Chicago Midway

Sat 11/7

12:10 pm-3:05 pm

Nonstop1h 55m

$237

PhiladelphiaChicago

PHL Philadelphia - MDW Chicago Midway

PHLMDW

Philadelphia

Tue 11/10

6:20 pm-7:35 pm

Nonstop2h 15m

Chicago Midway

Thu 11/12

3:50 pm-6:45 pm

Nonstop1h 55m

$237

PhiladelphiaChicago

PHL Philadelphia - MDW Chicago Midway

PHLMDW

Philadelphia

Sat 10/17

7:55 am-9:00 am

Nonstop2h 05m

Chicago Midway

Mon 10/19

6:55 pm-9:55 pm

Nonstop2h 00m

$237

PhiladelphiaChicago

PHL Philadelphia - MDW Chicago Midway

PHLMDW

Philadelphia

Mon 10/12

6:10 am-9:32 am

1 stop4h 22m

Chicago Midway

Sat 10/17

9:29 am-4:44 pm

1 stop6h 15m

$257

PhiladelphiaChicago

PHL Philadelphia - MDW Chicago Midway

PHLMDW

Philadelphia

Tue 12/8

10:35 am-4:17 pm

1 stop6h 42m

Chicago Midway

Thu 12/31

6:00 am-2:57 pm

1 stop7h 57m

$257

PhiladelphiaChicago

PHL Philadelphia - MDW Chicago Midway

PHLMDW

Philadelphia

Sun 10/11

6:00 am-12:17 pm

1 stop7h 17m

Chicago Midway

Mon 10/12

1:26 pm-6:41 pm

1 stop4h 15m

$320

PhiladelphiaChicago

PHL Philadelphia - MDW Chicago Midway

PHLMDW

Philadelphia

Fri 10/16

7:55 pm-11:43 pm

2 stops28h 48m

Chicago Midway

Sun 10/18

6:40 pm-7:21 am

1 stop11h 41m

$322

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 November is, on average, the cheapest month to fly to Chicago Midway Airport from Maryland, with most prices found around $188. If you are unable to visit Chicago Midway Airport during the month of November, then departing from Maryland during the month October is also very affordable. Most momondo users find prices during this month for around $221.

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 $340. 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 $428.

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 $319 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $390. 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 Airport flights?

There are 2 cabin classes available to choose from on Maryland to Chicago Midway Airport 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 Maryland to Chicago Midway Airport flights?

No. A direct flight is the cheapest option for a flight between Maryland 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	$95
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 $95. The best round-trip flight deal from Maryland to Chicago Midway Airport found on momondo in the last 72 hours is $178.

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?
The number of operators available for flights from Maryland to Chicago Midway Airport is 3 as of September 2026.
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 (20.47% of total bookings). The next most popular plane models are Boeing 737-800 Passenger/BBJ2 (winglets) (11.71%), Boeing 737-900 (10.63%), and Boeing 737-800 (8.72%).

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 $108	Free Cancellation	Rating 5.6 2,608 reviews		Search Frontier flights
Southwest	PriceFrom $179	Free Cancellation	Rating 8.0 4,194 reviews		Search Southwest flights

Merrillville

New Buffalo

Hammond

Portage

Benton Harbor

Lansing

Saint Joseph

Valparaiso

Schererville

Munster

Chesterton

Monticello

Porter

Crown Point

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 $95

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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Southwest flights from Maryland to Chicago Midway Airport

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

Frontier flights from Maryland to Chicago Midway Airport

Our best Frontier 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.

See travel insights to Chicago from

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

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?

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

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

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

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

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

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

Cheap Maryland to Chicago Midway Airport flight deals and tips

Best Price Found

Fastest flight time

Direct flights

Frequently asked questions about flying 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?

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

Maryland flight routes

According to popular flight searches on momondo this year

Chicago Midway Airport flight routes

According to popular flight searches on momondo this year

Fly your favorite airline to Chicago

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List of cabin classes available on flights landing in Chicago. Availability may vary depending on flight origin and airline.

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