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Cheap flights from Maryland to Chicago Midway Airport from $38

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 Midway Airport departing on 12/12. 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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Find the cheapest flights from Maryland to Chicago

Cheap round-trip flights

These are some of the best round-trip flight deals from Maryland to Chicago that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Maryland to Chicago.

Cheap last minute flights

Planning a quick getaway from Maryland to Chicago? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Chicago, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Maryland to Chicago

Find recent round-trip train or bus tickets from Maryland to Chicago.

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
12:14 pm - 1:40 pmPHL-MDW
2h 26mnonstop
7:45 am - 10:48 amMDW-PHL
2h 03mnonstop
$50Frontier
Find Deal
Mon, Dec 16 - Tue, Dec 17
2:21 pm - 3:33 pmBWI-MDW
2h 12mnonstop
1:16 pm - 4:11 pmMDW-BWI
1h 55mnonstop
$59Frontier
Find Deal
Sat, Mar 1 - Wed, Mar 5
10:57 pm - 12:20 amPHL-MDW
2h 23mnonstop
8:15 am - 11:18 amMDW-PHL
2h 03mnonstop
$62Frontier
Find Deal
Fri, Dec 13 - Mon, Dec 16
12:14 pm - 1:40 pmPHL-MDW
2h 26mnonstop
8:15 am - 11:18 amMDW-PHL
2h 03mnonstop
$63Frontier
Find Deal
Mon, Dec 9 - Mon, Dec 16
10:35 am - 11:45 amBWI-MDW
2h 10mnonstop
8:35 am - 11:20 amMDW-BWI
1h 45mnonstop
$140Southwest
Find Deal
Tue, Jan 28 - Sat, Feb 1
7:35 am - 8:45 amPHL-MDW
2h 10mnonstop
8:30 am - 11:25 amMDW-PHL
1h 55mnonstop
$157Southwest
Find Deal
Wed, Dec 11 - Tue, Dec 17
3:55 pm - 10:20 pmPHL-MDW
7h 25m1 stop
10:57 am - 7:45 pmMDW-PHL
7h 48m1 stop
$196Delta
Find Deal
Tue, Jan 21 - Thu, Feb 6
12:26 pm - 6:14 pmBWI-MDW
6h 48m1 stop
10:57 am - 6:12 pmMDW-BWI
6h 15m1 stop
$196Delta
Find Deal
Wed, Jan 8 - Tue, Jan 14
5:40 pm - 5:46 pmIAD-MDW
25h 06m3 stops
11:15 am - 10:24 pmMDW-IAD
10h 09m1 stop
Mon, Mar 31 - Fri, Apr 4
7:00 am - 4:40 pmIAD-MDW
10h 40m1 stop
11:15 am - 10:24 pmMDW-IAD
10h 09m1 stop
$745Porter Airlines
Find Deal
Fri, Dec 6 - Sun, Dec 8
4:50 pm - 6:12 pmPHL-MDW
2h 22mnonstop
$38Frontier
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Thu, Dec 12
4:18 pm - 5:22 pmBWI-MDW
2h 04mnonstop
$39Frontier
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Mon, Dec 16
8:10 pm - 9:25 pmBWI-MDW
2h 15mnonstop
$70Southwest
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Tue, Jan 7
5:25 pm - 6:35 pmPHL-MDW
2h 10mnonstop
$91Southwest
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Sat, Dec 14
6:00 am - 8:54 amPHL-MDW
3h 54m1 stop
$98Delta
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Tue, Feb 18
12:26 pm - 6:14 pmBWI-MDW
6h 48m1 stop
$98Delta
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Wed, Jan 8
5:40 pm - 5:35 pmIAD-MDW
24h 55m3 stops
Mon, Mar 3
12:40 pm - 3:03 pmIAD-MDW
27h 23m3 stops
Mon, Dec 23
7:00 am - 4:40 pmIAD-MDW
10h 40m1 stop
$295Porter Airlines
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Fri, Dec 20
7:00 am - 4:40 pmIAD-MDW
10h 40m1 stop
$307Porter Airlines
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Sun, Apr 6
8:00 am - 9:23 amPHL-MDW
2h 23mnonstop
12:36 pm - 3:42 pmMDW-PHL
2h 06mnonstop
$261Frontier
Find Deal
Thu, Nov 28 - Sun, Dec 15
4:42 pm - 11:15 pmPHL-MDW
7h 33m1 stop
12:36 pm - 3:42 pmMDW-PHL
2h 06mnonstop
$263Frontier
Find Deal
Thu, Nov 28 - Sun, Dec 15
4:09 pm - 11:15 pmBWI-MDW
8h 06m1 stop
12:15 pm - 3:07 pmMDW-BWI
1h 52mnonstop
$338Frontier
Find Deal
Thu, Nov 28 - Mon, Dec 2
4:00 pm - 5:01 pmBWI-MDW
2h 01mnonstop
12:15 pm - 3:07 pmMDW-BWI
1h 52mnonstop
$347Frontier
Find Deal
Wed, Nov 27 - Mon, Dec 2
7:30 pm - 8:35 pmBWI-MDW
2h 05mnonstop
5:55 pm - 8:45 pmMDW-BWI
1h 50mnonstop
$514Southwest
Find Deal
Sat, Nov 30 - Sat, Dec 7
9:15 am - 2:00 pmBWI-MDW
5h 45m2 stops
5:55 pm - 8:45 pmMDW-BWI
1h 50mnonstop
$528Southwest
Find Deal
Sat, Nov 30 - Sat, Dec 7
6:00 am - 8:50 amBWI-MDW
3h 50m1 stop
5:50 pm - 10:29 pmMDW-BWI
3h 39m1 stop
$547Delta
Find Deal
Sat, Nov 30 - Sat, Dec 7
6:00 am - 8:50 amIAD-MDW
3h 50m1 stop
6:00 am - 11:49 amMDW-IAD
4h 49m1 stop
$598Delta
Find Deal
Fri, Nov 29 - Thu, Dec 5
11:21 am - 11:46 amBWI-MDW
25h 25m2 stops
8:15 pm - 9:55 pmMDW-BWI
24h 40m2 stops
Sat, Nov 30 - Sun, Dec 1
5:20 am - 11:46 amBWI-MDW
31h 26m3 stops
8:15 pm - 9:55 pmMDW-BWI
24h 40m2 stops
Sat, Nov 30 - Sun, Dec 1
12:14 pm - 1:40 pmPHL-MDW
2h 26mnonstop
7:45 am - 10:48 amMDW-PHL
2h 03mnonstop
$49Frontier
Find Deal
Mon, Dec 16 - Tue, Dec 17
2:21 pm - 3:33 pmBWI-MDW
2h 12mnonstop
1:16 pm - 4:11 pmMDW-BWI
1h 55mnonstop
$59Frontier
Find Deal
Sat, Mar 1 - Wed, Mar 5
10:57 pm - 12:20 amPHL-MDW
2h 23mnonstop
8:15 am - 11:18 amMDW-PHL
2h 03mnonstop
$62Frontier
Find Deal
Fri, Dec 13 - Mon, Dec 16
12:14 pm - 1:40 pmPHL-MDW
2h 26mnonstop
8:15 am - 11:18 amMDW-PHL
2h 03mnonstop
$63Frontier
Find Deal
Mon, Dec 9 - Mon, Dec 16
4:50 pm - 6:12 pmPHL-MDW
2h 22mnonstop
8:15 am - 11:18 amMDW-PHL
2h 03mnonstop
$65Frontier
Find Deal
Thu, Dec 12 - Mon, Dec 16
12:14 pm - 1:40 pmPHL-MDW
2h 26mnonstop
7:45 am - 10:48 amMDW-PHL
2h 03mnonstop
$67Frontier
Find Deal
Mon, Dec 16 - Tue, Dec 17
11:43 am - 1:09 pmPHL-MDW
2h 26mnonstop
7:34 am - 10:37 amMDW-PHL
2h 03mnonstop
$73Frontier
Find Deal
Tue, Dec 17 - Thu, Dec 19
10:57 pm - 12:20 amPHL-MDW
2h 23mnonstop
8:15 am - 11:18 amMDW-PHL
2h 03mnonstop
$76Frontier
Find Deal
Fri, Dec 13 - Mon, Dec 16
8:15 am - 9:30 amBWI-MDW
2h 15mnonstop
6:25 pm - 9:15 pmMDW-BWI
1h 50mnonstop
$140Southwest
Find Deal
Sat, Jan 25 - Sat, Feb 1
7:35 am - 8:45 amPHL-MDW
2h 10mnonstop
8:30 am - 11:25 amMDW-PHL
1h 55mnonstop
$157Southwest
Find Deal
Wed, Dec 11 - Tue, Dec 17

Frontier flights from Maryland to Chicago Midway Airport

Our best Frontier deals on Maryland to Chicago Midway Airport flight tickets
Frontier
Dec 16
PHL12:14 pmPhiladelphia
2h 26m
MDW1:40 pmChicago Midway
Dec 17
MDW7:45 amChicago Midway
2h 03m
PHL10:48 amPhiladelphia
Frontier
Mar 1
BWI2:21 pmBaltimore/Washington
2h 12m
MDW3:33 pmChicago Midway
Mar 5
MDW1:16 pmChicago Midway
1h 55m
BWI4:11 pmBaltimore/Washington
Frontier
Dec 13
PHL10:57 pmPhiladelphia
2h 23m
MDW12:20 amChicago Midway
Dec 16
MDW8:15 amChicago Midway
2h 03m
PHL11:18 amPhiladelphia

Delta flights from Maryland to Chicago Midway Airport

Our best Delta deals on Maryland to Chicago Midway Airport flight tickets
Delta
Jan 21
PHL3:55 pmPhiladelphia
7h 25m
1 stop
MDW10:20 pmChicago Midway
Feb 6
MDW10:57 amChicago Midway
7h 48m
1 stop
PHL7:45 pmPhiladelphia
Delta
Jan 7
BWI6:00 amBaltimore/Washington
3h 54m
1 stop
MDW8:54 amChicago Midway
Jan 10
MDW6:28 pmChicago Midway
3h 51m
1 stop
BWI11:19 pmBaltimore/Washington
Delta
Dec 10
BWI8:00 amBaltimore/Washington
4h 58m
1 stop
MDW11:58 amChicago Midway
Jan 11
MDW5:05 pmChicago Midway
5h 14m
1 stop
BWI11:19 pmBaltimore/Washington

See travel insights to Chicago from

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?

The month of April is, on average, the cheapest month to fly to Chicago Midway Airport from Maryland, with most prices found around $69. If you are unable to visit Chicago Midway Airport during the month of April, then departing from Maryland during the month January is also very affordable. Most momondo users find prices during this month for around $124.

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 $229. 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, Tuesday 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 $315.

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 afternoon is the least expensive time of day to depart. momondo users have found prices as low as $192 when looking at flights departing in the afternoon. Try not to purchase tickets at noon because they tend to be around $318. 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

How far in advance should I book a flight to Chicago Midway Airport?

We recommend purchasing flights from Maryland to Chicago Midway Airport 58 days ahead of your departure date because this is when momondo users tend to see the best flight rates. On average, our users have found flights to Chicago Midway Airport for $235. In the past 72 hours, momondo users found flights from Maryland to Chicago Midway Airport for as low as $76.

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

There are 1 cabin classes 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.

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

You could potentially save up to 120% on your flight if you consider stops on a Maryland to Chicago Midway Airport flight.

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

$38

Fastest flight time

1h 59m

Direct flights

Mon, Tue, Thu, Fri and Sat
The best one-way flight to Chicago Midway Airport from Maryland in the past 72 hours is $38. The best round-trip flight deal from Maryland to Chicago Midway Airport found on momondo in the last 72 hours is $50.
The fastest flight from Maryland to Chicago Midway Airport takes 1h 59m
Direct flights go from Maryland to Chicago Midway Airport on Monday, Tuesday, Thursday, Friday and Saturday. Airlines offering direct flights are: Southwest and Frontier.

  • 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?

  • 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?


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
FrontierPriceFrom $58Free CancellationRating
6.1
3,524 reviews
Search Frontier flights
SouthwestPriceFrom $160Free CancellationRating
8.1
4,982 reviews
Search Southwest flights
DeltaPriceFrom $176Free CancellationRating
8.0
8,736 reviews
Search Delta flights

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.


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