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Cheap flights from Maryland to Chicago Midway Airport from $30

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 3/19. 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.
5:11 pm - 6:23 pmBWI-MDW
2h 12mnonstop
1:16 pm - 4:11 pmMDW-BWI
1h 55mnonstop
$57Frontier
Find Deal
Wed, Feb 12 - Wed, Feb 19
5:11 pm - 6:23 pmBWI-MDW
2h 12mnonstop
1:16 pm - 4:11 pmMDW-BWI
1h 55mnonstop
$58Frontier
Find Deal
Wed, Feb 12 - Wed, Feb 19
5:11 pm - 6:23 pmBWI-MDW
2h 12mnonstop
10:26 am - 1:21 pmMDW-BWI
1h 55mnonstop
$59Frontier
Find Deal
Wed, Feb 12 - Sat, Feb 22
7:53 pm - 9:05 pmBWI-MDW
2h 12mnonstop
1:16 pm - 4:11 pmMDW-BWI
1h 55mnonstop
$69Frontier
Find Deal
Mon, Feb 10 - Wed, Feb 12
8:10 pm - 9:25 pmBWI-MDW
2h 15mnonstop
5:05 pm - 7:50 pmMDW-BWI
1h 45mnonstop
$148Southwest
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Wed, Feb 5 - Wed, Feb 19
6:35 am - 7:55 amBWI-MDW
2h 20mnonstop
2:20 pm - 5:05 pmMDW-BWI
1h 45mnonstop
$158Southwest
Find Deal
Sat, Mar 1 - Mon, Mar 3
6:00 am - 10:12 amBWI-MDW
5h 12m1 stop
9:33 am - 4:43 pmMDW-BWI
6h 10m1 stop
$197Delta
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Wed, Feb 5 - Wed, Feb 12
6:07 pm - 10:20 pmPHL-MDW
5h 13m1 stop
10:19 am - 5:51 pmMDW-PHL
6h 32m1 stop
$201Delta
Find Deal
Tue, Feb 18 - Wed, Feb 19
7:32 pm - 10:19 pmBWI-MDW
27h 47m2 stops
3:37 pm - 5:35 pmMDW-BWI
24h 58m1 stop
Wed, Jan 29 - Fri, Jan 31
7:32 pm - 6:26 pmBWI-MDW
23h 54m1 stop
1:04 pm - 3:59 pmMDW-BWI
1h 55mnonstop
Wed, Jan 29 - Fri, Jan 31
4:11 pm - 5:23 pmBWI-MDW
2h 12mnonstop
$30Frontier
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Wed, Mar 19
6:31 pm - 7:51 pmPHL-MDW
2h 20mnonstop
$32Frontier
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Tue, Apr 8
6:31 pm - 7:51 pmPHL-MDW
2h 20mnonstop
$34Frontier
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Tue, Apr 8
5:11 pm - 6:23 pmBWI-MDW
2h 12mnonstop
$34Frontier
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Wed, Feb 26
6:05 pm - 7:15 pmBWI-MDW
2h 10mnonstop
$69Southwest
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Tue, Feb 18
7:40 pm - 8:50 pmBWI-MDW
2h 10mnonstop
$70Southwest
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Tue, Mar 18
9:33 am - 1:05 pmPHL-MDW
4h 32m1 stop
$101Delta
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Tue, Feb 4
6:00 am - 8:51 amBWI-MDW
3h 51m1 stop
$104Delta
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Fri, Feb 14
5:40 pm - 5:35 pmIAD-MDW
24h 55m3 stops
Mon, Mar 3
5:40 pm - 5:46 pmIAD-MDW
25h 06m3 stops
Mon, Mar 10
6:35 pm - 11:29 pmBWI-MDW
5h 54m1 stop
7:30 am - 7:41 pmMDW-BWI
11h 11m1 stop
$278Frontier
Find Deal
Sat, Jan 18 - Sat, Jan 25
6:35 pm - 11:29 pmBWI-MDW
5h 54m1 stop
7:30 am - 7:41 pmMDW-BWI
11h 11m1 stop
$279Frontier
Find Deal
Sat, Jan 18 - Sat, Jan 25
7:53 pm - 9:05 pmBWI-MDW
2h 12mnonstop
7:30 am - 7:41 pmMDW-BWI
11h 11m1 stop
$289Frontier
Find Deal
Mon, Jan 20 - Sat, Jan 25
1:01 pm - 12:17 amDCA-MDW
12h 16m1 stop
8:15 am - 9:59 pmMDW-DCA
12h 44m1 stop
$290Frontier
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Fri, Jan 17 - Wed, Jan 22
9:55 am - 1:08 pmDCA-MDW
4h 13m1 stop
5:07 pm - 10:35 pmMDW-DCA
4h 28m1 stop
$499Delta
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Mon, Jan 20 - Mon, Jan 27
10:00 am - 11:05 amDCA-MDW
2h 05mnonstop
8:15 pm - 11:05 pmMDW-DCA
1h 50mnonstop
$519Southwest
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Mon, Jan 20 - Thu, Jan 23
11:55 am - 1:05 pmDCA-MDW
2h 10mnonstop
4:10 pm - 10:05 pmMDW-DCA
4h 55m1 stop
$529Southwest
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Mon, Jan 20 - Thu, Jan 23
6:00 am - 8:54 amIAD-MDW
3h 54m1 stop
6:00 am - 11:57 amMDW-IAD
4h 57m1 stop
$549Delta
Find Deal
Mon, Jan 20 - Thu, Jan 23
8:50 pm - 10:00 pmBWI-MDW
2h 10mnonstop
5:05 pm - 7:50 pmMDW-BWI
1h 45mnonstop
$550Southwest
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Mon, Jan 20 - Thu, Jan 23
6:05 am - 12:46 pmIAD-MDW
7h 41m1 stop
5:05 pm - 12:22 amMDW-IAD
6h 17m1 stop
$604Delta
Find Deal
Fri, Jan 17 - Mon, Feb 3
5:11 pm - 6:23 pmBWI-MDW
2h 12mnonstop
1:16 pm - 4:11 pmMDW-BWI
1h 55mnonstop
$58Frontier
Find Deal
Wed, Feb 12 - Wed, Feb 19
5:11 pm - 6:23 pmBWI-MDW
2h 12mnonstop
10:26 am - 1:21 pmMDW-BWI
1h 55mnonstop
$59Frontier
Find Deal
Wed, Feb 12 - Sat, Feb 22
7:53 pm - 9:05 pmBWI-MDW
2h 12mnonstop
1:16 pm - 4:11 pmMDW-BWI
1h 55mnonstop
$69Frontier
Find Deal
Mon, Feb 10 - Wed, Feb 12
7:53 pm - 9:05 pmBWI-MDW
2h 12mnonstop
10:26 am - 1:21 pmMDW-BWI
1h 55mnonstop
$70Frontier
Find Deal
Mon, Feb 10 - Sat, Feb 22
4:21 pm - 5:33 pmBWI-MDW
2h 12mnonstop
1:16 pm - 4:11 pmMDW-BWI
1h 55mnonstop
$72Frontier
Find Deal
Fri, Feb 21 - Wed, Feb 26
5:11 pm - 6:23 pmBWI-MDW
2h 12mnonstop
12:26 pm - 3:21 pmMDW-BWI
1h 55mnonstop
$73Frontier
Find Deal
Wed, Feb 12 - Fri, Feb 14
4:21 pm - 5:33 pmBWI-MDW
2h 12mnonstop
10:26 am - 1:21 pmMDW-BWI
1h 55mnonstop
$74Frontier
Find Deal
Fri, Feb 21 - Sat, Feb 22
5:11 pm - 6:23 pmBWI-MDW
2h 12mnonstop
10:26 am - 1:21 pmMDW-BWI
1h 55mnonstop
$78Frontier
Find Deal
Wed, Feb 12 - Sat, Feb 15
10:35 am - 11:45 amBWI-MDW
2h 10mnonstop
5:05 pm - 7:50 pmMDW-BWI
1h 45mnonstop
$137Southwest
Find Deal
Tue, Mar 4 - Wed, Mar 5
7:40 pm - 8:50 pmBWI-MDW
2h 10mnonstop
3:35 pm - 6:20 pmMDW-BWI
1h 45mnonstop
$139Southwest
Find Deal
Tue, Mar 11 - Tue, Mar 18

Frontier flights from Maryland to Chicago Midway Airport

Our best Frontier deals on Maryland to Chicago Midway Airport flight tickets
Frontier
Feb 12
BWI5:11 pmBaltimore/Washington
2h 12m
MDW6:23 pmChicago Midway
Feb 19
MDW1:16 pmChicago Midway
1h 55m
BWI4:11 pmBaltimore/Washington
Frontier
Feb 12
BWI5:11 pmBaltimore/Washington
2h 12m
MDW6:23 pmChicago Midway
Feb 19
MDW1:16 pmChicago Midway
1h 55m
BWI4:11 pmBaltimore/Washington
Frontier
Feb 12
BWI5:11 pmBaltimore/Washington
2h 12m
MDW6:23 pmChicago Midway
Feb 22
MDW10:26 amChicago Midway
1h 55m
BWI1:21 pmBaltimore/Washington

Southwest flights from Maryland to Chicago Midway Airport

Our best Southwest deals on Maryland to Chicago Midway Airport flight tickets
Southwest
Feb 5
BWI8:10 pmBaltimore/Washington
2h 15m
MDW9:25 pmChicago Midway
Feb 19
MDW5:05 pmChicago Midway
1h 45m
BWI7:50 pmBaltimore/Washington
Southwest
Mar 1
BWI6:35 amBaltimore/Washington
2h 20m
MDW7:55 amChicago Midway
Mar 3
MDW2:20 pmChicago Midway
1h 45m
BWI5:05 pmBaltimore/Washington
Southwest
Feb 5
BWI8:10 pmBaltimore/Washington
2h 15m
MDW9:25 pmChicago Midway
Feb 12
MDW10:30 amChicago Midway
1h 45m
BWI1:15 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 $53. If you are unable to visit Chicago Midway Airport during the month of April, then departing from Maryland during the month July is also very affordable. Most momondo users find prices during this month for around $177.

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 $329.

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 $209 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?

You are more likely to see cheaper flights to Chicago Midway Airport from Maryland when booking 15 weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $215 when searching 15 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago Midway Airport from Maryland for as low as $81 on momondo.

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.

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

$30

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 $30. The best round-trip flight deal from Maryland to Chicago Midway Airport found on momondo in the last 72 hours is $57.
The fastest flight from Maryland to Chicago Midway Airport takes 1h 55m
Direct flights go from Maryland to Chicago Midway Airport every day.

  • 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
6.0
3,433 reviews
Search Frontier flights
SouthwestPriceFrom $170Free CancellationRating
8.1
4,659 reviews
Search Southwest flights
DeltaPriceFrom $176Free CancellationRating
8.0
8,511 reviews
Search Delta flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Hammond
New Buffalo
Portage
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Munster
Crown Point
Schererville
Monticello
Chesterton
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.


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