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Cheap flights from Maryland to Chicago from $94

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 8/20. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Maryland to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
6:30 am - 7:30 am
BWI
-
MDW
2h 00mnonstop
Southwest Logo
5:55 am - 8:40 am
MDW
-
BWI
1h 45mnonstop
$206Southwest
Thu, Sep 3 - Sat, Sep 5
Southwest Logo
6:35 am - 7:35 am
BWI
-
MDW
2h 00mnonstop
Southwest Logo
12:35 pm - 4:40 pm
MDW
-
BWI
3h 05m
1 stop
$207Southwest
Sat, Aug 15 - Wed, Aug 19
Southwest Logo
4:50 pm - 9:30 pm
BWI
-
MDW
5h 40m
2 stops
Southwest Logo
1:15 pm - 5:40 pm
MDW
-
BWI
3h 25m
1 stop
$208Southwest
Tue, Nov 3 - Wed, Nov 4
Southwest Logo
7:30 pm - 8:30 pm
BWI
-
MDW
2h 00mnonstop
Southwest Logo
8:00 am - 1:30 pm
MDW
-
BWI
4h 30m
1 stop
$211Southwest
Sat, Aug 15 - Mon, Aug 17
Frontier Logo
4:30 pm - 10:03 pm
PHL
-
MDW
6h 33m
1 stop
Frontier Logo
11:45 am - 8:28 pm
MDW
-
PHL
7h 43m
1 stop
$212Frontier
Tue, Aug 11 - Sat, Aug 29
Frontier Logo
4:30 pm - 10:03 pm
PHL
-
MDW
6h 33m
1 stop
Frontier Logo
11:06 am - 7:20 pm
MDW
-
PHL
7h 14m
1 stop
$214Frontier
Thu, Aug 6 - Fri, Aug 14
Frontier Logo
4:30 pm - 9:51 am
PHL
-
MDW
18h 21m
1 stop
Frontier Logo
11:06 am - 7:20 pm
MDW
-
PHL
7h 14m
1 stop
$215Frontier
Wed, Aug 5 - Thu, Aug 13
Delta Logo
5:47 pm - 10:36 pm
IAD
-
MDW
5h 49m
1 stop
Delta Logo
5:37 pm - 11:14 pm
MDW
-
IAD
4h 37m
1 stop
$231Delta
Sat, Sep 5 - Tue, Sep 8
Delta Logo
6:10 am - 9:17 am
DCA
-
MDW
4h 07m
1 stop
Delta Logo
6:42 pm - 10:59 pm
MDW
-
DCA
3h 17m
1 stop
$238Delta
Thu, Aug 20 - Mon, Aug 24
Delta Logo
10:10 am - 3:44 pm
DCA
-
MDW
6h 34m
1 stop
Delta Logo
5:37 pm - 11:02 pm
MDW
-
DCA
4h 25m
1 stop
$241Delta
Sun, Sep 6 - Tue, Sep 8

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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
Sep 3
BWI6:30 amBaltimore/Washington
2h 00m
MDW7:30 amChicago Midway
Sep 5
MDW5:55 amChicago Midway
1h 45m
BWI8:40 amBaltimore/Washington
$206
Southwest
Aug 15
BWI6:35 amBaltimore/Washington
2h 00m
MDW7:35 amChicago Midway
Aug 19
MDW12:35 pmChicago Midway
3h 05m
1 stop
BWI4:40 pmBaltimore/Washington
$207
Southwest
Nov 3
BWI4:50 pmBaltimore/Washington
5h 40m
2 stops
MDW9:30 pmChicago Midway
Nov 4
MDW1:15 pmChicago Midway
3h 25m
1 stop
BWI5:40 pmBaltimore/Washington
$208

Delta flights from Maryland to Chicago Midway Airport

Our best Delta deals on Maryland to Chicago Midway Airport flight tickets
Delta
Sep 5
IAD5:47 pmWashington, D.C. Dulles Intl
5h 49m
1 stop
MDW10:36 pmChicago Midway
Sep 8
MDW5:37 pmChicago Midway
4h 37m
1 stop
IAD11:14 pmWashington, D.C. Dulles Intl
$231
Delta
Nov 23
BWI6:10 pmBaltimore/Washington
5h 00m
1 stop
MDW10:10 pmChicago Midway
Dec 1
MDW6:30 pmChicago Midway
3h 25m
1 stop
BWI10:55 pmBaltimore/Washington
$234
Delta
Aug 20
IAD6:10 amWashington, D.C. Dulles Intl
4h 07m
1 stop
MDW9:17 amChicago Midway
Aug 24
MDW6:42 pmChicago Midway
3h 44m
1 stop
IAD11:26 pmWashington, D.C. Dulles Intl
$238

momondo Fare Finder

 
Customize your flight search to find flights from Maryland to Chicago Midway Airport that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated July 23, 2026.
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
Quickest round-trip

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Thu 9/3

6:30 am-7:30 am

Nonstop2h 00m

Chicago Midway

Sat 9/5

5:55 am-8:40 am

Nonstop1h 45m

$206

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Sat 8/15

6:35 am-7:35 am

Nonstop2h 00m

Chicago Midway

Wed 8/19

12:35 pm-4:40 pm

1 stop3h 05m

$207

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Tue 11/3

4:50 pm-9:30 pm

2 stops5h 40m

Chicago Midway

Wed 11/4

1:15 pm-5:40 pm

1 stop3h 25m

$208

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Sat 8/15

7:30 pm-8:30 pm

Nonstop2h 00m

Chicago Midway

Mon 8/17

8:00 am-1:30 pm

1 stop4h 30m

$211

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Tue 8/11

4:30 pm-10:03 pm

1 stop6h 33m

Chicago Midway

Sat 8/29

11:45 am-8:28 pm

1 stop7h 43m

$212

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Thu 8/6

4:30 pm-10:03 pm

1 stop6h 33m

Chicago Midway

Fri 8/14

11:06 am-7:20 pm

1 stop7h 14m

$214

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Wed 8/5

4:30 pm-9:51 am

1 stop18h 21m

Chicago Midway

Thu 8/13

11:06 am-7:20 pm

1 stop7h 14m

$215

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Sat 9/5

5:47 pm-10:36 pm

1 stop5h 49m

Chicago Midway

Tue 9/8

5:37 pm-11:14 pm

1 stop4h 37m

$231

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Thu 8/20

6:10 am-9:17 am

1 stop4h 07m

Chicago Midway

Mon 8/24

6:42 pm-10:59 pm

1 stop3h 17m

$238

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Sun 9/6

10:10 am-3:44 pm

1 stop6h 34m

Chicago Midway

Tue 9/8

5:37 pm-11:02 pm

1 stop4h 25m

$241

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 September is, on average, the cheapest month to fly to Chicago Midway Airport from Maryland, with most prices found around $171. If you are unable to visit Chicago Midway Airport during the month of September, then departing from Maryland during the month November is also very affordable. Most momondo users find prices during this month for around $186.

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 $305 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $383. 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?

You could potentially save up to 2% 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

$188

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 $188. The best round-trip flight deal from Maryland to Chicago Midway Airport found on momondo in the last 72 hours is $304.
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?

  • 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 $90Free CancellationRating
5.6
2,770 reviews
Search Frontier flights
SouthwestPriceFrom $177Free CancellationRating
8.0
4,240 reviews
Search Southwest flights

Traveling to a place near Chicago?

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