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Cheap flights from Maryland to Chicago from $57

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 8/31. 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

Frontier Logo
2:29 pm - 3:33 pmBWI-MDW
2h 04mnonstop
Frontier Logo
1:59 pm - 4:55 pmMDW-BWI
1h 56mnonstop
$102Frontier
Find Deal
Fri, Oct 17 - Mon, Oct 20
Frontier Logo
5:40 pm - 6:43 pmBWI-MDW
2h 03mnonstop
Frontier Logo
1:49 pm - 4:50 pmMDW-BWI
2h 01mnonstop
$114Frontier
Find Deal
Thu, Sep 11 - Mon, Sep 15
Frontier Logo
5:40 pm - 6:43 pmBWI-MDW
2h 03mnonstop
Frontier Logo
1:49 pm - 4:50 pmMDW-BWI
2h 01mnonstop
$117Frontier
Find Deal
Fri, Sep 19 - Mon, Sep 22
Frontier Logo
6:00 am - 7:11 amPHL-MDW
2h 11mnonstop
Frontier Logo
8:06 am - 11:07 amMDW-PHL
2h 01mnonstop
$120Frontier
Find Deal
Thu, Sep 25 - Sun, Sep 28
Frontier Logo
5:40 pm - 6:43 pmBWI-MDW
2h 03mnonstop
Frontier Logo
1:49 pm - 4:50 pmMDW-BWI
2h 01mnonstop
$120Frontier
Find Deal
Thu, Sep 11 - Thu, Sep 18
Southwest Logo
7:55 pm - 8:55 pmBWI-MDW
2h 00mnonstop
Southwest Logo
5:35 am - 8:20 amMDW-BWI
1h 45mnonstop
$161Southwest
Find Deal
Sat, Oct 11 - Tue, Oct 14
Southwest Logo
6:10 am - 7:10 amBWI-MDW
2h 00mnonstop
Southwest Logo
9:35 am - 12:25 pmMDW-BWI
1h 50mnonstop
$169Southwest
Find Deal
Mon, Sep 1 - Sat, Sep 6
Allegiant Air Logo
1:22 pm - 6:17 pmIAD-MDW
5h 55m1 stop
Allegiant Air Logo
9:32 am - 3:23 pmMDW-IAD
4h 51m1 stop
$174Allegiant Air
Find Deal
Mon, Aug 18 - Fri, Aug 22
Delta Logo
7:00 am - 1:36 pmPHL-MDW
7h 36m1 stop
Delta Logo
6:17 pm - 11:22 pmMDW-PHL
4h 05m1 stop
$197Delta
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Wed, Sep 3 - Sat, Sep 6
Delta Logo
5:25 pm - 9:12 pmIAD-MDW
4h 47m1 stop
Delta Logo
9:30 am - 11:26 pmMDW-IAD
12h 56m1 stop
$227Delta
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Sat, Aug 30 - Tue, Sep 2

Frontier flights from Maryland to Chicago Midway Airport

Our best Frontier deals on Maryland to Chicago Midway Airport flight tickets
Frontier
Oct 17
BWI2:29 pmBaltimore/Washington
2h 04m
MDW3:33 pmChicago Midway
Oct 20
MDW1:59 pmChicago Midway
1h 56m
BWI4:55 pmBaltimore/Washington
$102
Find similar
Frontier
Sep 11
BWI5:40 pmBaltimore/Washington
2h 03m
MDW6:43 pmChicago Midway
Sep 15
MDW1:49 pmChicago Midway
2h 01m
BWI4:50 pmBaltimore/Washington
$114
Find similar
Frontier
Sep 19
BWI5:40 pmBaltimore/Washington
2h 03m
MDW6:43 pmChicago Midway
Sep 22
MDW1:49 pmChicago Midway
2h 01m
BWI4:50 pmBaltimore/Washington
$117
Find similar

Delta flights from Maryland to Chicago Midway Airport

Our best Delta deals on Maryland to Chicago Midway Airport flight tickets
Delta
Sep 3
PHL7:00 amPhiladelphia
7h 36m
1 stop
MDW1:36 pmChicago Midway
Sep 6
MDW6:17 pmChicago Midway
4h 05m
1 stop
PHL11:22 pmPhiladelphia
$197
Find similar
Delta
Aug 30
IAD5:25 pmWashington, D.C. Dulles Intl
4h 47m
1 stop
MDW9:12 pmChicago Midway
Sep 2
MDW9:30 amChicago Midway
12h 56m
1 stop
IAD11:26 pmWashington, D.C. Dulles Intl
$227
Find similar
Delta
Aug 26
IAD3:26 pmWashington, D.C. Dulles Intl
7h 18m
1 stop
MDW9:44 pmChicago Midway
Sep 3
MDW6:17 pmChicago Midway
4h 09m
1 stop
IAD11:26 pmWashington, D.C. Dulles Intl
$237
Find similar

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 August 2, 2025.
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 10/17

2:29 pm-3:33 pm

Nonstop2h 04m

Chicago Midway

Mon 10/20

1:59 pm-4:55 pm

Nonstop1h 56m

$102

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Thu 9/11

5:40 pm-6:43 pm

Nonstop2h 03m

Chicago Midway

Mon 9/15

1:49 pm-4:50 pm

Nonstop2h 01m

$114

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Fri 9/19

5:40 pm-6:43 pm

Nonstop2h 03m

Chicago Midway

Mon 9/22

1:49 pm-4:50 pm

Nonstop2h 01m

$117

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Thu 9/25

6:00 am-7:11 am

Nonstop2h 11m

Chicago Midway

Sun 9/28

8:06 am-11:07 am

Nonstop2h 01m

$120

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Thu 9/11

5:40 pm-6:43 pm

Nonstop2h 03m

Chicago Midway

Thu 9/18

1:49 pm-4:50 pm

Nonstop2h 01m

$120

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Sat 10/11

7:55 pm-8:55 pm

Nonstop2h 00m

Chicago Midway

Tue 10/14

5:35 am-8:20 am

Nonstop1h 45m

$161

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Mon 9/1

6:10 am-7:10 am

Nonstop2h 00m

Chicago Midway

Sat 9/6

9:35 am-12:25 pm

Nonstop1h 50m

$169

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Mon 8/18

1:22 pm-6:17 pm

1 stop5h 55m

Chicago Midway

Fri 8/22

9:32 am-3:23 pm

1 stop4h 51m

$174

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Wed 9/3

7:00 am-1:36 pm

1 stop7h 36m

Chicago Midway

Sat 9/6

6:17 pm-11:22 pm

1 stop4h 05m

$197

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Sat 8/30

5:25 pm-9:12 pm

1 stop4h 47m

Chicago Midway

Tue 9/2

9:30 am-11:26 pm

1 stop12h 56m

$227

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 February is, on average, the cheapest month to fly to Chicago Midway Airport from Maryland, with most prices found around $181. If you are unable to visit Chicago Midway Airport during the month of February, then departing from Maryland during the month September is also very affordable. Most momondo users find prices during this month for around $200.

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 $325. 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 $393.

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 $316 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $352. 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 weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $236 when searching 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 $151 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

$57

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 $57. The best round-trip flight deal from Maryland to Chicago Midway Airport found on momondo in the last 72 hours is $102.
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?

  • 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 $61Free CancellationRating
5.8
3,241 reviews
Search Frontier flights
DeltaPriceFrom $98Free CancellationRating
8.0
7,983 reviews
Search Delta flights
SouthwestPriceFrom $161Free CancellationRating
8.0
4,246 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
Benton Harbor
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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