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Cheap flights from Maryland to Chicago from $33

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 2/22. 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.
8:56 am - 10:09 amPHL-MDW
2h 13mnonstop
10:59 am - 1:58 pmMDW-PHL
1h 59mnonstop
$57Frontier
Find Deal
Wed, Feb 12 - Wed, Feb 19
7:59 pm - 9:27 pmPHL-ORD
2h 28mnonstop
10:22 pm - 1:29 amORD-PHL
2h 07mnonstop
$58Frontier
Find Deal
Wed, Dec 18 - Wed, Dec 25
9:25 am - 10:51 amPHL-ORD
2h 26mnonstop
6:30 am - 9:27 amORD-PHL
1h 57mnonstop
$137American Airlines
Find Deal
Wed, Feb 12 - Wed, Feb 19
12:35 pm - 2:00 pmBWI-ORD
2h 25mnonstop
4:35 pm - 7:30 pmORD-BWI
1h 55mnonstop
$139Southwest
Find Deal
Wed, Jan 8 - Mon, Jan 13
6:11 am - 6:31 pmPHL-ORD
13h 20m1 stop
8:01 pm - 11:07 pmORD-PHL
2h 06mnonstop
Sun, Nov 24 - Wed, Nov 27
7:16 am - 8:15 pmPHL-ORD
13h 59m1 stop
6:07 pm - 9:14 pmORD-PHL
2h 07mnonstop
Wed, Dec 4 - Fri, Dec 6
8:15 am - 9:30 amBWI-MDW
2h 15mnonstop
7:10 am - 10:05 amMDW-BWI
1h 55mnonstop
$144Southwest
Find Deal
Sat, Feb 8 - Mon, Feb 10
10:10 am - 11:41 amPHL-ORD
2h 31mnonstop
6:30 pm - 9:40 pmORD-PHL
2h 10mnonstop
$147United Airlines
Find Deal
Wed, Jan 8 - Wed, Jan 15
7:30 am - 8:51 amBWI-ORD
2h 21mnonstop
6:00 pm - 9:03 pmORD-BWI
2h 03mnonstop
$148American Airlines
Find Deal
Sat, Feb 8 - Mon, Feb 10
5:15 pm - 6:39 pmPHL-ORD
2h 24mnonstop
6:15 pm - 9:25 pmORD-PHL
2h 10mnonstop
$159United Airlines
Find Deal
Sat, Dec 14 - Mon, Dec 16
10:41 pm - 12:05 amPHL-ORD
2h 24mnonstop
$33Frontier
Find Deal
Sat, Feb 22
8:56 am - 10:09 amPHL-MDW
2h 13mnonstop
$33Frontier
Find Deal
Sat, Feb 15
10:10 am - 11:29 amPHL-ORD
2h 19mnonstop
$69United Airlines
Find Deal
Sat, Dec 14
5:25 pm - 6:35 pmPHL-MDW
2h 10mnonstop
$69Southwest
Find Deal
Sat, Dec 14
10:35 am - 11:45 amBWI-MDW
2h 10mnonstop
$69Southwest
Find Deal
Wed, Jan 8
10:05 am - 11:24 amBWI-ORD
2h 19mnonstop
$70United Airlines
Find Deal
Thu, Jan 9
7:22 am - 8:15 pmPHL-ORD
13h 53m1 stop
$70Spirit Airlines
Find Deal
Wed, Nov 20
11:30 am - 8:15 pmBWI-ORD
9h 45m1 stop
$71Spirit Airlines
Find Deal
Wed, Nov 20
3:36 pm - 5:00 pmBWI-ORD
2h 24mnonstop
$85American Airlines
Find Deal
Wed, Dec 11
9:43 am - 11:03 amDCA-ORD
2h 20mnonstop
$99American Airlines
Find Deal
Tue, Dec 10
10:26 am - 11:52 amPHL-ORD
2h 26mnonstop
7:30 am - 10:29 amORD-PHL
1h 59mnonstop
$102Frontier
Find Deal
Mon, Nov 18 - Thu, Nov 21
12:07 pm - 1:24 pmPHL-MDW
2h 17mnonstop
6:48 pm - 9:49 pmMDW-PHL
2h 01mnonstop
$102Frontier
Find Deal
Mon, Nov 18 - Thu, Nov 21
10:26 am - 11:52 amPHL-ORD
2h 26mnonstop
1:09 pm - 1:17 amORD-PHL
11h 08m1 stop
Mon, Nov 18 - Mon, Nov 25
10:26 am - 11:52 amPHL-ORD
2h 26mnonstop
1:20 pm - 8:15 pmORD-PHL
5h 55m1 stop
Mon, Nov 18 - Thu, Nov 21
8:59 pm - 10:05 amBWI-ORD
14h 06m2 stops
11:51 am - 9:55 pmORD-BWI
9h 04m1 stop
$199Spirit Airlines
Find Deal
Tue, Nov 19 - Thu, Nov 21
8:59 pm - 10:05 amBWI-ORD
14h 06m2 stops
7:26 am - 1:13 amORD-BWI
16h 47m2 stops
$203Spirit Airlines
Find Deal
Tue, Nov 19 - Thu, Nov 21
6:00 am - 9:27 amPHL-ORD
4h 27m1 stop
1:35 pm - 7:36 pmORD-PHL
5h 01m1 stop
$256Delta
Find Deal
Tue, Nov 19 - Tue, Nov 19
6:00 am - 8:50 amPHL-MDW
3h 50m1 stop
5:42 pm - 11:15 pmMDW-PHL
4h 33m1 stop
$276Delta
Find Deal
Tue, Nov 19 - Wed, Nov 27
6:13 pm - 7:45 pmPHL-ORD
2h 32mnonstop
12:13 pm - 3:09 pmORD-PHL
1h 56mnonstop
$276American Airlines
Find Deal
Tue, Nov 19 - Thu, Nov 21
1:47 pm - 5:45 pmIAD-ORD
4h 58m1 stop
1:54 pm - 7:31 pmORD-IAD
4h 37m1 stop
$496American Airlines
Find Deal
Tue, Nov 19 - Thu, Nov 21
8:56 am - 10:09 amPHL-MDW
2h 13mnonstop
10:59 am - 1:58 pmMDW-PHL
1h 59mnonstop
$57Frontier
Find Deal
Wed, Feb 12 - Wed, Feb 19
7:59 pm - 9:27 pmPHL-ORD
2h 28mnonstop
10:22 pm - 1:29 amORD-PHL
2h 07mnonstop
$58Frontier
Find Deal
Wed, Dec 18 - Wed, Dec 25
11:43 am - 1:09 pmPHL-MDW
2h 26mnonstop
7:45 am - 10:48 amMDW-PHL
2h 03mnonstop
$58Frontier
Find Deal
Tue, Dec 17 - Tue, Dec 31
9:25 am - 10:51 amPHL-ORD
2h 26mnonstop
6:30 am - 9:27 amORD-PHL
1h 57mnonstop
$137American Airlines
Find Deal
Wed, Feb 12 - Wed, Feb 19
12:35 pm - 2:00 pmBWI-ORD
2h 25mnonstop
4:35 pm - 7:30 pmORD-BWI
1h 55mnonstop
$139Southwest
Find Deal
Wed, Jan 8 - Mon, Jan 13
12:35 pm - 2:00 pmBWI-ORD
2h 25mnonstop
7:00 am - 9:55 amORD-BWI
1h 55mnonstop
$140Southwest
Find Deal
Thu, Jan 30 - Mon, Feb 3
7:30 am - 8:51 amBWI-ORD
2h 21mnonstop
6:00 pm - 9:03 pmORD-BWI
2h 03mnonstop
$143American Airlines
Find Deal
Sat, Feb 8 - Mon, Feb 10
10:10 am - 11:41 amPHL-ORD
2h 31mnonstop
6:30 pm - 9:40 pmORD-PHL
2h 10mnonstop
$147United Airlines
Find Deal
Wed, Jan 8 - Wed, Jan 15
5:15 pm - 6:39 pmPHL-ORD
2h 24mnonstop
6:15 pm - 9:25 pmORD-PHL
2h 10mnonstop
$159United Airlines
Find Deal
Sat, Dec 14 - Mon, Dec 16
6:30 am - 7:54 amPHL-ORD
2h 24mnonstop
4:58 pm - 8:05 pmORD-PHL
2h 07mnonstop
Wed, Dec 4 - Mon, Dec 9

Southwest flights from Maryland to Chicago

Our best Southwest deals on Maryland to Chicago flight tickets
Southwest
Jan 8
BWI12:35 pmBaltimore/Washington
2h 25m
ORD2:00 pmChicago O'Hare Intl
Jan 13
ORD4:35 pmChicago O'Hare Intl
1h 55m
BWI7:30 pmBaltimore/Washington
Southwest
Feb 8
BWI8:15 amBaltimore/Washington
2h 15m
MDW9:30 amChicago Midway
Feb 10
MDW7:10 amChicago Midway
1h 55m
BWI10:05 amBaltimore/Washington
Southwest
Jan 9
BWI12:35 pmBaltimore/Washington
2h 25m
ORD2:00 pmChicago O'Hare Intl
Jan 13
ORD4:35 pmChicago O'Hare Intl
1h 55m
BWI7:30 pmBaltimore/Washington

Spirit Airlines flights from Maryland to Chicago

Our best Spirit Airlines deals on Maryland to Chicago flight tickets
Spirit Airlines
Nov 19
BWI5:28 amBaltimore/Washington
5h 22m
1 stop
ORD9:50 amChicago O'Hare Intl
Nov 20
ORD1:09 pmChicago O'Hare Intl
5h 58m
1 stop
BWI8:07 pmBaltimore/Washington
Spirit Airlines
Nov 21
BWI12:20 pmBaltimore/Washington
8h 55m
1 stop
ORD8:15 pmChicago O'Hare Intl
Nov 23
ORD1:09 pmChicago O'Hare Intl
5h 58m
1 stop
BWI8:07 pmBaltimore/Washington
Spirit Airlines
Nov 19
BWI8:59 pmBaltimore/Washington
14h 06m
2 stops
ORD10:05 amChicago O'Hare Intl
Nov 20
ORD1:09 pmChicago O'Hare Intl
5h 58m
1 stop
BWI8:07 pmBaltimore/Washington

How to get the cheapest flight ticket from Maryland to Chicago

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 airline that flies to Chicago from Maryland?

Frontier. Frontier, Spirit Airlines, and Delta are the most popular carriers operating from Maryland to Chicago

What is the cheapest Maryland to Chicago flight route?

Philadelphia - Chicago Midway. Fly from Philadelphia to Chicago Midway for the best Maryland - Chicago flight prices

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

There are 3 cabin classes available to choose from on Maryland to Chicago 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 flights?

No. A direct flight is the cheapest option for a flight between Maryland to Chicago.

Cheap Maryland to Chicago flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Maryland to Chicago

Best Price Found

$33

Fastest flight time

1h 59m

Direct flights

Every day

Airports in Chicago

2 airports
The best one-way flight to Chicago from Maryland in the past 72 hours is $33. The best round-trip flight deal from Maryland to Chicago found on momondo in the last 72 hours is $57.
The fastest flight from Maryland to Chicago takes 1h 59m
Direct flights go from Maryland to Chicago every day.
There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)

  • When did momondo last update prices for flights from Maryland to Chicago?

    Prices for flights from Maryland to Chicago are refreshed on a daily basis.

  • How many operators does momondo search for flights from Maryland to Chicago?

  • How old do you have to be to fly from Maryland to Chicago?

    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.

  • What documentation or ID do you need to fly to Chicago?

    The travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Maryland to Chicago?


Best airlines flying from Maryland to Chicago

Compare and see reviews for airlines that fly from Maryland to Chicago with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $58Free CancellationRating
6.1
3,551 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $101Free CancellationRating
6.3
8,167 reviews
Search Spirit Airlines flights
American AirlinesPriceFrom $136Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $153Free CancellationRating
7.4
9,194 reviews
Search United Airlines flights
SouthwestPriceFrom $160Free CancellationRating
8.1
5,045 reviews
Search Southwest flights
DeltaPriceFrom $176Free CancellationRating
8.0
8,788 reviews
Search Delta flights

Why use momondo?

Why should I use momondo to find a flight deal from Maryland to Chicago?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Maryland to Chicago. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Maryland to Chicago with flexible booking policies on momondo?

Yes. All flights to Chicago from Maryland on momondo can be compared and filtered by various policies on offer, including flexible booking.

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?

Of course. momondo tracks the price of Maryland to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.


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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago