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Cheap flights from Chicago to Maryland from $31

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Maryland departing on 2/12. 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 Chicago to Maryland

Cheap round-trip flights

These are some of the best round-trip flight deals from Chicago to Maryland 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 Chicago to Maryland.

Cheap last minute flights

Planning a quick getaway from Chicago to Maryland? 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 Maryland, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Chicago to Maryland

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

All round-trip flight deals to Maryland

The cheapest plane tickets to Maryland found on KAYAK recently.
7:45 am - 10:48 amMDW-PHL
2h 03mnonstop
5:15 am - 6:39 amPHL-MDW
2h 24mnonstop
$67Frontier
Find Deal
Tue, Dec 17 - Thu, Dec 19
10:26 am - 1:21 pmMDW-BWI
1h 55mnonstop
2:21 pm - 3:33 pmBWI-MDW
2h 12mnonstop
$68Frontier
Find Deal
Sat, Feb 15 - Sat, Feb 22
6:31 am - 9:32 amORD-PHL
2h 01mnonstop
9:30 am - 11:00 amPHL-ORD
2h 30mnonstop
$131American Airlines
Find Deal
Wed, Dec 11 - Mon, Dec 16
5:20 pm - 8:19 pmORD-PHL
1h 59mnonstop
9:25 am - 10:51 amPHL-ORD
2h 26mnonstop
$137American Airlines
Find Deal
Wed, Jan 8 - Wed, Jan 15
11:20 am - 2:20 pmORD-PHL
2h 00mnonstop
10:10 am - 11:29 amPHL-ORD
2h 19mnonstop
$156United Airlines
Find Deal
Wed, Dec 11 - Thu, Dec 12
7:45 am - 10:49 amORD-PHL
2h 04mnonstop
6:30 am - 7:54 amPHL-ORD
2h 24mnonstop
$171United Airlines
Find Deal
Tue, Dec 10 - Wed, Dec 11
12:09 pm - 12:05 amORD-PHL
10h 56m1 stop
8:33 am - 8:13 pmPHL-ORD
12h 40m1 stop
$185Spirit Airlines
Find Deal
Wed, Jan 8 - Wed, Jan 15
5:11 pm - 7:48 amORD-PHL
13h 37m2 stops
7:27 pm - 4:06 pmPHL-ORD
21h 39m2 stops
$186Spirit Airlines
Find Deal
Mon, Dec 9 - Tue, Dec 10
6:28 pm - 11:19 pmMDW-BWI
3h 51m1 stop
8:15 am - 11:59 amBWI-MDW
4h 44m1 stop
$196Delta
Find Deal
Wed, Jan 8 - Thu, Jan 30
6:00 am - 2:12 pmMDW-PHL
7h 12m1 stop
12:37 pm - 5:01 pmPHL-MDW
5h 24m1 stop
$196Delta
Find Deal
Sat, Dec 7 - Tue, Dec 17
1:16 pm - 4:11 pmMDW-BWI
1h 55mnonstop
$31Frontier
Find Deal
Wed, Feb 12
10:26 am - 1:21 pmMDW-BWI
1h 55mnonstop
$34Frontier
Find Deal
Sat, Feb 15
5:50 pm - 8:48 pmORD-BWI
1h 58mnonstop
$69United Airlines
Find Deal
Wed, Jan 15
9:45 am - 12:49 pmORD-PHL
2h 04mnonstop
$69American Airlines
Find Deal
Tue, Jan 7
5:50 pm - 8:48 pmORD-BWI
1h 58mnonstop
$70United Airlines
Find Deal
Tue, Jan 7
9:58 am - 11:15 amORD-BWI
24h 17m2 stops
$77Spirit Airlines
Find Deal
Tue, Dec 17
3:22 pm - 7:33 amORD-BWI
15h 11m2 stops
$87Spirit Airlines
Find Deal
Tue, Feb 11
6:30 am - 9:31 amORD-PHL
2h 01mnonstop
$89American Airlines
Find Deal
Mon, Feb 3
5:50 pm - 11:42 pmMDW-BWI
4h 52m1 stop
$98Delta
Find Deal
Fri, Dec 13
6:00 am - 11:58 amMDW-PHL
4h 58m1 stop
$98Delta
Find Deal
Tue, Jan 7
6:48 pm - 9:49 pmMDW-PHL
2h 01mnonstop
9:00 am - 10:21 amPHL-MDW
2h 21mnonstop
$155Frontier
Find Deal
Tue, Nov 26 - Wed, Nov 27
8:51 am - 11:57 amORD-PHL
2h 06mnonstop
5:30 pm - 6:56 pmPHL-ORD
2h 26mnonstop
$155Frontier
Find Deal
Tue, Nov 26 - Wed, Nov 27
4:45 pm - 11:31 pmORD-BWI
5h 46m1 stop
5:20 am - 10:21 amBWI-ORD
6h 01m1 stop
$344Spirit Airlines
Find Deal
Mon, Nov 25 - Tue, Dec 3
4:45 pm - 11:31 pmORD-BWI
5h 46m1 stop
7:35 pm - 10:32 amBWI-ORD
15h 57m2 stops
$345Spirit Airlines
Find Deal
Mon, Nov 25 - Tue, Dec 3
6:49 pm - 12:28 amMDW-BWI
4h 39m1 stop
12:24 pm - 5:02 pmBWI-MDW
5h 38m1 stop
$347Delta
Find Deal
Tue, Nov 26 - Tue, Dec 3
3:58 pm - 6:52 pmORD-IAD
1h 54mnonstop
10:14 pm - 3:12 pmIAD-ORD
17h 58m1 stop
$419United Airlines
Find Deal
Fri, Nov 22 - Fri, Nov 22
1:21 pm - 4:15 pmORD-IAD
1h 54mnonstop
10:16 pm - 11:20 pmIAD-ORD
2h 04mnonstop
$453United Airlines
Find Deal
Fri, Nov 22 - Fri, Dec 13
10:15 am - 4:30 pmORD-DCA
5h 15m1 stop
6:00 am - 9:09 amDCA-ORD
4h 09m1 stop
$488Delta
Find Deal
Tue, Nov 26 - Sat, Jan 4
9:24 am - 12:21 pmORD-BWI
1h 57mnonstop
12:41 pm - 2:00 pmBWI-ORD
2h 19mnonstop
$530American Airlines
Find Deal
Tue, Nov 26 - Wed, Dec 4
6:45 pm - 9:55 pmORD-BWI
2h 10mnonstop
5:00 am - 8:42 amBWI-ORD
4h 42m1 stop
$538American Airlines
Find Deal
Mon, Nov 25 - Wed, Nov 27
7:45 am - 10:48 amMDW-PHL
2h 03mnonstop
5:15 am - 6:39 amPHL-MDW
2h 24mnonstop
$67Frontier
Find Deal
Tue, Dec 17 - Thu, Dec 19
6:25 am - 9:17 amMDW-BWI
1h 52mnonstop
10:59 am - 12:03 pmBWI-MDW
2h 04mnonstop
$67Frontier
Find Deal
Wed, Dec 18 - Thu, Dec 19
6:25 am - 9:17 amMDW-BWI
1h 52mnonstop
10:59 am - 12:03 pmBWI-MDW
2h 04mnonstop
$68Frontier
Find Deal
Wed, Dec 18 - Thu, Dec 19
10:22 pm - 1:29 amORD-PHL
2h 07mnonstop
7:59 pm - 9:27 pmPHL-ORD
2h 28mnonstop
$73Frontier
Find Deal
Wed, Dec 18 - Wed, Dec 25
6:31 am - 9:32 amORD-PHL
2h 01mnonstop
9:30 am - 11:00 amPHL-ORD
2h 30mnonstop
$131American Airlines
Find Deal
Wed, Dec 11 - Mon, Dec 16
9:45 am - 12:49 pmORD-PHL
2h 04mnonstop
3:55 pm - 5:24 pmPHL-ORD
2h 29mnonstop
$132American Airlines
Find Deal
Tue, Jan 14 - Tue, Jan 14
10:30 am - 1:15 pmMDW-BWI
1h 45mnonstop
7:00 pm - 8:10 pmBWI-MDW
2h 10mnonstop
$144Southwest
Find Deal
Tue, Jan 7 - Sat, Jan 11
7:00 am - 9:55 amORD-BWI
1h 55mnonstop
12:35 pm - 2:00 pmBWI-ORD
2h 25mnonstop
$150Southwest
Find Deal
Thu, Jan 23 - Thu, Jan 30
6:15 pm - 9:25 pmORD-PHL
2h 10mnonstop
6:30 am - 7:54 amPHL-ORD
2h 24mnonstop
$184United Airlines
Find Deal
Sat, Dec 14 - Sun, Dec 15
7:45 am - 10:49 amORD-PHL
2h 04mnonstop
1:15 pm - 2:39 pmPHL-ORD
2h 24mnonstop
$196United Airlines
Find Deal
Mon, Dec 9 - Wed, Dec 11

Frontier flights from Chicago to Maryland

Our best Frontier deals on Chicago to Maryland flight tickets
Frontier
Dec 17
MDW7:45 amChicago Midway
2h 03m
PHL10:48 amPhiladelphia
Dec 19
PHL5:15 amPhiladelphia
2h 24m
MDW6:39 amChicago Midway
Frontier
Feb 15
MDW10:26 amChicago Midway
1h 55m
BWI1:21 pmBaltimore/Washington
Feb 22
BWI2:21 pmBaltimore/Washington
2h 12m
MDW3:33 pmChicago Midway
Frontier
Dec 18
MDW6:25 amChicago Midway
1h 52m
BWI9:17 amBaltimore/Washington
Jan 10
BWI4:48 pmBaltimore/Washington
2h 04m
MDW5:52 pmChicago Midway

American Airlines flights from Chicago to Maryland

Our best American Airlines deals on Chicago to Maryland flight tickets
American Airlines
Dec 11
ORD6:31 amChicago O'Hare Intl
2h 01m
PHL9:32 amPhiladelphia
Dec 16
PHL9:30 amPhiladelphia
2h 30m
ORD11:00 amChicago O'Hare Intl
American Airlines
Jan 8
ORD5:20 pmChicago O'Hare Intl
1h 59m
PHL8:19 pmPhiladelphia
Jan 15
PHL9:25 amPhiladelphia
2h 26m
ORD10:51 amChicago O'Hare Intl
American Airlines
Jan 7
ORD6:00 pmChicago O'Hare Intl
2h 03m
BWI9:03 pmBaltimore/Washington
Jan 14
BWI7:30 amBaltimore/Washington
2h 21m
ORD8:51 amChicago O'Hare Intl

See travel insights to Maryland from

How to get the cheapest flight ticket from Chicago to Maryland

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 day to depart on your flight to Maryland?

The cheapest day to depart from Chicago to Maryland is on a Wednesday. Travelers who choose to depart for Maryland on a Wednesday will often find tickets for as low as $269. The most expensive day to fly to Maryland is Sunday, with ticket prices averaging around $334.

What is the cheapest Chicago to Maryland flight route?

Fly from Chicago Midway to Baltimore/Washington for the best Chicago - Maryland flight prices

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

There are 4 cabin classes available to choose from on Chicago to Maryland 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 Chicago to Maryland flights?

You could potentially save up to 89% on your flight if you consider stops on a Chicago to Maryland flight.

Cheap Chicago to Maryland flight deals and tips

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

Best Price Found

$31

Fastest flight time

1h 45m

Direct flights

Every day

Airports in Maryland

4 airports
The best one-way flight to Maryland from Chicago in the past 72 hours is $31. The best round-trip flight deal from Chicago to Maryland found on momondo in the last 72 hours is $67.
The fastest flight from Chicago to Maryland takes 1h 45m
Direct flights go from Chicago to Maryland every day.
There are 4 airports near Maryland: Washington, D.C. Reagan-National (DCA), Baltimore/Washington (BWI), Philadelphia (PHL), Washington, D.C. Dulles Intl (IAD)

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

    Prices for flights from Chicago to Maryland were last updated today.

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

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

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago to Maryland.

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

    The travel and health documents required for your trip to Maryland 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 Maryland. 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 Chicago to Maryland?


Best airlines flying from Chicago to Maryland

Compare and see reviews for airlines that fly from Chicago to Maryland with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $65Free CancellationRating
6.1
3,536 reviews
Search Frontier flights
American AirlinesPriceFrom $121Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
Spirit AirlinesPriceFrom $135Free CancellationRating
6.3
8,169 reviews
Search Spirit Airlines flights
SouthwestPriceFrom $138Free CancellationRating
8.1
5,005 reviews
Search Southwest flights
United AirlinesPriceFrom $159Free CancellationRating
7.4
9,172 reviews
Search United Airlines flights
DeltaPriceFrom $176Free CancellationRating
8.0
8,755 reviews
Search Delta flights

Why use momondo?

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

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Chicago to Maryland for you.

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

Yes. momondo enables you to select and highlight flights to Maryland from Chicago with this policy.

How can momondo help me find flights from Chicago to Maryland?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Maryland from Chicago.

I’m not ready to book a flight from Chicago to Maryland right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Chicago to Maryland now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Maryland and let you know when they change.


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