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Cheap flights from Chicago to Maryland from $29

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.
1:16 pm - 4:11 pmMDW-BWI
1h 55mnonstop
5:11 pm - 6:23 pmBWI-MDW
2h 12mnonstop
$58Frontier
Find Deal
Wed, Feb 19 - Wed, Feb 26
10:26 am - 1:21 pmMDW-BWI
1h 55mnonstop
5:11 pm - 6:23 pmBWI-MDW
2h 12mnonstop
$59Frontier
Find Deal
Sat, Feb 22 - Wed, Feb 26
4:35 pm - 7:30 pmORD-BWI
1h 55mnonstop
11:25 am - 12:45 pmBWI-ORD
2h 20mnonstop
$139Southwest
Find Deal
Wed, Feb 26 - Sat, Mar 1
4:35 pm - 7:30 pmORD-BWI
1h 55mnonstop
8:55 pm - 10:20 pmBWI-ORD
2h 25mnonstop
$140Southwest
Find Deal
Tue, Jan 21 - Wed, Jan 22
8:20 am - 11:17 amORD-BWI
1h 57mnonstop
11:51 am - 1:12 pmBWI-ORD
2h 21mnonstop
$141American Airlines
Find Deal
Tue, Feb 4 - Tue, Feb 11
8:20 am - 11:17 amORD-BWI
1h 57mnonstop
7:30 am - 8:51 amBWI-ORD
2h 21mnonstop
$149American Airlines
Find Deal
Sat, Jan 25 - Tue, Jan 28
2:29 pm - 5:35 pmORD-PHL
2h 06mnonstop
10:10 am - 11:41 amPHL-ORD
2h 31mnonstop
$181United Airlines
Find Deal
Wed, Feb 12 - Tue, Feb 25
10:50 am - 1:51 pmORD-BWI
2h 01mnonstop
5:22 pm - 6:40 pmBWI-ORD
2h 18mnonstop
$184United Airlines
Find Deal
Wed, Jan 29 - Sat, Feb 1
10:57 am - 6:12 pmMDW-BWI
6h 15m1 stop
5:15 pm - 10:20 pmBWI-MDW
6h 05m1 stop
$196Delta
Find Deal
Wed, Feb 5 - Sat, Feb 8
6:35 pm - 12:35 amORD-BWI
5h 00m1 stop
6:00 am - 9:16 amBWI-ORD
4h 16m1 stop
$196Delta
Find Deal
Wed, Feb 5 - Wed, Feb 12
1:16 pm - 4:11 pmMDW-BWI
1h 55mnonstop
$29Frontier
Find Deal
Wed, Feb 12
1:16 pm - 4:11 pmMDW-BWI
1h 55mnonstop
$30Frontier
Find Deal
Wed, Feb 26
7:00 am - 9:55 amORD-BWI
1h 55mnonstop
$69United Airlines
Find Deal
Wed, Feb 19
2:20 pm - 5:05 pmMDW-BWI
1h 45mnonstop
$69Southwest
Find Deal
Tue, Feb 18
10:50 am - 1:51 pmORD-BWI
2h 01mnonstop
$70United Airlines
Find Deal
Wed, Jan 22
5:05 pm - 7:50 pmMDW-BWI
1h 45mnonstop
$70Southwest
Find Deal
Wed, Jan 22
6:00 am - 12:56 pmMDW-BWI
5h 56m1 stop
$98Delta
Find Deal
Wed, Feb 5
6:15 pm - 11:19 pmORD-BWI
4h 04m1 stop
$98Delta
Find Deal
Tue, Jan 21
8:10 am - 11:02 amORD-DCA
1h 52mnonstop
$116American Airlines
Find Deal
Thu, May 29
6:00 am - 8:55 amORD-DCA
1h 55mnonstop
$119American Airlines
Find Deal
Thu, Jan 9
6:25 am - 9:17 amMDW-BWI
1h 52mnonstop
10:07 am - 11:11 amBWI-MDW
2h 04mnonstop
$240Frontier
Find Deal
Wed, Dec 25 - Wed, Jan 1
4:11 pm - 12:07 amORD-PHL
6h 56m1 stop
6:00 am - 12:29 pmPHL-ORD
7h 29m1 stop
Wed, Dec 25 - Tue, Jan 14
9:05 pm - 11:59 pmORD-IAD
1h 54mnonstop
10:09 pm - 11:15 pmIAD-ORD
2h 06mnonstop
$428United Airlines
Find Deal
Sat, Dec 28 - Fri, Jan 10
6:01 pm - 9:00 pmORD-DCA
1h 59mnonstop
6:42 am - 8:03 amDCA-ORD
2h 21mnonstop
$428American Airlines
Find Deal
Sat, Dec 28 - Fri, Jan 10
6:15 am - 5:05 pmORD-BWI
9h 50m1 stop
8:55 pm - 10:20 pmBWI-ORD
2h 25mnonstop
$434Southwest
Find Deal
Sat, Dec 28 - Fri, Jan 10
11:41 am - 2:47 pmORD-DCA
2h 06mnonstop
7:29 am - 11:27 amDCA-ORD
4h 58m1 stop
$438American Airlines
Find Deal
Sat, Dec 28 - Fri, Jan 10
8:30 am - 3:00 pmMDW-DCA
5h 30m1 stop
9:20 pm - 10:25 pmDCA-MDW
2h 05mnonstop
$438Southwest
Find Deal
Sat, Dec 28 - Fri, Jan 10
8:10 pm - 11:09 pmORD-BWI
1h 59mnonstop
6:20 am - 7:39 amBWI-ORD
2h 19mnonstop
$444United Airlines
Find Deal
Sat, Dec 28 - Wed, Jan 1
5:50 pm - 11:55 pmORD-BWI
5h 05m1 stop
5:30 pm - 11:56 pmBWI-ORD
7h 26m1 stop
$463Delta
Find Deal
Sat, Dec 28 - Tue, Dec 31
2:55 pm - 9:40 pmORD-IAD
5h 45m1 stop
6:00 am - 9:55 amIAD-ORD
4h 55m1 stop
$472Delta
Find Deal
Thu, Dec 26 - Tue, Jan 7
1:16 pm - 4:11 pmMDW-BWI
1h 55mnonstop
5:11 pm - 6:23 pmBWI-MDW
2h 12mnonstop
$58Frontier
Find Deal
Wed, Feb 19 - Wed, Feb 26
10:26 am - 1:21 pmMDW-BWI
1h 55mnonstop
5:11 pm - 6:23 pmBWI-MDW
2h 12mnonstop
$59Frontier
Find Deal
Sat, Feb 22 - Wed, Feb 26
1:16 pm - 4:11 pmMDW-BWI
1h 55mnonstop
5:11 pm - 6:23 pmBWI-MDW
2h 12mnonstop
$65Frontier
Find Deal
Wed, Feb 12 - Wed, Feb 19
1:04 pm - 3:59 pmMDW-BWI
1h 55mnonstop
5:11 pm - 6:23 pmBWI-MDW
2h 12mnonstop
$69Frontier
Find Deal
Fri, Feb 7 - Wed, Feb 12
8:20 am - 11:17 amORD-BWI
1h 57mnonstop
12:30 pm - 1:47 pmBWI-ORD
2h 17mnonstop
$138American Airlines
Find Deal
Wed, Feb 12 - Tue, Feb 25
4:35 pm - 7:30 pmORD-BWI
1h 55mnonstop
11:25 am - 12:45 pmBWI-ORD
2h 20mnonstop
$139Southwest
Find Deal
Wed, Feb 26 - Sat, Mar 1
6:55 pm - 9:45 pmMDW-BWI
1h 50mnonstop
10:35 am - 11:45 amBWI-MDW
2h 10mnonstop
$140Southwest
Find Deal
Tue, Jan 21 - Tue, Jan 28
8:20 am - 11:17 amORD-BWI
1h 57mnonstop
11:51 am - 1:12 pmBWI-ORD
2h 21mnonstop
$141American Airlines
Find Deal
Tue, Feb 4 - Tue, Feb 11
6:30 pm - 9:40 pmORD-PHL
2h 10mnonstop
5:10 pm - 6:41 pmPHL-ORD
2h 31mnonstop
$181United Airlines
Find Deal
Tue, Jan 14 - Wed, Jan 15
10:50 am - 1:51 pmORD-BWI
2h 01mnonstop
5:22 pm - 6:40 pmBWI-ORD
2h 18mnonstop
$184United Airlines
Find Deal
Wed, Jan 29 - Sat, Feb 1

Frontier flights from Chicago to Maryland

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

Delta flights from Chicago to Maryland

Our best Delta deals on Chicago to Maryland flight tickets
Delta
Feb 5
MDW10:57 amChicago Midway
6h 15m
1 stop
BWI6:12 pmBaltimore/Washington
Feb 8
BWI5:15 pmBaltimore/Washington
6h 05m
1 stop
MDW10:20 pmChicago Midway
Delta
Jan 7
MDW9:34 amChicago Midway
5h 21m
1 stop
PHL3:55 pmPhiladelphia
Jan 8
PHL1:00 pmPhiladelphia
6h 14m
1 stop
MDW6:14 pmChicago Midway
Delta
Jan 6
ORD10:30 amChicago O'Hare Intl
4h 25m
1 stop
PHL3:55 pmPhiladelphia
Jan 8
PHL4:50 pmPhiladelphia
5h 03m
1 stop
ORD8:53 pmChicago 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 month to fly to Maryland?

The cheapest month to fly to Maryland from Chicago is in August. Flight prices, which tend to average around $221, are often lower during this time because this is during the off-season. If you don’t want to visit Maryland in August, then you should wait until September to fly from Chicago, when ticket prices are also cheap, with an average price of $235.

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 $338.

What is the cheapest time of day to depart on your flight to Maryland?

Our most recent data shows that the best time of day to fly to Maryland is in the morning. Flights from Chicago to Maryland during this time can be as low as $278. In contrast, the most expensive time of day to depart to Maryland is at noon when prices are around $298.

What is the cheapest Chicago to Maryland flight route?

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

How far in advance should I book a flight to Maryland?

Most flyers found that booking tickets 49 days in advance of their planned departure date is the best time to get cheap flights to Maryland. During this timeframe, flight prices are around $278. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Maryland from Chicago for as low as $173 on momondo.

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 95% 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

$29

Fastest flight time

1h 44m

Direct flights

Every day

Airports in Maryland

4 airports
The best one-way flight to Maryland from Chicago in the past 72 hours is $29. The best round-trip flight deal from Chicago to Maryland found on momondo in the last 72 hours is $58.
The fastest flight from Chicago to Maryland takes 1h 44m
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
3,469 reviews
Search Frontier flights
American AirlinesPriceFrom $120Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
Spirit AirlinesPriceFrom $135Free CancellationRating
6.3
8,113 reviews
Search Spirit Airlines flights
SouthwestPriceFrom $138Free CancellationRating
8.1
4,780 reviews
Search Southwest flights
United AirlinesPriceFrom $160Free CancellationRating
7.4
9,022 reviews
Search United Airlines flights
DeltaPriceFrom $176Free CancellationRating
8.0
8,588 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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Popular flights according to clicks in the last 7 days on momondo