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Cheap flights from Chicago to Maryland from $38

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 5/28. 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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0 bags

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Cheap round-trip flights

KAYAK's recommended round-trip deals from the most popular airlines that fly from Chicago to Maryland.
Frontier Logo
2:53 pm - 5:46 pmMDW-BWI
1h 53mnonstop
Frontier Logo
6:36 pm - 7:43 pmBWI-MDW
2h 07mnonstop
$87Frontier
Find Deal
Wed, May 28 - Fri, May 30
Frontier Logo
2:44 pm - 5:42 pmMDW-BWI
1h 58mnonstop
Frontier Logo
6:27 pm - 7:31 pmBWI-MDW
2h 04mnonstop
$96Frontier
Find Deal
Fri, Jun 6 - Wed, Jun 11
United Airlines Logo
7:10 am - 10:13 amORD-BWI
2h 03mnonstop
United Airlines Logo
6:40 am - 7:55 amBWI-ORD
2h 15mnonstop
$161United Airlines
Find Deal
Sat, May 24 - Sun, May 25
Southwest Logo
5:45 am - 8:30 amMDW-BWI
1h 45mnonstop
Southwest Logo
7:40 am - 8:40 amBWI-MDW
2h 00mnonstop
$161Southwest
Find Deal
Sat, May 24 - Sun, May 25
Southwest Logo
6:20 pm - 9:15 pmMDW-PHL
1h 55mnonstop
Southwest Logo
3:15 pm - 4:25 pmPHL-MDW
2h 10mnonstop
$161Southwest
Find Deal
Sat, May 24 - Sun, May 25
American Airlines Logo
8:22 am - 11:23 amORD-PHL
2h 01mnonstop
American Airlines Logo
6:55 pm - 8:33 pmPHL-ORD
2h 38mnonstop
$161American Airlines
Find Deal
Sun, May 25 - Sun, May 25
American Airlines Logo
5:40 pm - 8:40 pmORD-PHL
2h 00mnonstop
American Airlines Logo
7:20 am - 8:46 amPHL-ORD
2h 26mnonstop
$169American Airlines
Find Deal
Sat, May 24 - Tue, May 27
United Airlines Logo
9:31 pm - 12:30 amORD-IAD
1h 59mnonstop
United Airlines Logo
8:25 am - 9:38 amIAD-ORD
2h 13mnonstop
$195United Airlines
Find Deal
Sat, May 24 - Mon, May 26
Delta Logo
12:44 pm - 8:43 pmMDW-BWI
6h 59m1 stop
Delta Logo
6:00 am - 8:40 amBWI-MDW
3h 40m1 stop
$197Delta
Find Deal
Thu, Jul 3 - Wed, Jul 9
Delta Logo
5:55 pm - 12:49 amORD-BWI
5h 54m1 stop
Delta Logo
6:00 am - 9:18 amBWI-ORD
4h 18m1 stop
$197Delta
Find Deal
Sat, May 24 - Sun, May 25

Southwest flights from Chicago to Maryland

Our best Southwest deals on Chicago to Maryland flight tickets
Southwest
May 24
MDW6:20 pmChicago Midway
1h 55m
PHL9:15 pmPhiladelphia
May 25
PHL3:15 pmPhiladelphia
2h 10m
MDW4:25 pmChicago Midway
Southwest
Jul 4
MDW5:35 pmChicago Midway
2h 00m
PHL8:35 pmPhiladelphia
Jul 9
PHL5:55 amPhiladelphia
2h 05m
MDW7:00 amChicago Midway
Southwest
Jun 15
MDW5:15 amChicago Midway
1h 45m
BWI8:00 amBaltimore/Washington
Jun 17
BWI5:40 pmBaltimore/Washington
3h 55m
1 stop
MDW8:35 pmChicago Midway

JetBlue flights from Chicago to Maryland

Our best JetBlue deals on Chicago to Maryland flight tickets
JetBlue
May 20
ORD4:03 pmChicago O'Hare Intl
5h 55m
1 stop
DCA10:58 pmWashington, D.C. Reagan-National
May 21
DCA12:45 pmWashington, D.C. Reagan-National
6h 51m
1 stop
ORD6:36 pmChicago O'Hare Intl
JetBlue
Jul 8
ORD8:40 amChicago O'Hare Intl
8h 19m
1 stop
DCA5:59 pmWashington, D.C. Reagan-National
Jul 15
DCA10:30 amWashington, D.C. Reagan-National
7h 26m
1 stop
ORD4:56 pmChicago O'Hare Intl
JetBlue
May 7
ORD10:50 amChicago O'Hare Intl
4h 48m
1 stop
PHL4:38 pmPhiladelphia
May 14
PHL10:16 amPhiladelphia
9h 20m
1 stop
ORD6:36 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 September. Flight prices, which tend to average around $199, are often lower during this time because this is during the off-season. If you don’t want to visit Maryland in September, then you should wait until August to fly from Chicago, when ticket prices are also cheap, with an average price of $203.

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

The cheapest day to depart from Chicago to Maryland is on a Thursday. Travelers who choose to depart for Maryland on a Thursday will often find tickets for as low as $299. The most expensive day to fly to Maryland is Monday, with ticket prices averaging around $433.

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 $305. In contrast, the most expensive time of day to depart to Maryland is at noon when prices are around $595.

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?

You are more likely to see cheaper flights to Maryland from Chicago when booking 4 weeks ahead of your departure date. In general, you can expect to find flights to Maryland for around $307 when searching 4 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Maryland from Chicago for as low as $240 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.

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

$38

Fastest flight time

1h 40m

Direct flights

Every day

Airports in Maryland

4 airports
The best one-way flight to Maryland from Chicago in the past 72 hours is $38. The best round-trip flight deal from Chicago to Maryland found on momondo in the last 72 hours is $87.
The fastest flight from Chicago to Maryland takes 1h 40m
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 $68Free CancellationRating
5.9
3,283 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $101Free CancellationRating
6.3
7,942 reviews
Search Spirit Airlines flights
American AirlinesPriceFrom $122Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
SouthwestPriceFrom $140Free CancellationRating
8.0
4,287 reviews
Search Southwest flights
United AirlinesPriceFrom $173Free CancellationRating
7.4
8,685 reviews
Search United Airlines flights
DeltaPriceFrom $176Free CancellationRating
8.0
7,920 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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