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Cheap flights from Chicago to Maryland from $58

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 1/15. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
8:45 am - 11:45 am
ORD
-
BWI
2h 00mnonstop
Frontier Logo
12:40 pm - 2:07 pm
BWI
-
ORD
2h 27mnonstop
$88Frontier
Mon, Feb 2 - Mon, Feb 9
Frontier Logo
9:15 am - 6:50 pm
ORD
-
BWI
8h 35m1 stop
Frontier Logo
12:40 pm - 2:07 pm
BWI
-
ORD
2h 27mnonstop
$93Frontier
Sat, Jan 24 - Mon, Jan 26
Multiple Airlines Logo
5:15 am - 7:03 pm
ORD
-
BWI
12h 48m1 stop
Multiple Airlines Logo
12:05 pm - 1:32 pm
BWI
-
ORD
2h 27mnonstop
$97Multiple Airlines
Thu, Jan 29 - Thu, Feb 5
Multiple Airlines Logo
12:09 pm - 11:49 pm
ORD
-
BWI
10h 40m1 stop
Multiple Airlines Logo
8:07 pm - 9:31 pm
BWI
-
ORD
2h 24mnonstop
$98Multiple Airlines
Wed, Jan 7 - Thu, Jan 8
Multiple Airlines Logo
10:48 am - 11:47 pm
ORD
-
BWI
11h 59m1 stop
Multiple Airlines Logo
12:05 pm - 1:32 pm
BWI
-
ORD
2h 27mnonstop
$99Multiple Airlines
Wed, Jan 21 - Thu, Jan 29
Spirit Airlines Logo
8:43 pm - 8:47 am
ORD
-
PHL
11h 04m1 stop
Spirit Airlines Logo
1:40 pm - 9:03 pm
PHL
-
ORD
8h 23m1 stop
$115Spirit Airlines
Fri, Jan 23 - Tue, Jan 27
Southwest Logo
7:05 am - 10:00 am
MDW
-
BWI
1h 55mnonstop
Southwest Logo
1:45 pm - 2:55 pm
BWI
-
MDW
2h 10mnonstop
$139Southwest
Thu, Jan 15 - Sun, Jan 18
Southwest Logo
10:00 am - 12:55 pm
MDW
-
PHL
1h 55mnonstop
Southwest Logo
5:40 am - 7:00 am
PHL
-
MDW
2h 20mnonstop
$149Southwest
Wed, Jan 14 - Sun, Jan 18
American Airlines Logo
2:55 pm - 7:47 pm
ORD
-
SBY
3h 52m1 stop
American Airlines Logo
5:57 pm - 11:50 pm
SBY
-
ORD
6h 53m1 stop
$585American Airlines
Fri, May 1 - Sun, May 17
American Airlines Logo
1:10 pm - 7:47 pm
ORD
-
SBY
5h 37m2 stops
American Airlines Logo
12:01 pm - 3:03 pm
SBY
-
ORD
4h 02m1 stop
$872American Airlines
Fri, May 1 - Sun, May 17

Spirit Airlines flights from Chicago to Maryland

Our best Spirit Airlines deals on Chicago to Maryland flight tickets
Spirit Airlines
Jan 23
ORD8:43 pmChicago O'Hare Intl
11h 04m
1 stop
PHL8:47 amPhiladelphia
Jan 27
PHL1:40 pmPhiladelphia
8h 23m
1 stop
ORD9:03 pmChicago O'Hare Intl
$115
Find similar
Spirit Airlines
Jan 24
ORD10:48 amChicago O'Hare Intl
8h 00m
1 stop
PHL7:48 pmPhiladelphia
Jan 27
PHL1:40 pmPhiladelphia
11h 06m
1 stop
ORD11:46 pmChicago O'Hare Intl
$126
Find similar
Spirit Airlines
Jan 23
ORD8:43 pmChicago O'Hare Intl
11h 04m
1 stop
PHL8:47 amPhiladelphia
Jan 28
PHL1:40 pmPhiladelphia
8h 23m
1 stop
ORD9:03 pmChicago O'Hare Intl
$127
Find similar

United Airlines flights from Chicago to Maryland

Our best United Airlines deals on Chicago to Maryland flight tickets
United Airlines
Feb 18
ORD2:10 pmChicago O'Hare Intl
2h 04m
PHL5:14 pmPhiladelphia
Feb 25
PHL10:06 amPhiladelphia
2h 33m
ORD11:39 amChicago O'Hare Intl
$139
Find similar
United Airlines
Jan 14
ORD11:20 amChicago O'Hare Intl
2h 11m
PHL2:31 pmPhiladelphia
Jan 21
PHL5:00 pmPhiladelphia
2h 30m
ORD6:30 pmChicago O'Hare Intl
$149
Find similar
United Airlines
Jan 6
ORD6:20 pmChicago O'Hare Intl
2h 16m
PHL9:36 pmPhiladelphia
Jan 10
PHL5:00 pmPhiladelphia
2h 30m
ORD6:30 pmChicago O'Hare Intl
$159
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to Maryland 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 December 18, 2025.
Use the filters below to find and compare flights from Chicago to Maryland that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoBaltimore

ORD - BWI

ORDBWI

Chicago O'Hare Intl

Mon 2/2

8:45 am-11:45 am

Nonstop2h 00m

Baltimore/Washington

Mon 2/9

12:40 pm-2:07 pm

Nonstop2h 27m

$88

ChicagoBaltimore

ORD - BWI

ORDBWI

Chicago O'Hare Intl

Sat 1/24

9:15 am-6:50 pm

1 stop8h 35m

Baltimore/Washington

Mon 1/26

12:40 pm-2:07 pm

Nonstop2h 27m

$93

ChicagoBaltimore

ORD - BWI

ORDBWI

Chicago O'Hare Intl

Thu 1/29

5:15 am-7:03 pm

1 stop12h 48m

Baltimore/Washington

Thu 2/5

12:05 pm-1:32 pm

Nonstop2h 27m

$97

ChicagoBaltimore

ORD - BWI

ORDBWI

Chicago O'Hare Intl

Wed 1/7

12:09 pm-11:49 pm

1 stop10h 40m

Baltimore/Washington

Thu 1/8

8:07 pm-9:31 pm

Nonstop2h 24m

$98

ChicagoBaltimore

ORD - BWI

ORDBWI

Chicago O'Hare Intl

Wed 1/21

10:48 am-11:47 pm

1 stop11h 59m

Baltimore/Washington

Thu 1/29

12:05 pm-1:32 pm

Nonstop2h 27m

$99

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Fri 1/23

8:43 pm-8:47 am

1 stop11h 04m

Philadelphia

Tue 1/27

1:40 pm-9:03 pm

1 stop8h 23m

$115

ChicagoBaltimore

MDW - BWI

MDWBWI

Chicago Midway

Thu 1/15

7:05 am-10:00 am

Nonstop1h 55m

Baltimore/Washington

Sun 1/18

1:45 pm-2:55 pm

Nonstop2h 10m

$139

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Wed 1/14

10:00 am-12:55 pm

Nonstop1h 55m

Philadelphia

Sun 1/18

5:40 am-7:00 am

Nonstop2h 20m

$149

ChicagoSalisbury

ORD - SBY

ORDSBY

Chicago O'Hare Intl

Fri 5/1

2:55 pm-7:47 pm

1 stop3h 52m

Salisbury-Ocean City

Sun 5/17

5:57 pm-11:50 pm

1 stop6h 53m

$585

ChicagoSalisbury

ORD - SBY

ORDSBY

Chicago O'Hare Intl

Fri 5/1

1:10 pm-7:47 pm

2 stops5h 37m

Salisbury-Ocean City

Sun 5/17

12:01 pm-3:03 pm

1 stop4h 02m

$872

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 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 $164, 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 $183.

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

The cheapest day to depart from Chicago to Maryland is on a Friday. Travelers who choose to depart for Maryland on a Friday will often find tickets for as low as $344. The most expensive day to fly to Maryland is Sunday, with ticket prices averaging around $537.

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 $333. In contrast, the most expensive time of day to depart to Maryland is at noon when prices are around $754.

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 weeks ahead of your departure date. In general, you can expect to find flights to Maryland for around $311 when searching 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 $254 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?

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

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

$95

Fastest flight time

1h 45m

Direct flights

Every day

Airports in Maryland

112 airports
The best one-way flight to Maryland from Chicago in the past 72 hours is $95. The best round-trip flight deal from Chicago to Maryland found on momondo in the last 72 hours is $151.
The fastest flight from Chicago to Maryland takes 1h 45m
Direct flights go from Chicago to Maryland every day.
There are 112 airports in Maryland. From Chicago there are direct flights to Washington, D.C. Reagan-National (DCA), Baltimore/Washington (BWI), Philadelphia (PHL).
Search flight deals

  • 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
Spirit AirlinesPriceFrom $45Free CancellationRating
6.3
8,190 reviews
Search Spirit Airlines flights
FrontierPriceFrom $58Free CancellationRating
5.8
3,081 reviews
Search Frontier flights
United AirlinesPriceFrom $142Free CancellationRating
7.4
9,091 reviews
Search United Airlines flights
American AirlinesPriceFrom $149Free CancellationRating
7.2
11,054 reviews
Search American Airlines flights
SouthwestPriceFrom $157Free CancellationRating
7.9
4,250 reviews
Search Southwest 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.

An easier way to manage your Maryland trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
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Sat 1/17
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Find better results for your trip to Maryland

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