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Cheap flights from Chicago to Maryland from $66

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 4/27. 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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Find the cheapest flights from Chicago to Maryland

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
8:00 am - 11:06 am
ORD
-
BWI
2h 06mnonstop
Frontier Logo
4:55 pm - 6:18 pm
BWI
-
ORD
2h 23mnonstop
$103Frontier
Wed, Apr 1 - Wed, Apr 8
Frontier Logo
12:25 pm - 3:30 pm
ORD
-
BWI
2h 05mnonstop
Frontier Logo
4:25 pm - 5:51 pm
BWI
-
ORD
2h 26mnonstop
$106Frontier
Fri, May 1 - Mon, May 4
Multiple Airlines Logo
5:15 am - 8:24 am
ORD
-
BWI
2h 09mnonstop
Multiple Airlines Logo
12:30 pm - 9:13 pm
BWI
-
ORD
9h 43m
1 stop
$116Multiple Airlines
Thu, Mar 5 - Sun, Mar 8
Southwest Logo
7:40 am - 10:35 am
MDW
-
PHL
1h 55mnonstop
Southwest Logo
3:45 pm - 5:00 pm
PHL
-
MDW
2h 15mnonstop
$147Southwest
Sat, Apr 18 - Sat, Apr 25
United Airlines Logo
1:06 pm - 4:09 pm
ORD
-
IAD
2h 03mnonstop
United Airlines Logo
10:31 pm - 11:44 pm
IAD
-
ORD
2h 13mnonstop
$155United Airlines
Wed, Mar 11 - Sat, Mar 14
Southwest Logo
7:40 am - 10:35 am
MDW
-
PHL
1h 55mnonstop
Southwest Logo
2:15 pm - 3:25 pm
PHL
-
MDW
2h 10mnonstop
$162Southwest
Sat, Apr 18 - Thu, Apr 30
Multiple Airlines Logo
9:28 am - 12:31 am
ORD
-
IAD
14h 03m
1 stop
Multiple Airlines Logo
7:00 am - 5:15 pm
IAD
-
ORD
11h 15m
2 stops
$163Multiple Airlines
Tue, Mar 10 - Tue, Mar 17
American Airlines Logo
6:08 am - 8:59 am
ORD
-
DCA
1h 51mnonstop
American Airlines Logo
6:00 am - 7:25 am
DCA
-
ORD
2h 25mnonstop
$166American Airlines
Sat, Mar 14 - Sat, Mar 21
American Airlines Logo
8:00 am - 1:44 pm
ORD
-
DCA
4h 44m
1 stop
American Airlines Logo
7:50 pm - 9:15 pm
DCA
-
ORD
2h 25mnonstop
$173American Airlines
Wed, Mar 11 - Sat, Mar 14
United Airlines Logo
6:00 am - 8:51 am
ORD
-
DCA
1h 51mnonstop
United Airlines Logo
6:30 am - 7:50 am
DCA
-
ORD
2h 20mnonstop
$197United Airlines
Wed, Mar 18 - Tue, Mar 24

Frontier flights from Chicago to Maryland

Our best Frontier deals on Chicago to Maryland flight tickets
Frontier
Apr 1
ORD8:00 amChicago O'Hare Intl
2h 06m
BWI11:06 amBaltimore/Washington
Apr 8
BWI4:55 pmBaltimore/Washington
2h 23m
ORD6:18 pmChicago O'Hare Intl
$103
Frontier
May 1
ORD12:25 pmChicago O'Hare Intl
2h 05m
BWI3:30 pmBaltimore/Washington
May 4
BWI4:25 pmBaltimore/Washington
2h 26m
ORD5:51 pmChicago O'Hare Intl
$106
Frontier
Mar 9
ORD12:38 pmChicago O'Hare Intl
2h 09m
BWI3:47 pmBaltimore/Washington
Mar 10
BWI3:19 pmBaltimore/Washington
18h 04m
1 stop
ORD8:23 amChicago O'Hare Intl
$108

Spirit Airlines flights from Chicago to Maryland

Our best Spirit Airlines deals on Chicago to Maryland flight tickets
Spirit Airlines
Mar 17
ORD6:10 pmChicago O'Hare Intl
13h 29m
1 stop
PHL8:39 amPhiladelphia
Mar 24
PHL6:48 amPhiladelphia
14h 03m
1 stop
ORD7:51 pmChicago O'Hare Intl
$152
Spirit Airlines
Mar 5
ORD7:00 amChicago O'Hare Intl
11h 52m
1 stop
PHL7:52 pmPhiladelphia
Mar 11
PHL8:06 amPhiladelphia
12h 05m
1 stop
ORD7:11 pmChicago O'Hare Intl
$160
Spirit Airlines
Mar 4
ORD8:16 pmChicago O'Hare Intl
11h 28m
1 stop
PHL8:44 amPhiladelphia
Mar 11
PHL5:26 pmPhiladelphia
7h 21m
1 stop
ORD11:47 pmChicago O'Hare Intl
$161

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 February 19, 2026.
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

Wed 4/1

8:00 am-11:06 am

Nonstop2h 06m

Baltimore/Washington

Wed 4/8

4:55 pm-6:18 pm

Nonstop2h 23m

$103

ChicagoBaltimore

ORD - BWI

ORDBWI

Chicago O'Hare Intl

Fri 5/1

12:25 pm-3:30 pm

Nonstop2h 05m

Baltimore/Washington

Mon 5/4

4:25 pm-5:51 pm

Nonstop2h 26m

$106

ChicagoBaltimore

ORD - BWI

ORDBWI

Chicago O'Hare Intl

Thu 3/5

5:15 am-8:24 am

Nonstop2h 09m

Baltimore/Washington

Sun 3/8

12:30 pm-9:13 pm

1 stop9h 43m

$116

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Sat 4/18

7:40 am-10:35 am

Nonstop1h 55m

Philadelphia

Sat 4/25

3:45 pm-5:00 pm

Nonstop2h 15m

$147

ChicagoWashington, D.C.

ORD - IAD

ORDIAD

Chicago O'Hare Intl

Wed 3/11

1:06 pm-4:09 pm

Nonstop2h 03m

Washington, D.C. Dulles Intl

Sat 3/14

10:31 pm-11:44 pm

Nonstop2h 13m

$155

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Sat 4/18

7:40 am-10:35 am

Nonstop1h 55m

Philadelphia

Thu 4/30

2:15 pm-3:25 pm

Nonstop2h 10m

$162

ChicagoWashington, D.C.

ORD - IAD

ORDIAD

Chicago O'Hare Intl

Tue 3/10

9:28 am-12:31 am

1 stop14h 03m

Washington, D.C. Dulles Intl

Tue 3/17

7:00 am-5:15 pm

2 stops11h 15m

$163

ChicagoWashington, D.C.

ORD - DCA

ORDDCA

Chicago O'Hare Intl

Sat 3/14

6:08 am-8:59 am

Nonstop1h 51m

Washington, D.C. Reagan-National

Sat 3/21

6:00 am-7:25 am

Nonstop2h 25m

$166

ChicagoWashington, D.C.

ORD - DCA

ORDDCA

Chicago O'Hare Intl

Wed 3/11

8:00 am-1:44 pm

1 stop4h 44m

Washington, D.C. Reagan-National

Sat 3/14

7:50 pm-9:15 pm

Nonstop2h 25m

$173

ChicagoWashington, D.C.

ORD - DCA

ORDDCA

Chicago O'Hare Intl

Wed 3/18

6:00 am-8:51 am

Nonstop1h 51m

Washington, D.C. Reagan-National

Tue 3/24

6:30 am-7:50 am

Nonstop2h 20m

$197

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 $182.

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 $356. The most expensive day to fly to Maryland is Sunday, with ticket prices averaging around $547.

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 $342. In contrast, the most expensive time of day to depart to Maryland is at noon when prices are around $786.

What is the cheapest Chicago to Maryland flight route?

Fly from Chicago O'Hare Intl 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 $326 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 $258 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

$89

Fastest flight time

1h 41m

Direct flights

Every day

Airports in Maryland

112 airports
The best one-way flight to Maryland from Chicago in the past 72 hours is $89. The best round-trip flight deal from Chicago to Maryland found on momondo in the last 72 hours is $158.
The fastest flight from Chicago to Maryland takes 1h 41m
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), Washington, D.C. Dulles Intl (IAD).
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 $42Free CancellationRating
6.3
8,478 reviews
Search Spirit Airlines flights
FrontierPriceFrom $57Free CancellationRating
5.7
3,046 reviews
Search Frontier flights
United AirlinesPriceFrom $114Free CancellationRating
7.4
9,325 reviews
Search United Airlines flights
American AirlinesPriceFrom $148Free CancellationRating
7.2
11,321 reviews
Search American Airlines flights
SouthwestPriceFrom $158Free CancellationRating
8.0
4,295 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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