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Cheap flights from Chicago to Maryland from $90

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 5/14. 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
6:00 am - 4:58 pm
MDW
-
BWI
9h 58m
1 stop
Frontier Logo
9:59 pm - 3:57 pm
BWI
-
MDW
18h 58m
1 stop
$151Frontier
Sat, May 2 - Thu, May 7
Frontier Logo
4:28 pm - 12:44 am
ORD
-
BWI
7h 16m
1 stop
Frontier Logo
2:42 pm - 11:59 pm
BWI
-
ORD
10h 17m
1 stop
$151Frontier
Mon, Apr 27 - Sun, May 3
Frontier Logo
2:15 pm - 12:44 am
MDW
-
BWI
9h 29m
1 stop
Frontier Logo
5:35 pm - 4:13 pm
BWI
-
MDW
23h 38m
1 stop
$152Frontier
Wed, Apr 29 - Fri, May 1
Frontier Logo
5:45 pm - 10:51 am
ORD
-
BWI
16h 06m
1 stop
Frontier Logo
9:57 am - 9:27 am
BWI
-
ORD
24h 30m
1 stop
$152Frontier
Thu, May 7 - Sat, May 9
Spirit Airlines Logo
1:18 pm - 11:58 pm
ORD
-
PHL
9h 40m
1 stop
Spirit Airlines Logo
8:44 pm - 8:22 am
PHL
-
ORD
12h 38m
1 stop
$190Spirit Airlines
Sat, May 30 - Sun, May 31
Southwest Logo
2:40 pm - 11:00 pm
ORD
-
DCA
7h 20m
2 stops
Southwest Logo
6:00 am - 12:50 pm
DCA
-
ORD
7h 50m
1 stop
$208Southwest
Tue, May 19 - Wed, May 20
Southwest Logo
1:05 pm - 3:55 pm
MDW
-
DCA
1h 50mnonstop
Southwest Logo
12:00 pm - 5:05 pm
DCA
-
MDW
6h 05m
1 stop
$208Southwest
Sat, May 2 - Wed, May 6
United Airlines Logo
4:25 pm - 7:28 pm
ORD
-
IAD
2h 03mnonstop
United Airlines Logo
6:15 am - 7:26 am
IAD
-
ORD
2h 11mnonstop
$218United Airlines
Wed, May 6 - Mon, May 11
United Airlines Logo
11:15 am - 2:14 pm
ORD
-
DCA
1h 59mnonstop
United Airlines Logo
7:30 am - 8:47 am
DCA
-
ORD
2h 17mnonstop
$219United Airlines
Thu, May 14 - Mon, May 18
American Airlines Logo
6:08 am - 9:05 am
ORD
-
DCA
1h 57mnonstop
American Airlines Logo
5:55 am - 7:24 am
DCA
-
ORD
2h 29mnonstop
$220American Airlines
Thu, May 14 - Mon, May 18

Spirit Airlines flights from Chicago to Maryland

Our best Spirit Airlines deals on Chicago to Maryland flight tickets
Spirit Airlines
May 8
ORD7:33 pmChicago O'Hare Intl
12h 02m
1 stop
BWI8:35 amBaltimore/Washington
May 10
BWI7:27 pmBaltimore/Washington
13h 55m
1 stop
ORD8:22 amChicago O'Hare Intl
$165
Spirit Airlines
May 8
ORD7:33 pmChicago O'Hare Intl
12h 02m
1 stop
BWI8:35 amBaltimore/Washington
May 15
BWI7:48 pmBaltimore/Washington
13h 34m
1 stop
ORD8:22 amChicago O'Hare Intl
$179
Spirit Airlines
Apr 15
ORD7:15 pmChicago O'Hare Intl
13h 34m
1 stop
PHL9:49 amPhiladelphia
Apr 18
PHL6:12 pmPhiladelphia
7h 12m
1 stop
ORD12:24 amChicago O'Hare Intl
$186

Southwest flights from Chicago to Maryland

Our best Southwest deals on Chicago to Maryland flight tickets
Southwest
May 6
MDW5:00 pmChicago Midway
1h 50m
BWI7:50 pmBaltimore/Washington
May 13
BWI6:30 amBaltimore/Washington
2h 05m
MDW7:35 amChicago Midway
$177
Southwest
May 2
MDW5:25 pmChicago Midway
1h 50m
BWI8:15 pmBaltimore/Washington
May 12
BWI6:30 amBaltimore/Washington
2h 05m
MDW7:35 amChicago Midway
$179
Southwest
May 5
MDW12:45 pmChicago Midway
3h 55m
1 stop
BWI5:40 pmBaltimore/Washington
May 12
BWI9:35 amBaltimore/Washington
2h 05m
MDW10:40 amChicago Midway
$183

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 April 11, 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

Cheapest round-trip

ChicagoBaltimore

MDW - BWI

MDWBWI

Chicago Midway

Sat 5/2

6:00 am-4:58 pm

1 stop9h 58m

Baltimore/Washington

Thu 5/7

9:59 pm-3:57 pm

1 stop18h 58m

$151

ChicagoBaltimore

ORD - BWI

ORDBWI

Chicago O'Hare Intl

Mon 4/27

4:28 pm-12:44 am

1 stop7h 16m

Baltimore/Washington

Sun 5/3

2:42 pm-11:59 pm

1 stop10h 17m

$151

ChicagoBaltimore

MDW - BWI

MDWBWI

Chicago Midway

Wed 4/29

2:15 pm-12:44 am

1 stop9h 29m

Baltimore/Washington

Fri 5/1

5:35 pm-4:13 pm

1 stop23h 38m

$152

ChicagoBaltimore

ORD - BWI

ORDBWI

Chicago O'Hare Intl

Thu 5/7

5:45 pm-10:51 am

1 stop16h 06m

Baltimore/Washington

Sat 5/9

9:57 am-9:27 am

1 stop24h 30m

$152

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Sat 5/30

1:18 pm-11:58 pm

1 stop9h 40m

Philadelphia

Sun 5/31

8:44 pm-8:22 am

1 stop12h 38m

$190

ChicagoWashington, D.C.

ORD - DCA

ORDDCA

Chicago O'Hare Intl

Tue 5/19

2:40 pm-11:00 pm

2 stops7h 20m

Washington, D.C. Reagan-National

Wed 5/20

6:00 am-12:50 pm

1 stop7h 50m

$208

ChicagoWashington, D.C.

MDW - DCA

MDWDCA

Chicago Midway

Sat 5/2

1:05 pm-3:55 pm

Nonstop1h 50m

Washington, D.C. Reagan-National

Wed 5/6

12:00 pm-5:05 pm

1 stop6h 05m

$208
Quickest round-trip

ChicagoWashington, D.C.

ORD - IAD

ORDIAD

Chicago O'Hare Intl

Wed 5/6

4:25 pm-7:28 pm

Nonstop2h 03m

Washington, D.C. Dulles Intl

Mon 5/11

6:15 am-7:26 am

Nonstop2h 11m

$218

ChicagoWashington, D.C.

ORD - DCA

ORDDCA

Chicago O'Hare Intl

Thu 5/14

11:15 am-2:14 pm

Nonstop1h 59m

Washington, D.C. Reagan-National

Mon 5/18

7:30 am-8:47 am

Nonstop2h 17m

$219

ChicagoWashington, D.C.

ORD - DCA

ORDDCA

Chicago O'Hare Intl

Thu 5/14

6:08 am-9:05 am

Nonstop1h 57m

Washington, D.C. Reagan-National

Mon 5/18

5:55 am-7:24 am

Nonstop2h 29m

$220

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 $167, 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 $181.

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 $366. The most expensive day to fly to Maryland is Sunday, with ticket prices averaging around $600.

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 $370. In contrast, the most expensive time of day to depart to Maryland is at noon when prices are around $803.

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 $332 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 $247 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 7% 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

$153

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 $153. The best round-trip flight deal from Chicago to Maryland found on momondo in the last 72 hours is $237.
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).
Search flight deals

Frequently asked questions about flying from Chicago to Maryland

  • 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
8,609 reviews
Search Spirit Airlines flights
FrontierPriceFrom $57Free CancellationRating
5.7
2,998 reviews
Search Frontier flights
United AirlinesPriceFrom $114Free CancellationRating
7.4
9,569 reviews
Search United Airlines flights
American AirlinesPriceFrom $152Free CancellationRating
7.1
11,569 reviews
Search American Airlines flights
SouthwestPriceFrom $157Free CancellationRating
8.0
4,335 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

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