What is the cheapest airline that flies from Chicago to Maryland?

Frontier, Spirit Airlines, and Southwest are the most popular carriers operating from Chicago to Maryland

How many flights depart from Chicago to Maryland on average per day?

As of November 2025, there are 123 flights per day flying from Chicago to Maryland. The most common time of day flights depart is 8:00PM, with 42% of flights taking off in the evening.

How many flights depart from Chicago to Maryland on average per week?

864 flights are operational weekly from Chicago to Maryland as of November 2025. The most popular departure day for this route is Mon, with 18% of flights per week taking off on this day.

What airlines fly to Maryland?

United Airlines, Frontier and Southwest are the top three most popular airlines that fly to Maryland from Chicago according to our data. United Airlines is the first choice among our users, with 31% of people opting to fly with this airline when traveling to Maryland. Keep in mind that there are 5 different airlines that fly to Maryland on a routine basis, so you have a few additional options to choose from.

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?

The number of operators available for flights from Chicago to Maryland is 7 as of November 2025.

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.

$54 Cheap Flights from Chicago to Maryland in 2025/26

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Find the cheapest flights from Chicago to Maryland

Round-trip

One-way

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Cheap round-trip flights

Enter your travel dates to find the best prices.

5:11 am - 8:18 amORD-BWI

2h 07mnonstop

9:37 am - 10:55 amBWI-ORD

2h 18mnonstop

$96Frontier

Find Deal

Sun, Dec 7 - Tue, Dec 23

12:25 pm - 3:21 pmMDW-BWI

1h 56mnonstop

4:06 pm - 5:15 pmBWI-MDW

2h 09mnonstop

$98Frontier

Find Deal

Sat, Nov 22 - Mon, Nov 24

5:05 am - 5:47 pmORD-BWI

11h 42m1 stop

3:31 pm - 4:55 pmBWI-ORD

2h 24mnonstop

$98Frontier

Find Deal

Fri, Jan 9 - Sun, Jan 11

10:18 am - 8:32 pmORD-BWI

9h 14m1 stop

3:31 pm - 9:23 pmBWI-ORD

6h 52m1 stop

$111Spirit Airlines

Find Deal

Fri, Feb 20 - Mon, Feb 23

5:10 am - 2:15 pmORD-PHL

8h 05m1 stop

3:10 pm - 12:27 amPHL-ORD

10h 17m1 stop

$114Spirit Airlines

Find Deal

Tue, Nov 18 - Wed, Nov 19

11:05 am - 2:00 pmMDW-PHL

1h 55mnonstop

6:15 pm - 7:25 pmPHL-MDW

2h 10mnonstop

$139Southwest

Find Deal

Tue, Dec 2 - Tue, Dec 9

2:30 pm - 5:39 pmORD-PHL

2h 09mnonstop

5:07 pm - 6:35 pmPHL-ORD

2h 28mnonstop

$139United Airlines

Find Deal

Sat, Dec 6 - Tue, Dec 9

7:05 pm - 9:55 pmMDW-BWI

1h 50mnonstop

7:40 am - 9:00 amBWI-MDW

2h 20mnonstop

$148Southwest

Find Deal

Fri, Jan 16 - Mon, Jan 19

5:00 am - 7:57 amORD-PHL

1h 57mnonstop

9:25 pm - 10:56 pmPHL-ORD

2h 31mnonstop

$161American Airlines

Find Deal

Thu, Nov 27 - Tue, Dec 2

1:35 pm - 7:36 pmORD-DCA

5h 01m1 stop

9:13 pm - 10:34 pmDCA-ORD

2h 21mnonstop

$212American Airlines

Find Deal

Sun, Feb 8 - Sun, Feb 8

United Airlines flights from Chicago to Maryland

Our best United Airlines deals on Chicago to Maryland flight tickets

United Airlines

Dec 6

ORD2:30 pmChicago O'Hare Intl

2h 09m

PHL5:39 pmPhiladelphia

Dec 9

PHL5:07 pmPhiladelphia

2h 28m

ORD6:35 pmChicago O'Hare Intl

$139

Find similar

United Airlines

Nov 8

ORD7:25 amChicago O'Hare Intl

1h 59m

PHL10:24 amPhiladelphia

Dec 6

PHL5:07 pmPhiladelphia

2h 29m

ORD6:36 pmChicago O'Hare Intl

$234

Find similar

Spirit Airlines flights from Chicago to Maryland

Our best Spirit Airlines deals on Chicago to Maryland flight tickets

Spirit Airlines

Feb 20

ORD10:18 amChicago O'Hare Intl

9h 14m

1 stop

BWI8:32 pmBaltimore/Washington

Feb 23

BWI3:31 pmBaltimore/Washington

6h 52m

1 stop

ORD9:23 pmChicago O'Hare Intl

$111

Find similar

Spirit Airlines

Nov 18

ORD5:10 amChicago O'Hare Intl

8h 05m

1 stop

PHL2:15 pmPhiladelphia

Nov 19

PHL3:10 pmPhiladelphia

10h 17m

1 stop

ORD12:27 amChicago O'Hare Intl

$114

Find similar

Spirit Airlines

Nov 18

ORD10:52 amChicago O'Hare Intl

11h 34m

1 stop

PHL11:26 pmPhiladelphia

Nov 19

PHL6:00 amPhiladelphia

28h 01m

2 stops

ORD9:01 amChicago O'Hare Intl

$159

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoBaltimore

ORD - BWI

ORDBWI

Chicago O'Hare Intl

Sun 12/7

5:11 am-8:18 am

Nonstop2h 07m

Baltimore/Washington

Tue 12/23

9:37 am-10:55 am

Nonstop2h 18m

$96

ChicagoBaltimore

MDW - BWI

MDWBWI

Chicago Midway

Sat 11/22

12:25 pm-3:21 pm

Nonstop1h 56m

Baltimore/Washington

Mon 11/24

4:06 pm-5:15 pm

Nonstop2h 09m

$98

ChicagoBaltimore

ORD - BWI

ORDBWI

Chicago O'Hare Intl

Fri 1/9

5:05 am-5:47 pm

1 stop11h 42m

Baltimore/Washington

Sun 1/11

3:31 pm-4:55 pm

Nonstop2h 24m

$98

ChicagoBaltimore

ORD - BWI

ORDBWI

Chicago O'Hare Intl

Fri 2/20

10:18 am-8:32 pm

1 stop9h 14m

Baltimore/Washington

Mon 2/23

3:31 pm-9:23 pm

1 stop6h 52m

$111

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Tue 11/18

5:10 am-2:15 pm

1 stop8h 05m

Philadelphia

Wed 11/19

3:10 pm-12:27 am

1 stop10h 17m

$114

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Tue 12/2

11:05 am-2:00 pm

Nonstop1h 55m

Philadelphia

Tue 12/9

6:15 pm-7:25 pm

Nonstop2h 10m

$139

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Sat 12/6

2:30 pm-5:39 pm

Nonstop2h 09m

Philadelphia

Tue 12/9

5:07 pm-6:35 pm

Nonstop2h 28m

$139

ChicagoBaltimore

MDW - BWI

MDWBWI

Chicago Midway

Fri 1/16

7:05 pm-9:55 pm

Nonstop1h 50m

Baltimore/Washington

Mon 1/19

7:40 am-9:00 am

Nonstop2h 20m

$148

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Thu 11/27

5:00 am-7:57 am

Nonstop1h 57m

Philadelphia

Tue 12/2

9:25 pm-10:56 pm

Nonstop2h 31m

$161

ChicagoWashington, D.C.

ORD - DCA

ORDDCA

Chicago O'Hare Intl

Sun 2/8

1:35 pm-7:36 pm

1 stop5h 01m

Washington, D.C. Reagan-National

Sun 2/8

9:13 pm-10:34 pm

Nonstop2h 21m

$212

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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

Prices

Airlines

Other information

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 $184.

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 $325. The most expensive day to fly to Maryland is Monday, with ticket prices averaging around $498.

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 $326. In contrast, the most expensive time of day to depart to Maryland is at noon when prices are around $723.

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 $304 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 $241 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	$85
Fastest flight time	1h 44m
Direct flights	Every day
Airports in Maryland	3 airports

The best one-way flight to Maryland from Chicago in the past 72 hours is $85. The best round-trip flight deal from Chicago to Maryland found on momondo in the last 72 hours is $147.

The fastest flight from Chicago to Maryland takes 1h 44m

Direct flights go from Chicago to Maryland every day.

There are 3 airports near Maryland: 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?
The number of operators available for flights from Chicago to Maryland is 7 as of November 2025.
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?
Based on momondo bookings for flights between Chicago and Maryland, the leading plane model is Airbus A320neo, making up 11.10% of the total bookings. Other popular models include Boeing 737-900 with 10.35%, Airbus A320-100/200 with 9.24%, and Airbus A319 with 9.09%.

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 Airlines	PriceFrom $45	Free Cancellation	Rating 6.3 8,115 reviews	Search Spirit Airlines flights
Frontier	PriceFrom $63	Free Cancellation	Rating 5.8 3,117 reviews	Search Frontier flights
United Airlines	PriceFrom $143	Free Cancellation	Rating 7.4 8,997 reviews	Search United Airlines flights
American Airlines	PriceFrom $147	Free Cancellation	Rating 7.2 11,038 reviews	Search American Airlines flights
Southwest	PriceFrom $157	Free Cancellation	Rating 8.0 4,238 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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Popular cities in Maryland

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Cheap flights from Chicago to Maryland from $54

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 1/7. 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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Filter for what you want

Filter for what you want

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Find the cheapest flights from Chicago to Maryland

Cheap round-trip flights

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United Airlines flights from Chicago to Maryland

Our best United Airlines deals on Chicago to Maryland flight tickets

Spirit Airlines flights from Chicago to Maryland

Our best Spirit Airlines deals on Chicago to Maryland flight tickets

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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?

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 $325. The most expensive day to fly to Maryland is Monday, with ticket prices averaging around $498.

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 $326. In contrast, the most expensive time of day to depart to Maryland is at noon when prices are around $723.

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?

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.

What is the cheapest airline that flies from Chicago to Maryland?

Frontier, Spirit Airlines, and Southwest are the most popular carriers operating from Chicago to Maryland

What airlines fly to Maryland?

How many flights depart from Chicago to Maryland on average per day?

As of November 2025, there are 123 flights per day flying from Chicago to Maryland. The most common time of day flights depart is 8:00PM, with 42% of flights taking off in the evening.

How many flights depart from Chicago to Maryland on average per week?

864 flights are operational weekly from Chicago to Maryland as of November 2025. The most popular departure day for this route is Mon, with 18% of flights per week taking off on this day.

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

Fastest flight time

Direct flights

Airports in Maryland

When did momondo last update prices for flights from Chicago to Maryland?

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?

What documentation or ID do you need to fly to Maryland?

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

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Maryland?

Can I find flights from Chicago to Maryland with flexible booking policies on momondo?

How can momondo help me find flights from Chicago to Maryland?

I’m not ready to book a flight from Chicago to Maryland right now. Can momondo alert me if prices 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.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to Maryland

Popular cities in Maryland

Popular flights according to clicks in the last 7 days on momondo