What airlines fly to Maryland?

United Airlines, Southwest and American Airlines 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 32% 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.

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

776 flights are operational weekly from Chicago to Maryland as of July 2025. The most popular departure day for this route is Thu, with 23% of flights per week taking off on this day.

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

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

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

As of July 2025, there are 110 flights per day flying from Chicago to Maryland. The most common time of day flights depart is 7:00PM, with 37% of flights taking off in the evening.

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 6 as of July 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.

$39 Cheap Flights from Chicago to Maryland in 2025

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Find the cheapest flights from Chicago to Maryland

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

7:10 pm - 10:13 pmORD-BWI

2h 03mnonstop

10:58 pm - 12:14 amBWI-ORD

2h 16mnonstop

$59Frontier

Find Deal

Fri, Oct 17 - Mon, Oct 20

6:10 am - 9:02 amORD-BWI

1h 52mnonstop

9:57 am - 11:10 amBWI-ORD

2h 13mnonstop

$69Spirit Airlines

Find Deal

Thu, Oct 23 - Mon, Oct 27

12:05 pm - 11:59 pmORD-PHL

10h 54m1 stop

10:21 am - 11:52 amPHL-ORD

2h 31mnonstop

$154

Find Deal

Thu, Oct 2 - Thu, Oct 16

6:20 am - 9:26 amORD-PHL

2h 06mnonstop

9:47 am - 9:19 pmPHL-ORD

12h 32m1 stop

$158

Find Deal

Fri, Oct 24 - Sun, Oct 26

8:35 am - 11:30 amMDW-BWI

1h 55mnonstop

10:10 am - 11:10 amBWI-MDW

2h 00mnonstop

$161Southwest

Find Deal

Wed, Sep 10 - Sat, Sep 13

9:35 am - 12:25 pmMDW-BWI

1h 50mnonstop

7:30 am - 8:30 amBWI-MDW

2h 00mnonstop

$169Southwest

Find Deal

Sat, Aug 30 - Sun, Aug 31

7:24 pm - 10:38 pmORD-PHL

2h 14mnonstop

6:00 am - 7:25 amPHL-ORD

2h 25mnonstop

$177American Airlines

Find Deal

Sat, Aug 30 - Sun, Aug 31

11:30 am - 2:24 pmORD-DCA

1h 54mnonstop

3:28 pm - 7:05 pmDCA-ORD

4h 37m1 stop

$193American Airlines

Find Deal

Wed, Sep 10 - Wed, Sep 10

9:00 am - 11:59 amORD-DCA

1h 59mnonstop

6:00 pm - 7:15 pmDCA-ORD

2h 15mnonstop

$217United Airlines

Find Deal

Tue, Aug 26 - Tue, Sep 2

8:50 am - 11:55 amORD-IAD

2h 05mnonstop

6:40 pm - 7:48 pmIAD-ORD

2h 08mnonstop

$217United Airlines

Find Deal

Thu, Aug 28 - Tue, Sep 2

Frontier flights from Chicago to Maryland

Our best Frontier deals on Chicago to Maryland flight tickets

Frontier

Oct 17

ORD7:10 pmChicago O'Hare Intl

2h 03m

BWI10:13 pmBaltimore/Washington

Oct 20

BWI10:58 pmBaltimore/Washington

2h 16m

ORD12:14 amChicago O'Hare Intl

$59

Find similar

Frontier

Sep 25

MDW8:15 amChicago Midway

2h 01m

PHL11:16 amPhiladelphia

Sep 28

PHL6:00 amPhiladelphia

2h 11m

MDW7:11 amChicago Midway

$73

Find similar

Frontier

Sep 25

ORD6:10 amChicago O'Hare Intl

2h 15m

PHL9:25 amPhiladelphia

Sep 28

PHL10:21 amPhiladelphia

2h 37m

ORD11:58 amChicago O'Hare Intl

$76

Find similar

Delta flights from Chicago to Maryland

Our best Delta deals on Chicago to Maryland flight tickets

Delta

Aug 30

MDW6:17 pmChicago Midway

4h 05m

1 stop

PHL11:22 pmPhiladelphia

Sep 1

PHL5:25 amPhiladelphia

5h 11m

1 stop

MDW9:36 amChicago Midway

$197

Find similar

Delta

Sep 13

ORD10:30 amChicago O'Hare Intl

4h 43m

1 stop

DCA4:13 pmWashington, D.C. Reagan-National

Sep 27

DCA6:00 amWashington, D.C. Reagan-National

4h 10m

1 stop

ORD9:10 amChicago O'Hare Intl

$237

Find similar

Delta

Aug 13

MDW1:08 pmChicago Midway

5h 02m

1 stop

PHL7:10 pmPhiladelphia

Aug 14

PHL6:00 amPhiladelphia

3h 35m

1 stop

MDW8:35 amChicago Midway

$277

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoBaltimore

ORD - BWI

ORDBWI

Chicago O'Hare Intl

Fri 10/17

7:10 pm-10:13 pm

Nonstop2h 03m

Baltimore/Washington

Mon 10/20

10:58 pm-12:14 am

Nonstop2h 16m

$59

ChicagoBaltimore

ORD - BWI

ORDBWI

Chicago O'Hare Intl

Thu 10/23

6:10 am-9:02 am

Nonstop1h 52m

Baltimore/Washington

Mon 10/27

9:57 am-11:10 am

Nonstop2h 13m

$69

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Thu 10/2

12:05 pm-11:59 pm

1 stop10h 54m

Philadelphia

Thu 10/16

10:21 am-11:52 am

Nonstop2h 31m

$154

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Fri 10/24

6:20 am-9:26 am

Nonstop2h 06m

Philadelphia

Sun 10/26

9:47 am-9:19 pm

1 stop12h 32m

$158

ChicagoBaltimore

MDW - BWI

MDWBWI

Chicago Midway

Wed 9/10

8:35 am-11:30 am

Nonstop1h 55m

Baltimore/Washington

Sat 9/13

10:10 am-11:10 am

Nonstop2h 00m

$161

ChicagoBaltimore

MDW - BWI

MDWBWI

Chicago Midway

Sat 8/30

9:35 am-12:25 pm

Nonstop1h 50m

Baltimore/Washington

Sun 8/31

7:30 am-8:30 am

Nonstop2h 00m

$169

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Sat 8/30

7:24 pm-10:38 pm

Nonstop2h 14m

Philadelphia

Sun 8/31

6:00 am-7:25 am

Nonstop2h 25m

$177

ChicagoWashington, D.C.

ORD - DCA

ORDDCA

Chicago O'Hare Intl

Wed 9/10

11:30 am-2:24 pm

Nonstop1h 54m

Washington, D.C. Reagan-National

Wed 9/10

3:28 pm-7:05 pm

1 stop4h 37m

$193

ChicagoWashington, D.C.

ORD - DCA

ORDDCA

Chicago O'Hare Intl

Tue 8/26

9:00 am-11:59 am

Nonstop1h 59m

Washington, D.C. Reagan-National

Tue 9/2

6:00 pm-7:15 pm

Nonstop2h 15m

$217

ChicagoWashington, D.C.

ORD - IAD

ORDIAD

Chicago O'Hare Intl

Thu 8/28

8:50 am-11:55 am

Nonstop2h 05m

Washington, D.C. Dulles Intl

Tue 9/2

6:40 pm-7:48 pm

Nonstop2h 08m

$217

Flights are sorted by cheapest round-trip flights first.

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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 $183, 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 $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 Friday. Travelers who choose to depart for Maryland on a Friday will often find tickets for as low as $299. The most expensive day to fly to Maryland is Monday, with ticket prices averaging around $470.

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 $303. In contrast, the most expensive time of day to depart to Maryland is at noon when prices are around $650.

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 $273 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 $214 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	$39
Fastest flight time	1h 45m
Direct flights	Every day
Airports in Maryland	4 airports

The best one-way flight to Maryland from Chicago in the past 72 hours is $39. The best round-trip flight deal from Chicago to Maryland found on momondo in the last 72 hours is $59.

The fastest flight from Chicago to Maryland takes 1h 45m

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)

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 6 as of July 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 Boeing 737-900, making up 10.16% of the total bookings. Other popular models include Boeing 737-800 Passenger/BBJ2 (winglets) with 10.00%, Airbus A320neo with 9.87%, and Airbus A320-100/200 with 9.80%.

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 $42	Free Cancellation	Rating 6.3 8,048 reviews	Search Spirit Airlines flights
Frontier	PriceFrom $74	Free Cancellation	Rating 5.9 3,239 reviews	Search Frontier flights
American Airlines	PriceFrom $127	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights
Southwest	PriceFrom $140	Free Cancellation	Rating 8.0 4,246 reviews	Search Southwest flights
United Airlines	PriceFrom $153	Free Cancellation	Rating 7.4 8,900 reviews	Search United Airlines 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 $39

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 9/11. 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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Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

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Find the cheapest flights from Chicago to Maryland

Cheap round-trip flights

Cheap one-way flights

Cheap last minute flights

Cheap direct flights

Frontier flights from Chicago to Maryland

Our best Frontier deals on Chicago to Maryland flight tickets

Delta flights from Chicago to Maryland

Our best Delta deals on Chicago to Maryland flight tickets

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Use the filters below to find and compare flights from Chicago to Maryland that are best for you.

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?

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 $299. The most expensive day to fly to Maryland is Monday, with ticket prices averaging around $470.

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 $303. In contrast, the most expensive time of day to depart to Maryland is at noon when prices are around $650.

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?

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?

Spirit Airlines and Frontier 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 July 2025, there are 110 flights per day flying from Chicago to Maryland. The most common time of day flights depart is 7:00PM, with 37% of flights taking off in the evening.

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

776 flights are operational weekly from Chicago to Maryland as of July 2025. The most popular departure day for this route is Thu, with 23% 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