How long does it take to fly to Chicago?

Average flight duration from Maryland to Chicago depends on which airport you fly into and out of. Flying from Baltimore to Chicago O'Hare Intl Airport is 2h 09m on average, while flying from Salisbury to Chicago O'Hare Intl Airport is 4h 35m on average. Chicago O'Hare Intl Airport is the most popular airport in Chicago.

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

As of September 2025, 755 flights take off from Maryland and land in Chicago each week. The most common flight departure day for this route is Wed, with 22% of weekly flights taking off on this day.

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

As of September 2025, 107 flights take off from Maryland and land in Chicago each day. The most common flight departure time for this route is 6:00AM, with 61% of daily flights taking off at noon.

What airlines fly to Chicago?

United Airlines, Southwest and Frontier are the top three most popular airlines that fly to Chicago from Maryland 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 Chicago. Keep in mind that there are 6 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

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

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

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

Prices for flights from Maryland to Chicago are refreshed on a daily basis.

How many operators does momondo search for flights from Maryland to Chicago?

There are 6 operators available for flights from Maryland to Chicago as of September 2025.

How old do you have to be to fly from Maryland to Chicago?

The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Maryland to Chicago.

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

The travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

$59 Cheap Flights from Maryland to Chicago in 2025/26

1 adult

0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

Find the cheapest flights from Maryland to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

7:54 pm - 9:00 pmBWI-MDW

2h 06mnonstop

3:40 pm - 6:35 pmMDW-BWI

1h 55mnonstop

$106Frontier

Find Deal

Fri, Oct 24 - Fri, Oct 31

7:25 pm - 8:31 pmBWI-MDW

2h 06mnonstop

9:32 am - 8:16 pmMDW-BWI

9h 44m1 stop

$107Frontier

Find Deal

Thu, Oct 30 - Fri, Oct 31

9:12 am - 10:36 amBWI-ORD

2h 24mnonstop

7:56 pm - 10:54 pmORD-BWI

1h 58mnonstop

$110Multiple Airlines

Find Deal

Sun, Dec 7 - Sun, Dec 7

5:44 pm - 7:01 pmBWI-ORD

2h 17mnonstop

7:56 pm - 10:54 pmORD-BWI

1h 58mnonstop

$111Spirit Airlines

Find Deal

Thu, Feb 19 - Sun, Feb 22

6:18 am - 10:41 amBWI-ORD

5h 23m1 stop

7:56 pm - 10:54 pmORD-BWI

1h 58mnonstop

$122Multiple Airlines

Find Deal

Thu, Oct 30 - Thu, Nov 13

5:44 pm - 7:01 pmBWI-ORD

2h 17mnonstop

7:56 pm - 10:54 pmORD-BWI

1h 58mnonstop

$126Spirit Airlines

Find Deal

Thu, Nov 20 - Thu, Dec 4

10:05 am - 11:27 amPHL-ORD

2h 22mnonstop

2:15 pm - 5:35 pmORD-PHL

2h 20mnonstop

$134United Airlines

Find Deal

Sat, Oct 25 - Sat, Oct 25

6:29 am - 7:44 amBWI-ORD

2h 15mnonstop

2:20 pm - 5:14 pmORD-BWI

1h 54mnonstop

$139United Airlines

Find Deal

Sat, Oct 25 - Tue, Oct 28

12:44 pm - 2:11 pmPHL-ORD

2h 27mnonstop

11:20 am - 2:17 pmORD-PHL

1h 57mnonstop

$139American Airlines

Find Deal

Sat, Nov 1 - Wed, Nov 5

2:39 pm - 4:06 pmPHL-ORD

2h 27mnonstop

8:45 am - 11:44 amORD-PHL

1h 59mnonstop

$159American Airlines

Find Deal

Wed, Oct 15 - Sat, Oct 18

Frontier flights from Maryland to Chicago

Our best Frontier deals on Maryland to Chicago flight tickets

Frontier

Oct 24

BWI7:54 pmBaltimore/Washington

2h 06m

MDW9:00 pmChicago Midway

Oct 31

MDW3:40 pmChicago Midway

1h 55m

BWI6:35 pmBaltimore/Washington

$106

Find similar

Frontier

Oct 26

BWI6:37 pmBaltimore/Washington

13h 33m

1 stop

ORD7:10 amChicago O'Hare Intl

Oct 27

ORD12:53 pmChicago O'Hare Intl

2h 03m

BWI3:56 pmBaltimore/Washington

$107

Find similar

Frontier

Oct 24

BWI4:46 pmBaltimore/Washington

2h 29m

ORD6:15 pmChicago O'Hare Intl

Oct 31

ORD11:00 amChicago O'Hare Intl

2h 03m

BWI2:03 pmBaltimore/Washington

$108

Find similar

American Airlines flights from Maryland to Chicago

Our best American Airlines deals on Maryland to Chicago flight tickets

American Airlines

Nov 1

PHL12:44 pmPhiladelphia

2h 27m

ORD2:11 pmChicago O'Hare Intl

Nov 5

ORD11:20 amChicago O'Hare Intl

1h 57m

PHL2:17 pmPhiladelphia

$139

Find similar

American Airlines

Oct 15

PHL2:39 pmPhiladelphia

2h 27m

ORD4:06 pmChicago O'Hare Intl

Oct 18

ORD8:45 amChicago O'Hare Intl

1h 59m

PHL11:44 amPhiladelphia

$159

Find similar

Fly from

Fly to

Route

Depart

Return

Price

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Fri 10/24

7:54 pm-9:00 pm

Nonstop2h 06m

Chicago Midway

Fri 10/31

3:40 pm-6:35 pm

Nonstop1h 55m

$106

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Thu 10/30

7:25 pm-8:31 pm

Nonstop2h 06m

Chicago Midway

Fri 10/31

9:32 am-8:16 pm

1 stop9h 44m

$107

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Sun 12/7

9:12 am-10:36 am

Nonstop2h 24m

Chicago O'Hare Intl

Sun 12/7

7:56 pm-10:54 pm

Nonstop1h 58m

$110

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Thu 2/19

5:44 pm-7:01 pm

Nonstop2h 17m

Chicago O'Hare Intl

Sun 2/22

7:56 pm-10:54 pm

Nonstop1h 58m

$111

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Thu 10/30

6:18 am-10:41 am

1 stop5h 23m

Chicago O'Hare Intl

Thu 11/13

7:56 pm-10:54 pm

Nonstop1h 58m

$122

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Thu 11/20

5:44 pm-7:01 pm

Nonstop2h 17m

Chicago O'Hare Intl

Thu 12/4

7:56 pm-10:54 pm

Nonstop1h 58m

$126

PhiladelphiaChicago

PHL - ORD

PHLORD

Philadelphia

Sat 10/25

10:05 am-11:27 am

Nonstop2h 22m

Chicago O'Hare Intl

Sat 10/25

2:15 pm-5:35 pm

Nonstop2h 20m

$134

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Sat 10/25

6:29 am-7:44 am

Nonstop2h 15m

Chicago O'Hare Intl

Tue 10/28

2:20 pm-5:14 pm

Nonstop1h 54m

$139

PhiladelphiaChicago

PHL - ORD

PHLORD

Philadelphia

Sat 11/1

12:44 pm-2:11 pm

Nonstop2h 27m

Chicago O'Hare Intl

Wed 11/5

11:20 am-2:17 pm

Nonstop1h 57m

$139

PhiladelphiaChicago

PHL - ORD

PHLORD

Philadelphia

Wed 10/15

2:39 pm-4:06 pm

Nonstop2h 27m

Chicago O'Hare Intl

Sat 10/18

8:45 am-11:44 am

Nonstop1h 59m

$159

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Maryland to Chicago

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 Chicago?

The month of September is, on average, the cheapest month to fly to Chicago from Maryland, with most prices found around $222. If you’re not able to fly to Chicago in September, then August is your next best option. Flight prices from Maryland to Chicago during August average around $227.

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

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $384. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Maryland to Chicago for around $499.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Maryland to Chicago during this time can be as low as $336. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $434.

What is the cheapest Maryland to Chicago flight route?

Fly from Baltimore/Washington to Chicago Midway for the best Maryland - Chicago flight prices

How far in advance should I book a flight to Chicago?

You are more likely to see cheaper flights to Chicago from Maryland when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $328 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Maryland for as low as $254 on momondo.

What cabin class options are available on Maryland to Chicago flights?

There are 4 cabin classes available to choose from on Maryland to Chicago 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 Maryland to Chicago flights?

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

Cheap Maryland to Chicago flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Maryland to Chicago

Best Price Found	$73
Fastest flight time	1h 55m
Direct flights	Every day
Airports in Chicago	2 airports

The best one-way flight to Chicago from Maryland in the past 72 hours is $73. The best round-trip flight deal from Maryland to Chicago found on momondo in the last 72 hours is $139.

The fastest flight from Maryland to Chicago takes 1h 55m

Direct flights go from Maryland to Chicago every day.

There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)

Search flight deals

When did momondo last update prices for flights from Maryland to Chicago?
Prices for flights from Maryland to Chicago are refreshed on a daily basis.
How many operators does momondo search for flights from Maryland to Chicago?
There are 6 operators available for flights from Maryland to Chicago as of September 2025.
How old do you have to be to fly from Maryland to Chicago?
The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Maryland to Chicago.
What documentation or ID do you need to fly to Chicago?
The travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Maryland to Chicago?
momondo data reveals that the most frequently booked plane model on the route from Maryland to Chicago is Airbus A320neo, representing 11.37% of all bookings. The subsequent popular models are Boeing 737-900 at 9.54%, Boeing 737-800 Passenger/BBJ2 (winglets) at 9.46%, and Boeing 737 MAX 8 at 9.35%.

Best airlines flying from Maryland to Chicago

Compare and see reviews for airlines that fly from Maryland to Chicago with momondo

Airline	Rating	Free Cancellation	Price
Spirit Airlines	PriceFrom $46	Free Cancellation	Rating 6.3 8,042 reviews	Search Spirit Airlines flights
Frontier	PriceFrom $67	Free Cancellation	Rating 5.8 3,163 reviews	Search Frontier flights
Delta	PriceFrom $98	Free Cancellation	Rating 7.9 7,973 reviews	Search Delta flights
Southwest	PriceFrom $157	Free Cancellation	Rating 8.0 4,244 reviews	Search Southwest flights
American Airlines	PriceFrom $158	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights
United Airlines	PriceFrom $158	Free Cancellation	Rating 7.4 8,928 reviews	Search United Airlines flights

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

Schererville

Valparaiso

Crown Point

Munster

Chesterton

Monticello

Porter

Griffith

Saint John

Why use momondo?

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

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Maryland to Chicago. Millions of users trust and use momondo every year so you are in good hands.

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

Yes. All flights to Chicago from Maryland on momondo can be compared and filtered by various policies on offer, including flexible booking.

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

Once you have performed a search for Maryland to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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

Of course. momondo tracks the price of Maryland to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

An easier way to manage your Chicago 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.

Start using Trips

Find my bookings

Get notified when prices go down

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

1 adult

Fri 10/24

Fri 10/31

Email me momondo's favorite deals

By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the United States

Cheap flights from Maryland to Chicago from $59

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Maryland to Chicago departing on 10/20. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Big names and deals

Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

Price Alerts

Price Alerts

Find the cheapest flights from Maryland to Chicago

Cheap round-trip flights

Cheap one-way flights

Cheap last minute flights

Cheap direct flights

Frontier flights from Maryland to Chicago

Our best Frontier deals on Maryland to Chicago flight tickets

American Airlines flights from Maryland to Chicago

Our best American Airlines deals on Maryland to Chicago flight tickets

momondo Fare Finder

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

See travel insights to Chicago from

How to get the cheapest flight ticket from Maryland to Chicago

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 Chicago?

The month of September is, on average, the cheapest month to fly to Chicago from Maryland, with most prices found around $222. If you’re not able to fly to Chicago in September, then August is your next best option. Flight prices from Maryland to Chicago during August average around $227.

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

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Maryland to Chicago during this time can be as low as $336. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $434.

What is the cheapest Maryland to Chicago flight route?

Fly from Baltimore/Washington to Chicago Midway for the best Maryland - Chicago flight prices

How far in advance should I book a flight to Chicago?

What cabin class options are available on Maryland to Chicago flights?

There are 4 cabin classes available to choose from on Maryland to Chicago 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 Maryland to Chicago flights?

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

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

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

What airlines fly to Chicago?

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

As of September 2025, 107 flights take off from Maryland and land in Chicago each day. The most common flight departure time for this route is 6:00AM, with 61% of daily flights taking off at noon.

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

As of September 2025, 755 flights take off from Maryland and land in Chicago each week. The most common flight departure day for this route is Wed, with 22% of weekly flights taking off on this day.

How long does it take to fly to Chicago?

Cheap Maryland to Chicago flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Maryland to Chicago

Best Price Found

Fastest flight time

Direct flights

Airports in Chicago

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

How many operators does momondo search for flights from Maryland to Chicago?

How old do you have to be to fly from Maryland to Chicago?

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

What is the most popular plane model from Maryland to Chicago?

Best airlines flying from Maryland to Chicago

Compare and see reviews for airlines that fly from Maryland to Chicago with momondo

Traveling to a place near Chicago?

Why use momondo?

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

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

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

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

An easier way to manage your Chicago 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 the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago