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

As of May 2026, 919 flights take off from Maryland and land in Chicago each week. The most common flight departure day for this route is Fri, with 18% of weekly flights taking off on this day.

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

As of May 2026, 131 flights take off from Maryland and land in Chicago each day. The most common flight departure time for this route is 11:00AM, with 52% of daily flights taking off at noon.

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 12m on average, while flying from Salisbury to Chicago O'Hare Intl Airport is 5h 44m on average. Chicago O'Hare Intl Airport is the most popular airport in Chicago.

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

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

What airlines fly to Chicago?

United Airlines, Frontier and American Airlines 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 34% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 5 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

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 May 2026.

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.

$91 Cheap Flights from Maryland to Chicago in 2026

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Find the cheapest flights from Maryland to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

8:30 am - 7:53 pm

PHL

ORD

12h 23m

1 stop

8:05 pm - 11:31 pm

ORD

PHL

2h 26mnonstop

$184Frontier

Tue, Jun 30 - Mon, Jul 6

6:30 am - 11:09 am

PHL

MDW

5h 39m

1 stop

6:00 am - 12:25 pm

MDW

PHL

5h 25m

1 stop

$184Frontier

Fri, May 29 - Sat, May 30

8:00 am - 10:37 am

PHL

RFD

27h 37m

1 stop

11:27 am - 9:25 am

RFD

PHL

20h 58m

1 stop

$197Multiple Airlines

Wed, Jun 10 - Sun, Jun 14

8:00 am - 10:37 am

PHL

RFD

27h 37m

1 stop

11:27 am - 12:44 am

RFD

PHL

12h 17m

1 stop

$204Multiple Airlines

Wed, Jun 10 - Thu, Jun 25

9:15 pm - 10:20 pm

BWI

MDW

2h 05mnonstop

7:25 am - 10:15 am

MDW

BWI

1h 50mnonstop

$212Southwest

Mon, Jun 1 - Wed, Jun 10

7:11 pm - 8:35 pm

BWI

ORD

2h 24mnonstop

9:25 pm - 12:33 am

ORD

BWI

2h 08mnonstop

$212United Airlines

Sat, May 23 - Tue, May 26

7:10 pm - 8:20 pm

BWI

MDW

2h 10mnonstop

7:45 am - 11:50 am

MDW

BWI

3h 05m

1 stop

$218Southwest

Mon, Jun 1 - Wed, Jun 3

8:03 pm - 9:34 pm

DCA

ORD

2h 31mnonstop

10:00 am - 2:24 pm

ORD

DCA

3h 24m

1 stop

$223American Airlines

Tue, May 26 - Tue, Jun 2

3:52 pm - 5:27 pm

DCA

ORD

2h 35mnonstop

5:57 am - 9:13 am

ORD

DCA

2h 16mnonstop

$231American Airlines

Sat, May 23 - Tue, May 26

6:30 am - 7:46 am

DCA

ORD

2h 16mnonstop

6:00 am - 8:54 am

ORD

DCA

1h 54mnonstop

$233United Airlines

Tue, Jun 16 - Thu, Jun 18

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United Airlines flights from Maryland to Chicago

Our best United Airlines deals on Maryland to Chicago flight tickets

United Airlines

May 23

BWI7:11 pmBaltimore/Washington

2h 24m

ORD8:35 pmChicago O'Hare Intl

May 26

ORD9:25 pmChicago O'Hare Intl

2h 08m

BWI12:33 amBaltimore/Washington

$212

United Airlines

Jun 1

BWI10:40 amBaltimore/Washington

2h 16m

ORD11:56 amChicago O'Hare Intl

Jun 10

ORD6:20 amChicago O'Hare Intl

1h 57m

BWI9:17 amBaltimore/Washington

$226

United Airlines

May 29

BWI6:10 amBaltimore/Washington

2h 15m

ORD7:25 amChicago O'Hare Intl

Jun 2

ORD9:25 pmChicago O'Hare Intl

2h 08m

BWI12:33 amBaltimore/Washington

$227

Frontier flights from Maryland to Chicago

Our best Frontier deals on Maryland to Chicago flight tickets

Frontier

May 11

PHL5:06 pmPhiladelphia

2h 38m

ORD6:44 pmChicago O'Hare Intl

May 14

ORD8:39 amChicago O'Hare Intl

6h 59m

1 stop

PHL4:38 pmPhiladelphia

$184

Frontier

May 15

PHL5:04 pmPhiladelphia

7h 09m

1 stop

ORD11:13 pmChicago O'Hare Intl

Jun 10

ORD1:29 pmChicago O'Hare Intl

8h 00m

1 stop

PHL10:29 pmPhiladelphia

$185

Frontier

Aug 1

PHL5:18 pmPhiladelphia

2h 42m

ORD7:00 pmChicago O'Hare Intl

Aug 7

ORD1:50 pmChicago O'Hare Intl

7h 38m

1 stop

PHL10:28 pmPhiladelphia

$186

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

PhiladelphiaChicago

PHL - ORD

PHLORD

Philadelphia

Tue 6/30

8:30 am-7:53 pm

1 stop12h 23m

Chicago O'Hare Intl

Mon 7/6

8:05 pm-11:31 pm

Nonstop2h 26m

$184

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Fri 5/29

6:30 am-11:09 am

1 stop5h 39m

Chicago Midway

Sat 5/30

6:00 am-12:25 pm

1 stop5h 25m

$184

PhiladelphiaChicago

PHL - RFD

PHLRFD

Philadelphia

Wed 6/10

8:00 am-10:37 am

1 stop27h 37m

Chicago Greater Rockford

Sun 6/14

11:27 am-9:25 am

1 stop20h 58m

$197

PhiladelphiaChicago

PHL - RFD

PHLRFD

Philadelphia

Wed 6/10

8:00 am-10:37 am

1 stop27h 37m

Chicago Greater Rockford

Thu 6/25

11:27 am-12:44 am

1 stop12h 17m

$204

Quickest round-trip

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Mon 6/1

9:15 pm-10:20 pm

Nonstop2h 05m

Chicago Midway

Wed 6/10

7:25 am-10:15 am

Nonstop1h 50m

$212

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Sat 5/23

7:11 pm-8:35 pm

Nonstop2h 24m

Chicago O'Hare Intl

Tue 5/26

9:25 pm-12:33 am

Nonstop2h 08m

$212

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Mon 6/1

7:10 pm-8:20 pm

Nonstop2h 10m

Chicago Midway

Wed 6/3

7:45 am-11:50 am

1 stop3h 05m

$218

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Tue 5/26

8:03 pm-9:34 pm

Nonstop2h 31m

Chicago O'Hare Intl

Tue 6/2

10:00 am-2:24 pm

1 stop3h 24m

$223

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Sat 5/23

3:52 pm-5:27 pm

Nonstop2h 35m

Chicago O'Hare Intl

Tue 5/26

5:57 am-9:13 am

Nonstop2h 16m

$231

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Tue 6/16

6:30 am-7:46 am

Nonstop2h 16m

Chicago O'Hare Intl

Thu 6/18

6:00 am-8:54 am

Nonstop1h 54m

$233

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

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Other information

What is the cheapest month to fly to Chicago?

The month of May is, on average, the cheapest month to fly to Chicago from Maryland, with most prices found around $34. If you’re not able to fly to Chicago in May, then February is your next best option. Flight prices from Maryland to Chicago during February average around $43.

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 $389. 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 $512.

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 $383. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $424.

What is the cheapest Maryland to Chicago flight route?

Fly from Baltimore/Washington to Chicago O'Hare Intl for the best Maryland - Chicago flight prices

How far in advance should I book a flight from Maryland 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 $374 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 $201 on momondo.

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	$176
Fastest flight time	1h 55m
Direct flights	Every day
Airports in Chicago	3 airports

The best one-way flight to Chicago from Maryland in the past 72 hours is $176. The best round-trip flight deal from Maryland to Chicago found on momondo in the last 72 hours is $309.

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

Direct flights go from Maryland to Chicago every day.

There are 3 airports in Chicago. From Maryland there are direct flights to Chicago O'Hare Intl (ORD), Chicago Midway (MDW).

Search flight deals

Frequently asked questions about flying 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 May 2026.
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 Boeing 737 MAX 8, representing 14.05% of all bookings. The subsequent popular models are Boeing 737-800 at 9.95%, Boeing 737-900 at 9.58%, and Embraer 175 at 8.72%.

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 $43	Free Cancellation	Rating 6.3 8,640 reviews	Search Spirit Airlines flights
Frontier	PriceFrom $57	Free Cancellation	Rating 5.6 2,971 reviews	Search Frontier flights
Southwest	PriceFrom $134	Free Cancellation	Rating 8.0 4,314 reviews	Search Southwest flights
United Airlines	PriceFrom $152	Free Cancellation	Rating 7.4 9,679 reviews	Search United Airlines flights
American Airlines	PriceFrom $158	Free Cancellation	Rating 7.1 11,673 reviews	Search American Airlines flights

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Munster

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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.

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Cheap flights from Maryland to Chicago from $91

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 5/12. 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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United Airlines flights from Maryland to Chicago

Our best United Airlines deals on Maryland to Chicago flight tickets

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How to get the cheapest flight ticket from Maryland to Chicago

What is the cheapest month to fly to Chicago?

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?

What is the cheapest Maryland to Chicago flight route?

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

Can stopping save me money on Maryland to Chicago flights?

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

What airlines fly to Chicago?

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

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

How long does it take to fly to Chicago?

Cheap Maryland to Chicago flight deals and tips

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Frequently asked questions about flying from Maryland to Chicago

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Airports listed have a maximum distance of 78.5 mi from Chicago

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List of cabin classes available on flights landing in Chicago. Availability may vary depending on flight origin and airline.

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