What airlines fly to Chicago?

United Airlines, Frontier and Southwest 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 32% 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.

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 02m on average, while flying from Salisbury to Chicago O'Hare Intl Airport is 5h 06m 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 January 2026, 683 flights take off from Maryland and land in Chicago each week. The most common flight departure day for this route is Thu, with 19% of weekly flights taking off on this day.

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

As of January 2026, 97 flights take off from Maryland and land in Chicago each day. The most common flight departure time for this route is 6:00AM, with 53% of daily flights taking off at noon.

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

Frontier, Southwest, and United Airlines 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 January 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.

$55 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.

10:06 am - 9:13 pm

BWI

ORD

12h 07m

1 stop

10:44 am - 10:53 pm

ORD

BWI

11h 09m

1 stop

$102Spirit Airlines

Tue, Feb 24 - Tue, Mar 3

7:19 pm - 8:46 pm

BWI

ORD

2h 27mnonstop

4:42 pm - 12:31 am

ORD

BWI

6h 49m

1 stop

$103Frontier

Thu, Feb 19 - Sat, Feb 21

9:19 am - 10:46 am

BWI

ORD

2h 27mnonstop

8:16 pm - 9:06 am

ORD

BWI

11h 50m

1 stop

$104Multiple Airlines

Thu, Mar 5 - Mon, Mar 9

12:30 pm - 11:22 am

BWI

ORD

23h 52m

1 stop

3:15 pm - 6:24 pm

ORD

BWI

2h 09mnonstop

$105Multiple Airlines

Tue, Feb 17 - Thu, Feb 19

9:19 am - 10:46 am

BWI

ORD

2h 27mnonstop

3:21 pm - 8:26 am

ORD

BWI

16h 05m

1 stop

$106Frontier

Thu, Feb 26 - Thu, Mar 5

12:30 pm - 7:11 pm

BWI

ORD

7h 41m

1 stop

11:51 am - 12:31 am

ORD

BWI

11h 40m

1 stop

$107Multiple Airlines

Wed, Feb 25 - Wed, Mar 4

1:00 pm - 2:22 pm

DCA

ORD

2h 22mnonstop

7:00 am - 9:54 am

ORD

DCA

1h 54mnonstop

$197United Airlines

Wed, Feb 25 - Wed, Mar 4

6:55 pm - 8:00 pm

DCA

MDW

2h 05mnonstop

4:35 pm - 7:20 pm

MDW

DCA

1h 45mnonstop

$197Southwest

Tue, Mar 10 - Tue, Mar 17

7:59 pm - 9:24 pm

DCA

ORD

2h 25mnonstop

7:48 pm - 11:00 pm

ORD

DCA

2h 12mnonstop

$198American Airlines

Tue, Feb 24 - Tue, Mar 3

9:00 pm - 10:15 pm

DCA

MDW

2h 15mnonstop

2:35 pm - 10:00 pm

MDW

DCA

6h 25m

1 stop

$207Southwest

Tue, Feb 24 - Tue, Mar 3

JetBlue flights from Maryland to Chicago

Our best JetBlue deals on Maryland to Chicago flight tickets

JetBlue

Feb 24

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

6h 59m

1 stop

ORD11:59 amChicago O'Hare Intl

Mar 3

ORD10:00 amChicago O'Hare Intl

7h 55m

1 stop

DCA6:55 pmWashington, D.C. Reagan-National

$207

JetBlue

Mar 2

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

6h 49m

1 stop

ORD11:49 amChicago O'Hare Intl

Mar 6

ORD12:41 pmChicago O'Hare Intl

9h 18m

1 stop

DCA10:59 pmWashington, D.C. Reagan-National

$226

JetBlue

Feb 11

DCA10:05 amWashington, D.C. Reagan-National

7h 50m

1 stop

ORD4:55 pmChicago O'Hare Intl

Feb 12

ORD10:00 amChicago O'Hare Intl

5h 04m

1 stop

DCA4:04 pmWashington, D.C. Reagan-National

$233

Frontier flights from Maryland to Chicago

Our best Frontier deals on Maryland to Chicago flight tickets

Frontier

Feb 6

BWI10:00 amBaltimore/Washington

2h 27m

ORD11:27 amChicago O'Hare Intl

Feb 9

ORD8:45 amChicago O'Hare Intl

2h 00m

BWI11:45 amBaltimore/Washington

$102

Frontier

Feb 19

BWI7:19 pmBaltimore/Washington

2h 27m

ORD8:46 pmChicago O'Hare Intl

Feb 21

ORD4:42 pmChicago O'Hare Intl

6h 49m

1 stop

BWI12:31 amBaltimore/Washington

$103

Frontier

Feb 26

BWI9:19 amBaltimore/Washington

2h 27m

ORD10:46 amChicago O'Hare Intl

Mar 5

ORD3:21 pmChicago O'Hare Intl

16h 05m

1 stop

BWI8:26 amBaltimore/Washington

$106

Fly from

Fly to

Route

Depart

Return

Price

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Tue 2/24

10:06 am-9:13 pm

1 stop12h 07m

Chicago O'Hare Intl

Tue 3/3

10:44 am-10:53 pm

1 stop11h 09m

$102

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Thu 2/19

7:19 pm-8:46 pm

Nonstop2h 27m

Chicago O'Hare Intl

Sat 2/21

4:42 pm-12:31 am

1 stop6h 49m

$103

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Thu 3/5

9:19 am-10:46 am

Nonstop2h 27m

Chicago O'Hare Intl

Mon 3/9

8:16 pm-9:06 am

1 stop11h 50m

$104

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Tue 2/17

12:30 pm-11:22 am

1 stop23h 52m

Chicago O'Hare Intl

Thu 2/19

3:15 pm-6:24 pm

Nonstop2h 09m

$105

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Thu 2/26

9:19 am-10:46 am

Nonstop2h 27m

Chicago O'Hare Intl

Thu 3/5

3:21 pm-8:26 am

1 stop16h 05m

$106

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Wed 2/25

12:30 pm-7:11 pm

1 stop7h 41m

Chicago O'Hare Intl

Wed 3/4

11:51 am-12:31 am

1 stop11h 40m

$107

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Wed 2/25

1:00 pm-2:22 pm

Nonstop2h 22m

Chicago O'Hare Intl

Wed 3/4

7:00 am-9:54 am

Nonstop1h 54m

$197

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Tue 3/10

6:55 pm-8:00 pm

Nonstop2h 05m

Chicago Midway

Tue 3/17

4:35 pm-7:20 pm

Nonstop1h 45m

$197

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Tue 2/24

7:59 pm-9:24 pm

Nonstop2h 25m

Chicago O'Hare Intl

Tue 3/3

7:48 pm-11:00 pm

Nonstop2h 12m

$198

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Tue 2/24

9:00 pm-10:15 pm

Nonstop2h 15m

Chicago Midway

Tue 3/3

2:35 pm-10:00 pm

1 stop6h 25m

$207

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 $203. If you’re not able to fly to Chicago in September, then February is your next best option. Flight prices from Maryland to Chicago during February average around $218.

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 $378. 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 $500.

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 $353. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $418.

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 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 $334 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 $216 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	$121
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 $121. The best round-trip flight deal from Maryland to Chicago found on momondo in the last 72 hours is $219.

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

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 January 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 737-900, representing 9.60% of all bookings. The subsequent popular models are Boeing 737 MAX 8 at 9.24%, Embraer 175 at 8.53%, and Boeing 737-800 at 8.39%.

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 $41	Free Cancellation	Rating 6.3 8,394 reviews	Search Spirit Airlines flights
Frontier	PriceFrom $57	Free Cancellation	Rating 5.7 3,056 reviews	Search Frontier flights
Southwest	PriceFrom $148	Free Cancellation	Rating 8.0 4,267 reviews	Search Southwest flights
United Airlines	PriceFrom $153	Free Cancellation	Rating 7.4 9,215 reviews	Search United Airlines flights
American Airlines	PriceFrom $159	Free Cancellation	Rating 7.2 11,205 reviews	Search American Airlines flights

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Saint Joseph

Portage

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Valparaiso

Munster

Crown Point

Chesterton

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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.

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Cheap flights from Maryland to Chicago from $55

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 2/28. 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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Find the cheapest flights from Maryland to Chicago

Cheap round-trip flights

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JetBlue flights from Maryland to Chicago

Our best JetBlue deals on Maryland to Chicago flight tickets

Frontier flights from Maryland to Chicago

Our best Frontier deals on Maryland to Chicago flight tickets

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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

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 $203. If you’re not able to fly to Chicago in September, then February is your next best option. Flight prices from Maryland to Chicago during February average around $218.

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 $353. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $418.

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 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, Southwest, and United Airlines 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 January 2026, 97 flights take off from Maryland and land in Chicago each day. The most common flight departure time for this route is 6:00AM, with 53% of daily flights taking off at noon.

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

As of January 2026, 683 flights take off from Maryland and land in Chicago each week. The most common flight departure day for this route is Thu, with 19% 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