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

As of March 2026, 123 flights take off from Maryland and land in Chicago each day. The most common flight departure time for this route is 5:00PM, with 51% of daily flights taking off in the afternoon.

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 14m on average, while flying from Salisbury to Chicago O'Hare Intl Airport is 6h 27m 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?

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

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

As of March 2026, 867 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.

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 March 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.

$80 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.

12:17 pm - 7:31 pm

BWI

MDW

8h 14m

1 stop

2:15 pm - 12:44 am

MDW

BWI

9h 29m

1 stop

$145Frontier

Wed, Apr 15 - Wed, Apr 22

6:00 am - 5:00 pm

BWI

ORD

12h 00m

1 stop

6:08 pm - 11:22 am

ORD

BWI

16h 14m

1 stop

$145Frontier

Wed, Apr 22 - Tue, Apr 28

5:09 pm - 6:35 pm

BWI

ORD

2h 26mnonstop

12:45 pm - 11:59 pm

ORD

BWI

10h 14m

1 stop

$152Multiple Airlines

Thu, Apr 9 - Tue, Apr 14

5:53 pm - 10:23 am

BWI

ORD

17h 30m

1 stop

1:59 pm - 10:57 pm

ORD

BWI

7h 58m

1 stop

$153Multiple Airlines

Sat, May 2 - Wed, May 6

6:05 am - 10:44 am

BWI

ORD

5h 39m

1 stop

8:00 am - 11:06 am

ORD

BWI

2h 06mnonstop

$154Frontier

Tue, Apr 7 - Wed, Apr 8

1:45 pm - 3:09 pm

DCA

ORD

2h 24mnonstop

4:00 pm - 7:05 pm

ORD

DCA

2h 05mnonstop

$209American Airlines

Tue, Apr 14 - Tue, Apr 21

3:40 pm - 4:50 pm

DCA

MDW

2h 10mnonstop

1:30 pm - 4:15 pm

MDW

DCA

1h 45mnonstop

$209Southwest

Tue, Apr 14 - Tue, Apr 21

11:35 am - 12:55 pm

DCA

ORD

2h 20mnonstop

2:57 pm - 6:00 pm

ORD

DCA

2h 03mnonstop

$210American Airlines

Wed, Jun 3 - Wed, Jun 10

3:40 pm - 4:50 pm

DCA

MDW

2h 10mnonstop

1:55 pm - 6:40 pm

MDW

DCA

3h 45m

1 stop

$215Southwest

Tue, Apr 21 - Wed, Apr 22

3:30 pm - 4:50 pm

DCA

ORD

2h 20mnonstop

11:15 am - 2:14 pm

ORD

DCA

1h 59mnonstop

$224United Airlines

Tue, Apr 14 - Thu, Apr 16

Spirit Airlines flights from Maryland to Chicago

Our best Spirit Airlines deals on Maryland to Chicago flight tickets

Spirit Airlines

Mar 23

BWI10:09 amBaltimore/Washington

10h 54m

1 stop

ORD8:03 pmChicago O'Hare Intl

Mar 26

ORD12:45 pmChicago O'Hare Intl

5h 59m

1 stop

BWI7:44 pmBaltimore/Washington

$162

Spirit Airlines

Mar 23

BWI10:09 amBaltimore/Washington

10h 54m

1 stop

ORD8:03 pmChicago O'Hare Intl

Mar 31

ORD12:45 pmChicago O'Hare Intl

10h 14m

1 stop

BWI11:59 pmBaltimore/Washington

$163

Spirit Airlines

Apr 7

BWI10:19 amBaltimore/Washington

7h 56m

1 stop

ORD5:15 pmChicago O'Hare Intl

Apr 9

ORD7:17 amChicago O'Hare Intl

10h 28m

1 stop

BWI6:45 pmBaltimore/Washington

$167

Frontier flights from Maryland to Chicago

Our best Frontier deals on Maryland to Chicago flight tickets

Frontier

Apr 22

BWI6:00 amBaltimore/Washington

12h 00m

1 stop

ORD5:00 pmChicago O'Hare Intl

Apr 28

ORD6:08 pmChicago O'Hare Intl

16h 14m

1 stop

BWI11:22 amBaltimore/Washington

$145

Frontier

Apr 7

BWI6:05 amBaltimore/Washington

5h 39m

1 stop

ORD10:44 amChicago O'Hare Intl

Apr 8

ORD8:00 amChicago O'Hare Intl

2h 06m

BWI11:06 amBaltimore/Washington

$154

Frontier

Apr 9

BWI5:09 pmBaltimore/Washington

2h 26m

ORD6:35 pmChicago O'Hare Intl

Apr 13

ORD4:34 pmChicago O'Hare Intl

7h 10m

1 stop

BWI12:44 amBaltimore/Washington

$155

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Wed 4/15

12:17 pm-7:31 pm

1 stop8h 14m

Chicago Midway

Wed 4/22

2:15 pm-12:44 am

1 stop9h 29m

$145

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Wed 4/22

6:00 am-5:00 pm

1 stop12h 00m

Chicago O'Hare Intl

Tue 4/28

6:08 pm-11:22 am

1 stop16h 14m

$145

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Thu 4/9

5:09 pm-6:35 pm

Nonstop2h 26m

Chicago O'Hare Intl

Tue 4/14

12:45 pm-11:59 pm

1 stop10h 14m

$152

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Sat 5/2

5:53 pm-10:23 am

1 stop17h 30m

Chicago O'Hare Intl

Wed 5/6

1:59 pm-10:57 pm

1 stop7h 58m

$153

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Tue 4/7

6:05 am-10:44 am

1 stop5h 39m

Chicago O'Hare Intl

Wed 4/8

8:00 am-11:06 am

Nonstop2h 06m

$154

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Tue 4/14

1:45 pm-3:09 pm

Nonstop2h 24m

Chicago O'Hare Intl

Tue 4/21

4:00 pm-7:05 pm

Nonstop2h 05m

$209

Quickest round-trip

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Tue 4/14

3:40 pm-4:50 pm

Nonstop2h 10m

Chicago Midway

Tue 4/21

1:30 pm-4:15 pm

Nonstop1h 45m

$209

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Wed 6/3

11:35 am-12:55 pm

Nonstop2h 20m

Chicago O'Hare Intl

Wed 6/10

2:57 pm-6:00 pm

Nonstop2h 03m

$210

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Tue 4/21

3:40 pm-4:50 pm

Nonstop2h 10m

Chicago Midway

Wed 4/22

1:55 pm-6:40 pm

1 stop3h 45m

$215

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Tue 4/14

3:30 pm-4:50 pm

Nonstop2h 20m

Chicago O'Hare Intl

Thu 4/16

11:15 am-2:14 pm

Nonstop1h 59m

$224

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 August is your next best option. Flight prices from Maryland to Chicago during August average around $224.

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 $509.

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 $374. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $422.

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 $353 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 $199 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	$158
Fastest flight time	1h 55m
Direct flights	Mon, Wed, Thu, Fri, Sat and Sun
Airports in Chicago	3 airports

The best one-way flight to Chicago from Maryland in the past 72 hours is $158. The best round-trip flight deal from Maryland to Chicago found on momondo in the last 72 hours is $270.

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

Direct flights go from Maryland to Chicago on Monday, Wednesday, Thursday, Friday, Saturday and Sunday. Airlines offering direct flights are: Southwest and American Airlines.

There are 3 airports in Chicago. From Maryland there are direct flights to 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 March 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 12.81% of all bookings. The subsequent popular models are Boeing 737-900 at 10.46%, Embraer 175 at 10.01%, and Boeing 737-800 at 8.65%.

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 8,533 reviews	Search Spirit Airlines flights
Frontier	PriceFrom $57	Free Cancellation	Rating 5.7 3,023 reviews	Search Frontier flights
Southwest	PriceFrom $139	Free Cancellation	Rating 8.0 4,325 reviews	Search Southwest flights
United Airlines	PriceFrom $152	Free Cancellation	Rating 7.4 9,451 reviews	Search United Airlines flights
American Airlines	PriceFrom $158	Free Cancellation	Rating 7.1 11,488 reviews	Search American Airlines flights

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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 $80

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 4/15. 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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Spirit Airlines flights from Maryland to Chicago

Our best Spirit Airlines deals on Maryland to Chicago flight tickets

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Our best Frontier 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 to Chicago?

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

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

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

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Fastest flight time

Direct flights

Airports in 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?

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.

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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

Fly your favorite airline to Chicago

Airlines are sorted and displayed according to clicks in the past 7 days on momondo

Cabin classes currently available on flights to Chicago

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

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

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