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

United Airlines, Southwest, and American 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 August 2026, 769 flights take off from Maryland and land in Chicago each week. The most common flight departure day for this route is Fri, with 26% of weekly flights taking off on this day.

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 6h 31m 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 day?

As of August 2026, 109 flights take off from Maryland and land in Chicago each day. The most common flight departure time for this route is 10:00AM, with 51% of daily flights taking off at noon.

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 38% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 4 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 5 operators available for flights from Maryland to Chicago as of August 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.

$69 Cheap Flights from Maryland to Chicago in 2026

Discover deals from 900+ travel sites with momondo.

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.

11:54 am - 1:30 pm

PHL

ORD

2h 36mnonstop

6:00 am - 2:21 pm

ORD

PHL

7h 21m

1 stop

$175Frontier

Mon, Oct 5 - Wed, Oct 7

12:40 pm - 6:23 pm

PHL

ORD

6h 43m

1 stop

3:50 pm - 12:09 am

ORD

PHL

7h 19m

1 stop

$178Frontier

Mon, Sep 14 - Wed, Sep 16

4:47 pm - 6:24 pm

PHL

ORD

2h 37mnonstop

9:38 am - 5:59 pm

ORD

PHL

7h 21m

1 stop

$184Multiple Airlines

Sun, Oct 18 - Fri, Oct 23

6:00 am - 7:29 am

PHL

ORD

2h 29mnonstop

11:01 am - 8:01 pm

ORD

PHL

8h 00m

1 stop

$189Multiple Airlines

Mon, Aug 24 - Mon, Aug 24

6:00 am - 12:13 pm

DCA

ORD

7h 13m

1 stop

5:29 pm - 11:07 pm

ORD

DCA

4h 38m

1 stop

$197Delta

Sat, Oct 24 - Sat, Oct 24

1:30 pm - 6:03 pm

DCA

ORD

5h 33m

1 stop

5:18 pm - 10:59 pm

ORD

DCA

4h 41m

1 stop

$197Delta

Wed, Sep 2 - Sat, Sep 5

3:15 pm - 6:55 pm

DCA

MDW

4h 40m

1 stop

6:35 am - 11:35 am

MDW

DCA

4h 00m

1 stop

$197Southwest

Thu, Aug 27 - Sat, Aug 29

4:35 pm - 8:10 pm

DCA

MDW

4h 35m

1 stop

8:15 am - 2:55 pm

MDW

DCA

5h 40m

1 stop

$197Southwest

Thu, Sep 10 - Mon, Sep 14

3:30 pm - 4:52 pm

DCA

ORD

2h 22mnonstop

6:00 am - 8:55 am

ORD

DCA

1h 55mnonstop

$200United Airlines

Wed, Sep 2 - Mon, Sep 7

7:10 pm - 8:30 pm

DCA

ORD

2h 20mnonstop

6:00 am - 8:55 am

ORD

DCA

1h 55mnonstop

$200United Airlines

Sat, Sep 5 - Mon, Sep 7

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American Airlines flights from Maryland to Chicago

Our best American Airlines deals on Maryland to Chicago flight tickets

American Airlines

Sep 5

DCA8:32 amWashington, D.C. Reagan-National

4h 43m

1 stop

ORD12:15 pmChicago O'Hare Intl

Sep 12

ORD8:50 amChicago O'Hare Intl

2h 04m

DCA11:54 amWashington, D.C. Reagan-National

$216

American Airlines

Sep 3

BWI7:03 amBaltimore/Washington

2h 27m

ORD8:30 amChicago O'Hare Intl

Sep 9

ORD6:20 pmChicago O'Hare Intl

2h 10m

BWI9:30 pmBaltimore/Washington

$219

American Airlines

Aug 20

DCA10:18 amWashington, D.C. Reagan-National

2h 20m

ORD11:38 amChicago O'Hare Intl

Aug 24

ORD8:00 amChicago O'Hare Intl

1h 59m

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

$221

Frontier flights from Maryland to Chicago

Our best Frontier deals on Maryland to Chicago flight tickets

Frontier

Oct 5

PHL11:54 amPhiladelphia

2h 36m

ORD1:30 pmChicago O'Hare Intl

Oct 7

ORD6:00 amChicago O'Hare Intl

7h 21m

1 stop

PHL2:21 pmPhiladelphia

$175

Frontier

Aug 29

PHL1:00 pmPhiladelphia

11h 08m

1 stop

ORD11:08 pmChicago O'Hare Intl

Sep 2

ORD8:05 amChicago O'Hare Intl

13h 54m

1 stop

PHL10:59 pmPhiladelphia

$178

Frontier

Aug 27

PHL10:22 amPhiladelphia

2h 33m

ORD11:55 amChicago O'Hare Intl

Aug 30

ORD6:00 amChicago O'Hare Intl

2h 17m

PHL9:17 amPhiladelphia

$179

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

PhiladelphiaChicago

PHL - ORD

PHLORD

Philadelphia

Mon 10/5

11:54 am-1:30 pm

Nonstop2h 36m

Chicago O'Hare Intl

Wed 10/7

6:00 am-2:21 pm

1 stop7h 21m

$175

PhiladelphiaChicago

PHL - ORD

PHLORD

Philadelphia

Mon 9/14

12:40 pm-6:23 pm

1 stop6h 43m

Chicago O'Hare Intl

Wed 9/16

3:50 pm-12:09 am

1 stop7h 19m

$178

PhiladelphiaChicago

PHL - ORD

PHLORD

Philadelphia

Sun 10/18

4:47 pm-6:24 pm

Nonstop2h 37m

Chicago O'Hare Intl

Fri 10/23

9:38 am-5:59 pm

1 stop7h 21m

$184

PhiladelphiaChicago

PHL - ORD

PHLORD

Philadelphia

Mon 8/24

6:00 am-7:29 am

Nonstop2h 29m

Chicago O'Hare Intl

Mon 8/24

11:01 am-8:01 pm

1 stop8h 00m

$189

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Sat 10/24

6:00 am-12:13 pm

1 stop7h 13m

Chicago O'Hare Intl

Sat 10/24

5:29 pm-11:07 pm

1 stop4h 38m

$197

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Wed 9/2

1:30 pm-6:03 pm

1 stop5h 33m

Chicago O'Hare Intl

Sat 9/5

5:18 pm-10:59 pm

1 stop4h 41m

$197

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Thu 8/27

3:15 pm-6:55 pm

1 stop4h 40m

Chicago Midway

Sat 8/29

6:35 am-11:35 am

1 stop4h 00m

$197

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Thu 9/10

4:35 pm-8:10 pm

1 stop4h 35m

Chicago Midway

Mon 9/14

8:15 am-2:55 pm

1 stop5h 40m

$197

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Wed 9/2

3:30 pm-4:52 pm

Nonstop2h 22m

Chicago O'Hare Intl

Mon 9/7

6:00 am-8:55 am

Nonstop1h 55m

$200

Quickest round-trip

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Sat 9/5

7:10 pm-8:30 pm

Nonstop2h 20m

Chicago O'Hare Intl

Mon 9/7

6:00 am-8:55 am

Nonstop1h 55m

$200

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 $208. If you’re not able to fly to Chicago in September, then January is your next best option. Flight prices from Maryland to Chicago during January average around $219.

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 Saturday when prices can be found for as low as $400. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Maryland to Chicago for around $535.

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 $409. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $451.

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 $399 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 $284 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	$188
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 $188. The best round-trip flight deal from Maryland to Chicago found on momondo in the last 72 hours is $313.

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 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 5 operators available for flights from Maryland to Chicago as of August 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 16.37% of all bookings. The subsequent popular models are Boeing 737-900 at 11.27%, Boeing 737-800 at 11.15%, and Embraer 175 at 8.29%.

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
Frontier	PriceFrom $57	Free Cancellation	Rating 5.6 2,741 reviews	Search Frontier flights
Southwest	PriceFrom $134	Free Cancellation	Rating 8.0 4,230 reviews	Search Southwest flights
United Airlines	PriceFrom $158	Free Cancellation	Rating 7.4 10,061 reviews	Search United Airlines flights
American Airlines	PriceFrom $174	Free Cancellation	Rating 7.1 11,846 reviews	Search American Airlines flights

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Schererville

Munster

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Monticello

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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 $89

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 8/17. 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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American Airlines flights from Maryland to Chicago

Our best American Airlines 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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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?

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?

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

Best Price Found

Fastest flight time

Direct flights

Airports in Chicago

Frequently asked questions about flying 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?

An easier way to manage your Chicago trip

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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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