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$54+ Cheap flights from Chicago (CHI) to Maryland

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/1. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BWI
Jan 21 — Jan 281
Tue 1/21
Tue 1/28
1 adult, Economy
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Cheap flight deals from Chicago to Maryland

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Maryland (USMD). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 16, 2025.

Round-trip from

$109
(Frontier)

One-way from

$54
(Trip.com)
From Chicago (CHI) to Maryland
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One-way flight from Chicago (CHI) to Maryland
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Find flight deals from Chicago to Maryland

Cheapest flights from Chicago to Maryland
Explore the most affordable flight options available from Chicago to Maryland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 16, 2025.

This Frontier deal was found by Cheapflights users on 1/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/307:25 amMDW - PHL
1 stop10h 07mFrontier
Thu 3/201:23 pmPHL - MDW
1 stop7h 12mFrontier
Deal found 1/16$109
This Frontier deal was found by Cheapflights users on 1/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/3010:33 amORD - PHL
1 stop7h 32mFrontier
Sat 2/110:18 pmPHL - ORD
1 stop12h 34mFrontier
Deal found 1/15$109
This Kiwi.com deal was found by Cheapflights users on 1/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/307:25 amMDW - BWI
1 stop25h 34mFrontier
Mon 2/312:58 pmBWI - MDW
1 stop10h 41mFrontier
Deal found 1/15$127
This Frontier deal was found by Cheapflights users on 1/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/197:25 amORD - BWI
1 stop9h 01mFrontier
Fri 2/219:58 pmBWI - ORD
1 stop12h 17mFrontier
Deal found 1/16$129
This eDestinos deal was found by Cheapflights users on 1/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/45:31 pmMDW - BWI
1 stop22h 32mMultiple Airlines
Mon 2/107:05 pmBWI - MDW
1 stop22h 11mMultiple Airlines
Deal found 1/14$130
This Kiwi.com deal was found by Cheapflights users on 1/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/52:02 pmORD - PHL
1 stop7h 14mMultiple Airlines
Sat 2/810:18 pmPHL - ORD
1 stop12h 34mMultiple Airlines
Deal found 1/14$132
This United Airlines deal was found by Cheapflights users on 1/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/1510:55 amORD - BWI
Nonstop1h 58mUnited Airlines
Wed 2/196:30 amBWI - ORD
Nonstop2h 22mUnited Airlines
Deal found 1/16$138
This Southwest deal was found by Cheapflights users on 1/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/111:25 amORD - BWI
Nonstop1h 50mSouthwest
Tue 4/810:35 amBWI - ORD
Nonstop2h 15mSouthwest
Deal found 1/16$139
This Priceline deal was found by Cheapflights users on 1/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/55:11 amORD - BWI
1 stop8h 24mMultiple Airlines
Mon 2/103:22 pmBWI - ORD
1 stop7h 54mMultiple Airlines
Deal found 1/15$143
This eDestinos deal was found by Cheapflights users on 1/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/254:58 pmMDW - PHL
1 stop21h 02mMultiple Airlines
Tue 4/16:39 pmPHL - MDW
1 stop22h 14mMultiple Airlines
Deal found 1/16$145
This FlightHub deal was found by Cheapflights users on 1/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/116:15 amORD - BWI
1 stop5h 22mSpirit Airlines
Sat 5/174:15 pmBWI - ORD
1 stop7h 06mSpirit Airlines
Deal found 1/15$152
This Southwest deal was found by Cheapflights users on 1/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/187:35 amMDW - BWI
Nonstop1h 55mSouthwest
Tue 2/188:50 pmBWI - MDW
Nonstop2h 10mSouthwest
Deal found 1/16$153

Find flights from Chicago to Maryland within your budget

Customize your flight search to find flights from Chicago to Maryland that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 16, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Thu 1/30

7:25 am-6:32 pm

1 stop10h 07m

Philadelphia

Thu 3/20

1:23 pm-7:35 pm

1 stop7h 12m

$109

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Thu 1/30

10:33 am-9:23 pm

1 stop9h 50m

Philadelphia

Sat 2/1

10:18 pm-9:52 am

1 stop12h 34m

$109

ChicagoBaltimore

MDW - BWI

MDWBWI

Chicago Midway

Thu 1/30

7:25 am-9:59 am

1 stop25h 34m

Baltimore/Washington

Mon 2/3

12:58 pm-10:39 pm

1 stop10h 41m

$127

ChicagoBaltimore

ORD - BWI

ORDBWI

Chicago O'Hare Intl

Wed 2/19

7:25 am-5:26 pm

1 stop9h 01m

Baltimore/Washington

Fri 2/21

9:58 pm-9:15 am

1 stop12h 17m

$129

ChicagoBaltimore

MDW - BWI

MDWBWI

Chicago Midway

Wed 2/5

8:01 pm-6:59 pm

1 stop21h 58m

Baltimore/Washington

Tue 2/11

7:32 pm-7:07 am

1 stop12h 35m

$130

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Wed 3/19

7:07 pm-10:13 am

1 stop14h 06m

Philadelphia

Mon 3/24

5:05 am-12:01 pm

1 stop7h 56m

$135

ChicagoBaltimore

MDW - BWI

MDWBWI

Chicago Midway

Tue 2/25

6:55 pm-9:45 pm

Nonstop1h 50m

Baltimore/Washington

Wed 2/26

8:10 pm-9:25 pm

Nonstop2h 15m

$137

ChicagoBaltimore

ORD - BWI

ORDBWI

Chicago O'Hare Intl

Sat 2/15

10:55 am-1:53 pm

Nonstop1h 58m

Baltimore/Washington

Wed 2/19

6:30 am-7:52 am

Nonstop2h 22m

$138

ChicagoBaltimore

ORD - BWI

ORDBWI

Chicago O'Hare Intl

Tue 4/1

11:25 am-2:15 pm

Nonstop1h 50m

Baltimore/Washington

Tue 4/8

10:35 am-11:50 am

Nonstop2h 15m

$139

ChicagoBaltimore

ORD - BWI

ORDBWI

Chicago O'Hare Intl

Wed 2/5

5:11 am-2:35 pm

1 stop8h 24m

Baltimore/Washington

Mon 2/10

3:22 pm-10:16 pm

1 stop7h 54m

$143

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/16

Showing 1-10 of 60 results
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Best time to book a flight from Chicago to Maryland

Have a flexible travel schedule? Discover the best time to fly to Maryland from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Travel insights for flights from Chicago to Maryland

Get recent, data-driven insights about flights from Chicago to Maryland including ideal travel times, pricing trends, and more.

What is the cheapest month to book a flight from Chicago to Maryland?

Currently, August is the cheapest month in which you can book a flight from Chicago to Maryland (average of $241). Flying from Chicago to Maryland in March is currently the most expensive (average of $290). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to MD?

Find hourly flight availability from Chicago to Maryland. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated January 16, 2025.

When flying from Chicago to Maryland, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Weekly flight availability from Chicago to Maryland

Explore weekly flight availability from Chicago to Maryland. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated January 16, 2025.

The most flights from CHI to USMD are scheduled on a Wednesday (23 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (13 on average).

Rainfall in Maryland by month

Plan your trip to Maryland by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Maryland ranges from 2.9 - 4.1 inches per month. July is typically the wettest month, when rainfall can reach 4.1 in. February is typically the driest time to visit Maryland when rainfall is around 2.9 in.

Temperature in Maryland by month

Plan your trip to Maryland by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Maryland, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 77.0 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 33.8 F).

Reviews of airlines servicing Maryland

Get insights into the airlines that provide service to Maryland. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Maryland. Reviews last updated January 16, 2025.
Read through reviews of airlines operating flights from Chicago to Maryland, such as United Airlines, Southwest and Delta. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,659 reviews

Overall

8.1

Boarding

8.2

Entertainment

7.7

Food

7.2

Crew

8.7

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,659 reviews
Southwest
8.1
Very good
4,659 reviews

Overall

8.1

Boarding

8.2

Entertainment

7.7

Food

7.2

Crew

8.7

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,511 reviews
Southwest
8.1
Very good
4,659 reviews

Overall

8.1

Boarding

8.2

Entertainment

7.7

Food

7.2

Crew

8.7

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

JetBlue
7.4
Good
3,199 reviews
Southwest
8.1
Very good
4,659 reviews

Overall

8.1

Boarding

8.2

Entertainment

7.7

Food

7.2

Crew

8.7

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

United Airlines
7.4
Good
8,964 reviews
Southwest
8.1
Very good
4,659 reviews

Overall

8.1

Boarding

8.2

Entertainment

7.7

Food

7.2

Crew

8.7

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Allegiant Air
7.4
Good
801 reviews
Southwest
8.1
Very good
4,659 reviews

Overall

8.1

Boarding

8.2

Entertainment

7.7

Food

7.2

Crew

8.7

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Maryland. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What are the cheapest airlines to fly from Chicago to Maryland one-way?

    The cheapest airlines for a one-way flight from Chicago to Maryland are Frontier ($54), Southwest ($69), and United Airlines ($69).

  • What are the most popular routes from Chicago to Maryland?

    The most popular flight routes from Chicago to Maryland are Chicago O'Hare Intl - Washington, D.C. Dulles Intl, Chicago O'Hare Intl - Washington, D.C. Reagan-National and Chicago O'Hare Intl - Philadelphia.

  • What are the most reliable airlines from Chicago to Maryland?

    Consider Qatar Airways (85%), United Airlines (84%) or Envoy Air (83%) when booking your flight. These represent the most reliable airlines when flying from Chicago to Maryland.

  • What are the cheapest flights from Chicago to Maryland?

    While on average a flight from Chicago to Maryland is generally $290, our data shows the cheapest flight currently is $79. When looking at the most popular route, (Chicago O'Hare Intl - Washington, D.C. Dulles Intl), you can expect to pay $164 for that flight.

  • Can I find deals for flights from Chicago to Maryland that include hotel bookings?

    Yes. In addition to deals on Chicago to Maryland flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Maryland?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Maryland.

  • Can I find deals for business class flights from Chicago to Maryland?

    Yes. Cheapflights offers flight deals from Chicago to Maryland by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Maryland?

    Currently, August is the cheapest month in which you can book a flight from Chicago to Maryland (average of $241). Flying from Chicago to Maryland in March is currently the most expensive (average of $290). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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Alternative routes for Chicago to Maryland

See prices for flight routes from nearby airports that may be better suited for you.
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Top 6 airlines flying from Chicago to Maryland

Discover the top 6 airlines that operate flights from Chicago to Maryland. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$66Average$154FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$119Average$394FlexibilityNo cancel feeOn-time71%
Spirit AirlinesCheapest$135Average$174FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$138Average$276FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$160Average$291FlexibilityNo cancel feeOn-time69%
DeltaCheapest$176Average$264FlexibilityNo cancel feeOn-timeN/A
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