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$75+ 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 5/19. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BWI
Apr 22 — Apr 291
Tue 4/22
Tue 4/29
1 adult, Economy
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Cheap flight deals from Chicago to Maryland

Keep the following information in mind while searching for Chicago to Maryland flight deals. Data was last updated April 17, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$159
(Frontier)

One-way from

$76
(Trip.com)

Popular in

June

Cheapest in

September

Average price

$254

Good round-trip deal

$188 or less

Good one-way deal

$84 or less
Provider with most accurate pricing for Chicago (CHI)-Washington, D.C. (WAS) flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Washington, D.C. (WAS) flights.
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From Chicago (CHI) to Maryland
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One-way flight from Chicago (CHI) to Maryland
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Highest demand for flights based on searches. 3% potential increase in price ($8 potential increase over avg. RT price).
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Cheapest flight prices on average. 0% potential price decrease ($3 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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Price to beat on a round-trip flight from Chicago (CHI) to Maryland.
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Price to beat on a 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 April 17, 2025.

This Frontier deal was found by Cheapflights users on 4/16. 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 7/318:24 amORD - PHL
Nonstop2h 19mFrontier
Sun 8/35:45 amPHL - ORD
Nonstop2h 32mFrontier
Deal found 4/16$154
This Cheapflightsfares deal was found by Cheapflights users on 4/17. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/1612:15 pmMDW - PHL
Nonstop2h 02mFrontier
Mon 5/194:12 pmPHL - MDW
Nonstop2h 16mFrontier
Deal found 4/17$162
This Southwest deal was found by Cheapflights users on 4/16. 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.
Wed 6/256:20 amMDW - PHL
Nonstop1h 55mSouthwest
Tue 7/17:10 pmPHL - MDW
Nonstop2h 15mSouthwest
Deal found 4/16$169
This American Airlines deal was found by Cheapflights users on 4/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/259:36 pmORD - PHL
Nonstop2h 09mAmerican Airlines
Tue 7/14:23 pmPHL - ORD
Nonstop2h 32mAmerican Airlines
Deal found 4/16$169
This United Airlines deal was found by Cheapflights users on 4/16. 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 5/179:00 amORD - PHL
Nonstop2h 08mUnited Airlines
Sun 5/2512:25 pmPHL - ORD
Nonstop2h 24mUnited Airlines
Deal found 4/16$170
This CheapOair deal was found by Cheapflights users on 4/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/69:34 amMDW - BWI
1 stop9h 22mFrontier
Thu 5/81:38 pmBWI - MDW
Nonstop2h 07mFrontier
Deal found 4/17$172
This FlightHub deal was found by Cheapflights users on 4/17. 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.
Sat 5/1712:41 pmORD - BWI
1 stop9h 00mSpirit Airlines
Mon 5/197:57 pmBWI - ORD
1 stop13h 53mSpirit Airlines
Deal found 4/17$172
This FlightHub deal was found by Cheapflights users on 4/17. 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.
Wed 5/1412:41 pmORD - PHL
1 stop9h 02mMultiple Airlines
Sun 5/187:15 amPHL - ORD
Nonstop2h 28mMultiple Airlines
Deal found 4/17$175
This Southwest deal was found by Cheapflights users on 4/17. 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.
Fri 5/305:45 amMDW - BWI
Nonstop1h 45mSouthwest
Sun 6/16:20 amBWI - MDW
Nonstop2h 05mSouthwest
Deal found 4/17$177
This Southwest deal was found by Cheapflights users on 4/17. 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.
Fri 5/301:50 pmORD - BWI
Nonstop1h 55mSouthwest
Mon 6/210:35 amBWI - ORD
Nonstop2h 15mSouthwest
Deal found 4/17$177
This Frontier deal was found by Cheapflights users on 4/17. 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 5/1411:10 amORD - BWI
1 stop7h 46mFrontier
Sat 5/176:45 amBWI - ORD
1 stop7h 56mFrontier
Deal found 4/17$178
This FlightHub deal was found by Cheapflights users on 4/17. 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.
Thu 5/1510:33 amORD - BWI
Nonstop1h 46mMultiple Airlines
Tue 7/87:20 amBWI - ORD
1 stop10h 18mMultiple Airlines
Deal found 4/17$179

Cheapflights Fare Finder

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 April 17, 2025.
Use the filters below to find and compare flights from Chicago to Maryland that are best for you.

Fly from

Chicago

Fly to

Maryland

Route

Depart

Return

Price

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Sun 5/11

9:48 am-12:56 pm

Nonstop2h 08m

Philadelphia

Mon 5/12

5:01 pm-6:29 pm

Nonstop2h 28m

$159

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Fri 5/16

12:15 pm-3:17 pm

Nonstop2h 02m

Philadelphia

Mon 5/19

4:12 pm-5:28 pm

Nonstop2h 16m

$162

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Wed 6/25

6:20 am-9:15 am

Nonstop1h 55m

Philadelphia

Tue 7/1

7:10 pm-8:25 pm

Nonstop2h 15m

$169

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Wed 6/25

9:36 pm-12:45 am

Nonstop2h 09m

Philadelphia

Tue 7/1

4:23 pm-5:55 pm

Nonstop2h 32m

$169

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Sat 5/17

9:00 am-12:08 pm

Nonstop2h 08m

Philadelphia

Sun 5/25

12:25 pm-1:49 pm

Nonstop2h 24m

$170

ChicagoBaltimore

ORD - BWI

ORDBWI

Chicago O'Hare Intl

Mon 5/5

7:47 pm-9:22 am

1 stop12h 35m

Baltimore/Washington

Mon 5/12

7:57 pm-8:50 am

1 stop13h 53m

$172

ChicagoBaltimore

MDW - BWI

MDWBWI

Chicago Midway

Thu 5/1

9:51 am-12:48 pm

Nonstop1h 57m

Baltimore/Washington

Fri 5/9

10:03 am-11:09 am

Nonstop2h 06m

$173

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Wed 5/14

12:41 pm-10:43 pm

1 stop9h 02m

Philadelphia

Sun 5/18

7:15 am-8:43 am

Nonstop2h 28m

$175

ChicagoBaltimore

ORD - BWI

ORDBWI

Chicago O'Hare Intl

Sun 5/4

5:45 am-7:59 pm

1 stop13h 14m

Baltimore/Washington

Sun 5/18

8:10 am-9:24 am

Nonstop2h 14m

$175

ChicagoBaltimore

MDW - BWI

MDWBWI

Chicago Midway

Fri 5/23

7:50 pm-10:40 pm

Nonstop1h 50m

Baltimore/Washington

Mon 5/26

8:05 am-9:05 am

Nonstop2h 00m

$177

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/17

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.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Maryland

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 April 17, 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 April 17, 2025.

The most flights from CHI to USMD are scheduled on a Thursday (30 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (12 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 April 17, 2025.
Read through reviews of airlines operating flights from Chicago to Maryland, such as Alaska 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.
Alaska Airlines
8.0
Very good
9,887 reviews

Food

7.1

Comfort

7.9

Entertainment

7.1

Boarding

8.1

Overall

8.0

Crew

8.5

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Alaska Airlines
8.0
Very good
9,887 reviews
Alaska Airlines
8.0
Very good
9,887 reviews

Food

7.1

Comfort

7.9

Entertainment

7.1

Boarding

8.1

Overall

8.0

Crew

8.5

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Southwest
8.0
Very good
4,280 reviews
Alaska Airlines
8.0
Very good
9,887 reviews

Food

7.1

Comfort

7.9

Entertainment

7.1

Boarding

8.1

Overall

8.0

Crew

8.5

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Delta
8.0
Very good
7,916 reviews
Alaska Airlines
8.0
Very good
9,887 reviews

Food

7.1

Comfort

7.9

Entertainment

7.1

Boarding

8.1

Overall

8.0

Crew

8.5

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
United Airlines
7.4
Good
8,667 reviews
Alaska Airlines
8.0
Very good
9,887 reviews

Food

7.1

Comfort

7.9

Entertainment

7.1

Boarding

8.1

Overall

8.0

Crew

8.5

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
JetBlue
7.3
Good
2,926 reviews
Alaska Airlines
8.0
Very good
9,887 reviews

Food

7.1

Comfort

7.9

Entertainment

7.1

Boarding

8.1

Overall

8.0

Crew

8.5

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >

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 ($76), Spirit Airlines ($80), and Southwest ($81).

  • 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 - Philadelphia and Chicago O'Hare Intl - Washington, D.C. Reagan-National.

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

    Consider Southwest (87%), United Airlines (87%) or Qatar Airways (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 $303, 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 $161 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.

See more FAQs

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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 April 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$68Average$162FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$101Average$174FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$121Average$398FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$140Average$277FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$174Average$290FlexibilityNo cancel feeOn-time69%
DeltaCheapest$176Average$244FlexibilityNo cancel feeOn-timeN/A

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