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$59+ 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 10/9. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BWI
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
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 September 16, 2025.

Round-trip from

$88
(Cheapflightsfares)

One-way from

$59
(Frontier)

Popular in

January

Cheapest in

August

Average price

$212

Good round-trip deal

$111 or less

Good one-way deal

$89 or less
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. 5% potential increase in price ($13 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($3 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 16, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/1712:48 pmORD - BWI
Nonstop2h 03mFrontier
Mon 10/205:04 pmBWI - ORD
Nonstop2h 16mFrontier
Deal found 9/15$88
This Frontier deal was found by Cheapflights users on 9/15. 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.
Fri 10/1712:48 pmORD - BWI
Nonstop2h 03mFrontier
Sun 10/198:48 pmBWI - ORD
Nonstop2h 29mFrontier
Deal found 9/15$89
This Frontier deal was found by Cheapflights users on 9/16. 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 11/612:00 pmORD - BWI
Nonstop2h 03mFrontier
Sun 11/94:09 pmBWI - ORD
Nonstop2h 16mFrontier
Deal found 9/16$91
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 10/2312:30 pmMDW - BWI
Nonstop1h 57mFrontier
Sat 10/254:12 pmBWI - MDW
Nonstop2h 01mFrontier
Deal found 9/15$92
This Gotogate deal was found by Cheapflights users on 9/15. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1812:30 pmMDW - BWI
Nonstop1h 57mFrontier
Mon 10/207:54 pmBWI - MDW
Nonstop2h 06mFrontier
Deal found 9/15$94
This Booking.com deal was found by Cheapflights users on 9/13. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/73:47 pmMDW - BWI
Nonstop1h 55mFrontier
Sun 11/99:21 amBWI - MDW
Nonstop2h 05mFrontier
Deal found 9/13$96
This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/143:11 pmORD - BWI
Nonstop1h 54mSpirit Airlines
Sun 11/165:44 pmBWI - ORD
Nonstop2h 17mSpirit Airlines
Deal found 9/14$99
This Spirit deal was found by Cheapflights users on 9/16. 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 Spirit is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/73:11 pmORD - BWI
Nonstop1h 54mSpirit Airlines
Sun 11/95:44 pmBWI - ORD
Nonstop2h 17mSpirit Airlines
Deal found 9/16$100
This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1612:30 pmMDW - BWI
Nonstop1h 57mFrontier
Mon 10/207:54 pmBWI - MDW
Nonstop2h 06mFrontier
Deal found 9/15$101
This CheapOair deal was found by Cheapflights users on 9/14. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/73:47 pmMDW - BWI
Nonstop1h 55mFrontier
Mon 11/107:25 pmBWI - MDW
Nonstop2h 06mFrontier
Deal found 9/14$102
This Gotogate deal was found by Cheapflights users on 9/16. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/63:40 pmMDW - BWI
Nonstop1h 55mFrontier
Sun 11/99:21 amBWI - MDW
Nonstop2h 05mFrontier
Deal found 9/16$103
This Frontier deal was found by Cheapflights users on 9/15. 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 10/26:11 pmORD - BWI
Nonstop2h 03mFrontier
Sun 10/59:59 pmBWI - ORD
Nonstop2h 21mFrontier
Deal found 9/15$103

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 September 16, 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

ChicagoBaltimore

MDW - BWI

MDWBWI

Chicago Midway

Thu 10/30

3:40 pm-6:35 pm

Nonstop1h 55m

Baltimore/Washington

Mon 11/3

7:25 pm-8:31 pm

Nonstop2h 06m

$117

ChicagoBaltimore

MDW - BWI

MDWBWI

Chicago Midway

Fri 10/31

3:40 pm-6:35 pm

Nonstop1h 55m

Baltimore/Washington

Sun 11/2

8:21 pm-8:32 am

1 stop13h 11m

$123

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Tue 10/14

6:45 am-9:40 am

Nonstop1h 55m

Philadelphia

Sat 10/18

12:05 pm-1:10 pm

Nonstop2h 05m

$139

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Wed 12/10

2:30 pm-5:39 pm

Nonstop2h 09m

Philadelphia

Sat 12/13

5:07 pm-6:36 pm

Nonstop2h 29m

$139

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Sat 10/25

5:35 pm-8:30 pm

Nonstop1h 55m

Philadelphia

Tue 10/28

5:25 am-6:30 am

Nonstop2h 05m

$139

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Sat 11/1

6:13 pm-9:21 pm

Nonstop2h 08m

Philadelphia

Tue 11/11

5:07 pm-6:35 pm

Nonstop2h 28m

$139

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Sat 11/1

12:50 pm-3:40 pm

Nonstop1h 50m

Philadelphia

Tue 11/11

6:00 am-7:15 am

Nonstop2h 15m

$139

ChicagoBaltimore

ORD - BWI

ORDBWI

Chicago O'Hare Intl

Wed 10/22

2:22 pm-5:26 pm

Nonstop2h 04m

Baltimore/Washington

Wed 10/29

6:15 am-7:31 am

Nonstop2h 16m

$139

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Sat 10/18

5:35 pm-8:30 pm

Nonstop1h 55m

Philadelphia

Tue 10/21

6:05 pm-7:10 pm

Nonstop2h 05m

$139

ChicagoBaltimore

ORD - BWI

ORDBWI

Chicago O'Hare Intl

Wed 12/10

6:20 pm-9:19 pm

Nonstop1h 59m

Baltimore/Washington

Sat 12/13

10:20 am-11:28 am

Nonstop2h 08m

$139

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/13

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 September 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 September 16, 2025.

The most flights from CHI to USMD are scheduled on a Sunday (36 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (14 on average).

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 September 16, 2025.
See what other customers who have flown with Southwest, United Airlines, and American Airlines from Chicago to Maryland have to say. 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
8.0
Very good
4,242 reviews

Entertainment

7.5

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,924 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Spirit Airlines
6.3
Okay
8,019 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Frontier
5.8
Fair
3,174 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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.

  • How long is the flight from Chicago to Maryland?

    A quick flight from Chicago to Maryland can take about 1h 55m. Frontier provides one of the quickest options available for as low as $117. There are 609 mi between Chicago and Maryland. All flights are typically nonstop.

  • 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 Southwest ($70), United Airlines ($70), and Frontier ($78).

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

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

    Consider Republic Airways (83%), Spirit Airlines (80%) or Alaska Airlines (77%) 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 $218, our data shows the cheapest flight currently is $55. When looking at the most popular route, (Chicago O'Hare Intl - Washington, D.C. Reagan-National), you can expect to pay $133 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 5 airlines flying from Chicago to Maryland

Discover the top 5 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 September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$45Average$142FlexibilityNo cancel feeOn-time65%
FrontierCheapest$75Average$159FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$124Average$375FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$153Average$274FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$154Average$292FlexibilityNo cancel feeOn-time69%

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