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Salisbury

$295+ Cheap flights from Chicago (CHI) to Salisbury, MD (SBY)

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 12/29. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SBY
Jan 6 — Jan 131
Tue 1/6
Tue 1/13
1 adult, Economy
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Cheap flight deals from Chicago to Salisbury

Cheapest flights from Chicago to Salisbury
Explore the most affordable flight options available from Chicago to Salisbury. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 7, 2025.

This American Airlines deal was found by Cheapflights users on 12/6. 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.
Fri 12/195:00 amORD - SBY
1 stop7h 15mAmerican Airlines
Tue 12/237:55 amSBY - ORD
1 stop5h 04mAmerican Airlines
Deal found 12/6$575
This American Airlines deal was found by Cheapflights users on 12/6. 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.
Mon 12/221:54 pmORD - SBY
1 stop7h 19mAmerican Airlines
Sun 12/287:55 amSBY - ORD
1 stop5h 04mAmerican Airlines
Deal found 12/6$590
This American Airlines deal was found by Cheapflights users on 12/6. 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.
Sun 12/211:54 pmORD - SBY
1 stop7h 19mAmerican Airlines
Thu 12/256:00 amSBY - ORD
2 stops10h 40mAmerican Airlines
Deal found 12/6$869

Find flight deals from Chicago to Salisbury

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Salisbury (SBY). 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 December 7, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$575
(American Airlines)

One-way from

$295
(Kiwi.com)
Provider with most accurate pricing for Chicago (CHI)-Salisbury-Ocean City flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Salisbury-Ocean City flights.
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From Chicago (CHI) to Salisbury-Ocean City
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One-way flight from Chicago (CHI) to Salisbury-Ocean City
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Salisbury 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 December 7, 2025.
Use the filters below to find and compare flights from Chicago to Salisbury that are best for you.

Fly from

Chicago

Fly to

Salisbury

Route

Depart

Return

Price

ChicagoSalisbury

ORD - SBY

ORDSBY

Chicago O'Hare Intl

Fri 12/19

5:00 am-1:15 pm

1 stop7h 15m

Salisbury-Ocean City

Tue 12/23

7:55 am-11:59 am

1 stop5h 04m

$575

ChicagoSalisbury

ORD - SBY

ORDSBY

Chicago O'Hare Intl

Fri 5/1

2:55 pm-7:47 pm

1 stop3h 52m

Salisbury-Ocean City

Sun 5/17

5:57 pm-9:22 pm

1 stop4h 25m

$585

ChicagoSalisbury

ORD - SBY

ORDSBY

Chicago O'Hare Intl

Mon 12/22

1:54 pm-10:13 pm

1 stop7h 19m

Salisbury-Ocean City

Sun 12/28

7:55 am-11:59 am

1 stop5h 04m

$590

ChicagoSalisbury

ORD - SBY

ORDSBY

Chicago O'Hare Intl

Sun 12/21

1:54 pm-10:13 pm

1 stop7h 19m

Salisbury-Ocean City

Thu 12/25

6:00 am-3:40 pm

2 stops10h 40m

$869

ChicagoSalisbury

ORD - SBY

ORDSBY

Chicago O'Hare Intl

Mon 12/29

7:20 am-7:22 pm

1 stop11h 02m

$295

ChicagoSalisbury

ORD - SBY

ORDSBY

Chicago O'Hare Intl

Fri 12/19

7:20 am-7:22 pm

1 stop11h 02m

$329

ChicagoSalisbury

ORD - SBY

ORDSBY

Chicago O'Hare Intl

Mon 12/29

12:16 pm-8:34 pm

2 stops7h 18m

$690

ChicagoSalisbury

ORD - SBY

ORDSBY

Chicago O'Hare Intl

Fri 12/19

1:48 pm-10:13 pm

2 stops7h 25m

$776

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/5

Compare providers for flights from Chicago to Salisbury

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Salisbury in December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-Salisbury, Maryland flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago-Salisbury, Maryland flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Chicago-Salisbury, Maryland flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Salisbury, Maryland flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Salisbury, Maryland flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Chicago to Salisbury

Have a flexible travel schedule? Discover the best time to fly to Salisbury 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 Salisbury

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

Currently, February is the cheapest month in which you can book a flight from Chicago to Salisbury, Maryland (average of $58). Flying from Chicago to Salisbury, Maryland in April is currently the most expensive (average of $169). 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.

Reviews of airlines servicing Salisbury

Get insights into the airlines that provide service to Salisbury. 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 Salisbury. Reviews last updated December 7, 2025.
See what other customers who have flown with American Airlines from Chicago to Salisbury have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
11,046 reviews

Crew

8.0

Overall

7.2

Comfort

7.2

Entertainment

6.9

Boarding

7.5

Food

6.5

Reviews

1 / 20
10.0
Excellent

Jeremy,Dec 2025

OKC - CLT

Was an okay flight. Had extra seat empty beside me so was able to stretch a bit
American Airlines
7.2
Good
11,046 reviews
American Airlines
7.2
Good
11,046 reviews

Crew

8.0

Overall

7.2

Comfort

7.2

Entertainment

6.9

Boarding

7.5

Food

6.5

Reviews

1 / 20
10.0
Excellent

Jeremy,Dec 2025

OKC - CLT

Was an okay flight. Had extra seat empty beside me so was able to stretch a bit

Related info for your journey

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

  • What airport do you fly into for flights to Salisbury from Chicago?

    If you book a flight to Salisbury from Chicago, you will be flying to Salisbury-Ocean City, which is the city’s only airport. Salisbury-Ocean City (SBY) is located 5.0 mi from the center of Salisbury. There are 0 flights from Chicago to Salisbury-Ocean City per day from 1 airline.

  • How long is the flight from Chicago to Salisbury, Maryland?

    For as low as $575, American Airlines can have you in Salisbury, Maryland from Chicago in 7h 15m. There are 700 mi between Chicago and Salisbury, Maryland.

  • What is the cheapest airline to fly from Chicago to Salisbury, Maryland round-trip?

    Currently priced at $384, American Airlines will fly you from Chicago to Salisbury, Maryland and back. In addition to American Airlines, many other airlines offer competitively priced options for your trip.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Chicago to Salisbury 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 Salisbury, Maryland?

    Currently, February is the cheapest month in which you can book a flight from Chicago to Salisbury, Maryland (average of $58). Flying from Chicago to Salisbury, Maryland in April is currently the most expensive (average of $169). 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

Traveling to a place near Salisbury?

Book flights to Salisbury if you plan to visit one of these locations
Georgetown
Seaford
Chincoteague
Bethany Beach

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Top airline flying from Chicago to Salisbury

Discover the top airline that operate flights from Chicago to Salisbury. 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 December 7, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$384Average$473FlexibilityNo cancel feeOn-time71%

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