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Salisbury

$450+ Cheap flights from Chicago (CHI) to Salisbury, MD (SBY)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/27. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SBY
Aug 23 — Aug 301
Sat 8/23
Sat 8/30
1 adult, Economy
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Cheap 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 August 18, 2025.

Round-trip from

$450
(American Airlines)
From Chicago (CHI) to Salisbury-Ocean City
Search Deals

Find 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 August 18, 2025.

This American Airlines deal was found by Cheapflights users on 8/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/712:52 pmORD - SBY
1 stop7h 13mAmerican Airlines
Sun 10/128:00 amSBY - ORD
1 stop5h 04mAmerican Airlines
Deal found 8/17$450
This American Airlines deal was found by Cheapflights users on 8/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/264:45 pmORD - SBY
1 stop4h 26mAmerican Airlines
Mon 9/297:10 pmSBY - ORD
1 stop4h 29mAmerican Airlines
Deal found 8/17$470
This American Airlines deal was found by Cheapflights users on 8/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1911:45 amORD - SBY
1 stop4h 09mAmerican Airlines
Sat 8/235:01 amSBY - ORD
1 stop5h 24mAmerican Airlines
Deal found 8/17$476
This American Airlines deal was found by Cheapflights users on 8/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/210:00 amORD - SBY
2 stops5h 54mAmerican Airlines
Sat 9/68:00 amSBY - ORD
1 stop4h 30mAmerican Airlines
Deal found 8/17$776
This American Airlines deal was found by Cheapflights users on 8/16. 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.
Sat 9/279:16 amORD - SBY
2 stops6h 25mAmerican Airlines
Mon 9/296:37 amSBY - ORD
2 stops7h 18mAmerican Airlines
Deal found 8/16$1,269

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 August 18, 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

Sat 9/27

7:02 am-12:47 pm

1 stop4h 45m

Salisbury-Ocean City

Mon 9/29

7:10 pm-10:39 pm

1 stop4h 29m

$450

ChicagoSalisbury

ORD - SBY

ORDSBY

Chicago O'Hare Intl

Tue 10/7

12:52 pm-9:05 pm

1 stop7h 13m

Salisbury-Ocean City

Sun 10/12

7:03 pm-10:39 pm

1 stop4h 36m

$450

ChicagoSalisbury

ORD - SBY

ORDSBY

Chicago O'Hare Intl

Thu 12/4

5:10 am-10:50 am

1 stop4h 40m

Salisbury-Ocean City

Sun 12/7

12:01 pm-5:28 pm

1 stop6h 27m

$470

ChicagoSalisbury

ORD - SBY

ORDSBY

Chicago O'Hare Intl

Fri 9/26

4:45 pm-10:11 pm

1 stop4h 26m

Salisbury-Ocean City

Mon 9/29

7:10 pm-10:39 pm

1 stop4h 29m

$470

ChicagoSalisbury

ORD - SBY

ORDSBY

Chicago O'Hare Intl

Tue 9/2

11:45 am-4:54 pm

1 stop4h 09m

Salisbury-Ocean City

Sat 9/6

4:07 pm-8:27 pm

1 stop5h 20m

$476

ChicagoSalisbury

ORD - SBY

ORDSBY

Chicago O'Hare Intl

Mon 9/15

11:45 am-4:50 pm

1 stop4h 05m

$463

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/17

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 $367). Flying from Chicago to Salisbury, Maryland in October is currently the most expensive (average of $555). 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 August 18, 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
10,000 reviews

Comfort

7.2

Overall

7.2

Crew

8.0

Food

6.5

Boarding

7.5

Entertainment

6.9

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

MIA - DCA

Flight delayed 5 hours and was told it was due to mechanical issues. Instead of providing lodging due to missed connecting flight, American changed the cause of delay to weather, which meant they were not able required to provide a hotel. To make matters worse, one of our checked bags was lost even though its status said it was “by the plane” but no one at the service desk seemed able to locate it.
American Airlines
7.2
Good
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Comfort

7.2

Overall

7.2

Crew

8.0

Food

6.5

Boarding

7.5

Entertainment

6.9

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

MIA - DCA

Flight delayed 5 hours and was told it was due to mechanical issues. Instead of providing lodging due to missed connecting flight, American changed the cause of delay to weather, which meant they were not able required to provide a hotel. To make matters worse, one of our checked bags was lost even though its status said it was “by the plane” but no one at the service desk seemed able to locate it.

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 $450, American Airlines can have you in Salisbury, Maryland from Chicago in 4h 45m. 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 $367). Flying from Chicago to Salisbury, Maryland in October is currently the most expensive (average of $555). 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
Chincoteague
Seaford
Georgetown
Fenwick Island

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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 August 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$384Average$500FlexibilityNo cancel feeOn-time71%

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