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Salisbury

$188+ 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 3/6. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SBY
Mar 20 — Mar 271
Fri 3/20
Fri 3/27
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 February 18, 2026.

This Kiwi.com deal was found by Cheapflights users on 2/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/303:15 pm
ORD
-
SBY
2 stops27h 13m
Multiple Airlines
Mon 5/48:08 pm
SBY
-
ORD
1 stop12h 55m
Multiple Airlines
Deal found 2/17$342
This Kiwi.com deal was found by Cheapflights users on 2/15. 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.
Fri 3/1311:21 am
ORD
-
SBY
1 stop7h 07m
Multiple Airlines
Mon 3/168:08 pm
SBY
-
ORD
1 stop28h 30m
Multiple Airlines
Deal found 2/15$369
This Kiwi.com deal was found by Cheapflights users on 2/14. 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.
Fri 5/16:57 am
ORD
-
SBY
1 stop11h 31m
Multiple Airlines
Mon 5/48:08 pm
SBY
-
ORD
1 stop12h 55m
Multiple Airlines
Deal found 2/14$374
This Kiwi.com deal was found by Cheapflights users on 2/14. 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.
Mon 3/210:44 am
ORD
-
SBY
1 stop7h 44m
Multiple Airlines
Fri 3/68:08 pm
SBY
-
ORD
1 stop21h 44m
Multiple Airlines
Deal found 2/14$449
This American Airlines deal was found by Cheapflights users on 2/17. 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.
Sat 9/55:15 pm
ORD
-
SBY
1 stop4h 45m
American Airlines
Sat 9/125:00 am
SBY
-
ORD
1 stop5h 24m
American Airlines
Deal found 2/17$450
This American Airlines deal was found by Cheapflights users on 2/17. 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 3/203:16 pm
ORD
-
SBY
1 stop6h 05m
American Airlines
Sun 3/222:38 pm
SBY
-
ORD
1 stop4h 26m
American Airlines
Deal found 2/17$490
This American Airlines deal was found by Cheapflights users on 2/17. 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.
Sat 6/131:17 pm
ORD
-
SBY
1 stop7h 47m
American Airlines
Sat 6/204:34 pm
SBY
-
ORD
1 stop6h 03m
American Airlines
Deal found 2/17$493
This American Airlines deal was found by Cheapflights users on 2/17. 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 5/15:00 am
ORD
-
SBY
1 stop7h 21m
American Airlines
Sun 5/176:00 am
SBY
-
ORD
1 stop5h 12m
American Airlines
Deal found 2/17$510

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 February 18, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$342
(Kiwi.com)

One-way from

$188
(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.
Search Deals
From Chicago (CHI) to Salisbury-Ocean City
Search Deals
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 February 18, 2026.
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

Thu 4/30

3:15 pm-7:28 pm

2 stops27h 13m

Salisbury-Ocean City

Mon 5/4

8:08 pm-8:03 am

1 stop12h 55m

$342

ChicagoSalisbury

ORD - SBY

ORDSBY

Chicago O'Hare Intl

Fri 5/1

6:57 am-7:28 pm

1 stop11h 31m

Salisbury-Ocean City

Mon 5/4

8:08 pm-8:03 am

1 stop12h 55m

$374

ChicagoSalisbury

ORD - SBY

ORDSBY

Chicago O'Hare Intl

Mon 3/2

10:44 am-7:28 pm

1 stop7h 44m

Salisbury-Ocean City

Fri 3/6

8:08 pm-4:52 pm

1 stop21h 44m

$449

ChicagoSalisbury

ORD - SBY

ORDSBY

Chicago O'Hare Intl

Fri 3/20

3:16 pm-10:21 pm

1 stop6h 05m

Salisbury-Ocean City

Sun 3/22

2:38 pm-6:04 pm

1 stop4h 26m

$490

ChicagoSalisbury

ORD - SBY

ORDSBY

Chicago O'Hare Intl

Fri 5/1

3:31 pm-10:54 pm

1 stop6h 23m

Salisbury-Ocean City

Sun 5/17

6:00 am-10:12 am

1 stop5h 12m

$510

ChicagoSalisbury

ORD - SBY

ORDSBY

Chicago O'Hare Intl

Tue 3/3

3:16 pm-11:13 pm

1 stop6h 57m

Salisbury-Ocean City

Sat 3/7

1:51 pm-7:40 pm

1 stop6h 49m

$536

ChicagoSalisbury

ORD - SBY

ORDSBY

Chicago O'Hare Intl

Sat 2/21

8:03 am-4:01 pm

1 stop6h 58m

Salisbury-Ocean City

Mon 2/23

7:18 am-12:05 pm

1 stop5h 47m

$595

ChicagoSalisbury

ORD - SBY

ORDSBY

Chicago O'Hare Intl

Fri 3/6

7:00 am-7:28 pm

2 stops11h 28m

$188

ChicagoSalisbury

ORD - SBY

ORDSBY

Chicago O'Hare Intl

Thu 4/30

3:15 pm-7:28 pm

2 stops27h 13m

$200

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/16

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 February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Salisbury, Maryland flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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 $57). Flying from Chicago to Salisbury, Maryland in April is currently the most expensive (average of $157). 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 February 18, 2026.
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
11,304 reviews

Overall

7.2

Boarding

7.5

Comfort

7.2

Food

6.4

Crew

8.0

Entertainment

6.9

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.
American Airlines
7.2
Good
11,304 reviews
American Airlines
7.2
Good
11,304 reviews

Overall

7.2

Boarding

7.5

Comfort

7.2

Food

6.4

Crew

8.0

Entertainment

6.9

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.

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.

  • 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 $57). Flying from Chicago to Salisbury, Maryland in April is currently the most expensive (average of $157). 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

Browse thousands of different options on Cheapflights for your next trip

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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 February 18, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$384Average$473FlexibilityNo cancel feeOn-time71%

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