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Salisbury

$315+ 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 11/24. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SBY
Nov 21 — Nov 281
Fri 11/21
Fri 11/28
1 adult, Economy
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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 October 22, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/20. 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 11/246:48 amORD - SBY
1 stop11h 34mMultiple Airlines
Mon 12/18:02 pmSBY - ORD
1 stop28h 04mMultiple Airlines
Deal found 10/20$315
This Kiwi.com deal was found by Cheapflights users on 10/20. 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 11/276:23 pmORD - SBY
1 stop23h 59mMultiple Airlines
Mon 12/18:02 pmSBY - ORD
1 stop21h 01mMultiple Airlines
Deal found 10/20$361
This Kiwi.com deal was found by Cheapflights users on 10/20. 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.
Sun 11/237:09 pmORD - SBY
1 stop23h 13mMultiple Airlines
Mon 12/18:02 pmSBY - ORD
1 stop21h 01mMultiple Airlines
Deal found 10/20$369
This Kiwi.com deal was found by Cheapflights users on 10/20. 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 11/286:48 amORD - SBY
1 stop11h 34mMultiple Airlines
Mon 12/18:02 pmSBY - ORD
1 stop28h 04mMultiple Airlines
Deal found 10/20$371
This American Airlines deal was found by Cheapflights users on 10/21. 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 12/171:45 pmORD - SBY
1 stop4h 25mAmerican Airlines
Sat 12/201:51 pmSBY - ORD
1 stop6h 31mAmerican Airlines
Deal found 10/21$430
This Kiwi.com deal was found by Cheapflights users on 10/20. 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 11/246:48 amORD - SBY
1 stop11h 34mMultiple Airlines
Fri 11/288:02 pmSBY - ORD
1 stop14h 04mMultiple Airlines
Deal found 10/20$475
This American Airlines deal was found by Cheapflights users on 10/21. 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 12/64:05 pmORD - SBY
1 stop4h 53mAmerican Airlines
Sat 12/138:08 amSBY - ORD
1 stop5h 32mAmerican Airlines
Deal found 10/21$502
This American Airlines deal was found by Cheapflights users on 10/20. 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 11/262:03 pmORD - SBY
1 stop6h 55mAmerican Airlines
Fri 11/288:30 amSBY - ORD
1 stop6h 29mAmerican Airlines
Deal found 10/20$520
This American Airlines deal was found by Cheapflights users on 10/20. 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 11/244:40 pmORD - SBY
1 stop4h 49mAmerican Airlines
Tue 12/26:30 amSBY - ORD
1 stop6h 58mAmerican Airlines
Deal found 10/20$532

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 October 22, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$315
(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

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 October 22, 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

Thu 11/27

6:23 pm-7:22 pm

1 stop23h 59m

Salisbury-Ocean City

Mon 12/1

8:02 pm-4:03 pm

1 stop21h 01m

$361

ChicagoSalisbury

ORD - SBY

ORDSBY

Chicago O'Hare Intl

Fri 11/28

6:48 am-7:22 pm

1 stop11h 34m

Salisbury-Ocean City

Mon 12/1

8:02 pm-11:06 pm

1 stop28h 04m

$371

ChicagoSalisbury

ORD - SBY

ORDSBY

Chicago O'Hare Intl

Wed 12/17

1:45 pm-7:10 pm

1 stop4h 25m

Salisbury-Ocean City

Sat 12/20

1:51 pm-7:22 pm

1 stop6h 31m

$430

ChicagoSalisbury

ORD - SBY

ORDSBY

Chicago O'Hare Intl

Sat 12/6

4:05 pm-9:58 pm

1 stop4h 53m

Salisbury-Ocean City

Sat 12/13

8:08 am-12:40 pm

1 stop5h 32m

$502

ChicagoSalisbury

ORD - SBY

ORDSBY

Chicago O'Hare Intl

Wed 11/26

2:03 pm-9:58 pm

1 stop6h 55m

Salisbury-Ocean City

Fri 11/28

8:30 am-1:59 pm

1 stop6h 29m

$520

ChicagoSalisbury

ORD - SBY

ORDSBY

Chicago O'Hare Intl

Thu 11/27

5:00 am-11:32 am

1 stop5h 32m

Salisbury-Ocean City

Fri 11/28

8:30 am-1:59 pm

1 stop6h 29m

$520

ChicagoSalisbury

ORD - SBY

ORDSBY

Chicago O'Hare Intl

Mon 11/24

4:40 pm-10:29 pm

1 stop4h 49m

Salisbury-Ocean City

Tue 12/2

6:30 am-12:28 pm

1 stop6h 58m

$532

ChicagoSalisbury

ORD - SBY

ORDSBY

Chicago O'Hare Intl

Fri 10/31

12:52 pm-6:38 pm

1 stop4h 46m

Salisbury-Ocean City

Sun 11/2

5:30 am-11:30 am

1 stop7h 00m

$535

ChicagoSalisbury

ORD - SBY

ORDSBY

Chicago O'Hare Intl

Sun 11/23

4:40 pm-10:29 pm

1 stop4h 49m

Salisbury-Ocean City

Fri 11/28

8:30 am-12:28 pm

1 stop4h 58m

$545

ChicagoSalisbury

ORD - SBY

ORDSBY

Chicago O'Hare Intl

Fri 11/28

4:40 pm-10:29 pm

1 stop4h 49m

Salisbury-Ocean City

Tue 12/2

6:30 am-12:28 pm

1 stop6h 58m

$552

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/20

Showing 1-10 of 12 results
1
2

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 October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
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 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 $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 October 22, 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
11,029 reviews

Boarding

7.5

Comfort

7.2

Crew

8.0

Entertainment

6.9

Food

6.4

Overall

7.2

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac
American Airlines
7.2
Good
11,029 reviews
American Airlines
7.2
Good
11,029 reviews

Boarding

7.5

Comfort

7.2

Crew

8.0

Entertainment

6.9

Food

6.4

Overall

7.2

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac

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 $430, American Airlines can have you in Salisbury, Maryland from Chicago in 4h 25m. 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 $57). 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
Seaford
Chincoteague
Georgetown
Bethany Beach

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Alternative routes for Chicago to Salisbury

See prices for flight routes from nearby airports that may be better suited for you.
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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 October 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$384Average$473FlexibilityNo cancel feeOn-time71%

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