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$154+ Cheap flights from Salisbury, MD (SBY) to Chicago (CHI)

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 5/15. Fares are subject to change and may not be available on all flights or dates of travel.
SBY — CHI
Mar 6 — Mar 131
Fri 3/6
Fri 3/13
1 adult, Economy
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Cheap flight deals from Salisbury to Chicago

Cheapest flights from Salisbury to Chicago
Explore the most affordable flight options available from Salisbury to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 4, 2026.

This American Airlines deal was found by Cheapflights users on 2/2. 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 2/177:20 am
SBY
-
ORD
1 stop6h 45m
American Airlines
Sat 2/217:10 am
ORD
-
SBY
1 stop5h 15m
American Airlines
Deal found 2/2$536
This American Airlines deal was found by Cheapflights users on 2/3. 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 7/1011:26 am
SBY
-
ORD
1 stop6h 17m
American Airlines
Thu 7/237:50 am
ORD
-
SBY
1 stop7h 17m
American Airlines
Deal found 2/3$610
This Kiwi.com deal was found by Cheapflights users on 2/3. 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 7/108:09 pm
SBY
-
ORD
2 stops17h 31m
Multiple Airlines
Thu 7/234:10 pm
ORD
-
SBY
1 stop26h 19m
Multiple Airlines
Deal found 2/3$611
This American Airlines deal was found by Cheapflights users on 2/3. 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.
Thu 2/198:03 am
SBY
-
ORD
2 stops6h 58m
American Airlines
Mon 2/232:40 pm
ORD
-
SBY
1 stop7h 01m
American Airlines
Deal found 2/3$850
This American Airlines deal was found by Cheapflights users on 2/1. 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 3/317:26 am
SBY
-
ORD
1 stop6h 09m
American Airlines
Wed 4/11:39 pm
ORD
-
SBY
1 stop5h 34m
American Airlines
Deal found 2/1$902

Find flight deals from Salisbury to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Salisbury (SBY) to Chicago (CHI). 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 4, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$536
(American Airlines)

One-way from

$154
(Kiwi.com)
Provider with most accurate pricing for Salisbury-Ocean City-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Salisbury-Ocean City-Chicago (CHI) flights.
Search Deals
From Salisbury-Ocean City to Chicago (CHI)
Search Deals
One-way flight from Salisbury-Ocean City to Chicago (CHI)
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Salisbury to Chicago 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 4, 2026.
Use the filters below to find and compare flights from Salisbury to Chicago that are best for you.

Fly from

Salisbury

Fly to

Chicago

Route

Depart

Return

Price

SalisburyChicago

SBY - ORD

SBYORD

Salisbury-Ocean City

Tue 2/17

7:20 am-1:05 pm

1 stop6h 45m

Chicago O'Hare Intl

Sat 2/21

7:10 am-1:25 pm

1 stop5h 15m

$536

SalisburyChicago

SBY - ORD

SBYORD

Salisbury-Ocean City

Thu 2/19

7:18 am-12:05 pm

1 stop5h 47m

Chicago O'Hare Intl

Mon 2/23

8:10 am-4:01 pm

1 stop6h 51m

$610

SalisburyChicago

SBY - ORD

SBYORD

Salisbury-Ocean City

Fri 7/10

11:26 am-4:43 pm

1 stop6h 17m

Chicago O'Hare Intl

Thu 7/23

1:17 pm-9:58 pm

1 stop7h 41m

$610

SalisburyChicago

SBY - ORD

SBYORD

Salisbury-Ocean City

Fri 7/10

8:09 pm-12:40 pm

2 stops17h 31m

Chicago O'Hare Intl

Thu 7/23

4:10 pm-7:29 pm

1 stop26h 19m

$611

SalisburyChicago

SBY - ORD

SBYORD

Salisbury-Ocean City

Tue 3/31

7:26 am-12:35 pm

1 stop6h 09m

Chicago O'Hare Intl

Wed 4/1

1:39 pm-8:13 pm

1 stop5h 34m

$902

SalisburyChicago

SBY - ORD

SBYORD

Salisbury-Ocean City

Fri 5/15

8:09 pm-11:27 am

2 stops16h 18m

$154

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/3

Compare providers for flights from Salisbury to Chicago

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 Salisbury to Chicago 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 Salisbury, Maryland-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Salisbury, Maryland-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Salisbury, Maryland-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Salisbury, Maryland-Chicago 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 Salisbury, Maryland-Chicago 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 Salisbury to Chicago

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

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

Currently, March is the cheapest month in which you can book a flight from Salisbury, Maryland to Chicago (average of $56). Flying from Salisbury, Maryland to Chicago in June is currently the most expensive (average of $133). 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.

Related info for your journey

Find useful and relevant information for your journey from Salisbury to Chicago. 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 from for flights from Salisbury to Chicago?

    If you book a flight to Chicago from Salisbury, you will be flying from 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 Salisbury-Ocean City to Chicago per day from 1 airline.

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

    A quick flight from Salisbury, Maryland to Chicago can take about 6h 45m. American Airlines provides one of the quickest options available for as low as $536. Salisbury, Maryland and Chicago are separated by a distance of 700 mi.

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

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

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

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

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

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

    Currently, March is the cheapest month in which you can book a flight from Salisbury, Maryland to Chicago (average of $56). Flying from Salisbury, Maryland to Chicago in June is currently the most expensive (average of $133). 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 Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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Top airline flying from Salisbury to Chicago

Discover the top airline that operate flights from Salisbury to Chicago. 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 4, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$388Average$448FlexibilityNo cancel feeOn-time71%

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