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$361+ Cheap flights from Salisbury, MD (SBY) to Chicago (CHI)

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 11/21. Fares are subject to change and may not be available on all flights or dates of travel.
SBY — CHI
Dec 2 — Dec 91
Tue 12/2
Tue 12/9
1 adult, Economy
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Find 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 November 2, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/218:02 pmSBY - ORD
1 stop14h 04mMultiple Airlines
Sun 11/237:09 pmORD - SBY
1 stop23h 13mMultiple Airlines
Deal found 11/1$361
This American Airlines deal was found by Cheapflights users on 11/1. 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.
Thu 11/276:30 amSBY - ORD
1 stop6h 58mAmerican Airlines
Wed 12/31:45 pmORD - SBY
1 stop6h 22mAmerican Airlines
Deal found 11/1$431
This American Airlines deal was found by Cheapflights users on 11/2. 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.
Fri 11/216:30 amSBY - ORD
2 stops7h 45mAmerican Airlines
Sun 11/233:30 pmORD - SBY
2 stops5h 59mAmerican Airlines
Deal found 11/2$1,039

Cheap 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 November 2, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$361
(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

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 November 2, 2025.
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

Fri 11/21

8:02 pm-9:06 am

1 stop14h 04m

Chicago O'Hare Intl

Sun 11/23

7:09 pm-7:22 pm

1 stop23h 13m

$361

SalisburyChicago

SBY - ORD

SBYORD

Salisbury-Ocean City

Thu 11/27

6:30 am-12:28 pm

1 stop6h 58m

Chicago O'Hare Intl

Wed 12/3

1:45 pm-9:07 pm

1 stop6h 22m

$431

SalisburyChicago

SBY - ORD

SBYORD

Salisbury-Ocean City

Fri 4/24

5:00 am-8:49 am

1 stop4h 49m

Chicago O'Hare Intl

Sun 4/26

11:53 am-7:47 pm

1 stop6h 54m

$490

SalisburyChicago

SBY - ORD

SBYORD

Salisbury-Ocean City

Wed 3/11

5:56 pm-12:13 am

1 stop7h 17m

Chicago O'Hare Intl

Sat 3/14

5:00 am-10:43 am

1 stop4h 43m

$530

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/1

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 November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

*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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Salisbury, Maryland-Chicago flight deals on Cheapflights vs. eDreams >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 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 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 $50). Flying from Salisbury, Maryland to Chicago in June is currently the most expensive (average of $132). 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 0 different airlines.

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

    A quick flight from Salisbury, Maryland to Chicago can take about 6h 58m. American Airlines provides one of the quickest options available for as low as $431. 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 $50). Flying from Salisbury, Maryland to Chicago in June is currently the most expensive (average of $132). 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
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Porter
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