$215 Cheap Flights from Chicago (ORD) to Salisbury (SBY)

View $215 flight on Wed, Jul 30, 2025Opens in a new window

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Find available prices by choosing your travel dates.

Cheap Flights from Chicago to Salisbury (ORD-SBY)

Prices were available within the past 7 days and start at $215 for one-way flights and $430 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Sat, Aug 16 - Sat, Aug 23
ORD
Chicago
SBY
Salisbury
$430 Roundtrip, found 5 hours ago
$430
Roundtrip
found 5 hours ago
Select American Airlines flight, departing Sat, Aug 16 from Chicago to Salisbury, returning Sat, Aug 23, priced at $430 found 5 hours ago
American Airlines
Sat, Jul 26 - Wed, Jul 30
ORD
Chicago
SBY
Salisbury
$439 Roundtrip, found 1 day ago
$439
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Jul 26 from Chicago to Salisbury, returning Wed, Jul 30, priced at $439 found 1 day ago
American Airlines
Wed, Jul 9 - Sat, Jul 12
ORD
Chicago
SBY
Salisbury
$447 Roundtrip, found 13 hours ago
$447
Roundtrip
found 13 hours ago
Select American Airlines flight, departing Wed, Jul 9 from Chicago to Salisbury, returning Sat, Jul 12, priced at $447 found 13 hours ago
American Airlines
Sat, Jul 26 - Wed, Jul 30
ORD
Chicago
SBY
Salisbury
$450 Roundtrip, found 1 day ago
$450
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Jul 26 from Chicago to Salisbury, returning Wed, Jul 30, priced at $450 found 1 day ago
American Airlines
Wed, Aug 6 - Mon, Aug 11
ORD
Chicago
SBY
Salisbury
$450 Roundtrip, found 3 hours ago
$450
Roundtrip
found 3 hours ago
Select American Airlines flight, departing Wed, Aug 6 from Chicago to Salisbury, returning Mon, Aug 11, priced at $450 found 3 hours ago
American Airlines
Wed, Jul 9 - Sat, Jul 12
ORD
Chicago
SBY
Salisbury
$453 Roundtrip, found 13 hours ago
$453
Roundtrip
found 13 hours ago
Select American Airlines flight, departing Wed, Jul 9 from Chicago to Salisbury, returning Sat, Jul 12, priced at $453 found 13 hours ago
American Airlines
Sat, Sep 27 - Sun, Sep 28
ORD
Chicago
SBY
Salisbury
$459 Roundtrip, found 8 hours ago
$459
Roundtrip
found 8 hours ago
Select American Airlines flight, departing Sat, Sep 27 from Chicago to Salisbury, returning Sun, Sep 28, priced at $459 found 8 hours ago
American Airlines
Sat, Mar 7 - Sat, Mar 14
ORD
Chicago
SBY
Salisbury
$460 Roundtrip, found 2 days ago
$460
Roundtrip
found 2 days ago
Select American Airlines flight, departing Sat, Mar 7 from Chicago to Salisbury, returning Sat, Mar 14, priced at $460 found 2 days ago
American Airlines
Wed, Jul 2 - Sat, Jul 5
ORD
Chicago
SBY
Salisbury
$463 Roundtrip, found 1 day ago
$463
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, Jul 2 from Chicago to Salisbury, returning Sat, Jul 5, priced at $463 found 1 day ago
American Airlines
Wed, Aug 6 - Mon, Aug 11
ORD
Chicago
SBY
Salisbury
$467 Roundtrip, found 3 hours ago
$467
Roundtrip
found 3 hours ago
Select American Airlines flight, departing Wed, Aug 6 from Chicago to Salisbury, returning Mon, Aug 11, priced at $467 found 3 hours ago
Flights from Chicago (ORD) to Salisbury (SBY)
Origin airport
O'Hare Intl.
Destination airport
Salisbury - Ocean City Wicomico Regional
Airlines serving
American Airlines
Roundtrip price
$430
Distance
699 mi

Chicago to Salisbury Flights

The cheapest times to fly from Chicago to Salisbury

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Salisbury are during the month of August. You can find some of the cheapest flights from Chicago to Salisbury with Expedia's search tool and vast selection of airlines.

The best time to book a flight from Chicago to Salisbury

Sunday is one of the best days to book for cheap flights from Chicago to Salisbury: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

How to find cheap round-trip tickets from Chicago to Salisbury

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Salisbury in 2025. You can also book with separate airlines for your outbound and return journeys, from $215 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Salisbury flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Salisbury airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

*Terms apply.

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

Frequently asked questions

How much does a flight from O'Hare Intl. Airport (ORD) to Salisbury - Ocean City Wicomico Regional Airport (SBY) cost?
Discover the latest flight deals from ORD to SBY by entering your preferred travel dates and searching on Expedia. Easily compare prices by departure date if you have flexibility with your schedule and use handy filters to explore prices for your preferred journey. As a member of One Key™, our free loyalty program, you can use Price Tracking to watch fares and receive notifications if prices go up or down.
What is the cheapest month to fly from ORD to SBY?
The cheapest flights from ORD to SBY are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
What is the cheapest airline that flies from ORD to SBY?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that’ll take you from ORD to SBY. Sort your results by “Price (lowest to highest)” to snap up a great deal.
How many flights per day from O'Hare Intl. Airport (ORD) to Salisbury - Ocean City Wicomico Regional Airport (SBY)?
You’ll have to take a flight with a layover when traveling from O’Hare Intl. Airport (ORD) to Salisbury - Ocean City Wicomico Regional Airport (SBY). Direct flights don’t operate daily on this route. However, simply filter your search to include one or more stops to discover an option that works for you.
What day of the week has the most flights from ORD to SBY?
Usually you’ll find the widest variety of flight choices on a Friday. Tuesdays tend to be the quietest.* However, this can change depending on the airline, season and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from O'Hare Intl. Airport (ORD) to Salisbury - Ocean City Wicomico Regional Airport (SBY)?
To avoid potential delays on the O’Hare Intl. Airport (ORD) to Salisbury - Ocean City Wicomico Regional Airport (SBY) route, fly before 3 PM. Later departures have a 22% higher chance of cancellation.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG’s global flight data platform.
Is it cheaper to buy a plane ticket from O'Hare Intl. Airport (ORD) to Salisbury - Ocean City Wicomico Regional Airport (SBY) last-minute?
Last-minute bookings from ORD to SBY are usually more expensive. To lock in the best rates, start looking for flights early. That being said, if you can play around with your travel dates, you may score a cheap fare right before your trip.
Is it cheaper to book an ORD to SBY flight and hotel package?
Compared with arranging flights and hotels separately, booking an ORD to SBY flight and hotel package with Expedia could lead to significant savings. What’s more, having everything in one place will take the hassle out of travel planning. Simply pick your flights and select from our extensive range of stays, then tailor your trip with other add-ons like activities and car rentals.
Can I cancel or change the date of my flight from O'Hare Intl. Airport (ORD) to Salisbury - Ocean City Wicomico Regional Airport (SBY)?
If you booked your ORD to SBY flight in the last 24 hours, you may be able to modify or cancel it without fees. Depending on the airline and the ticket type you purchased, additional charges may apply for changes after that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you’d like more information.

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*Available to One Key members.