Cheap Flights from Salisbury (SBY) to Chicago (MDW)

Popular airlines from Salisbury, MD (SBY-Salisbury - Ocean City Wicomico Regional) to Chicago Midway Airport (MDW)

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Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $476
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $476

Frequently asked questions

How much does a flight from Salisbury - Ocean City Wicomico Regional Airport (SBY) to Midway Intl. Airport (MDW) cost?
Snag a cheap one-way flight or cheap return flight from Salisbury - Ocean City Wicomico Regional Airport (SBY) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight deals on this route.
What is the cheapest month to fly from Salisbury - Ocean City Wicomico Regional Airport (SBY) to Midway Intl. Airport (MDW)?
The cheapest month to fly from SBY to MDW is , when demand is low. Off-peak season is usually when you'll find cheap fares for travel between these airports.
What is the cheapest airline that flies from Salisbury - Ocean City Wicomico Regional Airport (SBY) to Midway Intl. Airport (MDW)?
Expedia's filter tool lets you easily compare different airlines, travel time and fares all in one place. Tailor the search to your trip, then sort by "Price (lowest to highest)" to find out which carrier offers the cheapest SBY to MDW flight.
How many flights per day from Salisbury - Ocean City Wicomico Regional Airport (SBY) to Midway Intl. Airport (MDW)?
There aren't any daily nonstop flights available from Salisbury - Ocean City Wicomico Regional Airport (SBY) to Midway Intl. Airport (MDW). But you can opt for flights with layovers. Filter your search results on Expedia to include one or more stops, and you'll be on your way in no time.
What day of the week has the most flights from SBY to MDW?
You'll usually find Tuesday the quietest day for flights, while Fridays are often the busiest.* However this can change from season to season and during public holidays or peak travel times.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Salisbury - Ocean City Wicomico Regional Airport (SBY) to Midway Intl. Airport (MDW)?
Opt for a flight from Salisbury - Ocean City Wicomico Regional Airport (SBY) to Midway Intl. Airport (MDW) that takes off before 3 PM to reduce the likelihood of delays. Later departures have a 22% higher chance of being canceled, on average.**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 Salisbury - Ocean City Wicomico Regional Airport (SBY) to Midway Intl. Airport (MDW) last-minute?
Booking your ticket from SBY to MDW shortly before your trip is usually more expensive. However, if you're flexible with your departure dates and times, you could score a cheap last-minute fare.
Is it cheaper to book a SBY to MDW flight and hotel package?
Compared with arranging flights and hotels separately, booking a SBY to MDW flight and hotel package with Expedia could result in significant savings. Better still, having it all in one place takes the hassle out of planning your trip. Simply secure your flights and select from our wide range of stays, then tailor your trip with other add-ons like tours, activities and car rentals.
Can I cancel or change the date of my flight from Salisbury - Ocean City Wicomico Regional Airport (SBY) to Midway Intl. Airport (MDW)?
Typically, you can cancel or modify your SBY to MDW flight. However, additional charges may apply, especially if you booked more than 24 hours ago. Double-check your itinerary for the airline's guidelines and fees on flight changes, or if you need more information, visit our Customer Service portal.

Travel information

Origin airport
Salisbury - Ocean City Wicomico Regional
Destination airport
Midway Intl.
Distance
688 mi

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Salisbury to Chicago Flights

The cheapest times to fly from Salisbury to Chicago

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 Salisbury to Chicago are during the month of . You can find some of the cheapest flights from Salisbury to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Salisbury to Chicago

Sunday is one of the best days to book for cheap flights from Salisbury to Chicago: 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 Salisbury to Chicago

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 Salisbury to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from 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 Salisbury to Chicago 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 Salisbury to Chicago 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.

 

Salisbury to Chicago Flights

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