$104 Cheap Flights from Syracuse (SYR) to Chicago (MDW)

View $104 flight on Fri, May 30, 2025Opens in a new window

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Cheap Flights from Syracuse to Chicago (SYR-MDW)

Prices were available within the past 7 days and start at $104 for one-way flights and $208 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Fri, Jun 6 - Sun, Jun 8
SYR
Syracuse
MDW
Chicago
$208 Roundtrip, found 9 hours ago
$208
Roundtrip
found 9 hours ago
Select Frontier Airlines flight, departing Fri, Jun 6 from Syracuse to Chicago, returning Sun, Jun 8, priced at $208 found 9 hours ago
Frontier Airlines
Sun, May 18 - Thu, Jun 5
SYR
Syracuse
MDW
Chicago
$228 Roundtrip, found 3 days ago
$228
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sun, May 18 from Syracuse to Chicago, returning Thu, Jun 5, priced at $228 found 3 days ago
Delta
Thu, Sep 25 - Fri, Oct 3
SYR
Syracuse
MDW
Chicago
$229 Roundtrip, just found
$229
Roundtrip
just found
Select Delta flight, departing Thu, Sep 25 from Syracuse to Chicago, returning Fri, Oct 3, priced at $229 just found
Delta
Tue, May 13 - Tue, May 20
SYR
Syracuse
MDW
Chicago
$239 Roundtrip, found 17 hours ago
$239
Roundtrip
found 17 hours ago
Select Delta flight, departing Tue, May 13 from Syracuse to Chicago, returning Tue, May 20, priced at $239 found 17 hours ago
Frontier Airlines
Fri, May 23 - Mon, Jun 2
SYR
Syracuse
MDW
Chicago
$240 Roundtrip, found 4 days ago
$240
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Fri, May 23 from Syracuse to Chicago, returning Mon, Jun 2, priced at $240 found 4 days ago
Frontier Airlines
Sun, May 11 - Sun, May 18
SYR
Syracuse
MDW
Chicago
$248 Roundtrip, found 3 days ago
$248
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sun, May 11 from Syracuse to Chicago, returning Sun, May 18, priced at $248 found 3 days ago
Frontier Airlines
Mon, Jun 9 - Sun, Jun 15
SYR
Syracuse
MDW
Chicago
$251 Roundtrip, found 2 days ago
$251
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Mon, Jun 9 from Syracuse to Chicago, returning Sun, Jun 15, priced at $251 found 2 days ago
Frontier Airlines
Sun, May 18 - Thu, May 22
SYR
Syracuse
MDW
Chicago
$260 Roundtrip, found 3 days ago
$260
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sun, May 18 from Syracuse to Chicago, returning Thu, May 22, priced at $260 found 3 days ago
Delta
Thu, Sep 25 - Thu, Oct 2
SYR
Syracuse
MDW
Chicago
$264 Roundtrip, just found
$264
Roundtrip
just found
Select Delta flight, departing Thu, Sep 25 from Syracuse to Chicago, returning Thu, Oct 2, priced at $264 just found
Delta
Mon, Aug 4 - Wed, Aug 13
SYR
Syracuse
MDW
Chicago
$267 Roundtrip, found 16 hours ago
$267
Roundtrip
found 16 hours ago
Select Delta flight, departing Mon, Aug 4 from Syracuse to Chicago, returning Wed, Aug 13, priced at $267 found 16 hours ago
Flights from Syracuse (SYR) to Chicago (MDW)
Origin airport
Hancock Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Frontier Airlines
Roundtrip price
$208
Distance
599 mi

Syracuse to Chicago Flights

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

The best time to book a flight from Syracuse to Chicago

Sunday is one of the best days to book for cheap flights from Syracuse 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 Syracuse 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 Syracuse to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $104 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 Syracuse 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 Syracuse 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.

Frequently asked questions

How much does a flight from Hancock Intl. Airport (SYR) to Midway Intl. Airport (MDW) cost?
Discover the latest flight deals from SYR to MDW 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 SYR to MDW?
The cheapest flights from SYR to MDW 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 SYR to MDW?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that’ll take you from SYR to MDW. Sort your results by “Price (lowest to highest)” to snap up a great deal.
How many flights per day from Hancock Intl. Airport (SYR) to Midway Intl. Airport (MDW)?
You’ll need to hop on a flight with a layover when traveling from Hancock Intl. Airport (SYR) to Midway Intl. Airport (MDW). Direct flights don’t operate daily on this route. However, just filter your search to include one or more stops to find the best option for your trip.
What day of the week has the most flights from SYR to MDW?
You’ll usually find Tuesday the quietest day for flights, while Fridays are often the busiest.* However this can vary 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 Hancock Intl. Airport (SYR) to Midway Intl. Airport (MDW)?
To touch down at Midway Intl. Airport (MDW) on schedule, opt for a flight that takes off from Hancock Intl. Airport (SYR) before 3 PM. The chance of cancellations is 22% higher, on average, for departures after this time.**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.
What airports do you fly into for Chicago from Hancock Intl. Airport (SYR)?
O’Hare Intl. Airport (ORD) is the only airport in Chicago with direct flights from Hancock Intl. Airport (SYR). Browse your options and discover affordable fares on Expedia.
Is it cheaper to buy a plane ticket from Hancock Intl. Airport (SYR) to Midway Intl. Airport (MDW) last-minute?
Booking your plane ticket from SYR to MDW shortly before your getaway is typically more expensive. However, if you’re flexible with your itinerary, you could snag a cheap last-minute fare.
Is it cheaper to book a SYR to MDW flight and hotel package?
You’ll generally save money by booking a SYR to MDW flight and hotel package compared to booking separately. In fact, you could save hundreds of dollars by bundling with Expedia. And it’s easy to manage everything in one convenient place. Once you’ve chosen your preferred flights and accommodations, consider adding extras including car rentals, tours and activities.
Can I cancel or change the date of my flight from Hancock Intl. Airport (SYR) to Midway Intl. Airport (MDW)?
If you reserved your SYR to MDW flight in the last 24 hours, you may be able to cancel or modify it at no cost. Depending on the airline and the type of fare you purchased, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal for more details.

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*Available to One Key members.