$77 Cheap Flights from Syracuse (SYR) to Chicago (MDW)

View $77 flight on Mon, Nov 3, 2025Opens in a new window

Popular airlines from Hancock Intl. Airport (SYR) to Chicago Midway Airport (MDW)

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Cheap Flights from Syracuse to Chicago (SYR-MDW)

Prices were available within the past 7 days and start at $77 for one-way flights and $154 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Fri, Sep 26 - Mon, Sep 29
SYR
Syracuse
MDW
Chicago
$154 Roundtrip, just found
$154
Roundtrip
just found
Select Frontier Airlines flight, departing Fri, Sep 26 from Syracuse to Chicago, returning Mon, Sep 29, priced at $154 just found
Frontier Airlines
Mon, Oct 6 - Thu, Oct 16
SYR
Syracuse
MDW
Chicago
$164 Roundtrip, found 12 hours ago
$164
Roundtrip
found 12 hours ago
Select Frontier Airlines flight, departing Mon, Oct 6 from Syracuse to Chicago, returning Thu, Oct 16, priced at $164 found 12 hours ago
Frontier Airlines
Thu, Oct 23 - Sat, Oct 25
SYR
Syracuse
MDW
Chicago
$182 Roundtrip, found 1 day ago
$182
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, Oct 23 from Syracuse to Chicago, returning Sat, Oct 25, priced at $182 found 1 day ago
Frontier Airlines
Thu, Oct 16 - Thu, Oct 30
SYR
Syracuse
MDW
Chicago
$192 Roundtrip, found 3 days ago
$192
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Thu, Oct 16 from Syracuse to Chicago, returning Thu, Oct 30, priced at $192 found 3 days ago
Frontier Airlines
Mon, Sep 22 - Mon, Sep 29
SYR
Syracuse
MDW
Chicago
$195 Roundtrip, found 4 hours ago
$195
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Mon, Sep 22 from Syracuse to Chicago, returning Mon, Sep 29, priced at $195 found 4 hours ago
Frontier Airlines
Sun, Nov 2 - Sun, Nov 9
SYR
Syracuse
MDW
Chicago
$202 Roundtrip, found 6 days ago
$202
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Sun, Nov 2 from Syracuse to Chicago, returning Sun, Nov 9, priced at $202 found 6 days ago
Frontier Airlines
Mon, Oct 6 - Sun, Oct 12
SYR
Syracuse
MDW
Chicago
$205 Roundtrip, found 12 hours ago
$205
Roundtrip
found 12 hours ago
Select Frontier Airlines flight, departing Mon, Oct 6 from Syracuse to Chicago, returning Sun, Oct 12, priced at $205 found 12 hours ago
Frontier Airlines
Thu, Oct 30 - Thu, Nov 6
SYR
Syracuse
MDW
Chicago
$207 Roundtrip, found 21 hours ago
$207
Roundtrip
found 21 hours ago
Select Frontier Airlines flight, departing Thu, Oct 30 from Syracuse to Chicago, returning Thu, Nov 6, priced at $207 found 21 hours ago
Frontier Airlines
Fri, Sep 26 - Mon, Sep 29
SYR
Syracuse
MDW
Chicago
$210 Roundtrip, just found
$210
Roundtrip
just found
Select Frontier Airlines flight, departing Fri, Sep 26 from Syracuse to Chicago, returning Mon, Sep 29, priced at $210 just found
Delta
Thu, Oct 23 - Sat, Oct 25
SYR
Syracuse
MDW
Chicago
$222 Roundtrip, found 1 day ago
$222
Roundtrip
found 1 day ago
Select Delta flight, departing Thu, Oct 23 from Syracuse to Chicago, returning Sat, Oct 25, priced at $222 found 1 day ago

Find the cheapest month to fly from Syracuse (SYR) to Chicago (MDW)

December is typically the cheapest month to fly

From $134 - $674 per traveler.

Frequently asked questions

How much does a flight from Hancock Intl. Airport (SYR) to Midway Intl. Airport (MDW) cost?
Snag a cheap one-way flight from $77 or cheap return flight from $154 from Hancock Intl. Airport (SYR) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight deals on this route.
What is the cheapest month to fly from Hancock Intl. Airport (SYR) to Midway Intl. Airport (MDW)?
The cheapest month to fly from SYR to MDW is September, when demand is low. Off-peak season is typically when you'll find lower airfares between these airports.
What is the cheapest airline that flies from Hancock Intl. Airport (SYR) to Midway Intl. Airport (MDW)?
Use the filters on Expedia to compare different airlines and find the cheapest carrier that'll take you from SYR to MDW. Then, sort your results by "Price (lowest to highest)" to score a good 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.

Travel information

Travel information

Origin airport
Hancock Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Frontier Airlines
Roundtrip price
$154
Distance
599 mi

Book with confidence

Book with confidence

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 September. 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 $77 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.

 

Syracuse to Chicago Flights

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*Available to One Key members.