CA $235 Cheap Flights from Syracuse (SYR) to Chicago (MDW)

View CA $235 flight on Wed, Jun 10, 2026Opens in a new window

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

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Cheap flights from Syracuse (SYR) to Chicago (MDW)

Prices were available within the past 7 days and start at CA $235 for one-way flights and CA $392 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Wed, Jun 10 - Sat, Jun 13
SYR
Syracuse
MDW
Chicago
CA $392 Roundtrip, found 2 days ago
CA $392
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Jun 10 from Syracuse to Chicago, returning Sat, Jun 13, priced at CA $392 found 2 days ago
Delta
Thu, Jul 2 - Sat, Jul 4
SYR
Syracuse
MDW
Chicago
CA $396 Roundtrip, found 6 days ago
CA $396
Roundtrip
found 6 days ago
Select Delta flight, departing Thu, Jul 2 from Syracuse to Chicago, returning Sat, Jul 4, priced at CA $396 found 6 days ago
Delta
Mon, Jun 8 - Tue, Jun 30
SYR
Syracuse
MDW
Chicago
CA $406 Roundtrip, found 23 hours ago
CA $406
Roundtrip
found 23 hours ago
Select Delta flight, departing Mon, Jun 8 from Syracuse to Chicago, returning Tue, Jun 30, priced at CA $406 found 23 hours ago
Delta
Wed, Jul 1 - Sat, Jul 4
SYR
Syracuse
MDW
Chicago
CA $430 Roundtrip, found 6 days ago
CA $430
Roundtrip
found 6 days ago
Select Delta flight, departing Wed, Jul 1 from Syracuse to Chicago, returning Sat, Jul 4, priced at CA $430 found 6 days ago
Delta
Wed, Jul 1 - Wed, Jul 8
SYR
Syracuse
MDW
Chicago
CA $464 Roundtrip, found 6 days ago
CA $464
Roundtrip
found 6 days ago
Select Delta flight, departing Wed, Jul 1 from Syracuse to Chicago, returning Wed, Jul 8, priced at CA $464 found 6 days ago
Delta
Sun, Jun 7 - Thu, Jun 11
SYR
Syracuse
MDW
Chicago
CA $469 Roundtrip, found 2 days ago
CA $469
Roundtrip
found 2 days ago
Select Delta flight, departing Sun, Jun 7 from Syracuse to Chicago, returning Thu, Jun 11, priced at CA $469 found 2 days ago
Delta
Thu, May 21 - Mon, Jun 8
SYR
Syracuse
MDW
Chicago
CA $481 Roundtrip, found 23 hours ago
CA $481
Roundtrip
found 23 hours ago
Select Delta flight, departing Thu, May 21 from Syracuse to Chicago, returning Mon, Jun 8, priced at CA $481 found 23 hours ago
Delta
Fri, Jul 3 - Wed, Jul 8
SYR
Syracuse
MDW
Chicago
CA $491 Roundtrip, found 6 days ago
CA $491
Roundtrip
found 6 days ago
Select Delta flight, departing Fri, Jul 3 from Syracuse to Chicago, returning Wed, Jul 8, priced at CA $491 found 6 days ago
Delta
Fri, Jun 12 - Tue, Jun 16
SYR
Syracuse
MDW
Chicago
CA $495 Roundtrip, found 2 days ago
CA $495
Roundtrip
found 2 days ago
Select Delta flight, departing Fri, Jun 12 from Syracuse to Chicago, returning Tue, Jun 16, priced at CA $495 found 2 days ago
Delta
Sat, May 16 - Mon, May 18
SYR
Syracuse
MDW
Chicago
CA $496 Roundtrip, found 3 days ago
CA $496
Roundtrip
found 3 days ago
Select Delta flight, departing Sat, May 16 from Syracuse to Chicago, returning Mon, May 18, priced at CA $496 found 3 days ago

Alternative airports near Chicago

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

Select flight to Midway Intl. MDW. Cheapest and Closest option available. Average driving time to city centre is 16 minutes. Flights from CA $481
MDW
Midway Intl.
CheapestClosest
Average driving time to city centre16 min
Flights from CA $481

Frequently asked questions

What is the cheapest month to fly from Syracuse, NY (SYR-Hancock Intl.) to Chicago, IL (MDW-Midway Intl.)?
September is typically the cheapest month to fly from Syracuse, NY (SYR-Hancock Intl.) to Chicago, IL (MDW-Midway Intl.), with average round-trip fares around 511 CAD. This is about 40% lower than the average price throughout the year. September often sees lower prices as the summer travel rush ends and before the holiday season begins, leading to reduced demand. Other cheap months to fly from Syracuse, NY (SYR-Hancock Intl.) to Chicago, IL (MDW-Midway Intl.) include February and June.*Averages based on flights available on Expedia in the last year.
How do I find cheap flights from Syracuse, NY (SYR-Hancock Intl.) to Chicago, IL (MDW-Midway Intl.)?
To find a cheap flight from Syracuse, NY (SYR-Hancock Intl.) to Chicago, IL (MDW-Midway Intl.), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.
What is the best time to fly from Syracuse, NY (SYR-Hancock Intl.) to Chicago, IL (MDW-Midway Intl.)?
Based on booking data from the past year, the cheapest months to fly from Syracuse, NY (SYR-Hancock Intl.) to Chicago, IL (MDW-Midway Intl.) are typically September and February, with average round-trip flights costing around 511 CAD. These months often offer lower prices because they fall outside of peak travel seasons, giving you a better chance to find a good deal.*Prices based on flights available on Expedia in the last year.
How many flights per day from Syracuse, NY (SYR-Hancock Intl.) to Chicago, IL (MDW-Midway Intl.)?
There are approximately 10 connecting flights per day from Syracuse, NY (SYR-Hancock Intl.) (SYR) to Chicago, IL (MDW-Midway Intl.) (MDW). Some common connection points include Detroit Metropolitan Wayne County (DTW), Washington Dulles Intl. (IAD), and Hartsfield-Jackson Atlanta Intl. (ATL).
What is the earliest flight from Syracuse, NY (SYR-Hancock Intl.) to Chicago, IL (MDW-Midway Intl.)?
The earliest flight from Syracuse, NY (SYR-Hancock Intl.) to Chicago, IL (MDW-Midway Intl.) typically departs at approximately 5:25 AM local time, operated by Delta. This is a seasonal service active in May. An early departure like this can help you make the most of your time at your destination. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.
What day of the week has the most flights from Syracuse, NY (SYR-Hancock Intl.) to Chicago, IL (MDW-Midway Intl.)?
You'll typically find the most flights from Syracuse, NY (SYR-Hancock Intl.) to Chicago, IL (MDW-Midway Intl.) on a Tuesday, with around 10 flights available. This gives you a good selection of options for your travel plans. Major airlines on this route include Delta Air Lines, United Airlines, and Frontier Airlines. Flight schedules are consistent throughout the week.
What are the most popular departure times for flights from Syracuse, NY (SYR-Hancock Intl.) to Chicago, IL (MDW-Midway Intl.)?
The most popular departure times for flights from Syracuse Hancock Intl. (SYR) to Chicago Midway Intl. (MDW) are in the early morning, from 6am to 9am. About 43% of passengers prefer this time. Many major carriers, including Delta and United, offer flights during this window. This timing works well because it allows you to get an early start on your travel day and arrive at your destination with plenty of time.
How long does it take to fly from Syracuse, NY (SYR-Hancock Intl.) to Chicago, IL (MDW-Midway Intl.)?
Flights from SYR to MDW with one stop typically take around 4 hours, covering approximately 599 miles. Keep in mind that actual flight times can vary due to wind patterns, weather, and air traffic.
Can you fly business or first class from Syracuse, NY (SYR-Hancock Intl.) to Chicago, IL (MDW-Midway Intl.)?
Select the "Business class" and "First class" filters when looking for SYR to MDW flights on Expedia. This is the easiest way to compare prices, routes and flight times for your trip.
How do I earn miles on a Syracuse, NY (SYR-Hancock Intl.) to Chicago, IL (MDW-Midway Intl.) flight with Expedia?
It's easy to earn miles on a Syracuse, NY (SYR-Hancock Intl.) to Chicago, IL (MDW-Midway Intl.) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia.*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
What airports do you fly into for Chicago from Hancock Intl. (SYR)?
From Hancock Intl. (SYR), you can fly into O'Hare Intl. (ORD) and Midway Intl. (MDW) in Chicago. Some flights may connect through major hubs like Ronald Reagan Washington National (DCA), Charlotte-Douglas Intl. (CLT), Philadelphia Intl. (PHL) before reaching Chicago. Compare routes and airports on Expedia to find the best flight options for your travel plans.
Is it cheaper to buy a plane ticket from Syracuse, NY (SYR-Hancock Intl.) to Chicago, IL (MDW-Midway Intl.) at the last minute?
Typically, booking a last minute flight from Syracuse, NY (SYR-Hancock Intl.) to Chicago, IL (MDW-Midway Intl.) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a Syracuse, NY (SYR-Hancock Intl.) to Chicago, IL (MDW-Midway Intl.) flight and hotel package?
Securing a Syracuse, NY (SYR-Hancock Intl.) to Chicago, IL (MDW-Midway Intl.) flight and hotel package is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Syracuse, NY (SYR-Hancock Intl.) to Chicago, IL (MDW-Midway Intl.)?
If you booked your Syracuse, NY (SYR-Hancock Intl.) to Chicago, IL (MDW-Midway Intl.) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, 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 if you'd like more information.

Travel information

Origin airport
Hancock Intl.
Destination airport
Midway Intl.
Airlines serving
Delta
Roundtrip price
CA $387
Distance
958 km

Book with confidence

North Syracuse to Chicago Flights

The easy way to book your flights from Syracuse to Chicago 

With Expedia, it’s simple to find and book flights to Chicago from Syracuse whether you’re traveling for business or pleasure. Enter your travel dates, hit search, and choose your flight from 20 airlines that cover this route. There are nonstop flights to Midway Intl., too.  

Choose your preferred carrier and cabin class with the advanced search tool and select your ideal departure time. Then, if you want, you can see just nonstop or refundable flights. And if you’re traveling last minute, just enter the date to check out flights from Syracuse to Chicago today, tomorrow, or this week.  

 

Save dollars with cheap flights from Hancock Intl., SYR to Midway Intl., MDW 

Sort your search results by price to find great deals on your flight from Syracuse to Chicago—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Chicago from Syracuse currently is just CA $392 rising to CA $496.  

Here are more money-saving tips: 

  • Fly in June when flight prices are normally at their lowest 
  • Book about a month to 6 weeks before you travel for the best prices to Chicago  
  • Avoid peak season and weekends when flights can cost more
  • Early morning and late-night flights are sometimes cheaper, so try varying your travel times 
  • One surefire way to save money on your flight is to book your flight and hotel together with Expedia. Sometimes, the savings are so large that the flight is basically free! 

 

Reasons to choose Expedia for your flight to Chicago from Syracuse 

Whatever your destination, budget, or reason to travel, in just one quick search, you can choose from loads of flights, airlines, and cabin classes. The filters make it quick and easy to find your ideal flights, and if you choose one of the flexible options, you won’t be charged to change your flight. So book your flight to Chicago with Expedia today.

North Syracuse to Chicago Flights

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