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CA $376 Cheap Flights from Syracuse (SYR) to Chicago (MDW)

View CA $376 flight on Wed, Sep 16, 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 $376 for one-way flights and CA $418 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Sat, Oct 24 - Mon, Nov 9
SYR
Syracuse
MDW
Chicago
CA $418 Roundtrip, found 2 days ago
CA $418
Roundtrip
found 2 days ago
Select Delta flight, departing Sat, Oct 24 from Syracuse to Chicago, returning Mon, Nov 9, priced at CA $418 found 2 days ago
Delta
Wed, Oct 21 - Sat, Oct 24
SYR
Syracuse
MDW
Chicago
CA $419 Roundtrip, found 1 day ago
CA $419
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Oct 21 from Syracuse to Chicago, returning Sat, Oct 24, priced at CA $419 found 1 day ago
Delta
Wed, Oct 21 - Sat, Oct 24
SYR
Syracuse
MDW
Chicago
CA $447 Roundtrip, found 1 day ago
CA $447
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Oct 21 from Syracuse to Chicago, returning Sat, Oct 24, priced at CA $447 found 1 day ago
Delta
Fri, Aug 28 - Sat, Aug 29
SYR
Syracuse
MDW
Chicago
CA $450 Roundtrip, found 6 days ago
CA $450
Roundtrip
found 6 days ago
Select Delta flight, departing Fri, Aug 28 from Syracuse to Chicago, returning Sat, Aug 29, priced at CA $450 found 6 days ago
Delta
Mon, Aug 17 - Sat, Aug 22
SYR
Syracuse
MDW
Chicago
CA $475 Roundtrip, found 2 days ago
CA $475
Roundtrip
found 2 days ago
Select Delta flight, departing Mon, Aug 17 from Syracuse to Chicago, returning Sat, Aug 22, priced at CA $475 found 2 days ago
Delta
Sat, Aug 22 - Wed, Aug 26
SYR
Syracuse
MDW
Chicago
CA $489 Roundtrip, found 1 day ago
CA $489
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Aug 22 from Syracuse to Chicago, returning Wed, Aug 26, priced at CA $489 found 1 day ago
Delta
Thu, Aug 20 - Mon, Aug 24
SYR
Syracuse
MDW
Chicago
CA $503 Roundtrip, found 2 days ago
CA $503
Roundtrip
found 2 days ago
Select Delta flight, departing Thu, Aug 20 from Syracuse to Chicago, returning Mon, Aug 24, priced at CA $503 found 2 days ago
Delta
Wed, Oct 21 - Sat, Oct 24
SYR
Syracuse
MDW
Chicago
CA $531 Roundtrip, found 1 day ago
CA $531
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Oct 21 from Syracuse to Chicago, returning Sat, Oct 24, priced at CA $531 found 1 day ago
Delta
Wed, Oct 21 - Sat, Oct 24
SYR
Syracuse
MDW
Chicago
CA $545 Roundtrip, found 1 day ago
CA $545
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Oct 21 from Syracuse to Chicago, returning Sat, Oct 24, priced at CA $545 found 1 day ago
Delta
Fri, Nov 6 - Mon, Nov 9
SYR
Syracuse
MDW
Chicago
CA $547 Roundtrip, found 5 hours ago
CA $547
Roundtrip
found 5 hours ago
Select Delta flight, departing Fri, Nov 6 from Syracuse to Chicago, returning Mon, Nov 9, priced at CA $547 found 5 hours ago

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. Average driving time to city centre is 23 minutes. Flights from CA $448
ORD
O'Hare Intl.
Average driving time to city centre23 min
Flights from CA $448

Frequently asked questions

How much does a flight from Syracuse, NY (SYR-Hancock Intl.) to Chicago, IL (MDW-Midway Intl.) cost?
You can find one-way and return flights from SYR to MDW with Expedia. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see our cheapest fares first, and use the Price Tracking tool to receive alerts when SYR to MDW ticket fares go up or down.
What is the cheapest month to fly from Syracuse, NY (SYR-Hancock Intl.) to Chicago, IL (MDW-Midway Intl.)?
If you're looking for the cheapest time to fly from Syracuse, NY (SYR-Hancock Intl.) to Chicago, IL (MDW-Midway Intl.), September is typically your best bet. You can expect average return flights to be around CA$292 during this month. Other budget-friendly months for this route include February and June.
Which airlines fly direct from Syracuse, NY (SYR-Hancock Intl.) to Chicago, IL (MDW-Midway Intl.)?
Enter SYR to MDW and your travel dates, then apply the 'Nonstop' filter to see only direct flights.
What is the cheapest airline that flies from Syracuse, NY (SYR-Hancock Intl.) to Chicago, IL (MDW-Midway Intl.)?
Frontier Airlines is one of the cheapest airlines offering connecting return flights from Syracuse, NY (SYR-Hancock Intl.) to Chicago, IL (MDW-Midway Intl.), with tickets starting from around CA$688 for flights that can be booked for departure within the next year. These prices are per adult, for economy/coach class. Use Expedia's search tool to compare the prices and schedules of airlines that fly this route to find the best option for your plans and budget.
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.)?
The best time to fly from Syracuse, NY (SYR-Hancock Intl.) to Chicago, IL (MDW-Midway Intl.) is typically September or February. These months offer a great balance, with average return flight prices around CA$292. While these are the cheapest months, they also tend to be popular times to travel, meaning you'll likely find plenty of flight options to suit your schedule. September offers pleasant early autumn weather, and February can be a good option for those looking to travel before the spring rush.
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 Hancock International (SYR) to Chicago Midway International (MDW). Some common connection points include Detroit Metropolitan Wayne County (DTW), Washington Dulles International (IAD), and Hartsfield-Jackson Atlanta International (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 around 5:30 AM local time. This flight is operated by Delta and is a seasonal service, active only in August. 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 Wednesday, with around 11 flights available. This gives you a good selection of options for your travel plans. Major airlines on this route include Delta, United, and Frontier Airlines. Flight schedules are fairly consistent throughout the week, so you'll have several flight options regardless of the day you choose to fly.
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, NY (SYR-Hancock Intl.) to Chicago, IL (MDW-Midway Intl.) are in the early morning, from 6am to 9am. Many major carriers, including Delta and United, offer flights during this window. Many travelers prefer these times because it allows for an early start to their day in Chicago.
How long does it take to fly from Syracuse, NY (SYR-Hancock Intl.) to Chicago, IL (MDW-Midway Intl.)?
There are no nonstop flights from Syracuse, NY (SYR-Hancock Intl.) to Chicago, IL (MDW-Midway Intl.). For this route, which covers a distance of about 964 kilometres, flights with one stop typically take around 6 hours 48 minutes. If your journey involves two or more stops, you can expect the travel time to be longer, usually around 13 hours. Keep in mind that actual flight times can vary based on factors like layover duration, routing, and wind patterns.
Can you fly business or first class from Syracuse, NY (SYR-Hancock Intl.) to Chicago, IL (MDW-Midway Intl.)?
You can fly business class or first class between SYR and MDW.First class cabins are available on Delta.
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, IL (MDW) from Syracuse, NY (SYR)?
If you're planning to travel to Chicago from Hancock Intl. (SYR), you can fly directly into Midway Intl. (MDW). Some flights may connect through major hubs like Washington Dulles Intl. (IAD), Liberty Intl. (EWR), or John F. Kennedy Intl. (JFK) 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 $418
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 $418 rising to CA $547.  

Here are more money-saving tips: 

  • Fly in October 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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