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$72+ Cheap flights from Syracuse (SYR) to Midway (MDW)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/3. Fares are subject to change and may not be available on all flights or dates of travel.
SYR — MDW
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheap flight deals from Syracuse to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Syracuse (SYR) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated September 11, 2025.

Round-trip from

$226
(Kiwi.com)

One-way from

$72
(Priceline)

Popular in

August

Cheapest in

October

Average price

$583
From Syracuse Hancock Intl to Chicago Midway
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One-way flight from Syracuse Hancock Intl to Chicago Midway
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Highest demand for flights based on searches. 23% potential increase in price ($150 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($30 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Syracuse to Midway

Cheapest flights from Syracuse to Midway
Explore the most affordable flight options available from Syracuse to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 11, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/1012:03 pmSYR - MDW
2 stops13h 27mFrontier
Thu 11/1310:12 amMDW - SYR
1 stop7h 33mFrontier
Deal found 9/9$222
This Booking.com deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/912:16 pmSYR - MDW
1 stop12h 30mFrontier
Wed 10/158:05 amMDW - SYR
1 stop26h 16mFrontier
Deal found 9/8$225
This Kiwi.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/209:56 amSYR - MDW
2 stops14h 50mFrontier
Sat 10/2511:31 amMDW - SYR
1 stop7h 37mFrontier
Deal found 9/10$226
This Kiwi.com deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/256:58 pmSYR - MDW
2 stops26h 48mMultiple Airlines
Mon 9/298:19 amMDW - SYR
1 stop7h 24mMultiple Airlines
Deal found 9/8$227
This Delta deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/46:00 amSYR - MDW
1 stop3h 40mDelta
Wed 10/89:35 amMDW - SYR
1 stop5h 23mDelta
Deal found 9/11$229
This Booking.com deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/137:40 pmSYR - MDW
1 stop27h 30mFrontier
Sun 11/161:37 pmMDW - SYR
1 stop20h 31mFrontier
Deal found 9/11$231
This Kiwi.com deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/312:03 pmSYR - MDW
1 stop7h 36mFrontier
Wed 11/122:06 pmMDW - SYR
2 stops27h 39mFrontier
Deal found 9/8$235
This Delta deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/256:00 amSYR - MDW
1 stop3h 40mDelta
Mon 9/296:15 pmMDW - SYR
1 stop3h 36mDelta
Deal found 9/8$239
This Frontier deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1912:12 pmSYR - MDW
2 stops22h 39mFrontier
Mon 9/228:19 amMDW - SYR
1 stop7h 24mFrontier
Deal found 9/8$241
This Booking.com deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/1412:03 pmSYR - MDW
1 stop11h 05mFrontier
Sun 11/161:37 pmMDW - SYR
1 stop20h 31mFrontier
Deal found 9/8$242
This Frontier deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/129:32 pmSYR - MDW
1 stop13h 19mFrontier
Mon 9/158:19 amMDW - SYR
1 stop7h 24mFrontier
Deal found 9/11$248
This Delta deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/266:00 amSYR - MDW
1 stop3h 40mDelta
Sat 9/276:15 pmMDW - SYR
1 stop3h 36mDelta
Deal found 9/11$249

Cheapflights Fare Finder

 
Customize your flight search to find flights from Syracuse to Midway that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 11, 2025.
Use the filters below to find and compare flights from Syracuse to Chicago Midway Airport that are best for you.

Fly from

Syracuse

Fly to

Midway

Route

Depart

Return

Price

SyracuseChicago

SYR - MDW

SYRMDW

Syracuse Hancock Intl

Mon 10/20

9:56 am-11:46 pm

2 stops14h 50m

Chicago Midway

Sat 10/25

11:31 am-8:08 pm

1 stop7h 37m

$226

SyracuseChicago

SYR - MDW

SYRMDW

Syracuse Hancock Intl

Fri 12/5

7:02 pm-11:32 pm

1 stop5h 30m

Chicago Midway

Sun 12/7

6:40 pm-11:10 pm

1 stop3h 30m

$229

SyracuseChicago

SYR - MDW

SYRMDW

Syracuse Hancock Intl

Tue 10/21

1:00 pm-6:25 pm

1 stop6h 25m

Chicago Midway

Sat 10/25

6:23 pm-11:04 pm

1 stop3h 41m

$229

SyracuseChicago

SYR - MDW

SYRMDW

Syracuse Hancock Intl

Wed 11/26

7:02 pm-11:32 pm

1 stop5h 30m

Chicago Midway

Tue 12/2

6:40 pm-11:10 pm

1 stop3h 30m

$229

SyracuseChicago

SYR - MDW

SYRMDW

Syracuse Hancock Intl

Wed 11/12

6:00 am-8:52 am

1 stop3h 52m

Chicago Midway

Sat 11/15

6:00 am-1:18 pm

1 stop6h 18m

$229

SyracuseChicago

SYR - MDW

SYRMDW

Syracuse Hancock Intl

Thu 10/30

6:00 am-8:40 am

1 stop3h 40m

Chicago Midway

Sat 11/1

6:00 am-1:12 pm

1 stop6h 12m

$229

SyracuseChicago

SYR - MDW

SYRMDW

Syracuse Hancock Intl

Mon 11/24

7:02 pm-11:32 pm

1 stop5h 30m

Chicago Midway

Tue 12/2

6:40 pm-11:10 pm

1 stop3h 30m

$229

SyracuseChicago

SYR - MDW

SYRMDW

Syracuse Hancock Intl

Sat 10/4

6:00 am-8:40 am

1 stop3h 40m

Chicago Midway

Wed 10/8

9:35 am-3:58 pm

1 stop5h 23m

$229

SyracuseChicago

SYR - MDW

SYRMDW

Syracuse Hancock Intl

Sat 9/27

6:00 am-8:40 am

1 stop3h 40m

Chicago Midway

Mon 9/29

6:15 pm-10:51 pm

1 stop3h 36m

$249

SyracuseChicago

SYR - MDW

SYRMDW

Syracuse Hancock Intl

Fri 9/26

6:00 am-8:40 am

1 stop3h 40m

Chicago Midway

Sat 9/27

6:15 pm-10:51 pm

1 stop3h 36m

$249

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

Showing 1-10 of 21 results
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Best time to book a flight from Syracuse to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Syracuse with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Syracuse to Chicago Midway Airport

What is the cheapest month to book a flight from Syracuse to Chicago Midway Airport?

Currently, April is the cheapest month in which you can book a flight from Syracuse to Chicago Midway Airport (average of $160). Flying from Syracuse to Chicago Midway Airport in November is currently the most expensive (average of $249). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from SYR to MDW?

Find hourly flight availability from Syracuse to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 11, 2025.

When flying from Syracuse to Chicago Midway Airport, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated September 11, 2025.
Read through reviews of airlines operating flights from Syracuse to Chicago Midway Airport, such as Delta. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,960 reviews

Comfort

7.9

Overall

8.0

Boarding

8.2

Food

7.3

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.
Delta
8.0
Very good
7,960 reviews
Delta
8.0
Very good
7,960 reviews

Comfort

7.9

Overall

8.0

Boarding

8.2

Food

7.3

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.

Related info for your journey

Find useful and relevant information for your journey from Syracuse to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Syracuse to Chicago Midway?

    Syracuse Hancock Intl (SYR), located 4.8 mi from the city center, is the airport you fly out of when you book flights from Syracuse to Chicago Midway. 1 airline have flights from Hancock Intl to Chicago Midway on a regular basis. Booking flights from Syracuse Hancock Intl to Chicago Midway should not be difficult; the airport handles an average of 0 outbound flights to Chicago Midway per day.

  • How long is the flight from Syracuse to Chicago Midway Airport?

    A quick flight from Syracuse to Chicago Midway Airport can take about 5h 30m. Frontier provides one of the quickest options available for as low as $229. Syracuse and Chicago Midway Airport are separated by a distance of 599 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What is the cheapest airline to fly from Syracuse to Chicago Midway Airport round-trip?

    Flying on Delta is currently your cheapest option to Chicago Midway Airport, with prices starting at $298. Delta is currently priced 39% below the average price you’ll pay for this route.

  • Can I find deals for flights from Syracuse to Midway that include hotel bookings?

    Yes. In addition to deals on Syracuse to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Syracuse to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Syracuse to Midway.

  • Can I find deals for business class flights from Syracuse to Midway?

    Yes. Cheapflights offers flight deals from Syracuse to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Syracuse to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Syracuse to Chicago Midway Airport (average of $160). Flying from Syracuse to Chicago Midway Airport in November is currently the most expensive (average of $249). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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Alternative routes for Syracuse to Midway

See prices for flight routes from nearby airports that may be better suited for you.
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Top airline flying from Syracuse to Midway

Discover the top airline that operate flights from Syracuse to Midway. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$298Average$428FlexibilityNo cancel feeOn-timeN/A

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