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$111+ 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 11/2. Fares are subject to change and may not be available on all flights or dates of travel.
SYR — MDW
Nov 15 — Nov 221
Sat 11/15
Sat 11/22
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 October 16, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$228
(Kiwi.com)

One-way from

$111
(Trip.com)

Popular in

February

Cheapest in

September

Average price

$439
Provider with most accurate pricing for Syracuse Hancock Intl-Chicago Midway flight deals.
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Provider most trusted by Cheapflights users for Syracuse Hancock Intl-Chicago Midway flights.
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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. 5% potential increase in price ($26 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($18 potential savings vs. average RT price).
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Average for round-trip flights in October 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 October 16, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/15. 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 10/307:54 pmSYR - MDW
1 stop13h 38mFrontier
Sat 11/811:36 amMDW - SYR
1 stop30h 18mFrontier
Deal found 10/15$228
This Delta deal was found by Cheapflights users on 10/14. 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.
Wed 11/51:00 pmSYR - MDW
1 stop6h 25mDelta
Sat 11/84:23 pmMDW - SYR
1 stop6h 57mDelta
Deal found 10/14$229
This Frontier deal was found by Cheapflights users on 10/14. 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.
Thu 10/307:54 pmSYR - MDW
1 stop13h 38mFrontier
Sun 11/210:12 amMDW - SYR
1 stop7h 33mFrontier
Deal found 10/14$243
This Delta deal was found by Cheapflights users on 10/15. 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 10/306:00 amSYR - MDW
1 stop3h 40mDelta
Mon 11/35:09 pmMDW - SYR
1 stop6h 11mDelta
Deal found 10/15$249
This Delta deal was found by Cheapflights users on 10/14. 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 11/206:00 amSYR - MDW
1 stop3h 54mDelta
Mon 11/246:48 pmMDW - SYR
1 stop3h 22mDelta
Deal found 10/14$254
This Delta deal was found by Cheapflights users on 10/13. 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 12/186:00 amSYR - MDW
1 stop3h 54mDelta
Mon 12/226:08 pmMDW - SYR
1 stop4h 09mDelta
Deal found 10/13$284
This Delta deal was found by Cheapflights users on 10/14. 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.
Wed 11/51:00 pmSYR - MDW
1 stop6h 25mDelta
Fri 11/76:23 pmMDW - SYR
1 stop3h 41mDelta
Deal found 10/14$287
This Kiwi.com deal was found by Cheapflights users on 10/14. 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 10/279:45 pmSYR - MDW
2 stops26h 40mMultiple Airlines
Thu 10/3010:12 amMDW - SYR
1 stop7h 47mMultiple Airlines
Deal found 10/14$288
This Kiwi.com deal was found by Cheapflights users on 10/16. 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.
Sat 10/259:03 pmSYR - MDW
1 stop14h 54mMultiple Airlines
Mon 10/279:45 amMDW - SYR
1 stop23h 32mMultiple Airlines
Deal found 10/16$291
This Delta deal was found by Cheapflights users on 10/15. 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 12/186:00 amSYR - MDW
1 stop3h 54mDelta
Fri 12/266:08 pmMDW - SYR
1 stop4h 09mDelta
Deal found 10/15$309
This Kiwi.com deal was found by Cheapflights users on 10/15. 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 11/67:40 pmSYR - MDW
1 stop27h 40mFrontier
Sun 11/910:12 amMDW - SYR
1 stop7h 42mFrontier
Deal found 10/15$313

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 October 16, 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

Sun 1/18

6:00 am-8:50 am

1 stop3h 50m

Chicago Midway

Sat 1/31

9:30 am-4:21 pm

1 stop5h 51m

$229

SyracuseChicago

SYR - MDW

SYRMDW

Syracuse Hancock Intl

Fri 1/16

6:00 am-8:50 am

1 stop3h 50m

Chicago Midway

Wed 1/28

9:30 am-4:21 pm

1 stop5h 51m

$229

SyracuseChicago

SYR - MDW

SYRMDW

Syracuse Hancock Intl

Sun 3/15

6:00 am-8:50 am

1 stop3h 50m

Chicago Midway

Fri 3/27

5:59 pm-11:01 pm

1 stop4h 02m

$229

SyracuseChicago

SYR - MDW

SYRMDW

Syracuse Hancock Intl

Sun 1/18

6:00 am-8:50 am

1 stop3h 50m

Chicago Midway

Tue 2/3

9:30 am-4:21 pm

1 stop5h 51m

$229

SyracuseChicago

SYR - MDW

SYRMDW

Syracuse Hancock Intl

Thu 1/15

6:00 am-8:50 am

1 stop3h 50m

Chicago Midway

Sat 1/31

5:59 pm-11:01 pm

1 stop4h 02m

$229

SyracuseChicago

SYR - MDW

SYRMDW

Syracuse Hancock Intl

Wed 3/18

6:00 am-8:50 am

1 stop3h 50m

Chicago Midway

Fri 3/27

5:59 pm-11:01 pm

1 stop4h 02m

$229

SyracuseChicago

SYR - MDW

SYRMDW

Syracuse Hancock Intl

Wed 3/18

9:30 am-12:35 pm

1 stop4h 05m

Chicago Midway

Sat 3/28

9:30 am-4:21 pm

1 stop5h 51m

$229

SyracuseChicago

SYR - MDW

SYRMDW

Syracuse Hancock Intl

Sun 1/18

6:00 am-8:50 am

1 stop3h 50m

Chicago Midway

Thu 1/29

9:30 am-4:21 pm

1 stop5h 51m

$229

SyracuseChicago

SYR - MDW

SYRMDW

Syracuse Hancock Intl

Wed 4/1

6:00 am-8:50 am

1 stop3h 50m

Chicago Midway

Tue 4/7

5:25 pm-11:59 pm

1 stop5h 34m

$229

SyracuseChicago

SYR - MDW

SYRMDW

Syracuse Hancock Intl

Wed 12/17

7:01 pm-11:49 pm

1 stop5h 48m

Chicago Midway

Sun 1/11

5:59 pm-11:01 pm

1 stop4h 02m

$229

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/14

Showing 1-10 of 22 results
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Compare providers for flights from Syracuse to Midway

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Syracuse to Midway in October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Syracuse-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Syracuse-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Syracuse-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Syracuse-Chicago Midway Airport flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Syracuse-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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, October is the cheapest month in which you can book a flight from Syracuse to Chicago Midway Airport (average of $233). Flying from Syracuse to Chicago Midway Airport in February is currently the most expensive (average of $446). 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 October 16, 2025.

It’s optimal to fly from Syracuse to Chicago Midway Airport in the evening. By choosing this option you can save up to 56% on the cost of your flight, compared to a flight in the morning.

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 October 16, 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
7,984 reviews

Food

7.3

Boarding

8.2

Entertainment

7.9

Overall

8.0

Comfort

7.9

Crew

8.5

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
7,984 reviews
Delta
8.0
Very good
7,984 reviews

Food

7.3

Boarding

8.2

Entertainment

7.9

Overall

8.0

Comfort

7.9

Crew

8.5

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 3h 50m. Delta 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.

  • 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 34% 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, October is the cheapest month in which you can book a flight from Syracuse to Chicago Midway Airport (average of $233). Flying from Syracuse to Chicago Midway Airport in February is currently the most expensive (average of $446). 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
Porter
Benton Harbor
Chesterton

Browse thousands of different options on Cheapflights for your next trip

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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 October 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$298Average$428FlexibilityNo cancel feeOn-timeN/A

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