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$104+ Cheap flights from Syracuse (SYR) to Chicago (CHI)

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 6/3. Fares are subject to change and may not be available on all flights or dates of travel.
SYR — CHI
Apr 22 — Apr 291
Wed 4/22
Wed 4/29
1 adult, Economy
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Cheapflights Tip: The best prices from Syracuse Hancock Intl to Chicago are usually found in September or January, booked 87 days in advance, depart on a Friday or Wednesday and return on a Wednesday

Cheap flight deals from Syracuse to Chicago

Cheapest flights from Syracuse to Chicago
Explore the most affordable flight options available from Syracuse to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 23, 2026.

This United Airlines deal was found by Cheapflights users on 3/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/186:30 am
SYR
-
ORD
Nonstop2h 13m
United Airlines
Sat 4/255:49 pm
ORD
-
SYR
Nonstop1h 59m
United Airlines
Deal found 3/21$269
This American Airlines deal was found by Cheapflights users on 3/19. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/1511:30 am
SYR
-
ORD
Nonstop2h 24m
American Airlines
Fri 5/158:02 pm
ORD
-
SYR
Nonstop2h 03m
American Airlines
Deal found 3/19$270
This Kiwi.com deal was found by Cheapflights users on 3/20. 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.
Fri 5/111:31 am
SYR
-
ORD
1 stop13h 23m
Multiple Airlines
Tue 5/51:59 pm
ORD
-
SYR
2 stops22h 45m
Multiple Airlines
Deal found 3/20$271
This Kiwi.com deal was found by Cheapflights users on 3/19. 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.
Fri 5/811:31 am
SYR
-
ORD
1 stop23h 00m
Multiple Airlines
Sun 5/103:05 pm
ORD
-
SYR
1 stop18h 36m
Multiple Airlines
Deal found 3/19$273
This Kiwi.com deal was found by Cheapflights users on 3/19. 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.
Sun 5/38:04 pm
SYR
-
ORD
2 stops27h 35m
Multiple Airlines
Thu 5/77:45 pm
ORD
-
SYR
1 stop13h 56m
Multiple Airlines
Deal found 3/19$274
This KAYAK deal was found by Cheapflights users on 3/21. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/297:00 am
SYR
-
ORD
1 stop6h 59m
JetBlue
Sat 9/55:12 pm
ORD
-
SYR
1 stop5h 51m
JetBlue
Deal found 3/21$275
This American Airlines deal was found by Cheapflights users on 3/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/185:46 pm
SYR
-
ORD
1 stop7h 08m
American Airlines
Tue 4/216:00 am
ORD
-
SYR
1 stop8h 45m
American Airlines
Deal found 3/20$276
This United Airlines deal was found by Cheapflights users on 3/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/296:15 am
SYR
-
ORD
1 stop5h 28m
United Airlines
Sun 5/35:52 pm
ORD
-
SYR
Nonstop1h 58m
United Airlines
Deal found 3/17$279
This Kiwi.com deal was found by Cheapflights users on 3/19. 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.
Sun 5/38:04 pm
SYR
-
ORD
2 stops36h 51m
Multiple Airlines
Sun 5/103:05 pm
ORD
-
SYR
1 stop18h 36m
Multiple Airlines
Deal found 3/19$280
This Kiwi.com deal was found by Cheapflights users on 3/20. 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 5/411:31 am
SYR
-
ORD
1 stop13h 24m
Multiple Airlines
Mon 5/116:55 am
ORD
-
SYR
2 stops53h 49m
Multiple Airlines
Deal found 3/20$281
This CheapOair deal was found by Cheapflights users on 3/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/296:00 am
SYR
-
ORD
1 stop16h 36m
JetBlue
Sat 5/26:00 am
ORD
-
SYR
1 stop15h 57m
JetBlue
Deal found 3/17$284
This United Airlines deal was found by Cheapflights users on 3/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/106:30 am
SYR
-
ORD
Nonstop2h 16m
United Airlines
Sun 4/126:45 am
ORD
-
SYR
Nonstop1h 55m
United Airlines
Deal found 3/19$285

Find flight deals from Syracuse to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Syracuse (SYR) to Chicago (CHI). 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 March 23, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$269
(United Airlines)

One-way from

$104
(Priceline)

Popular in

November

Cheapest in

September

Average price

$374

Good round-trip deal

$377 or less

Good one-way deal

$259 or less
Provider with most accurate pricing for Syracuse Hancock Intl-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Syracuse Hancock Intl-Chicago (CHI) flights.
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From Syracuse Hancock Intl to Chicago (CHI)
Search Deals
One-way flight from Syracuse Hancock Intl to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($33 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($14 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
Search Deals
Price to beat on a round-trip flight from Syracuse Hancock Intl to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Syracuse Hancock Intl to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Syracuse to Chicago 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 March 23, 2026.
Use the filters below to find and compare flights from Syracuse to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

SyracuseChicago

SYR - ORD

SYRORD

Syracuse Hancock Intl

Fri 5/1

6:15 am-7:32 am

Nonstop2h 17m

Chicago O'Hare Intl

Mon 5/4

5:52 pm-8:50 pm

Nonstop1h 58m

$269

SyracuseChicago

SYR - ORD

SYRORD

Syracuse Hancock Intl

Wed 5/27

2:21 pm-3:38 pm

Nonstop2h 17m

Chicago O'Hare Intl

Sat 5/30

6:19 pm-9:19 pm

Nonstop2h 00m

$269

SyracuseChicago

SYR - ORD

SYRORD

Syracuse Hancock Intl

Sat 4/18

6:30 am-7:43 am

Nonstop2h 13m

Chicago O'Hare Intl

Sat 4/25

5:49 pm-8:48 pm

Nonstop1h 59m

$269

SyracuseChicago

SYR - ORD

SYRORD

Syracuse Hancock Intl

Fri 4/24

7:40 pm-11:43 pm

1 stop5h 03m

Chicago O'Hare Intl

Sun 4/26

6:45 am-9:40 am

Nonstop1h 55m

$279

SyracuseChicago

SYR - ORD

SYRORD

Syracuse Hancock Intl

Wed 4/29

6:15 am-10:43 am

1 stop5h 28m

Chicago O'Hare Intl

Sun 5/3

5:52 pm-8:50 pm

Nonstop1h 58m

$279
Quickest round-trip

SyracuseChicago

SYR - ORD

SYRORD

Syracuse Hancock Intl

Fri 4/10

6:30 am-7:46 am

Nonstop2h 16m

Chicago O'Hare Intl

Sun 4/12

6:45 am-9:40 am

Nonstop1h 55m

$285

SyracuseChicago

SYR - MDW

SYRMDW

Syracuse Hancock Intl

Thu 7/23

6:00 am-8:42 am

1 stop3h 42m

Chicago Midway

Mon 7/27

5:59 pm-10:56 pm

1 stop3h 57m

$289

SyracuseChicago

SYR - MDW

SYRMDW

Syracuse Hancock Intl

Fri 9/18

3:11 pm-9:46 pm

1 stop7h 35m

Chicago Midway

Mon 9/21

6:00 am-2:11 pm

1 stop7h 11m

$289

SyracuseChicago

SYR - MDW

SYRMDW

Syracuse Hancock Intl

Sat 5/9

6:15 am-8:43 am

1 stop3h 28m

Chicago Midway

Sun 5/10

6:36 pm-11:49 pm

1 stop4h 13m

$289

SyracuseChicago

SYR - MDW

SYRMDW

Syracuse Hancock Intl

Fri 5/1

5:50 am-8:47 am

1 stop3h 57m

Chicago Midway

Tue 5/5

6:38 pm-11:10 pm

1 stop3h 32m

$289

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/22

Showing 1-10 of 59 resultsSorted by cheapest first
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Compare providers for flights from Syracuse to Chicago

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 Chicago in March.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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 flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Syracuse-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Syracuse-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Syracuse-Chicago 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 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 Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago 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

How far ahead should I book a flight from Syracuse to Chicago?

Use this chart to determine the optimal time to book a round-trip flight from Syracuse to Chicago. Price data was last updated on March 13, 2026.

The price you pay for your flight from Syracuse to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 40 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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

Currently, May is the cheapest month in which you can book a flight from Syracuse to Chicago (average of $141). Flying from Syracuse to Chicago in July is currently the most expensive (average of $271). 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 CHI?

Find hourly flight availability from Syracuse to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated March 23, 2026.

One of the essential ways to save on airfare from Syracuse to Chicago is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the evening could potentially save you up to 21% on airfare.

What is the cheapest day to fly from Syracuse to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Syracuse to Chicago. Price data was last updated on March 14, 2026.

Travelers seeking maximum savings on their Syracuse to Chicago flight should consider departing on Wednesday evenings when fares are most often at their lowest. Monday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Syracuse to Chicago

Explore weekly flight availability from Syracuse to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated March 23, 2026.

The most flights from SYR to CHI are scheduled on a Friday (21 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (15 on average).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated March 23, 2026.
Read through reviews of airlines operating flights from Syracuse to Chicago, such as Delta,United Airlines, andAmerican Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,319 reviews

Comfort

7.9

Food

7.2

Entertainment

7.8

Overall

7.9

Boarding

8.1

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
7.9
Good
8,319 reviews
Delta
7.9
Good
8,319 reviews

Comfort

7.9

Food

7.2

Entertainment

7.8

Overall

7.9

Boarding

8.1

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.
United Airlines
7.4
Good
9,460 reviews
Delta
7.9
Good
8,319 reviews

Comfort

7.9

Food

7.2

Entertainment

7.8

Overall

7.9

Boarding

8.1

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.
American Airlines
7.1
Good
11,489 reviews
Delta
7.9
Good
8,319 reviews

Comfort

7.9

Food

7.2

Entertainment

7.8

Overall

7.9

Boarding

8.1

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 Chicago. 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?

    Most people fly from Syracuse Hancock Intl (SYR) if they book a flight from Syracuse to Chicago. On average, Hancock Intl has 17 outbound flights to Chicago per day from 3 airlines. Syracuse Hancock Intl is conveniently located just 4.8 mi from Syracuse’s city center.

  • How long is the flight from Syracuse to Chicago?

    Departing from Syracuse to Chicago will take you 2h 17m. There are 605 mi between Syracuse and Chicago. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines flying from Syracuse to Chicago round-trip?

    Our cheapest airline available from Syracuse to Chicago is Delta. Our recent data shows that you can find tickets from as low as $153 on this airline. Additional options worth looking into are American Airlines and United Airlines, starting at $209 and $209 round-trip. These flights start at 52% lower than the current average price 3 months from now.

  • What are the cheapest airlines to fly from Syracuse to Chicago one-way?

    The cheapest airlines for a one-way flight from Syracuse to Chicago are Frontier ($72), American Airlines ($143), and United Airlines ($158).

  • What are the most popular routes from Syracuse to Chicago?

    While some choose either Syracuse Hancock Intl - Chicago Midway or Syracuse Hancock Intl - Chicago Greater Rockford, Syracuse Hancock Intl - Chicago O'Hare Intl is the most popular route from Syracuse to Chicago.

  • What are the most reliable airlines from Syracuse to Chicago?

    Before booking your flight to Chicago from Syracuse, check out the most reliable airlines to get you to your destination on time: Japan Airlines (80%), Envoy Air (77%), Alaska Airlines( 74%).

  • What are the cheapest flights from Syracuse to Chicago?

    While on average a flight from Syracuse to Chicago is generally $972, our data shows the cheapest flight currently is $173. When looking at the most popular route, (Syracuse Hancock Intl - Chicago O'Hare Intl), you can expect to pay $218 for that flight.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Syracuse to Chicago 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?

    Currently, May is the cheapest month in which you can book a flight from Syracuse to Chicago (average of $141). Flying from Syracuse to Chicago in July is currently the most expensive (average of $271). 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?

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

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Top 3 airlines flying from Syracuse to Chicago

Discover the top 3 airlines that operate flights from Syracuse to Chicago. 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 March 23, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$153Average$323FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$209Average$330FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$209Average$338FlexibilityNo cancel feeOn-time71%

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