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$77+ 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 1/27. Fares are subject to change and may not be available on all flights or dates of travel.
SYR — CHI
Nov 28 — Dec 51
Fri 11/28
Fri 12/5
1 adult, Economy
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Cheapflights Tip: The best prices from Syracuse Hancock Intl to Chicago are usually found in September or October, booked 87 days in advance, depart on a Wednesday or Friday and return on a Wednesday

Cheap 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 October 29, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$209
(United Airlines)

One-way from

$77
(JetBlue)

Popular in

January

Cheapest in

September

Average price

$295

Good round-trip deal

$305 or less

Good one-way deal

$225 or less
Provider with most accurate pricing for Syracuse Hancock Intl-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Syracuse Hancock Intl-Chicago (CHI) flights.
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From Syracuse Hancock Intl to Chicago (CHI)
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One-way flight from Syracuse Hancock Intl to Chicago (CHI)
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Highest demand for flights based on searches. 7% potential increase in price ($26 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Price to beat on a round-trip flight from Syracuse Hancock Intl to Chicago (CHI).
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Price to beat on a one-way flight from Syracuse Hancock Intl to Chicago (CHI).
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Find 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 October 29, 2025.

This United Airlines deal was found by Cheapflights users on 10/27. 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 11/196:15 amSYR - ORD
Nonstop2h 22mUnited Airlines
Sun 11/236:08 pmORD - SYR
Nonstop1h 54mUnited Airlines
Deal found 10/27$209
This American Airlines deal was found by Cheapflights users on 10/27. 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.
Thu 12/117:33 pmSYR - ORD
Nonstop2h 42mAmerican Airlines
Thu 12/184:19 pmORD - SYR
Nonstop1h 57mAmerican Airlines
Deal found 10/27$210
This United Airlines deal was found by Cheapflights users on 10/28. 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 11/195:27 pmSYR - ORD
Nonstop2h 28mUnited Airlines
Fri 11/288:50 amORD - SYR
1 stop4h 21mUnited Airlines
Deal found 10/28$219
This lastminute.com deal was found by Cheapflights users on 10/27. 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 lastminute.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/116:00 amSYR - ORD
1 stop5h 35mJetBlue
Thu 12/187:41 pmORD - SYR
1 stop26h 08mJetBlue
Deal found 10/27$220
This Frontier deal was found by Cheapflights users on 10/27. 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 11/712:03 pmSYR - MDW
1 stop11h 05mFrontier
Sun 11/910:12 amMDW - SYR
1 stop7h 42mFrontier
Deal found 10/27$222
This Frontier deal was found by Cheapflights users on 10/27. 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 11/712:03 pmSYR - ORD
1 stop5h 53mFrontier
Sun 11/95:25 amORD - SYR
1 stop12h 29mFrontier
Deal found 10/27$222
This Expedia deal was found by Cheapflights users on 10/27. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/116:00 amSYR - ORD
1 stop5h 35mJetBlue
Sat 11/1510:00 amORD - SYR
1 stop11h 07mJetBlue
Deal found 10/27$223
This Kiwi.com deal was found by Cheapflights users on 10/26. 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 12/411:34 amSYR - ORD
1 stop11h 17mMultiple Airlines
Mon 12/87:20 amORD - SYR
1 stop9h 30mMultiple Airlines
Deal found 10/26$226
This Frontier deal was found by Cheapflights users on 10/28. 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 10/3112:03 pmSYR - ORD
1 stop12h 36mFrontier
Sun 11/25:25 amORD - SYR
1 stop12h 20mFrontier
Deal found 10/28$228
This Delta deal was found by Cheapflights users on 10/29. 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 12/177:01 pmSYR - MDW
1 stop5h 46mDelta
Sun 1/115:31 pmMDW - SYR
1 stop5h 28mDelta
Deal found 10/29$229
This Expedia deal was found by Cheapflights users on 10/28. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/196:00 amSYR - ORD
1 stop5h 35mJetBlue
Thu 11/208:20 amORD - SYR
2 stops13h 54mJetBlue
Deal found 10/28$230
This American Airlines deal was found by Cheapflights users on 10/27. 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 11/1512:00 pmSYR - ORD
1 stop8h 36mAmerican Airlines
Sun 11/167:53 pmORD - SYR
Nonstop2h 03mAmerican Airlines
Deal found 10/27$236

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 October 29, 2025.
Use the filters below to find and compare flights from Syracuse to Chicago that are best for you.

Fly from

Syracuse

Fly to

Chicago

Route

Depart

Return

Price

SyracuseChicago

SYR - ORD

SYRORD

Syracuse Hancock Intl

Wed 11/19

6:15 am-7:37 am

Nonstop2h 22m

Chicago O'Hare Intl

Mon 11/24

6:08 pm-9:02 pm

Nonstop1h 54m

$209

SyracuseChicago

SYR - ORD

SYRORD

Syracuse Hancock Intl

Fri 1/23

8:00 am-9:44 am

Nonstop2h 44m

Chicago O'Hare Intl

Mon 1/26

6:10 pm-9:20 pm

Nonstop2h 10m

$209

SyracuseChicago

SYR - ORD

SYRORD

Syracuse Hancock Intl

Thu 12/4

6:00 am-10:44 am

1 stop5h 44m

Chicago O'Hare Intl

Mon 12/8

9:15 am-12:18 pm

Nonstop2h 03m

$219

SyracuseChicago

SYR - MDW

SYRMDW

Syracuse Hancock Intl

Fri 1/23

6:00 am-8:54 am

1 stop3h 54m

Chicago Midway

Mon 1/26

6:35 pm-11:15 pm

1 stop3h 40m

$229

SyracuseChicago

SYR - MDW

SYRMDW

Syracuse Hancock Intl

Wed 12/17

6:00 am-8:54 am

1 stop3h 54m

Chicago Midway

Sun 1/11

5:31 pm-11:59 pm

1 stop5h 28m

$229

SyracuseChicago

SYR - MDW

SYRMDW

Syracuse Hancock Intl

Fri 1/23

6:00 am-12:01 pm

1 stop7h 01m

Chicago Midway

Sun 1/25

6:35 pm-11:15 pm

1 stop3h 40m

$229

SyracuseChicago

SYR - MDW

SYRMDW

Syracuse Hancock Intl

Thu 2/26

6:00 am-8:50 am

1 stop3h 50m

Chicago Midway

Mon 3/2

5:59 pm-11:01 pm

1 stop4h 02m

$229

SyracuseChicago

SYR - ORD

SYRORD

Syracuse Hancock Intl

Wed 11/19

6:00 am-11:46 am

1 stop6h 46m

Chicago O'Hare Intl

Sun 11/23

6:20 pm-11:42 pm

1 stop4h 22m

$229

SyracuseChicago

SYR - MDW

SYRMDW

Syracuse Hancock Intl

Thu 12/11

6:00 am-11:55 am

1 stop6h 55m

Chicago Midway

Sun 12/14

5:13 pm-11:33 pm

1 stop5h 20m

$229

SyracuseChicago

SYR - ORD

SYRORD

Syracuse Hancock Intl

Tue 11/11

6:15 am-7:37 am

Nonstop2h 22m

Chicago O'Hare Intl

Sat 11/15

1:40 pm-4:40 pm

Nonstop2h 00m

$229

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/26

Showing 1-10 of 54 results
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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 October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
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 flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Syracuse-Chicago flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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 October 24, 2025.

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 October 29, 2025.

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 38% 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 December 16, 2024.

Travelers seeking maximum savings on their Syracuse to Chicago flight should consider departing on Saturday 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.

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 October 29, 2025.
Read through reviews of airlines operating flights from Syracuse to Chicago, such as Delta, United Airlines, and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
7,992 reviews

Comfort

7.9

Overall

7.9

Food

7.3

Crew

8.5

Entertainment

7.9

Boarding

8.2

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
7,992 reviews
Delta
7.9
Good
7,992 reviews

Comfort

7.9

Overall

7.9

Food

7.3

Crew

8.5

Entertainment

7.9

Boarding

8.2

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
8,999 reviews
Delta
7.9
Good
7,992 reviews

Comfort

7.9

Overall

7.9

Food

7.3

Crew

8.5

Entertainment

7.9

Boarding

8.2

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
7.2
Good
11,032 reviews
Delta
7.9
Good
7,992 reviews

Comfort

7.9

Overall

7.9

Food

7.3

Crew

8.5

Entertainment

7.9

Boarding

8.2

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 13 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 22m. 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 American Airlines. Our recent data shows that you can find tickets from as low as $209 on this airline. Additional options worth looking into are United Airlines and Delta, starting at $209 and $298 round-trip. These flights start at 36% 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 JetBlue ($77), Frontier ($88), and Allegiant Air ($151).

  • 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: ANA (94%), GoJet (83%), Air Canada( 81%).

  • What are the cheapest flights from Syracuse to Chicago?

    While on average a flight from Syracuse to Chicago is generally $909, our data shows the cheapest flight currently is $133. When looking at the most popular route, (Syracuse Hancock Intl - Chicago O'Hare Intl), you can expect to pay $209 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
Merrillville
Lansing
Hammond
Porter
Benton Harbor

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Alternative routes for Syracuse to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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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 October 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$209Average$359FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$209Average$344FlexibilityNo cancel feeOn-time71%
DeltaCheapest$298Average$428FlexibilityNo cancel feeOn-timeN/A

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