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$102+ 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 8/26. Fares are subject to change and may not be available on all flights or dates of travel.
SYR — CHI
Aug 4 — Aug 111
Mon 8/4
Mon 8/11
1 adult, Economy
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Cheapflights Tip: The best prices from Syracuse Hancock Intl to Chicago are usually found in November or September, 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 July 30, 2025.

Round-trip from

$215
(FlightHub)

One-way from

$102
(JetBlue)

Popular in

January

Cheapest in

November

Average price

$359

Good round-trip deal

$342 or less

Good one-way deal

$243 or less
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. 2% potential increase in price ($6 potential increase over avg. RT price).
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Cheapest flight prices on average. 0% potential price decrease ($2 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 30, 2025.

This FlightHub deal was found by Cheapflights users on 7/30. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/231:48 pmSYR - ORD
1 stop29h 53mFrontier
Mon 8/2511:34 amORD - SYR
1 stop8h 08mFrontier
Deal found 7/30$215
This Frontier deal was found by Cheapflights users on 7/30. 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 9/199:32 pmSYR - MDW
1 stop13h 19mFrontier
Mon 9/228:19 amMDW - SYR
1 stop7h 24mFrontier
Deal found 7/30$218
This United Airlines deal was found by Cheapflights users on 7/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/46:00 amSYR - ORD
1 stop4h 36mUnited Airlines
Wed 9/107:10 amORD - SYR
Nonstop2h 08mUnited Airlines
Deal found 7/29$219
This Delta deal was found by Cheapflights users on 7/30. 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 8/276:10 amSYR - MDW
1 stop3h 25mDelta
Wed 9/34:25 pmMDW - SYR
1 stop6h 26mDelta
Deal found 7/30$229
This Delta deal was found by Cheapflights users on 7/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/225:00 pmSYR - ORD
1 stop6h 20mDelta
Wed 11/268:55 amORD - SYR
1 stop6h 24mDelta
Deal found 7/28$229
This Mytrip deal was found by Cheapflights users on 7/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/44:50 pmSYR - ORD
2 stops25h 49mMultiple Airlines
Wed 9/106:44 pmORD - SYR
2 stops20h 16mMultiple Airlines
Deal found 7/29$236
This American Airlines deal was found by Cheapflights users on 7/30. 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.
Mon 12/154:45 pmSYR - ORD
Nonstop2h 15mAmerican Airlines
Thu 1/158:20 pmORD - SYR
Nonstop1h 54mAmerican Airlines
Deal found 7/30$249
This Mytrip deal was found by Cheapflights users on 7/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/178:36 pmSYR - RFD
2 stops18h 34mAllegiant Air
Wed 8/206:03 pmRFD - SYR
1 stop14h 55mAllegiant Air
Deal found 7/30$296
This Mytrip deal was found by Cheapflights users on 7/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2011:44 amSYR - RFD
3 stops25h 24mMultiple Airlines
Wed 8/276:03 pmRFD - SYR
1 stop13h 51mMultiple Airlines
Deal found 7/29$507

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 July 30, 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

Sat 8/23

1:48 pm-6:41 pm

1 stop29h 53m

Chicago O'Hare Intl

Mon 8/25

11:34 am-8:42 pm

1 stop8h 08m

$215

SyracuseChicago

SYR - MDW

SYRMDW

Syracuse Hancock Intl

Fri 9/19

9:32 pm-9:51 am

1 stop13h 19m

Chicago Midway

Mon 9/22

8:19 am-4:43 pm

1 stop7h 24m

$218

SyracuseChicago

SYR - ORD

SYRORD

Syracuse Hancock Intl

Thu 9/4

6:00 am-9:36 am

1 stop4h 36m

Chicago O'Hare Intl

Wed 9/10

7:10 am-10:18 am

Nonstop2h 08m

$219

SyracuseChicago

SYR - MDW

SYRMDW

Syracuse Hancock Intl

Wed 8/27

6:10 am-8:35 am

1 stop3h 25m

Chicago Midway

Wed 9/3

4:25 pm-11:51 pm

1 stop6h 26m

$229

SyracuseChicago

SYR - ORD

SYRORD

Syracuse Hancock Intl

Fri 8/22

5:00 pm-10:20 pm

1 stop6h 20m

Chicago O'Hare Intl

Wed 11/26

8:55 am-4:19 pm

1 stop6h 24m

$229

SyracuseChicago

SYR - ORD

SYRORD

Syracuse Hancock Intl

Thu 9/4

4:50 pm-5:39 pm

2 stops25h 49m

Chicago O'Hare Intl

Wed 9/10

6:44 pm-4:00 pm

2 stops20h 16m

$236

SyracuseChicago

SYR - ORD

SYRORD

Syracuse Hancock Intl

Fri 9/19

7:40 am-8:54 am

Nonstop2h 14m

Chicago O'Hare Intl

Mon 9/22

8:08 am-11:08 am

Nonstop2h 00m

$249

SyracuseChicago

SYR - RFD

SYRRFD

Syracuse Hancock Intl

Sun 8/17

8:36 pm-2:10 pm

2 stops18h 34m

Chicago Greater Rockford

Wed 8/20

6:03 pm-9:58 am

1 stop14h 55m

$296

SyracuseChicago

SYR - RFD

SYRRFD

Syracuse Hancock Intl

Wed 8/20

11:44 am-12:08 pm

3 stops25h 24m

Chicago Greater Rockford

Wed 8/27

6:03 pm-8:54 am

1 stop13h 51m

$507

SyracuseChicago

SYR - ORD

SYRORD

Syracuse Hancock Intl

Tue 8/26

6:00 am-11:18 am

1 stop6h 18m

$102

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/28

Showing 1-10 of 22 results
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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 July 25, 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 87 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, August is the cheapest month in which you can book a flight from Syracuse to Chicago (average of $245). Flying from Syracuse to Chicago in March is currently the most expensive (average of $321). 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 July 30, 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 29% 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 Thursday 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 July 30, 2025.

The most flights from SYR to CHI are scheduled on a Monday (24 on average). You will have fewer flight options on Friday, which is when the least amount of flights are scheduled (5 on average).

How much does it cost to fly round-trip from Syracuse to Chicago?

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 July 30, 2025.
Read through reviews of airlines operating flights from Syracuse to Chicago, such as Delta, United Airlines, and JetBlue. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,980 reviews

Entertainment

7.9

Comfort

7.9

Overall

8.0

Boarding

8.2

Food

7.3

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
7,980 reviews
Delta
8.0
Very good
7,980 reviews

Entertainment

7.9

Comfort

7.9

Overall

8.0

Boarding

8.2

Food

7.3

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
8,896 reviews
Delta
8.0
Very good
7,980 reviews

Entertainment

7.9

Comfort

7.9

Overall

8.0

Boarding

8.2

Food

7.3

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.
JetBlue
7.3
Good
2,913 reviews
Delta
8.0
Very good
7,980 reviews

Entertainment

7.9

Comfort

7.9

Overall

8.0

Boarding

8.2

Food

7.3

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
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,980 reviews

Entertainment

7.9

Comfort

7.9

Overall

8.0

Boarding

8.2

Food

7.3

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.
Allegiant Air
7.2
Good
703 reviews
Delta
8.0
Very good
7,980 reviews

Entertainment

7.9

Comfort

7.9

Overall

8.0

Boarding

8.2

Food

7.3

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 14 outbound flights to Chicago per day from 3 airlines. Syracuse Hancock Intl is conveniently located just 4.8 mi from Syracuse’s city center.

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

    Our cheapest airline available from Syracuse to Chicago is Frontier. Our recent data shows that you can find tickets from as low as $215 on this airline. Additional options worth looking into are United Airlines and Delta, starting at $219 and $229 round-trip. These flights start at 37% 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 ($102), Frontier ($107), and Delta ($147).

  • 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: Emirates (100%), ANA (90%), Japan Airlines( 84%).

  • What are the cheapest flights from Syracuse to Chicago?

    While on average a flight from Syracuse to Chicago is generally $880, our data shows the cheapest flight currently is $172. 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, August is the cheapest month in which you can book a flight from Syracuse to Chicago (average of $245). Flying from Syracuse to Chicago in March is currently the most expensive (average of $321). 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
Benton Harbor
Porter
Valparaiso
Chesterton

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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 July 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$209Average$346FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$247Average$388FlexibilityNo cancel feeOn-time69%
DeltaCheapest$248Average$468FlexibilityNo cancel feeOn-timeN/A

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