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$101+ 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 9/21. Fares are subject to change and may not be available on all flights or dates of travel.
SYR — CHI
Jul 24 — Jul 311
Fri 7/24
Fri 7/31
1 adult, Economy
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Cheapflights Tip: The best prices from Syracuse Hancock Intl to Chicago are usually found in October or September, booked 88 days in advance, depart on a Friday or Wednesday and return on a Saturday

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 June 24, 2026.

This American Airlines deal was found by Cheapflights users on 6/23. 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 7/238:19 pm
SYR
-
ORD
Nonstop2h 30m
American Airlines
Thu 7/309:02 pm
ORD
-
SYR
Nonstop2h 01m
American Airlines
Deal found 6/23$269
This JetBlue deal was found by Cheapflights users on 6/23. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/276:00 am
SYR
-
ORD
1 stop6h 56m
JetBlue
Fri 10/302:15 pm
ORD
-
SYR
1 stop7h 37m
JetBlue
Deal found 6/23$270
This CheapOair deal was found by Cheapflights users on 6/20. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/86:00 am
SYR
-
ORD
1 stop16h 55m
JetBlue
Fri 9/112:15 pm
ORD
-
SYR
1 stop7h 36m
JetBlue
Deal found 6/20$272
This Travelocity deal was found by Cheapflights users on 6/21. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/166:00 am
SYR
-
ORD
1 stop6h 47m
JetBlue
Mon 10/192:15 pm
ORD
-
SYR
1 stop7h 36m
JetBlue
Deal found 6/21$273
This Orbitz deal was found by Cheapflights users on 6/22. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/227:00 am
SYR
-
ORD
2 stops11h 34m
JetBlue
Sat 7/255:27 pm
ORD
-
SYR
1 stop5h 38m
JetBlue
Deal found 6/22$275
This American Airlines deal was found by Cheapflights users on 6/20. 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.
Tue 8/47:19 pm
SYR
-
ORD
1 stop5h 11m
American Airlines
Tue 8/118:00 am
ORD
-
SYR
Nonstop2h 05m
American Airlines
Deal found 6/20$278
This American Airlines deal was found by Cheapflights users on 6/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/67:52 pm
SYR
-
ORD
1 stop4h 45m
American Airlines
Sun 8/97:54 pm
ORD
-
SYR
Nonstop2h 01m
American Airlines
Deal found 6/21$280
This CheapOair deal was found by Cheapflights users on 6/21. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/77:00 am
SYR
-
ORD
1 stop13h 31m
JetBlue
Sat 7/115:27 pm
ORD
-
SYR
1 stop5h 38m
JetBlue
Deal found 6/21$282
This Kiwi.com deal was found by Cheapflights users on 6/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/307:26 pm
SYR
-
ORD
1 stop17h 49m
Multiple Airlines
Thu 8/68:05 am
ORD
-
SYR
1 stop9h 31m
Multiple Airlines
Deal found 6/21$283
This CheapOair deal was found by Cheapflights users on 6/23. 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.
Thu 10/297:00 am
SYR
-
ORD
1 stop13h 12m
JetBlue
Sat 10/312:15 pm
ORD
-
SYR
1 stop7h 37m
JetBlue
Deal found 6/23$285
This CheapOair deal was found by Cheapflights users on 6/20. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/47:00 am
SYR
-
ORD
1 stop7h 00m
JetBlue
Mon 7/68:21 pm
ORD
-
SYR
1 stop25h 30m
JetBlue
Deal found 6/20$286
This Delta deal was found by Cheapflights users on 6/22. 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 8/61:42 pm
SYR
-
MDW
1 stop5h 51m
Delta
Thu 8/136:42 pm
MDW
-
SYR
1 stop3h 26m
Delta
Deal found 6/22$289

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 June 24, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$269
(American Airlines)

One-way from

$101
(JetBlue)

Popular in

November

Cheapest in

October

Average price

$309

Good round-trip deal

$363 or less

Good one-way deal

$304 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.
Search Deals
From Syracuse Hancock Intl to Chicago (CHI)
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One-way flight from Syracuse Hancock Intl to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($20 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 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).
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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 June 24, 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 - MDW

SYRMDW

Syracuse Hancock Intl

Thu 8/6

1:42 pm-6:33 pm

1 stop5h 51m

Chicago Midway

Tue 8/11

6:42 pm-11:08 pm

1 stop3h 26m

$289

SyracuseChicago

SYR - MDW

SYRMDW

Syracuse Hancock Intl

Fri 8/21

4:02 pm-10:36 pm

1 stop7h 34m

Chicago Midway

Tue 8/25

6:42 pm-11:08 pm

1 stop3h 26m

$289

SyracuseChicago

SYR - MDW

SYRMDW

Syracuse Hancock Intl

Thu 8/6

1:42 pm-6:33 pm

1 stop5h 51m

Chicago Midway

Mon 8/10

6:42 pm-11:08 pm

1 stop3h 26m

$289

SyracuseChicago

SYR - ORD

SYRORD

Syracuse Hancock Intl

Thu 8/6

1:42 pm-6:29 pm

1 stop5h 47m

Chicago O'Hare Intl

Mon 8/10

5:20 pm-11:08 pm

1 stop4h 48m

$289

SyracuseChicago

SYR - ORD

SYRORD

Syracuse Hancock Intl

Mon 7/13

6:54 pm-11:53 pm

1 stop5h 59m

Chicago O'Hare Intl

Tue 7/21

5:30 am-11:25 am

1 stop4h 55m

$309

SyracuseChicago

SYR - ORD

SYRORD

Syracuse Hancock Intl

Fri 7/31

7:52 pm-11:31 pm

1 stop4h 39m

Chicago O'Hare Intl

Sun 8/2

6:09 pm-9:09 pm

Nonstop2h 00m

$315

SyracuseChicago

SYR - MDW

SYRMDW

Syracuse Hancock Intl

Wed 8/5

1:42 pm-6:33 pm

1 stop5h 51m

Chicago Midway

Sat 8/8

6:42 pm-11:08 pm

1 stop3h 26m

$324

SyracuseChicago

SYR - ORD

SYRORD

Syracuse Hancock Intl

Fri 7/17

6:15 am-7:29 am

Nonstop2h 14m

Chicago O'Hare Intl

Sun 7/19

6:09 pm-9:09 pm

Nonstop2h 00m

$329

SyracuseChicago

SYR - MDW

SYRMDW

Syracuse Hancock Intl

Fri 8/7

4:02 pm-10:36 pm

1 stop7h 34m

Chicago Midway

Mon 8/10

6:42 pm-11:08 pm

1 stop3h 26m

$364

SyracuseChicago

SYR - ORD

SYRORD

Syracuse Hancock Intl

Wed 11/25

6:50 pm-11:50 pm

1 stop6h 00m

Chicago O'Hare Intl

Sun 12/27

5:55 pm-11:55 pm

1 stop5h 00m

$364

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/22

Showing 1-10 of 47 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 June.
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

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 $124). Flying from Syracuse to Chicago in March is currently the most expensive (average of $238). 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 June 24, 2026.

One of the essential ways to save on airfare from Syracuse to Chicago is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the evening could potentially save you up to 22% on airfare.

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 June 24, 2026.

The most flights from SYR to CHI are scheduled on a Tuesday (29 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (8 on average).

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

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

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 22 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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 June 20, 2026.

Travelers seeking maximum savings on their Syracuse to Chicago flight should consider departing on Saturday at noon 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 June 24, 2026.
Read through reviews of airlines operating flights from Syracuse to Chicago, such as United Airlines and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,881 reviews

Entertainment

7.1

Overall

7.4

Boarding

7.7

Comfort

7.3

Crew

8.1

Food

6.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
United Airlines
7.4
Good
9,881 reviews
United Airlines
7.4
Good
9,881 reviews

Entertainment

7.1

Overall

7.4

Boarding

7.7

Comfort

7.3

Crew

8.1

Food

6.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
American Airlines
7.1
Good
11,751 reviews
United Airlines
7.4
Good
9,881 reviews

Entertainment

7.1

Overall

7.4

Boarding

7.7

Comfort

7.3

Crew

8.1

Food

6.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.

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 20 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 4h 39m. 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 53% lower than the current average price 3 months from now.

  • 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 (91%), GoJet (91%), Emirates( 91%).

  • What are the cheapest flights from Syracuse to Chicago?

    While on average a flight from Syracuse to Chicago is generally $805, our data shows the cheapest flight currently is $177. When looking at the most popular route, (Syracuse Hancock Intl - Chicago O'Hare Intl), you can expect to pay $239 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 $124). Flying from Syracuse to Chicago in March is currently the most expensive (average of $238). 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
Benton Harbor
Lansing
Merrillville
Hammond
Porter

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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 June 24, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$153Average$410FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$209Average$339FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$209Average$346FlexibilityNo cancel feeOn-time71%

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