$81 Cheap flight deals from Chicago (CHI) to Upstate New York (NYC)

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This Weekend's Flight Deals from Chicago to Upstate New York

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, Aug 9 - Sat, Aug 23
MDW
Midway Intl.
BUF
Buffalo Niagara Intl.
$211 Roundtrip, found 3 days ago
$211
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sat, Aug 9 from Midway Intl. to Buffalo Niagara Intl., returning Sat, Aug 23, priced at $211 found 3 days ago
Fri, Aug 8 - Mon, Aug 11
ORD
O'Hare Intl.
SYR
Hancock Intl.
$225 Roundtrip, found 5 hours ago
$225
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Fri, Aug 8 from O'Hare Intl. to Hancock Intl., returning Mon, Aug 11, priced at $225 found 5 hours ago
Sat, Aug 9 - Wed, Aug 27
MDW
Midway Intl.
BTV
Burlington Intl.
$265 Roundtrip, found 5 days ago
$265
Roundtrip
found 5 days ago
Select Delta flight, departing Sat, Aug 9 from Midway Intl. to Burlington Intl., returning Wed, Aug 27, priced at $265 found 5 days ago
Sat, Aug 9 - Wed, Aug 13
ORD
O'Hare Intl.
BTV
Burlington Intl.
$285 Roundtrip, found 4 days ago
$285
Roundtrip
found 4 days ago
Select Delta flight, departing Sat, Aug 9 from O'Hare Intl. to Burlington Intl., returning Wed, Aug 13, priced at $285 found 4 days ago

Airfares from $81 One Way, $177 Round Trip from Chicago to Upstate New York

Prices starting at $177 for return flights and $81 for one-way flights to Upstate New York were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Thu, Oct 9 - Mon, Oct 13
ORD
Chicago
BUF
Buffalo
$177 Roundtrip, found 2 days ago
$177
Roundtrip
found 2 days ago
Select United flight, departing Thu, Oct 9 from Chicago to Buffalo, returning Mon, Oct 13, priced at $177 found 2 days ago
Thu, Aug 28 - Sat, Aug 30
ORD
Chicago
ROC
Rochester
$182 Roundtrip, found 2 days ago
$182
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Thu, Aug 28 from Chicago to Rochester, returning Sat, Aug 30, priced at $182 found 2 days ago
Sun, Aug 31 - Sat, Sep 6
ORD
Chicago
BTV
Burlington
$185 Roundtrip, found 3 days ago
$185
Roundtrip
found 3 days ago
Select United flight, departing Sun, Aug 31 from Chicago to Burlington, returning Sat, Sep 6, priced at $185 found 3 days ago
Wed, Oct 29 - Sat, Nov 1
MDW
Chicago
BUF
Buffalo
$187 Roundtrip, found 4 days ago
$187
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Wed, Oct 29 from Chicago to Buffalo, returning Sat, Nov 1, priced at $187 found 4 days ago
Tue, Aug 26 - Sat, Aug 30
MDW
Chicago
BTV
Burlington
$208 Roundtrip, found 4 days ago
$208
Roundtrip
found 4 days ago
Select Delta flight, departing Tue, Aug 26 from Chicago to Burlington, returning Sat, Aug 30, priced at $208 found 4 days ago

Upstate New York economy flight packages

Price found within the past 48 hours. Click for updated prices.
Outsite Chelsea
2.0-star property

Outsite Chelsea

9.6/10 Exceptional! (8 reviews)

Sep 12 - Sep 15

3 night stay

Chicago (CHI) to New York (JFK)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
1 Hotel Brooklyn Bridge
5.0-star property

1 Hotel Brooklyn Bridge

8.8/10 Excellent! (1,001 reviews)

Sep 26 - Sep 28

2 night stay

Chicago (CHI) to New York (JFK)

Spirit Airlines • Coach

New York (JFK) to Chicago (CHI)

United • Coach
Save 100% on your flight
per person
found 14 hours ago
The hotel is beautiful looking forward to visiting again.

Reviewed on Feb 21, 2023

Omni Berkshire Place
4.0-star property

Omni Berkshire Place

9.2/10 Wonderful! (1,897 reviews)

Sep 12 - Sep 15

3 night stay

Chicago (CHI) to New York (JFK)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
Quiet and clean, a little older but well kept. Great location and friendly staff, did not use house keeping during our stay or eat onsite so I can’t speak to those things - if you’re going to the MOMA or anything in midtown really the location is perfect

Reviewed on May 26, 2025

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Upstate New York packages with premium economy flights

Price found within the past 48 hours. Click for updated prices.
The Lexington Hotel, Autograph Collection
4.0-star property

The Lexington Hotel, Autograph Collection

8.4/10 Very Good! (1,397 reviews)

Sep 5 - Sep 8

3 night stay

Chicago (ORD) to New York (JFK)

Delta • Roundtrip • PremiumEconomy
per person
found 5 hours ago
The hotel was lovely. The room was clean & well appointed. I didn’t like the odd toilet flush but the shower was great. The happy hour cocktail offerings were bad. Yet the appetizers were great.

Reviewed on Jul 15, 2025

Outsite Chelsea
2.0-star property

Outsite Chelsea

9.6/10 Exceptional! (8 reviews)

Sep 5 - Sep 8

3 night stay

Chicago (ORD) to New York (JFK)

Delta • Roundtrip • PremiumEconomy
Save 100% on your flight
per person
found 5 hours ago
NobleDEN Hotel
4.0-star property

NobleDEN Hotel

9.8/10 Exceptional! (1,259 reviews)

Sep 5 - Sep 8

3 night stay

Chicago (ORD) to New York (JFK)

Delta • Roundtrip • PremiumEconomy
per person
found 5 hours ago
The place was awesome close to everything clean. Staff is very helpful.

Reviewed on Jul 1, 2025

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Upstate New York first class flight packages

Price found within the past 48 hours. Click for updated prices.
1 Hotel Central Park
5.0-star property

1 Hotel Central Park

9.2/10 Wonderful! (1,003 reviews)

Sep 17 - Sep 23

6 night stay

Chicago (ORD) to New York (JFK)

Delta • Roundtrip • FirstClass
Save 100% on your flight
per person
found 3 hours ago
We have traditionally always stayed in the theater district area however more recently the area has changed. More homeless, dirtier and just not as enjoyable for us. We decided to stay more uptown in the central park area and the Orbitz site recommended the 1 Hotel Central Park. From the moment we checked in it was truly like a zen feeling and experience. Less hustle and bustle checking in, the staff was super friendly, attentive and helpful in every way from the check to the concierge. The room was modern (in a zen way), mini bar was stocked with wines, drinks and snacks. A coffee pod machine as well. The restaurant Jams, was excellent for breakfast and always packed! We HIGHLY recommend staying here and as a matter of fact tyhis will be our new go to staying in NYC.

Reviewed on Jul 13, 2025

The Fifth Avenue Hotel
5.0-star property

The Fifth Avenue Hotel

9.6/10 Exceptional! (125 reviews)

Sep 17 - Sep 23

6 night stay

Chicago (ORD) to New York (JFK)

Delta • Roundtrip • FirstClass
Save 100% on your flight
per person
found 3 hours ago
WestHouse New York
5.0-star property

WestHouse New York

8.4/10 Very Good! (1,003 reviews)

Sep 17 - Sep 23

6 night stay

Chicago (ORD) to New York (JFK)

Delta • Roundtrip • FirstClass
Save 100% on your flight
per person
found 3 hours ago
Love that the Breakfast and Tapas are included - saves so much time trying to figure out where to go

Reviewed on Mar 28, 2025

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More About Flying To Upstate New York from Chicago

Route Information for Flights from Chicago to Upstate New York

Origin Airport IATA Code
CHI
Destination Airport IATA Code
NYC
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Chicago to Upstate New York

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Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.