$154 Cheap flight deals from Chicago (CHI) to Cornwall (NYC)

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This Weekend's Flight Deals from Chicago to Cornwall

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.

Fri, Oct 23 - Mon, Oct 26
ORD
O'Hare Intl.
HPN
Westchester County
$557 Roundtrip, found 2 days ago
$557
Roundtrip
found 2 days ago
Select American Airlines flight, departing Fri, Oct 23 from O'Hare Intl. to Westchester County, returning Mon, Oct 26, priced at $557 found 2 days ago
Sun, Oct 25 - Tue, Oct 27
MDW
Midway Intl.
HPN
Westchester County
$1,109 Roundtrip, found 22 hours ago
$1,109
Roundtrip
found 22 hours ago
Select Delta flight, departing Sun, Oct 25 from Midway Intl. to Westchester County, returning Tue, Oct 27, priced at $1,109 found 22 hours ago

Airfares from $154 One Way, $307 Round Trip from Chicago to Cornwall

Prices starting at $307 for return flights and $154 for one-way flights to Cornwall 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, Nov 12 - Sat, Nov 14
ORD
Chicago
HPN
White Plains
$307 Roundtrip, found 3 days ago
$307
Roundtrip
found 3 days ago
Select Delta flight, departing Thu, Nov 12 from Chicago to White Plains, returning Sat, Nov 14, priced at $307 found 3 days ago
Thu, Nov 12 - Sat, Nov 14
ORD
Chicago
HPN
White Plains
$313 Roundtrip, found 3 days ago
$313
Roundtrip
found 3 days ago
Select Delta flight, departing Thu, Nov 12 from Chicago to White Plains, returning Sat, Nov 14, priced at $313 found 3 days ago
Sat, Nov 7 - Mon, Nov 9
ORD
Chicago
HPN
White Plains
$338 Roundtrip, found 19 hours ago
$338
Roundtrip
found 19 hours ago
Select Delta flight, departing Sat, Nov 7 from Chicago to White Plains, returning Mon, Nov 9, priced at $338 found 19 hours ago
Sat, Oct 31 - Sat, Nov 7
ORD
Chicago
HPN
White Plains
$339 Roundtrip, found 1 day ago
$339
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Oct 31 from Chicago to White Plains, returning Sat, Nov 7, priced at $339 found 1 day ago
Fri, Nov 13 - Sun, Nov 15
ORD
Chicago
HPN
White Plains
$343 Roundtrip, found 1 day ago
$343
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Nov 13 from Chicago to White Plains, returning Sun, Nov 15, priced at $343 found 1 day ago

Cornwall economy flight packages

Price found within the past 48 hours. Click for updated prices.
East Norwich Inn
2.5-star property

East Norwich Inn

8/10 Very Good! (1,809 reviews)

Dec 3 - Dec 8

5 night stay

Chicago (CHI) to New York (JFK)

Frontier Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $774, price is now $519 per person
$519
per person
found 1 day ago
Classic hotel, clean and comfortable.

Reviewed on Oct 17, 2026

Hotel Riu Plaza New York Times Square
4.0-star property

Hotel Riu Plaza New York Times Square

9/10 Wonderful! (3,389 reviews)

Dec 8 - Dec 13

5 night stay

Chicago (CHI) to New York (JFK)

Southwest Airlines • Coach

New York (JFK) to Chicago (CHI)

Frontier Airlines • Coach
Save 100% on your flight
Price was $3,390, price is now $2,212 per person
$2,212
per person
found 1 day ago
We had a nice stay. Most of the staff was very friendly. Breakfast was good, but seemed fairly strict concerning seating and taking coffee back to the rooms. The glass wall and door in the bathroom made it difficult for five people to get ready. Glass?!! Also, there was a shower leak onto the floor. Location is great.

Reviewed on Oct 19, 2026

1 Hotel Brooklyn Bridge
5.0-star property

1 Hotel Brooklyn Bridge

9/10 Wonderful! (1,007 reviews)

Dec 14 - Dec 17

3 night stay

Chicago (CHI) to New York (JFK)

Southwest Airlines • Coach

New York (JFK) to Chicago (CHI)

Frontier Airlines • Coach
Save 100% on your flight
Price was $2,240, price is now $1,474 per person
$1,474
per person
found 21 hours ago
My room had great views and was clean and fun.

Reviewed on Oct 15, 2026

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Cornwall packages with premium economy flights

Price found within the past 48 hours. Click for updated prices.
Margaritaville Resort Times Square
4.0-star property

Margaritaville Resort Times Square

9/10 Wonderful! (4,269 reviews)

Nov 19 - Nov 22

3 night stay

Chicago (MDW) to New York (JFK)

Frontier Airlines • Non-stop roundtrip • PremiumEconomy
Price was $1,130, price is now $975 per person
$975
per person
found 1 day ago
The room was quite spacious for NYC. The room was cleaned and stocked daily without asking. My one issue was the gym. The only two bikes were broken. I went to the gym everyday and the equipment surface cleaner was never available. I had to use hand sanitizer to clean my equipment before and after use.

Reviewed on Oct 19, 2026

Hotel Riu Plaza Manhattan Times Square
4.0-star property

Hotel Riu Plaza Manhattan Times Square

9.2/10 Wonderful! (4,026 reviews)

Nov 19 - Nov 22

3 night stay

Chicago (MDW) to New York (JFK)

Frontier Airlines • Non-stop roundtrip • PremiumEconomy
Save 100% on your flight
Price was $1,836, price is now $1,271 per person
$1,271
per person
found 1 day ago
Location is incredible - right in the heart of Times Square. Nice lobby, helpful staff, and rooms were very clean! Bed was comfy (linens could be softer - but I’m spoiled and prefer bamboo linens). We did as for additional pillows (which arrived very quickly) as there were only 2 on the bed. Shower was stocked with shampoo, conditioner and body soap and counter had hand soap and lotion dispenser. Safe in room and mini fridge as well as coffee maker. Will DEF stay here again.

Reviewed on Oct 19, 2026

Hyatt Centric Times Square New York
4.5-star property

Hyatt Centric Times Square New York

9.4/10 Exceptional! (2,199 reviews)

Nov 19 - Nov 22

3 night stay

Chicago (MDW) to New York (JFK)

Frontier Airlines • Non-stop roundtrip • PremiumEconomy
Price was $1,178, price is now $1,048 per person
$1,048
per person
found 1 day ago
The property and the staff were all lovely and very helpful, particularly Dayana, Jovan, and Yenny. The hotel can’t be any more convenient for a stay in the city. However, I had a very unfortunate incident which seemed to stem from miscommunication and then a lack of nighttime protocol. A maintenance person was sent to my room at 1 AM based on an online survey I completed that only stated that the toilet had difficulty flushing. Someone interpreted that as a toilet overflowing and took unnecessary and inappropriate steps to send maintenance, extremely late at night, and who then proceeded to knock aggressively for several minutes, scaring my niece and causing panic between my sister and I. I have to say that this was a serious oversight and while everything else was great, I would caution anyone staying here solely due to this incident.

Reviewed on Oct 19, 2026

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Cornwall first class flight packages

Price found within the past 48 hours. Click for updated prices.
Hotel Beacon
4.0-star property

Hotel Beacon

9.4/10 Exceptional! (1,530 reviews)

Dec 10 - Dec 13

3 night stay

Chicago (ORD) to New York (JFK)

Delta • Roundtrip • FirstClass
Save 100% on your flight
Price was $2,054, price is now $1,568 per person
$1,568
per person
found 1 day ago
The Bevin was clean, quiet and comfortable but is undergoing renovations o just felt like a place to sleep not a luxury NYC hotel.

Reviewed on Oct 18, 2026

Park Lane New York
5.0-star property

Park Lane New York

8.4/10 Very Good! (1,813 reviews)

Dec 10 - Dec 13

3 night stay

Chicago (ORD) to New York (JFK)

Delta • Roundtrip • FirstClass
Save 100% on your flight
Price was $2,713, price is now $1,865 per person
$1,865
per person
found 1 day ago

PUBLIC, an Ian Schrager hotel
4.0-star property

PUBLIC, an Ian Schrager hotel

8.8/10 Excellent! (4,011 reviews)

Dec 10 - Dec 13

3 night stay

Chicago (ORD) to New York (JFK)

Delta • Roundtrip • FirstClass
Save 100% on your flight
Price was $2,068, price is now $1,574 per person
$1,574
per person
found 1 day ago
The hotel was very lively and had amazing views from the rooftop deck. Pretty good location. We generally love Ian Schrager designed hotels. The cocktails were mid but very expensive ($25/ea). The service was average. However, we paid for an upgraded loft close to $750/night and the cable tv didn’t work and had some issues with the ac that was fixed. The tv never worked for the entire stay but we did receive an amenities credit and were offered a lower floor room on the final night that had a working tv. We’re in the city a few times a year and will probably look for another option next time.

Reviewed on Oct 19, 2026

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More About Flying To Cornwall from Chicago

Route Information for Flights from Chicago to Cornwall

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

Chicago to Cornwall

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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.