$113 Cheap flight deals from New York (NYC) to Orland Park (CHI)

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This Weekend's Flight Deals from New York to Orland Park

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.

Sun, Oct 4 - Tue, Oct 6
LGA
LaGuardia
MDW
Midway Intl.
$270 Roundtrip, found 4 hours ago
$270
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Sun, Oct 4 from LaGuardia to Midway Intl., returning Tue, Oct 6, priced at $270 found 4 hours ago
Sat, Oct 3 - Mon, Oct 5
LGA
LaGuardia
ORD
O'Hare Intl.
$270 Roundtrip, found 1 hour ago
$270
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Sat, Oct 3 from LaGuardia to O'Hare Intl., returning Mon, Oct 5, priced at $270 found 1 hour ago
Fri, Oct 2 - Sat, Oct 3
LGA
LaGuardia
RFD
Greater Rockford
$333 Roundtrip, found 14 hours ago
$333
Roundtrip
found 14 hours ago
Select American Airlines flight, departing Fri, Oct 2 from LaGuardia to Greater Rockford, returning Sat, Oct 3, priced at $333 found 14 hours ago
Sat, Oct 3 - Tue, Oct 6
JFK
John F. Kennedy Intl.
MDW
Midway Intl.
$340 Roundtrip, found 3 days ago
$340
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sat, Oct 3 from John F. Kennedy Intl. to Midway Intl., returning Tue, Oct 6, priced at $340 found 3 days ago

Airfares from $113 One Way, $225 Round Trip from New York to Orland Park

Prices starting at $225 for return flights and $113 for one-way flights to Orland Park were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Wed, Oct 28 - Sat, Oct 31
LGA
New York
ORD
Chicago
$225 Roundtrip, found 5 hours ago
$225
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Wed, Oct 28 from New York to Chicago, returning Sat, Oct 31, priced at $225 found 5 hours ago
Wed, Oct 28 - Wed, Nov 4
EWR
New York
ORD
Chicago
$235 Roundtrip, found 8 hours ago
$235
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Wed, Oct 28 from New York to Chicago, returning Wed, Nov 4, priced at $235 found 8 hours ago
Wed, Nov 4 - Wed, Nov 11
LGA
New York
MDW
Chicago
$238 Roundtrip, just found
$238
Roundtrip
just found
Select Frontier Airlines flight, departing Wed, Nov 4 from New York to Chicago, returning Wed, Nov 11, priced at $238 just found
Wed, Dec 2 - Tue, Dec 8
EWR
New York
MDW
Chicago
$238 Roundtrip, found 2 hours ago
$238
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Wed, Dec 2 from New York to Chicago, returning Tue, Dec 8, priced at $238 found 2 hours ago
Tue, Nov 3 - Wed, Nov 4
JFK
New York
ORD
Chicago
$277 Roundtrip, found 4 hours ago
$277
Roundtrip
found 4 hours ago
Select American Airlines flight, departing Tue, Nov 3 from New York to Chicago, returning Wed, Nov 4, priced at $277 found 4 hours ago

Orland Park economy flight packages

Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

9.6/10 Exceptional! (2,025 reviews)

Nov 13 - Nov 15

2 night stay

Newark Liberty Intl. Airport (EWR) to Chicago (ORD)

American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,102, price is now $717 per person
$717
per person
found 1 day ago
The Trump hotel is right in the middle of downtown, but it's on the quieter side of the river from the other hotels. It offers direct access to the river where you can join the architecture river tour and is overall quieter than the hotels on the other side of the river. The self parking is a bit of a tricky drive up very narrow and curving ramps. If you drive a Suburban or a Cybertruck, you might have difficulty.

Reviewed on Sep 29, 2026

Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

9.4/10 Exceptional! (5,340 reviews)

Nov 12 - Nov 15

3 night stay

Newark Liberty Intl. Airport (EWR) to Chicago (ORD)

American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,123, price is now $801 per person
$801
per person
found 1 day ago

Villa Christina
3.0-star property

Villa Christina

10/10 Exceptional! (1 review)

Nov 3 - Nov 7

4 night stay

New York (LGA) to Chicago (ORD)

Delta • Coach

Chicago (ORD) to New York (LGA)

Frontier Airlines • Coach
Save 100% on your flight
Price was $1,106, price is now $804 per person
$804
per person
found 1 day ago
Property was maintained very well, very clean with some artful style. Staff reaponsed quickly fie any needs or inquiry. Feels like a home. Community is safe and neighbors are nice. Street parking is reletively easy.

Reviewed on Aug 4, 2026

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Orland Park first class flight packages

Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

9.6/10 Exceptional! (2,025 reviews)

Nov 7 - Nov 9

2 night stay

New York (LGA) to Chicago (ORD)

Delta • FirstClass

Chicago (ORD) to New York (LGA)

Frontier Airlines • FirstClass
Price was $1,303, price is now $997 per person
$997
per person
found 1 day ago
The Trump hotel is right in the middle of downtown, but it's on the quieter side of the river from the other hotels. It offers direct access to the river where you can join the architecture river tour and is overall quieter than the hotels on the other side of the river. The self parking is a bit of a tricky drive up very narrow and curving ramps. If you drive a Suburban or a Cybertruck, you might have difficulty.

Reviewed on Sep 29, 2026

Level Chicago – Old Town
4.0-star property

Level Chicago – Old Town

9.2/10 Wonderful! (527 reviews)

Nov 17 - Nov 20

3 night stay

New York (LGA) to Chicago (ORD)

Delta • Roundtrip • FirstClass
Price was $1,254, price is now $1,016 per person
$1,016
per person
found 1 day ago
The location is perfect and the building is quite nice. The rooms are also comfortable. This is not a hotel, but rather occupies several floors in a large apartment building. We had a couple issues with our room (malfunctioning, smoke alarm and empty body wash) and neither were dealt with despite a asking multiple times.

Reviewed on Sep 27, 2026

Stay One Chicago
4.0-star property

Stay One Chicago

8/10 Very Good! (14 reviews)

Nov 17 - Nov 20

3 night stay

New York (LGA) to Chicago (ORD)

Delta • Roundtrip • FirstClass
Price was $1,611, price is now $1,308 per person
$1,308
per person
found 1 day ago
Very nice and clean property. Beds were extremely comfortable and the room was spacious! Loved it!

Reviewed on Sep 20, 2026

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More About Flying To Orland Park from New York

Route Information for Flights from New York to Orland Park

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

New York to Orland Park

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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.