$25 Cheap flight deals from New York (NYC) to Highland Park (CHI)
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This Weekend's Flight Deals from New York to Highland 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.
JFK
John F. Kennedy Intl.
MDW
Midway Intl.
$176 Roundtrip, found 3 days ago
$176
Roundtrip
found 3 days ago
LGA
LaGuardia
MDW
Midway Intl.
$193 Roundtrip, just found
$193
Roundtrip
just found
EWR
Newark Liberty Intl. Airport
MDW
Midway Intl.
$227 Roundtrip, found 3 days ago
$227
Roundtrip
found 3 days ago
JFK
John F. Kennedy Intl.
ORD
O'Hare Intl.
$255 Roundtrip, just found
$255
Roundtrip
just found
Airfares from $25 One Way, $49 Round Trip from New York to Highland Park
Prices starting at $49 for return flights and $25 for one-way flights to Highland 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.
LGA
New York
ORD
Chicago
$49 Roundtrip, just found
$49
Roundtrip
just found
EWR
New York
MDW
Chicago
$89 Roundtrip, just found
$89
Roundtrip
just found
EWR
New York
ORD
Chicago
$90 Roundtrip, found 5 days ago
$90
Roundtrip
found 5 days ago
JFK
New York
ORD
Chicago
$106 Roundtrip, found 5 days ago
$106
Roundtrip
found 5 days ago
LGA
New York
MDW
Chicago
$139 Roundtrip, found 20 hours ago
$139
Roundtrip
found 20 hours ago
Highland Park economy flight packages
Price found within the past 48 hours. Click for updated prices.
4.0-star property
Hotel Riu Plaza Chicago
9.4/10 Exceptional! (2,427 reviews)
Nov 14 - Nov 17
3 night stay
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $690, price is now $394 per person
$394
per person
found 1 day ago
One day didn’t receive room service
Reviewed on Sep 2, 2025
4.5-star property
Fairmont Chicago at Millennium Park
8.6/10 Excellent! (1,920 reviews)
Nov 7 - Nov 10
3 night stay
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $649, price is now $426 per person
$426
per person
found 1 day ago
This property really wants to be a luxury hotel, but they repeatedly missed the mark. Everyone who worked there was really nice and apologetic, but they made promises they did not keep.
One gets charged an "urban experience fee" of $25/ day for staying at this hotel. This fee gives you $15 towards food at the restaurants (which are okay, but the service is incredibly slow because there is only one kitchen across the restaurants), and the fee also covers guest passes to a health club that wasn't open during the times I was free, so I was basically forced to pay $25/ day for $15 credit towards their restaurants.
My room had a nice view.
Reviewed on Sep 21, 2025
5.0-star property
Trump International Hotel & Tower Chicago
9.4/10 Exceptional! (1,716 reviews)
Nov 7 - Nov 10
3 night stay
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,196, price is now $787 per person
$787
per person
found 1 day ago
Every employee makes every guest feel like a rockstar. Commitment to quality and guest experience is evident.
Reviewed on Sep 14, 2025
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See all available trips from New York to Highland Park
View all tripsHighland Park packages with premium economy flights
Price found within the past 48 hours. Click for updated prices.
4.5-star property
Fairmont Chicago at Millennium Park
8.6/10 Excellent! (1,920 reviews)
Nov 14 - Nov 16
2 night stay
New York (JFK) to Chicago (ORD)
Delta • Roundtrip • PremiumEconomy
Price was $818, price is now $669 per person
$669
per person
found 17 hours ago
This property really wants to be a luxury hotel, but they repeatedly missed the mark. Everyone who worked there was really nice and apologetic, but they made promises they did not keep.
One gets charged an "urban experience fee" of $25/ day for staying at this hotel. This fee gives you $15 towards food at the restaurants (which are okay, but the service is incredibly slow because there is only one kitchen across the restaurants), and the fee also covers guest passes to a health club that wasn't open during the times I was free, so I was basically forced to pay $25/ day for $15 credit towards their restaurants.
My room had a nice view.
Reviewed on Sep 21, 2025
4.0-star property
Hotel Riu Plaza Chicago
9.4/10 Exceptional! (2,427 reviews)
Nov 14 - Nov 16
2 night stay
New York (JFK) to Chicago (ORD)
Delta • Roundtrip • PremiumEconomy
Price was $919, price is now $677 per person
$677
per person
found 17 hours ago
One day didn’t receive room service
Reviewed on Sep 2, 2025
5.0-star property
Trump International Hotel & Tower Chicago
9.4/10 Exceptional! (1,716 reviews)
Nov 14 - Nov 16
2 night stay
New York (JFK) to Chicago (ORD)
Delta • Roundtrip • PremiumEconomy
Price was $1,153, price is now $862 per person
$862
per person
found 17 hours ago
Every employee makes every guest feel like a rockstar. Commitment to quality and guest experience is evident.
Reviewed on Sep 14, 2025
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See all available trips from New York to Highland Park
View all tripsHighland Park first class flight packages
Price found within the past 48 hours. Click for updated prices.
2.5-star property
Quality Inn Near Interstate I94
8.4/10 Very Good! (1,010 reviews)
Nov 6 - Nov 9
3 night stay
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
American Airlines • Non-stop roundtrip • FirstClass
Price was $1,122, price is now $1,079 per person
$1,079
per person
found 14 hours ago
We had never stayed at a Quality Inn. The AC in the room was great!
Reviewed on Aug 13, 2025
2.5-star property
Holiday Inn Express Hotel & Suites Niles by IHG
9/10 Wonderful! (681 reviews)
Nov 6 - Nov 9
3 night stay
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
American Airlines • Non-stop roundtrip • FirstClass
Price was $1,306, price is now $1,228 per person
$1,228
per person
found 14 hours ago
This hotel was spotless, the front desk person was super nice and quick
Reviewed on Jul 27, 2024
2.5-star property
Holiday Inn Express & Suites New Buffalo by IHG
8.8/10 Excellent! (1,006 reviews)
Nov 6 - Nov 9
3 night stay
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
American Airlines • Non-stop roundtrip • FirstClass
Price was $1,223, price is now $1,164 per person
$1,164
per person
found 14 hours ago
The staff was so friendly and accommodating! Easy and convenient to get to the beach and surrounding communities.
Reviewed on Jul 27, 2025
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See all available trips from New York to Highland Park
View all tripsMore About Flying To Highland Park from New York
Route Information for Flights from New York to Highland Park
Origin Airport IATA Code | NYC |
|---|---|
Destination Airport IATA Code | CHI |
Distance | 737 mi |
Direct Flight Airlines | American Airlines, KLM, Qatar Airways, Air Europa, Air France, China Airlines, China Eastern Airlines, Delta Air Lines, Gol, El Al, Alaska Airlines, JetBlue, LATAM Airlines, SAS, Iberia, Korean Air, Malaysia Airlines, WestJet, Virgin Atlantic, Gulf Air, British Airways |
Earliest Flight Arrival | 1:27PM UTC |
Latest Flight Arrival | 1:39AM UTC |
New York to Highland 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.