Highland Park Holidays
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Top Flight + Hotel Deals in Highland Park
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was €1,670, price is now €1,016 per person
€1,016
per person
29 Jul - 3 Aug
found 17 hours ago
Return direct flight included
New York (NYC) to Chicago (ORD)
8.2/10 Very Good! (2,711 reviews)
A decent buisness class hotel. No frills. Rooms are smaller, the queen beds are not true queens, and much smaller.
Reviewed on 22 May 2026
Swissotel - Chicago
Downtown Chicago
Price was €2,088, price is now €1,072 per person
€1,072
per person
29 Jul - 3 Aug
found 17 hours ago
Return direct flight included
New York (NYC) to Chicago (ORD)
9/10 Wonderful! (3,332 reviews)
Great location and very convenient to river walk and vicinity.
Reviewed on 22 May 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was €2,197, price is now €1,315 per person
€1,315
per person
29 Jul - 3 Aug
found 17 hours ago
Return direct flight included
New York (NYC) to Chicago (ORD)
9.4/10 Exceptional! (2,507 reviews)
I’m not sure if the hotel had a lack of staff but I called for towels and never received any, the next day they brought towels shortly after I called again.
Reviewed on 21 May 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was €2,214, price is now €1,359 per person
€1,359
per person
29 Jul - 3 Aug
found 17 hours ago
Return direct flight included
New York (NYC) to Chicago (ORD)
9.4/10 Exceptional! (3,727 reviews)
Can't beat the location; it's next to Michigan Avenue and across from the Riverwalk; we'd stay there again.
Reviewed on 21 May 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was €2,250, price is now €1,436 per person
€1,436
per person
29 Jul - 3 Aug
found 17 hours ago
Return direct flight included
New York (NYC) to Chicago (ORD)
9.4/10 Exceptional! (1,872 reviews)
Great experience! Would stay here agin
Reviewed on 18 May 2026
Top hotels in Highland Park
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
The price is €260 per night from 24 May to 25 May
€260
24 May - 25 May
includes taxes & fees
8.4/10 Very Good! (2,295 reviews)
"Very nice place. The room was great and spacious."
Reviewed on 22 May 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is €160 per night from 22 Jun to 23 Jun
€160
22 Jun - 23 Jun
includes taxes & fees
8.2/10 Very Good! (1,483 reviews)
"Close to everything, beautiful views, helpful staff-what more could you want!"
Reviewed on 21 May 2026
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is €166 per night from 25 May to 26 May
€166
25 May - 26 May
includes taxes & fees
8.8/10 Excellent! (2,554 reviews)
"."
Reviewed on 22 May 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Popular places to visit
Wrigley Field
4.5/5(40 reviews)
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Naval Base Great Lakes
5/5(1 review)
After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.
Navy Pier
4/5(127 reviews)
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
What to do in Highland Park
Skydeck - Willis Tower Admission
€38
per adult
96% of travellers recommend
Chicago Sightseeing River and Lake Cruise
€39
per adult
100% of travellers recommend
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
