Highwood Trip
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Top Highwood Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was ₹58,140, price is now ₹44,788 per person
₹44,788
per person
9 Apr - 12 Apr
found 1 day ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
8.2/10 Very Good! (2,365 reviews)
I liked the hotel. The staff was very courteous and friendly. The room was cute. The location is fantastic.
Reviewed on 20 Jan 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was ₹78,710, price is now ₹52,248 per person
₹52,248
per person
9 Apr - 12 Apr
found 1 day ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Great breakfast buffet, incredible staff, very clean, close to everything we wanted to do! 10/10 and will certainly stay here again!
Reviewed on 26 Jan 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was ₹109,038, price is now ₹82,069 per person
₹82,069
per person
9 Apr - 12 Apr
found 1 day ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
The room was boring thought it would be cleaner updated for the price best part was the view
Reviewed on 24 Jan 2026
Level Chicago – Old Town
Downtown Chicago
Price was ₹72,087, price is now ₹54,358 per person
₹54,358
per person
9 Apr - 12 Apr
found 1 day ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Property was clean, welcoming, pet friendly
Reviewed on 18 Jan 2026
Top hotels in Highwood
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
The price is ₹18,022 per night from 21 Feb to 22 Feb
₹18,022
₹21,156 total
21 Feb - 22 Feb
includes taxes & fees
8.2/10 Very Good! (2,202 reviews)
Room was great and so was the service.
Reviewed on 25 Jan 2026
Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
5440 N River Rd Rosemont IL
Fully refundable
The price is ₹10,115 per night from 1 Feb to 2 Feb
₹10,115
₹11,529 total
1 Feb - 2 Feb
includes taxes & fees
8.6/10 Excellent! (2,719 reviews)
Room was clean and the restaurant was good
Reviewed on 26 Jan 2026
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is ₹12,428 per night from 28 Jan to 29 Jan
₹12,428
₹14,165 total
28 Jan - 29 Jan
includes taxes & fees
8.8/10 Excellent! (2,352 reviews)
Cleanest hotel and amazing staff!
Reviewed on 25 Jan 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
Chicago’s world-renowned baseball ground, Wrigley Field is an iconic stadium where you can learn about the all-American sport and even catch a game.
Michigan Avenue
You can find the perfect gifts to bring home when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.
Navy Pier
A waterfront entertainment strip with fun diversions for both young and old, with shops, restaurants and even a Ferris wheel.
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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.
