Highwood Packages (Flight + Hotel)
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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
per person
21 Aug - 23 Aug
found 1 day ago
Return flight included
Boston (BOS) to Chicago (ORD)
8.2/10 Very Good! (1,842 reviews)
The property and room was nicely decorated. The beautiful aids were nice. Rooms are small no dresser to put your things in. I called and asked about a having access to a refrigerator. I was told that there was not one in the my room and that I could get one apron request for 20 dollars. When I checked in I requested a refrigerator and was told there was not one available or I could upgrade my room that included one for 17 dollars a night. I brought with me parishable food items because I was on a budget. Half of my food items went to waist and I could not store my left overs. Needless to say I was disappointed. The staff were helpful, nice and courteous.
Reviewed on 9 Jul 2025
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
per person
21 Aug - 23 Aug
found 1 day ago
Return flight included
Boston (BOS) to Chicago (ORD)
9.4/10 Exceptional! (2,053 reviews)
WE LIKE CLEANLINESS & CHILDREN MUSEUM AND AROUND THE HOTEL
Reviewed on 8 Jul 2025
Top hotels in Highwood
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave, Rosemont, IL
Fully refundableReserve now, pay when you stay
The price is ฿4,936 per night from 21 Jul to 22 Jul
฿4,936
฿5,626 total
21 Jul - 22 Jul
includes taxes & fees
8.6/10 Excellent! (1,722 reviews)
"This was a last minute booking as our flight got cancelled. Airport shuttle was a life saver!!"
Reviewed on 12 Jul 2025
Hilton Chicago O'Hare Airport
O'Hare International Airport, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ฿5,815 per night from 8 Aug to 9 Aug
฿5,815
฿6,826 total
8 Aug - 9 Aug
includes taxes & fees
8/10 Very Good! (2,074 reviews)
Business trip
"Flights were canceled so we booked the Hilton at the airport. Very friendly staff and smooth check in."
Reviewed on 12 Jul 2025
Marriott Chicago O'Hare
8535 West Higgins Road, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ฿5,226 per night from 26 Jul to 27 Jul
฿5,226
฿6,135 total
26 Jul - 27 Jul
includes taxes & fees
8.4/10 Very Good! (1,083 reviews)
"For the price we paid, i was disappointed to find that our room smelt like cigarettes. A few fixtures in the room seem to be stained from smoke and the carpet didn’t feel clean. But aside from that, the pool was clean, bathroom was nice, breakfast was expensive but it was okay. Stayed for two days. ..."
Reviewed on 11 Jul 2025
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.
Navy Pier
4/5(125 reviews)
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
Millennium Park
4.5/5(147 reviews)
A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.
What to do in Highwood
Chicago CityPASS®: Experience 5 must-see attractions
฿4,634
per adult
92% of travellers recommend
Frequently asked questions
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.