Highland Park Vacations from ￥344,016
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The Latest Highland Park Vacation Packages
Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was ￥419,975, price is now ￥344,016 per person
￥344,016
per person
Mar 22 - Mar 28
found 4 hours ago
Roundtrip flight included
Tokushima (TKS) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
Perfect location, comfortable and clean room
Reviewed on Jan 5, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥565,091, price is now ￥431,406 per person
￥431,406
per person
Mar 22 - Mar 28
found 4 hours ago
Roundtrip flight included
Tokushima (TKS) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Stayed in a river view room over NYE and had a great view of the fireworks show on the river! The staff was superb and went above and beyond for us. Extremely kind and knowledgeable. Cannot wait to stay again!
Reviewed on Jan 3, 2026
The Peninsula Chicago
Downtown Chicago
Price was ￥581,636, price is now ￥458,678 per person
￥458,678
per person
Mar 22 - Mar 28
found 4 hours ago
Roundtrip flight included
Tokushima (TKS) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Upon check-in, it was magical! The doormen were amazing, the 'go as often as you'd like' Santa's candy shop, overall hotel decorations and the professionalism of the staff will blow you away!!! This hotel is next level up and puts the Ritz Carlton down a notch, for sure. Our room was truly magnificent and I wish we could have stayed longer!
Reviewed on Jan 6, 2026
Level Chicago – Old Town
Downtown Chicago
Price was ￥450,266, price is now ￥368,169 per person
￥368,169
per person
Mar 22 - Mar 28
found 4 hours ago
Roundtrip flight included
Tokushima (TKS) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Staff was friendly did amazing job with checking us in
Reviewed on Dec 25, 2025
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Price was ￥445,109, price is now ￥367,908 per person
￥367,908
per person
Mar 22 - Mar 28
found 4 hours ago
Roundtrip flight included
Tokushima (TKS) to Chicago (ORD)
9.2/10 Wonderful! (317 reviews)
Room was very spacious and clean. The location was perfect walking distance from a lot great eating and tourists spots.
Reviewed on Dec 18, 2025
Find the Best Highland Park Vacation Packages
Highland Park Hotel Deals
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥30,690 per night from Feb 6 to Feb 7
￥30,690
￥36,027 total
Feb 6 - Feb 7
includes taxes & fees
8.2/10 Very Good! (2,199 reviews)
Our check in between flights was so friendly , efficient and competent . Ella is great . This easiest to access the property form terminal 2 .
Reviewed on Jan 5, 2026
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is ￥18,502 per night from Jan 11 to Jan 12
￥18,502
￥21,088 total
Jan 11 - Jan 12
includes taxes & fees
8.8/10 Excellent! (2,307 reviews)
Comfortable and elegant, the only thing missing was a free breakfast
Reviewed on Jan 6, 2026
Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
5440 N River Rd Rosemont IL
Fully refundable
The price is ￥16,444 per night from Jan 11 to Jan 12
￥16,444
￥18,744 total
Jan 11 - Jan 12
includes taxes & fees
8.6/10 Excellent! (2,685 reviews)
Overall the room was fine but there were insufficient blankets on the bed! Upped the room temp to 72 (and I'm used to 68 at home) and still used a bath towel as an added blanket!
Reviewed on Dec 31, 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.
Discover the most popular places to visit in Highland Park
Michigan Avenue
4.5/5(332 reviews)
You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.
Wrigley Field
4.5/5(2,128 reviews)
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Navy Pier
4.5/5(4,870 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
￥6,889
per adult
100% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
￥3,845
per adult
88% 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.
