Highland Park Vacations from ￥99,036
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The Latest Highland Park Vacation Packages
Price found within the past 48 hours. Click for updated prices.
The Chicago Hotel Collection Ambassador Gold Coast
Downtown Chicago
Price was ￥116,173, price is now ￥99,036 per person
￥99,036
per person
Jul 11 - Jul 13
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
8.2/10 Very Good! (1,532 reviews)
Beautiful property in a great location. Staff was very friendly and help. The room was spacing clean, but all of the furniture was very low to tue ground. If you have back or knee issues, you would have trouble staying here.
Reviewed on Jun 9, 2026
Level Chicago Fulton Market
Downtown Chicago
Price was ￥508,926, price is now ￥399,982 per person
￥399,982
per person
Aug 12 - Aug 18
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (491 reviews)
Room was not cleaned/ towels weren't replaced for the duration of our 3 night stay which I found rather peculiar. They also only provided 1 key for our room. I had believed it was common practice to provide 2. Other than that, the room was clean when we arrived, the bedding was comfortable, and the gym was lovely.
Reviewed on May 22, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥456,972, price is now ￥372,300 per person
￥372,300
per person
Jul 16 - Jul 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (4,319 reviews)
The staff is wonderful, as is the breakfast, the rooms are clean and comfortable.
Reviewed on Jun 9, 2026
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was ￥132,392, price is now ￥109,316 per person
￥109,316
per person
Jul 11 - Jul 13
found 16 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
8.8/10 Excellent! (2,176 reviews)
Clean room, overall nice hotel, restaurant was nice for happy hour. Lobby smelled like an old lady and peltons in gym were broken. Overall lovely stay.
Reviewed on Jun 9, 2026
The Godfrey Hotel Chicago
Downtown Chicago
Price was ￥144,187, price is now ￥119,856 per person
￥119,856
per person
Jul 11 - Jul 13
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
8.8/10 Excellent! (2,242 reviews)
The room size, location, and comfortable bed were excellent.
Reviewed on Jun 8, 2026
Find the Best Highland Park Vacation Packages
Highland Park Hotel Deals
Courtyard by Marriott Chicago Highland Park/Northbrook
1505 Lake Cook Road Highland Park IL
Fully refundableReserve now, pay when you stay
The price is ￥17,137 per night from Jul 2 to Jul 3
￥17,137
￥19,019 total
Jul 2 - Jul 3
includes taxes & fees
9/10 Wonderful! (1,002 reviews)
"Great location, nice place to stay! Would stay there again."
Reviewed on Jun 7, 2026
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is ￥25,465 per night from Jun 28 to Jun 29
￥25,465
￥29,024 total
Jun 28 - Jun 29
includes taxes & fees
8.8/10 Excellent! (2,638 reviews)
"Upsetting that I was given a room that I had to haul all of my luggage up 16 steep stairs. No other room options. I had reserved a room months in advance. The front desk lady said a few stairs, which I found odd being that there is an elevator. Beware…the top floor is by stairs only! Front desk lady ..."
Reviewed on Jun 9, 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥26,396 per night from Jun 29 to Jun 30
￥26,396
￥31,383 total
Jun 29 - Jun 30
includes taxes & fees
8.2/10 Very Good! (1,570 reviews)
"Beautiful property in a great location. Staff was very friendly and help. The room was spacing clean, but all of the furniture was very low to tue ground. If you have back or knee issues, you would have trouble staying here."
Reviewed on Jun 9, 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.
Discover the most popular places to visit in Highland Park
Wrigley Field
4.5/5(2,149 reviews)
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Naval Base Great Lakes
4.5/5(461 reviews)
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
4.5/5(4,925 reviews)
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
What to do in Highland Park
Wendella's 90-min Chicago River Architecture Tour
￥6,354
per adult
94% 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.
