Hillside Vacations from ￥376,196
Book a Hotel + Flight or Car together to unlock savings
The Latest Hillside Vacation Packages
Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Chicago O'Hare Airport - Rosemont
Price was ￥411,655, price is now ￥376,196 per person
￥376,196
per person
Jun 5 - Jun 11
found 1 day ago
Roundtrip flight included
Osaka (OSA) to Chicago (ORD)
8.6/10 Excellent! (1,006 reviews)
Clean king size bed but the full double beds I had at first had an a/c problem
Reviewed on Apr 16, 2026
Club Quarters Hotel Wacker at Michigan, Chicago
Downtown Chicago
Price was ￥509,183, price is now ￥424,518 per person
￥424,518
per person
Jun 5 - Jun 11
found 1 day ago
Roundtrip flight included
Osaka (OSA) to Chicago (ORD)
8.8/10 Excellent! (2,141 reviews)
Perfectly located. The staff was amazing. Room was clean. Will stay again
Reviewed on Apr 16, 2026
Claridge House Chicago, Tapestry Collection by Hilton
Downtown Chicago
Price was ￥490,324, price is now ￥422,500 per person
￥422,500
per person
Jun 5 - Jun 11
found 1 day ago
Roundtrip flight included
Osaka (OSA) to Chicago (ORD)
9/10 Wonderful! (1,520 reviews)
This is our favorite hotel in Chicago. The only thing that was different on our last trip was the parking garage next door. It is under new ownership, and they made it very difficult to leave and come back, even though we bought a three-day pass with in-and-out privileges. The management at Claridge House is aware of the situation and is working on a solution.
Reviewed on Apr 12, 2026
Find the Best Hillside Vacation Packages
Hillside Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥18,280 per night from Apr 26 to Apr 27
￥18,280
￥21,461 total
Apr 26 - Apr 27
includes taxes & fees
8/10 Very Good! (10,126 reviews)
We did self park. Parking lot was right behind the hotel. The room and view were fine. Only issue was the tv, safe and refrigerator were all unplugged. We had to call maintenance. Also, the bathrooms appeared clean but there were several hairs in the shower. I hate seeing that.
Reviewed on Apr 16, 2026
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥21,812 per night from Apr 26 to Apr 27
￥21,812
￥25,607 total
Apr 26 - Apr 27
includes taxes & fees
9/10 Wonderful! (4,136 reviews)
Great location. Clean room. Friendly staff. Pool was kinda chilly. But that’s the only little criticism
Reviewed on Apr 16, 2026
Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥24,740 per night from Apr 26 to Apr 27
￥24,740
￥29,043 total
Apr 26 - Apr 27
includes taxes & fees
8.6/10 Excellent! (5,850 reviews)
They didn’t clean our room even when I requested to be cleaned and we had to go and request towels and paper, breakfast is not good at all.
Reviewed on Apr 16, 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 Hillside
Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Naval Base Great Lakes
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
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
What to do in Hillside
Skydeck - Willis Tower Admission
￥6,982
per adult
98% of travellers recommend
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
