Roseland Vacations from ￥266,174
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The Latest Roseland Vacation Packages
Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was ￥304,722, price is now ￥266,174 per person
￥266,174
per person
Jan 1 - Jan 6
found 13 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (1,011 reviews)
My room was very clean. The stay was very friendly and helpful. Check-in was a breeze. Since my room was ready they even let me check in early!
There are 2 restaurants in this hotel. We had drinks at the one near the lobby and we ate at the ROOF. The food was delish! The environment was fun. We were worried that it was going to be more for the 20 something crowd, but there were adults of every age there.
This hotel is also just steps from The Chicago Theatre which makes it super convenient when seeing an event there.
Reviewed on Nov 10, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥348,951, price is now ￥293,788 per person
￥293,788
per person
Jan 18 - Jan 21
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,761 reviews)
The staff was very kind and the hotel was amazing
Reviewed on Nov 10, 2025
Park Hyatt Chicago
Downtown Chicago
Price was ￥354,356, price is now ￥301,018 per person
￥301,018
per person
Jan 18 - Jan 21
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,006 reviews)
This is a beautiful hotel with lots of amenities that feel kind of luxurious. We especially loved the huge tub in our room. Also, the staff was amazing. One gripe we had is that we paid quite a bit more for a lake view room and we were on the eighth floor, which did not really afford much of a view. We called the front desk to see if we could get a higher floor and they said there was nothing available, but they did bring us a bottle of wine to compensate. I know someone has to be on the lower floors, but it seems that if you are going to pay more for a view they should make sure you are on a higher floor. Other than that, we would definitely stay here again and would recommend!
Reviewed on Oct 20, 2025
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Price was ￥345,035, price is now ￥293,264 per person
￥293,264
per person
Jan 1 - Jan 6
found 13 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (303 reviews)
I love the decor and it was very clean. My only problem is they did not clean the room every day other than that is was very clean facility. Very safe location.
Reviewed on Oct 28, 2025
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥320,001, price is now ￥275,657 per person
￥275,657
per person
Jan 1 - Jan 6
found 13 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,602 reviews)
We had a great stay at the Riu Hotel in Chicago! The staff were very friendly and helpful. Tje cleanliness of the room stood out to me the most! Lastly, the breakfast buffet was great with a variety of food. I will be definitely coming back to Riu!
Reviewed on Nov 10, 2025
Where to stay in Roseland
Find the best Roseland areas and neighborhoods for the activities you enjoy most. Learn more about Roseland
Downtown Chicago
5 out of top 10 points of interest in this area
The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.
Roseland Hotel Deals
Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ￥16,569 per night from Dec 8 to Dec 9
￥16,569
￥19,450 total
Dec 8 - Dec 9
includes taxes & fees
8.4/10 Very Good! (5,208 reviews)
Friendly staff, well appointed room, needed more pillows and received very quickly.
Reviewed on Nov 8, 2025
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ￥15,518 per night from Dec 7 to Dec 8
￥15,518
￥18,217 total
Dec 7 - Dec 8
includes taxes & fees
8.8/10 Excellent! (3,253 reviews)
Room was clean and spacious, a little dated but comfortable. Staff friendly and helpful.
Reviewed on Nov 9, 2025
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ￥15,679 per night from Nov 13 to Nov 14
￥15,679
￥18,405 total
Nov 13 - Nov 14
includes taxes & fees
8/10 Very Good! (9,528 reviews)
It took 10 min to get hot shower. Other than that, the hotel was excellent.
Reviewed on Nov 8, 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.
Frequently asked questions
Discover the most popular places to visit in Roseland
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.
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.
Navy Pier
4.5/5(4,870 reviews)
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
Things to do
Skydeck - Willis Tower Admission
￥6,717
per adult
96% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
￥3,749
per adult
84% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.