Clearing Vacations from ￥251,786
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The Latest Clearing Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town
Downtown Chicago
Price was ￥319,960, price is now ￥251,786 per person
￥251,786
per person
Mar 26 - Mar 31
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
I stayed 5 nights total, 4 nights in a two BR, 1 bath with a balcony and the last night in a one BR. The 2BR was great. It faced East, received a lot of sunlight, was clean, modern and the bed was very comfortable. The gym had what I needed too. actually liked sleeping with the sound of the el nearby because I used to live in the area. I did not give it 5 stars because the walls are super thin. Someone had a party next to me and it was impossible to sleep hearing voices straight through the walls. Being a newer building, I don’t think the best quality appliances or fixtures were chosen. My ice machine wasn’t working and the heat/fan only worked in certain areas in the 2BR. Additional lighting should be added. The 1BR shower fixtures and drain needed some attention. That said, Mihajlo and the front desk staff were very helpful and attentive and helped me with whatever I needed. The 1BR seemed more like a studio to m. I’d prefer to book directly through Level, but it was a better price with Expedia. I still thought it was pricey but I was overall happy with my stay.
Reviewed on Jan 12, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥422,086, price is now ￥307,846 per person
￥307,846
per person
Mar 26 - Mar 31
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
The staff was super friendly and accommodating. The rooms were immaculately clean, and the spa was amazing
Reviewed on Jan 13, 2026
Waldorf Astoria Chicago
Downtown Chicago
Price was ￥446,626, price is now ￥344,356 per person
￥344,356
per person
Mar 27 - Mar 31
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
When we arrived at check in time, we were informed that our room was not ready but that we could upgrade at a discounted additional cost to a suite. At first, we didn't want to do that and decided to wait. The host provided complimentary round of drinks and meal for the wait. We decided to upgrade and I'm so glad that we did. The room was incredible and the service, from concierge, staff and valets, here is top notch. We ordered the Waldorf salad and Waldorf chocolate chip cookies because you have to if you stay here. Loved this place and will definitely return.
Reviewed on Jan 5, 2026
The Peninsula Chicago
Downtown Chicago
Price was ￥430,438, price is now ￥337,900 per person
￥337,900
per person
Mar 26 - Mar 31
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
The staff was great. Everybody was friendly. The room was beautifully appointed, although maybe a little too heavy on electronics. I don't think every light switch needs to be a touch pad. And there were one or two things we couldn't figure out, such as the lighted mirror on the credenza: don't know where the controls for that were hiding. These are minor issues and do not take away from the splendid funishings in the room.
Reviewed on Jan 11, 2026
Where to stay in Clearing
Find the best Clearing areas and neighborhoods for the activities you enjoy most. Learn more about Clearing
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.
Clearing Hotel Deals
Hilton Chicago
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥20,756 per night from Feb 1 to Feb 2
￥20,756
￥29,040 total
Feb 1 - Feb 2
includes taxes & fees
8.4/10 Very Good! (2,527 reviews)
THe staff was very efficient and professional and the breakfast was great.
Reviewed on Jan 13, 2026
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥14,229 per night from Jan 25 to Jan 26
￥14,229
￥16,705 total
Jan 25 - Jan 26
includes taxes & fees
8.8/10 Excellent! (3,706 reviews)
10/10
Reviewed on Jan 14, 2026
Club Quarters Hotel Wacker at Michigan, Chicago
75 E Wacker Dr Chicago IL
The price is ￥12,991 per night from Jan 27 to Jan 28
￥12,991
￥15,251 total
Jan 27 - Jan 28
includes taxes & fees
8.6/10 Excellent! (2,063 reviews)
Helpful staff! Great view of the river from our room.
Reviewed on Jan 13, 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.
Frequently asked questions
Discover the most popular places to visit in Clearing
Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Michigan Avenue
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
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
Things to do
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
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.