East Side Vacations from ￥295,012
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The Latest East Side Vacation Packages
Price found within the past 48 hours. Click for updated prices.
The Buckingham Hotel
Downtown Chicago
Price was ￥337,531, price is now ￥295,012 per person
￥295,012
per person
Sep 18 - Sep 22
found 8 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (1,003 reviews)
The view from our suite was excellent, especially during a thunderstorm. We loved our stay. The only (very minor) downside was neither TV worked correctly. One had very low volume, the other had no picture but good volume. The location was very good, very easy walk to public transportation. The room was clean, the bed was comfortable, and the A/C worked really well. The building security was Would definitely stay here again.
Reviewed on Jul 11, 2026
Sports Illustrated Resorts Chicago
Downtown Chicago
Price was ￥370,063, price is now ￥321,758 per person
￥321,758
per person
Sep 18 - Sep 22
found 8 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (1,429 reviews)
The staff was super friendly and helpful
Reviewed on Jul 10, 2026
Where to stay in East Side
Find the best East Side areas and neighborhoods for the activities you enjoy most. Learn more about East Side
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.
East Side Hotel Deals
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥24,883 per night from Jul 27 to Jul 28
￥24,883
￥29,585 total
Jul 27 - Jul 28
includes taxes & fees
8.2/10 Very Good! (1,734 reviews)
"Surprise fees upfront when you book with third party sites like, Expedia. Expect to cough up a few hundred dollars before you even get to the elevator. Other than that it’s a gorgeous hotel with incredible surrounding areas. Not too far from the beach as well. The breakfast buffet was also ..."
Reviewed on Jul 11, 2026
Omni Chicago Hotel
676 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥36,056 per night from Jul 26 to Jul 27
￥36,056
￥48,249 total
Jul 26 - Jul 27
includes taxes & fees
9.2/10 Wonderful! (1,908 reviews)
"Great location and a friendly staff made this a great experience. The rooms are very nice, but a little dated, which made it feel a little less clean. The staff was amazing, especially the doorman/bellman, Ham. He went out of his way help everytime we arrived or departed, he asked how our day was ..."
Reviewed on Jul 11, 2026
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥30,558 per night from Aug 10 to Aug 11
￥30,558
￥36,332 total
Aug 10 - Aug 11
includes taxes & fees
8/10 Very Good! (10,229 reviews)
"Older hotel, but nice"
Reviewed on Jul 11, 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
Stay near popular East Side attractions
Things to do
Chicago: Navy Pier Centennial Wheel Ticket
￥3,992
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.