Chicago Beach Vacations
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Top Beach vacation packages in Chicago
Price found within the past 48 hours. Click for updated prices.
Millennium Hotel Knickerbocker Chicago
Downtown Chicago
Price was ￥345,930, price is now ￥316,623 per person
￥316,623
per person
Jun 11 - Jun 15
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.6/10 Excellent! (1,965 reviews)
Clean room, very nice staff, small gym but got the job done
Reviewed on Apr 25, 2026
Four Seasons Hotel Chicago
Downtown Chicago
Price was ￥432,440, price is now ￥388,808 per person
￥388,808
per person
Jul 9 - Jul 13
found 23 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,003 reviews)
Beautiful and in walking distance to so many shops and cafes! We had a great stay.
Reviewed on Apr 6, 2026
The Chicago Hotel Collection Ambassador Gold Coast
Downtown Chicago
Price was ￥380,887, price is now ￥356,792 per person
￥356,792
per person
Jun 11 - Jun 15
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (1,370 reviews)
Bathrooms need some updating.
Reviewed on Apr 24, 2026
5* Beach vacations in Chicago
Price found within the past 48 hours. Click for updated prices.
Four Seasons Hotel Chicago
Downtown Chicago
Price was ￥432,440, price is now ￥388,808 per person
￥388,808
per person
Jul 9 - Jul 13
found 23 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,003 reviews)
Beautiful and in walking distance to so many shops and cafes! We had a great stay.
Reviewed on Apr 6, 2026
3 Night Beach vacations in Chicago
Price found within the past 48 hours. Click for updated prices.
Millennium Hotel Knickerbocker Chicago
Downtown Chicago
Price was ￥329,302, price is now ￥304,908 per person
￥304,908
per person
Jun 12 - Jun 15
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.6/10 Excellent! (1,965 reviews)
Clean room, very nice staff, small gym but got the job done
Reviewed on Apr 25, 2026
Eurostars Magnificent Mile
Downtown Chicago
Price was ￥348,086, price is now ￥313,486 per person
￥313,486
per person
Jun 12 - Jun 15
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (3,441 reviews)
It is an incredible place to spend a vacation it is very clean, and the staff were always very attentive to the guests' needs.
Reviewed on Apr 26, 2026
The Chicago Hotel Collection Ambassador Gold Coast
Downtown Chicago
Price was ￥353,569, price is now ￥334,537 per person
￥334,537
per person
Jun 12 - Jun 15
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (1,370 reviews)
Bathrooms need some updating.
Reviewed on Apr 24, 2026
4 Night Beach vacations in Chicago
Price found within the past 48 hours. Click for updated prices.
Holiday Inn & Suites Chicago - Downtown by IHG
Downtown Chicago
Price was ￥362,240, price is now ￥331,506 per person
￥331,506
per person
Jun 11 - Jun 15
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.6/10 Excellent! (1,009 reviews)
missing the microwave. But other then that it was a good place for my family to stay there.
Reviewed on Apr 25, 2026
Eurostars Magnificent Mile
Downtown Chicago
Price was ￥376,216, price is now ￥331,860 per person
￥331,860
per person
Jun 11 - Jun 15
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (3,441 reviews)
It is an incredible place to spend a vacation it is very clean, and the staff were always very attentive to the guests' needs.
Reviewed on Apr 26, 2026
Four Seasons Hotel Chicago
Downtown Chicago
Price was ￥432,440, price is now ￥388,808 per person
￥388,808
per person
Jul 9 - Jul 13
found 23 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,003 reviews)
Beautiful and in walking distance to so many shops and cafes! We had a great stay.
Reviewed on Apr 6, 2026
Top Beach Chicago Hotels
Millennium Hotel Knickerbocker Chicago
163 East Walton Place Chicago IL
Recharge at this hotel and get ready to stroll along the shore in Chicago, as you'll be near Oak Street Beach. Amenities at Millennium Hotel Knickerbocker Chicago ...
8.6/10 Excellent! (1,960 reviews)
Clean room, very nice staff, small gym but got the job done
Reviewed on Apr 25, 2026
The Whitehall Hotel, BW Premier Collection
105 E Delaware Pl Chicago IL
Enjoy sunsets on the beach in Chicago, as you'll be a short walk from Oak Street Beach with a vacation at this boutique hotel. A restaurant and a bar are just ...
8.4/10 Very Good! (3,981 reviews)
Just what we needed!
Reviewed on Apr 25, 2026
Chicago Lake Shore Hotel
4900 S Lake Shore Dr Chicago IL
Settle in and relax at this hotel and get ready to lounge by the shoreline in Chicago, as you'll be close to the beach.
6.8/10 (1,001 reviews)
The outside area was okay. The inside was clean, bed was comfortable. There was a microwave (didn’t use) and refrigerator. Large screen tv was nice. Water pressure was just okay. Had some issues checking in because I used my initials (which is what I go by) on my reservation and my ID has my name ...
Reviewed on Apr 21, 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
