South Suburbs Beach Vacations
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Top Beach vacation packages in South Suburbs
Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was ￥419,975, price is now ￥344,016 per person
￥344,016
per person
Mar 22 - Mar 28
found 5 hours ago
Roundtrip flight included
Tokushima (TKS) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
Perfect location, comfortable and clean room
Reviewed on Jan 5, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥565,091, price is now ￥431,406 per person
￥431,406
per person
Mar 22 - Mar 28
found 5 hours ago
Roundtrip flight included
Tokushima (TKS) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Stayed in a river view room over NYE and had a great view of the fireworks show on the river! The staff was superb and went above and beyond for us. Extremely kind and knowledgeable. Cannot wait to stay again!
Reviewed on Jan 3, 2026
The Peninsula Chicago
Downtown Chicago
Price was ￥581,636, price is now ￥458,678 per person
￥458,678
per person
Mar 22 - Mar 28
found 5 hours ago
Roundtrip flight included
Tokushima (TKS) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Upon check-in, it was magical! The doormen were amazing, the 'go as often as you'd like' Santa's candy shop, overall hotel decorations and the professionalism of the staff will blow you away!!! This hotel is next level up and puts the Ritz Carlton down a notch, for sure. Our room was truly magnificent and I wish we could have stayed longer!
Reviewed on Jan 6, 2026
Level Chicago – Old Town
Downtown Chicago
Price was ￥450,266, price is now ￥368,169 per person
￥368,169
per person
Mar 22 - Mar 28
found 5 hours ago
Roundtrip flight included
Tokushima (TKS) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Staff was friendly did amazing job with checking us in
Reviewed on Dec 25, 2025
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥411,452, price is now ￥345,150 per person
￥345,150
per person
Mar 22 - Mar 28
found 5 hours ago
Roundtrip flight included
Tokushima (TKS) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Everything is ok but no parking lot and too much fee
Reviewed on Jan 6, 2026
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View all trips5* Beach vacations in South Suburbs
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥565,091, price is now ￥431,406 per person
￥431,406
per person
Mar 22 - Mar 28
found 5 hours ago
Roundtrip flight included
Tokushima (TKS) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Stayed in a river view room over NYE and had a great view of the fireworks show on the river! The staff was superb and went above and beyond for us. Extremely kind and knowledgeable. Cannot wait to stay again!
Reviewed on Jan 3, 2026
The Peninsula Chicago
Downtown Chicago
Price was ￥581,636, price is now ￥458,678 per person
￥458,678
per person
Mar 22 - Mar 28
found 5 hours ago
Roundtrip flight included
Tokushima (TKS) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Upon check-in, it was magical! The doormen were amazing, the 'go as often as you'd like' Santa's candy shop, overall hotel decorations and the professionalism of the staff will blow you away!!! This hotel is next level up and puts the Ritz Carlton down a notch, for sure. Our room was truly magnificent and I wish we could have stayed longer!
Reviewed on Jan 6, 2026
3 Night Beach vacations in South Suburbs
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥228,040, price is now ￥199,076 per person
￥199,076
per person
Mar 17 - Mar 20
found 9 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Everything is ok but no parking lot and too much fee
Reviewed on Jan 6, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥303,137, price is now ￥250,502 per person
￥250,502
per person
Mar 17 - Mar 20
found 9 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Stayed in a river view room over NYE and had a great view of the fireworks show on the river! The staff was superb and went above and beyond for us. Extremely kind and knowledgeable. Cannot wait to stay again!
Reviewed on Jan 3, 2026
Level Chicago – Old Town
Downtown Chicago
Price was ￥245,634, price is now ￥218,524 per person
￥218,524
per person
Mar 17 - Mar 20
found 9 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Staff was friendly did amazing job with checking us in
Reviewed on Dec 25, 2025
4 Night Beach vacations in South Suburbs
Price found within the past 48 hours. Click for updated prices.
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Price was ￥310,730, price is now ￥249,464 per person
￥249,464
per person
Mar 16 - Mar 20
found 2 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (317 reviews)
Room was very spacious and clean. The location was perfect walking distance from a lot great eating and tourists spots.
Reviewed on Dec 18, 2025
The Peninsula Chicago
Downtown Chicago
Price was ￥395,658, price is now ￥312,870 per person
￥312,870
per person
Mar 26 - Mar 30
found 2 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Upon check-in, it was magical! The doormen were amazing, the 'go as often as you'd like' Santa's candy shop, overall hotel decorations and the professionalism of the staff will blow you away!!! This hotel is next level up and puts the Ritz Carlton down a notch, for sure. Our room was truly magnificent and I wish we could have stayed longer!
Reviewed on Jan 6, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥428,324, price is now ￥339,200 per person
￥339,200
per person
Mar 28 - Apr 1
found 1 hour ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Stayed in a river view room over NYE and had a great view of the fireworks show on the river! The staff was superb and went above and beyond for us. Extremely kind and knowledgeable. Cannot wait to stay again!
Reviewed on Jan 3, 2026
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
