South Suburbs Beach Vacations 2026

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Top Beach vacation packages in South Suburbs

Price found within the past 48 hours. Click for updated prices.

Fairmont Chicago at Millennium Park

Downtown Chicago

￥263,672

per person

Jun 12 - Jun 14

found 21 hours ago

Roundtrip non-stop flight included

Tokyo (TYO) to Chicago (ORD)

8.8/10 Excellent! (2,131 reviews)

Great location, nice property, extremely slow breakfast at in house restaurant Toro. Didn’t appreciate paying an “urban experience fee” with associated taxes.

Reviewed on Apr 24, 2026

Level Chicago – Old Town

Downtown Chicago

￥314,786

per person

Jun 12 - Jun 14

found 21 hours ago

Roundtrip non-stop flight included

Tokyo (TYO) to Chicago (ORD)

9/10 Wonderful! (466 reviews)

Great spot for small families that may need a space for than just sleeping

Reviewed on Apr 27, 2026

Hotel Riu Plaza Chicago

Downtown Chicago

￥287,961

per person

Jun 12 - Jun 14

found 22 hours ago

Roundtrip non-stop flight included

Tokyo (TYO) to Chicago (ORD)

9.4/10 Exceptional! (3,914 reviews)

Very clean! Great location! Nice roof top terrasse!

Reviewed on Apr 28, 2026

Trump International Hotel & Tower Chicago

Downtown Chicago

￥317,442

per person

Jun 12 - Jun 14

found 21 hours ago

Roundtrip non-stop flight included

Tokyo (TYO) to Chicago (ORD)

9.4/10 Exceptional! (1,853 reviews)

Absolutely fantastic will be back

Reviewed on Apr 27, 2026

Level Chicago - River North

Downtown Chicago

￥324,062

per person

Jun 12 - Jun 14

found 22 hours ago

Roundtrip non-stop flight included

Tokyo (TYO) to Chicago (ORD)

9.2/10 Wonderful! (946 reviews)

Espectacular todo limpio seguro amables

Reviewed on Apr 27, 2026

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5* Beach vacations in South Suburbs

Price found within the past 48 hours. Click for updated prices.

Trump International Hotel & Tower Chicago

Downtown Chicago

￥317,442

per person

Jun 12 - Jun 14

found 21 hours ago

Roundtrip non-stop flight included

Tokyo (TYO) to Chicago (ORD)

9.4/10 Exceptional! (1,853 reviews)

Absolutely fantastic will be back

Reviewed on Apr 27, 2026

The Peninsula Chicago

Downtown Chicago

￥468,270

per person

Jun 7 - Jun 10

found 5 hours ago

Roundtrip non-stop flight included

Tokyo (TYO) to Chicago (ORD)

9.8/10 Exceptional! (1,015 reviews)

Best Hotel in Chicago

Reviewed on Apr 27, 2026

The Langham, Chicago

Downtown Chicago

￥465,876

per person

Jun 12 - Jun 14

found 21 hours ago

Roundtrip non-stop flight included

Tokyo (TYO) to Chicago (ORD)

9.8/10 Exceptional! (1,010 reviews)

Such a gorgeous and relaxing stay! Everyone we encountered was accommodating and helpful. Our visit to the spa was nothing short of delightful. It was one of the best massages I've had in a long time and we enjoyed the use of the facilities.

Reviewed on Apr 27, 2026

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3 Night Beach vacations in South Suburbs

Price found within the past 48 hours. Click for updated prices.

Swissotel - Chicago

Downtown Chicago

￥344,999

per person

Jun 7 - Jun 10

found 5 hours ago

Roundtrip non-stop flight included

Tokyo (TYO) to Chicago (ORD)

9/10 Wonderful! (3,280 reviews)

Corner room with breath taking view. It was my second time in this hotel, it never disappoints.

Reviewed on Apr 27, 2026

Trump International Hotel & Tower Chicago

Downtown Chicago

￥399,113

per person

Jun 7 - Jun 10

found 5 hours ago

Roundtrip non-stop flight included

Tokyo (TYO) to Chicago (ORD)

9.4/10 Exceptional! (1,853 reviews)

Absolutely fantastic will be back

Reviewed on Apr 27, 2026

Thompson Chicago, by Hyatt

Downtown Chicago

￥365,688

per person

Jun 7 - Jun 10

found 5 hours ago

Roundtrip non-stop flight included

Tokyo (TYO) to Chicago (ORD)

9.2/10 Wonderful! (1,347 reviews)

Conveniently located, cute bars and restaurants nearby and within walking distance of a tour bus stop. The room was clean, comfortable beds and the staff was pleasant.

Reviewed on Apr 22, 2026

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