South Side All inclusive Vacations

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    Save up to ₩1,660,000 when you book a flight and hotel together*
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Top All inclusive vacation packages in South Side

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

Swissotel - Chicago

Downtown Chicago
₩593,308
per person
Nov 24 - Nov 27
found 13 hours ago
Roundtrip non-stop flight included
Des Moines (DSM) to Chicago (ORD)
9/10 Wonderful! (3,523 reviews)
Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

Downtown Chicago
₩704,555
per person
Nov 24 - Nov 27
found 13 hours ago
Roundtrip non-stop flight included
Des Moines (DSM) to Chicago (ORD)
8.6/10 Excellent! (1,841 reviews)
We unfortunately came to stay when the staff decided to strike. No room service , no cleaning service for a 4 night stay. Barely got towels on the last day. Disappointing. The only upside was the location.

Reviewed on Oct 22, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
₩1,190,004
per person
Nov 24 - Nov 27
found 13 hours ago
Roundtrip non-stop flight included
Des Moines (DSM) to Chicago (ORD)
9.6/10 Exceptional! (2,057 reviews)
A+++ Worth every penny amazing place

Reviewed on Oct 23, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
₩611,938
per person
Nov 24 - Nov 27
found 13 hours ago
Roundtrip non-stop flight included
Des Moines (DSM) to Chicago (ORD)
9.4/10 Exceptional! (5,404 reviews)
Pendry Chicago

Pendry Chicago

Downtown Chicago
₩771,580
per person
Nov 24 - Nov 27
found 13 hours ago
Roundtrip non-stop flight included
Des Moines (DSM) to Chicago (ORD)
9.2/10 Wonderful! (1,163 reviews)
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5* All inclusive vacations in South Side

Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
₩1,190,004
per person
Nov 24 - Nov 27
found 13 hours ago
Roundtrip non-stop flight included
Des Moines (DSM) to Chicago (ORD)
9.6/10 Exceptional! (2,057 reviews)
A+++ Worth every penny amazing place

Reviewed on Oct 23, 2026

Don't see what you're looking for?
See all available trips from Des Moines to South Side
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3 Night All inclusive vacations in South Side

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
₩611,938
per person
Nov 24 - Nov 27
found 13 hours ago
Roundtrip non-stop flight included
Des Moines (DSM) to Chicago (ORD)
9.4/10 Exceptional! (5,404 reviews)
Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

Downtown Chicago
₩704,555
per person
Nov 24 - Nov 27
found 13 hours ago
Roundtrip non-stop flight included
Des Moines (DSM) to Chicago (ORD)
8.6/10 Excellent! (1,841 reviews)
We unfortunately came to stay when the staff decided to strike. No room service , no cleaning service for a 4 night stay. Barely got towels on the last day. Disappointing. The only upside was the location.

Reviewed on Oct 22, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
₩1,190,004
per person
Nov 24 - Nov 27
found 13 hours ago
Roundtrip non-stop flight included
Des Moines (DSM) to Chicago (ORD)
9.6/10 Exceptional! (2,057 reviews)
A+++ Worth every penny amazing place

Reviewed on Oct 23, 2026

Don't see what you're looking for?
See all available trips from Des Moines to South Side
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.