Far Southeast Side All inclusive Holidays

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Top flight + All inclusive hotel deals in Far Southeast Side

Price found within the past 48 hours. Click for updated prices.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
NZ$1,333
per person
24 Nov - 29 Nov
found 1 day ago
Return flight included
Pittsburgh (PIT) to Chicago (ORD)
9.4/10 Exceptional! (165 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
Save 100% on your flight
NZ$1,540
per person
24 Nov - 29 Nov
found 1 day ago
Return flight included
Pittsburgh (PIT) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
Great location. Clean rooms and common areas.

Reviewed on 17 Sept 2026

The Emily Hotel

The Emily Hotel

Downtown Chicago
NZ$1,365
per person
24 Nov - 29 Nov
found 1 day ago
Return flight included
Pittsburgh (PIT) to Chicago (ORD)
9.2/10 Wonderful! (1,338 reviews)
The staff was super helpful and the room was clean and beautiful!

Reviewed on 16 Sept 2026

Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

Downtown Chicago
NZ$1,408
per person
24 Nov - 29 Nov
found 1 day ago
Return flight included
Pittsburgh (PIT) to Chicago (ORD)
9.4/10 Exceptional! (1,010 reviews)
Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

Downtown Chicago
NZ$1,472
per person
24 Nov - 29 Nov
found 1 day ago
Return flight included
Pittsburgh (PIT) to Chicago (ORD)
9.2/10 Wonderful! (2,381 reviews)
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Activities

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

NZ$45
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

NZ$67
per adult
92% of travellers recommend
Art Institute of Chicago
Flyover in Chicago

Flyover in Chicago

NZ$47
per adult
98% of travellers recommend
Flyover in Chicago
See all activities in Far Southeast Side
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.