Central Chicago All inclusive Holidays

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Top flight + All inclusive hotel deals in Central Chicago

Price found within the past 48 hours. Click for updated prices.
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

Downtown Chicago
NZ$1,018
per person
8 Dec - 13 Dec
found 1 day ago
Return flight included
Boston (BOS) to Chicago (ORD)
8.6/10 Excellent! (2,334 reviews)
St. Clair hotel lists the room as premium, even though the two windows in the room had no view. Both windows faced the building outter exterior brick walls from all sides. Dim lightning with no direct sunlight, very depressing to look out. The room should have been listened and offered as standard, at best, not premium.

Reviewed on 24 Oct 2026

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

Downtown Chicago
NZ$1,383
per person
8 Dec - 13 Dec
found 1 day ago
Return flight included
Boston (BOS) to Chicago (ORD)
8.6/10 Excellent! (1,873 reviews)
The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
Save 100% on your flight
NZ$1,395
per person
8 Dec - 13 Dec
found 1 day ago
Return flight included
Boston (BOS) to Chicago (ORD)
9.4/10 Exceptional! (185 reviews)
Nice property overall Room was very nice Location excellent

Reviewed on 19 Oct 2026

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

Downtown Chicago
NZ$1,488
per person
8 Dec - 13 Dec
found 1 day ago
Return flight included
Boston (BOS) to Chicago (ORD)
9.4/10 Exceptional! (3,881 reviews)
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

Downtown Chicago
NZ$1,146
per person
8 Dec - 13 Dec
found 1 day ago
Return flight included
Boston (BOS) to Chicago (ORD)
8.6/10 Excellent! (1,015 reviews)
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Activities

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

NZ$42
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

NZ$70
per adult
92% of travellers recommend
Art Institute of Chicago
Skydeck Chicago at Willis Tower

Skydeck Chicago at Willis Tower

NZ$74
per adult
88% of travellers recommend
Skydeck Chicago at Willis Tower
See all activities in Central Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.