West Side Adults Only Holidays

Book a Adults Only Hotel + Flight or Car together to unlock savings

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    Save up to £750 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Packages with flights are ATOL protected

Top flight + Adults Only hotel deals in West Side

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

Swissotel - Chicago

Downtown Chicago
£782
per person
26 Dec - 31 Dec
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9/10 Wonderful! (3,518 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
£1,305
per person
26 Dec - 31 Dec
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
£818
per person
26 Dec - 31 Dec
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (5,340 reviews)
The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
£834
per person
26 Dec - 31 Dec
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (179 reviews)
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

Downtown Chicago
£863
per person
26 Dec - 31 Dec
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (3,877 reviews)
I loved this hotel from top to Bottom

Reviewed on 3 Oct 2026

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5* Adults Only holidays in West Side

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

Trump International Hotel & Tower Chicago

Downtown Chicago
£1,305
per person
26 Dec - 31 Dec
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
Don't see what you're looking for?
See all available trips from London to West Side
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4 Night Adults Only holidays in West Side

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

Hotel Riu Plaza Chicago

Downtown Chicago
£840
per person
16 Dec - 20 Dec
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (5,340 reviews)
The Emily Hotel

The Emily Hotel

Downtown Chicago
£906
per person
16 Dec - 20 Dec
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,346 reviews)
Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

Downtown Chicago
£937
per person
16 Dec - 20 Dec
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
Don't see what you're looking for?
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Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£18
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Flyover in Chicago

Flyover in Chicago

£28
per adult
98% of travellers recommend
Flyover in Chicago
Skydeck Chicago at Willis Tower

Skydeck Chicago at Willis Tower

£32
per adult
88% of travellers recommend
Skydeck Chicago at Willis Tower
See all activities in West Side

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Where to go when
Where to go when

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.