West Side Adventure Holidays

Book a Adventure Hotel + Flight or Car together to unlock savings

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    Packages with flights are ATOL protected

Top flight + Adventure hotel deals in West Side

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

Hotel Saint Clair- Magnificent Mile

Downtown Chicago
£795
per person
1 Oct - 6 Oct
found 3 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
8.4/10 Very good! (2,079 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
Save 100% on your flight
£1,055
per person
1 Oct - 6 Oct
found 3 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

Downtown Chicago
Save 100% on your flight
£2,406
per person
9 Oct - 15 Oct
found 21 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
Eurostars Magnificent Mile

Eurostars Magnificent Mile

Downtown Chicago
Save 100% on your flight
£1,900
per person
7 Oct - 14 Oct
found 22 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9/10 Wonderful! (3,779 reviews)
Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
Save 100% on your flight
£992
per person
1 Oct - 6 Oct
found 3 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (544 reviews)
Great staff, great place!

Reviewed on 5 Aug 2026

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5* Adventure 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
Save 100% on your flight
£1,870
per person
7 Sept - 13 Sept
just found
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.6/10 Exceptional! (1,957 reviews)
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

Downtown Chicago
Save 100% on your flight
£2,406
per person
9 Oct - 15 Oct
found 21 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
Nobu Hotel Chicago

Nobu Hotel Chicago

Downtown Chicago
£2,523
per person
9 Oct - 15 Oct
found 21 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (891 reviews)
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3 Night Adventure holidays in West Side

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

Swissotel - Chicago

Downtown Chicago
£929
per person
10 Sept - 13 Sept
found 5 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9/10 Wonderful! (3,512 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
£1,034
per person
10 Sept - 13 Sept
found 5 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago
£1,391
per person
9 Oct - 12 Oct
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (2,631 reviews)
Great beautiful rooms. Nice beds

Reviewed on 7 Aug 2026

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4 Night Adventure holidays in West Side

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

Downtown Chicago
£1,114
per person
26 Sept - 30 Sept
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
8.2/10 Very good! (2,879 reviews)
Eurostars Magnificent Mile

Eurostars Magnificent Mile

Downtown Chicago
£1,168
per person
26 Sept - 30 Sept
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9/10 Wonderful! (3,779 reviews)
Hilton Garden Inn Chicago Downtown Riverwalk

Hilton Garden Inn Chicago Downtown Riverwalk

Downtown Chicago
£1,203
per person
26 Sept - 30 Sept
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9/10 Wonderful! (2,055 reviews)
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Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£20
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

£35
per adult
88% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

£18
per adult
90% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
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.