Northwest Side Adventure Holidays

Book a Adventure 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

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    Packages with flights are ATOL protected

Top flight + Adventure hotel deals in Northwest 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
£635
per person
23 Nov - 28 Nov
found 3 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
8.2/10 Very good! (3,012 reviews)
Level Chicago - River North

Level Chicago - River North

Downtown Chicago
£1,261
per person
27 Oct - 2 Nov
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (1,077 reviews)
The Emily Hotel

The Emily Hotel

Downtown Chicago
£732
per person
23 Nov - 28 Nov
found 3 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,338 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
£1,095
per person
12 Nov - 15 Nov
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (1,995 reviews)
Can’t wait to come back.

Reviewed on 21 Sept 2026

Viceroy Chicago

Viceroy Chicago

Downtown Chicago
£1,344
per person
27 Oct - 2 Nov
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,282 reviews)
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5* Adventure holidays in Northwest Side

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

Trump International Hotel & Tower Chicago

Downtown Chicago
£1,095
per person
12 Nov - 15 Nov
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (1,995 reviews)
Can’t wait to come back.

Reviewed on 21 Sept 2026

The Peninsula Chicago

The Peninsula Chicago

Downtown Chicago
£1,465
per person
14 Nov - 18 Nov
found 7 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.8/10 Exceptional! (1,001 reviews)
Absolutely amazing. Warm welcomes, great atmosphere, beautiful city

Reviewed on 20 Sept 2026

The Ritz-Carlton, Chicago

The Ritz-Carlton, Chicago

Downtown Chicago
£1,895
per person
27 Oct - 2 Nov
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (1,001 reviews)
Staff was excellent.

Reviewed on 17 Sept 2026

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3 Night Adventure holidays in Northwest Side

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

Hotel Riu Plaza Chicago

Downtown Chicago
£941
per person
12 Nov - 15 Nov
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
Only the wall outlet near the beds didn't work ...just that...everything was great !! Excelent hotel

Reviewed on 21 Sept 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
£1,095
per person
12 Nov - 15 Nov
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (1,995 reviews)
Can’t wait to come back.

Reviewed on 21 Sept 2026

Pendry Chicago

Pendry Chicago

Downtown Chicago
£993
per person
12 Nov - 15 Nov
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (1,146 reviews)
Don't see what you're looking for?
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4 Night Adventure holidays in Northwest Side

Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
£1,161
per person
22 Oct - 26 Oct
found 13 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (561 reviews)
Amazing place to stay in Chicago!

Reviewed on 18 Sept 2026

The Emily Hotel

The Emily Hotel

Downtown Chicago
£1,315
per person
22 Oct - 26 Oct
found 13 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,338 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
£1,564
per person
22 Oct - 26 Oct
found 13 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.6/10 Exceptional! (1,995 reviews)
Can’t wait to come back.

Reviewed on 21 Sept 2026

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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
Flyover in Chicago

Flyover in Chicago

£23
per adult
98% of travellers recommend
Flyover in Chicago
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 Northwest 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.