Northwest Side Adventure Holidays

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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
£993
per person
22 Oct - 28 Oct
found 1 day ago
Return direct flight included
Birmingham (BHX) to Chicago (ORD)
8.2/10 Very good! (3,012 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
Save 100% on your flight
£1,418
per person
22 Oct - 28 Oct
found 1 day ago
Return direct flight included
Birmingham (BHX) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
The hotel was truly remarkable! I can’t wait to go back in the future, the staff was truly amazing as well!

Reviewed on 22 Sept 2026

Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
£1,262
per person
22 Oct - 28 Oct
found 1 day ago
Return direct flight included
Birmingham (BHX) to Chicago (ORD)
9/10 Wonderful! (3,512 reviews)
Good location, close to everything

Reviewed on 21 Sept 2026

The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
£1,287
per person
22 Oct - 28 Oct
found 1 day ago
Return direct flight included
Birmingham (BHX) to Chicago (ORD)
9.4/10 Exceptional! (165 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
Save 100% on your flight
£1,857
per person
22 Oct - 28 Oct
found 1 day ago
Return direct flight included
Birmingham (BHX) to Chicago (ORD)
9.6/10 Exceptional! (1,995 reviews)
I like the service from valet to check out

Reviewed on 22 Sept 2026

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5* Adventure holidays in Northwest Side

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

Nobu Hotel Chicago

Downtown Chicago
£1,592
per person
28 Nov - 2 Dec
found 22 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (922 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
Save 100% on your flight
£1,857
per person
22 Oct - 28 Oct
found 1 day ago
Return direct flight included
Birmingham (BHX) to Chicago (ORD)
9.6/10 Exceptional! (1,995 reviews)
I like the service from valet to check out

Reviewed on 22 Sept 2026

The Peninsula Chicago

The Peninsula Chicago

Downtown Chicago
£2,418
per person
22 Oct - 28 Oct
found 1 day ago
Return direct flight included
Birmingham (BHX) to Chicago (ORD)
9.8/10 Exceptional! (1,001 reviews)
Don't see what you're looking for?
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3 Night Adventure holidays in Northwest Side

Price found within the past 48 hours. Click for updated prices.
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

O'Hare
£842
per person
31 Oct - 3 Nov
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
8.4/10 Very good! (2,463 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.
Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
£1,120
per person
22 Oct - 26 Oct
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9/10 Wonderful! (3,512 reviews)
Good location, close to everything

Reviewed on 21 Sept 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
£1,306
per person
22 Oct - 26 Oct
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
The hotel was truly remarkable! I can’t wait to go back in the future, the staff was truly amazing as well!

Reviewed on 22 Sept 2026

The Emily Hotel

The Emily Hotel

Downtown Chicago
£1,315
per person
22 Oct - 26 Oct
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,338 reviews)
It was ok

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

More holidays you might like

* 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.