West Side Mountain Holidays
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Packages with flights are ATOL protected
Top flight + Mountain hotel deals in West Side
Price found within the past 48 hours. Click for updated prices.
Park Hyatt Chicago
Downtown Chicago
Save 100% on your flight
Price was £1,483, price is now £999 per person
£999
per person
10 Nov - 14 Nov
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!
Reviewed on 10 Aug 2025
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was £2,303, price is now £1,465 per person
£1,465
per person
8 Oct - 15 Oct
found 24 hours ago
Return direct flight included
London (LGW) to Chicago (ORD)
9.4/10 Exceptional! (2,087 reviews)
it is great for the pier
Reviewed on 26 Aug 2025
The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Price was £2,172, price is now £1,399 per person
£1,399
per person
8 Oct - 15 Oct
found 24 hours ago
Return direct flight included
London (LGW) to Chicago (ORD)
9/10 Wonderful! (1,962 reviews)
The restrooms do not have built in ventilation and the hotel needs to be updated overall.
Reviewed on 25 Aug 2025
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was £2,020, price is now £1,307 per person
£1,307
per person
8 Oct - 15 Oct
found 24 hours ago
Return direct flight included
London (LGW) to Chicago (ORD)
8.2/10 Very Good! (2,061 reviews)
Great property. Clean and convenient. Only unsightly thing is that there was a dirty t shirt laying in the hallway that nobody seemed to pick up.
Reviewed on 26 Aug 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was £1,554, price is now £1,014 per person
£1,014
per person
27 Oct - 31 Oct
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
It is a beautiful, well maintained property. The staff is the true gem of the property. They elevate the visitors experience to a new level of excellence.
Reviewed on 25 Aug 2025
5* Mountain holidays in West Side
Price found within the past 48 hours. Click for updated prices.
Park Hyatt Chicago
Downtown Chicago
Save 100% on your flight
Price was £1,483, price is now £999 per person
£999
per person
10 Nov - 14 Nov
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!
Reviewed on 10 Aug 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was £1,554, price is now £1,014 per person
£1,014
per person
27 Oct - 31 Oct
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
It is a beautiful, well maintained property. The staff is the true gem of the property. They elevate the visitors experience to a new level of excellence.
Reviewed on 25 Aug 2025
3 Night Mountain holidays in West Side
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was £1,296, price is now £995 per person
£995
per person
8 Nov - 11 Nov
found 1 day ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
It is a beautiful, well maintained property. The staff is the true gem of the property. They elevate the visitors experience to a new level of excellence.
Reviewed on 25 Aug 2025
The Royal Sonesta Chicago River North
Downtown Chicago
Price was £1,874, price is now £1,431 per person
£1,431
per person
10 Oct - 13 Oct
found 17 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (2,028 reviews)
Great location and room was fantastic! Only negatives were a lengthy check in and access to the outside deck was closed at 10 PM. Probably a good idea for that, but it would’ve been nice to go out there for a nightcap.
Reviewed on 26 Aug 2025
Fairmont Chicago at Millennium Park Gold Experience
Downtown Chicago
Price was £1,814, price is now £1,420 per person
£1,420
per person
10 Oct - 13 Oct
found 17 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (131 reviews)
You can walk to restaurants and Michigan ave and the area is nice and safe
Reviewed on 16 Jul 2025
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View all trips4 Night Mountain holidays in West Side
Price found within the past 48 hours. Click for updated prices.
The Emily Hotel
Downtown Chicago
Price was £1,224, price is now £829 per person
£829
per person
27 Oct - 31 Oct
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,182 reviews)
The staff here are absolutely the most helpful and sweetest. The hotel is perfect for a boutique hotel. The night life seemed to quite popular as well and right around Fulton market! I definitely recommend.
Also the coffee bags ? PERFECTION. Just had to add that
Reviewed on 22 Aug 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was £1,554, price is now £1,014 per person
£1,014
per person
27 Oct - 31 Oct
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
It is a beautiful, well maintained property. The staff is the true gem of the property. They elevate the visitors experience to a new level of excellence.
Reviewed on 25 Aug 2025
Park Hyatt Chicago
Downtown Chicago
Save 100% on your flight
Price was £1,631, price is now £1,087 per person
£1,087
per person
29 Sept - 3 Oct
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!
Reviewed on 10 Aug 2025
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* 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.