West Side Mountain Holidays
Book a Mountain Hotel + Flight or Car together to unlock savings
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- Plan, book, travel with confidence
- Better togetherSave up to £335 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPackages with flights are ATOL protected
Top flight + Mountain hotel deals in West Side
Price found within the past 48 hours. Click for updated prices.
Arlo Chicago
Downtown Chicago
Save 100% on your flight
Price was £1,400, price is now £959 per person
£959
per person
30 Apr - 6 May
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,862 reviews)
Beautiful hotel, very nice staff and amazing location. Will stay again!
Reviewed on 9 Feb 2026
Pendry Chicago
Downtown Chicago
Save 100% on your flight
Price was £1,834, price is now £1,141 per person
£1,141
per person
30 Apr - 6 May
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
Muriel at the front desk was extremely helpful and courteous, wonderful historic art deco building right on Michigan Ave., great location and views, really nice, spacious and clean room. Chateau Carbide on the 24th floor is definitely worth checking out, nice cozy areas to hang out, sit on a couch and have a drink while enjoying great views of the city. We also got a free ride from the hotel to the Shedd Aquarium.
Reviewed on 31 Jan 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was £1,492, price is now £1,063 per person
£1,063
per person
12 Mar - 16 Mar
found 10 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Lovely room. Excellent staff.
Reviewed on 3 Feb 2026
Staypineapple, An Iconic Hotel, The Loop
Downtown Chicago
Price was £1,328, price is now £966 per person
£966
per person
30 Apr - 6 May
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,003 reviews)
Staff was excellent and the building is literally iconic. Our only negative is that the bathrooms were a bit tired. Ours had a yellowed, loose fitting toilet seat and a light out on the mirror.
Reviewed on 2 Feb 2026
5* 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 £1,492, price is now £1,063 per person
£1,063
per person
12 Mar - 16 Mar
found 10 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Lovely room. Excellent staff.
Reviewed on 3 Feb 2026
Waldorf Astoria Chicago
Downtown Chicago
Price was £1,688, price is now £1,267 per person
£1,267
per person
4 May - 8 May
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Completely loved our stay. Probably the best hotel in all Chicago. Amenities are great and the staff are even better.
Reviewed on 26 Jan 2026
3 Night Mountain holidays in West Side
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was £1,002, price is now £817 per person
£817
per person
20 Mar - 23 Mar
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Room was clean, staff was so polite and kind and very helpful. We took our 3 year old daughter with us and they were kind to her and welcoming! (That means a lot - not all hotels are welcoming to small children.) they made sure to open the doors for us each time we came in with our stroller. We will absolutely be back to the Riu in Chicago! 10/10
Reviewed on 9 Feb 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was £1,293, price is now £1,026 per person
£1,026
per person
23 Mar - 26 Mar
found 18 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Lovely room. Excellent staff.
Reviewed on 3 Feb 2026
Pendry Chicago
Downtown Chicago
Price was £1,037, price is now £892 per person
£892
per person
20 Mar - 23 Mar
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
Muriel at the front desk was extremely helpful and courteous, wonderful historic art deco building right on Michigan Ave., great location and views, really nice, spacious and clean room. Chateau Carbide on the 24th floor is definitely worth checking out, nice cozy areas to hang out, sit on a couch and have a drink while enjoying great views of the city. We also got a free ride from the hotel to the Shedd Aquarium.
Reviewed on 31 Jan 2026
4 Night Mountain holidays in West Side
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was £1,144, price is now £803 per person
£803
per person
12 Mar - 16 Mar
found 10 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Room was clean, staff was so polite and kind and very helpful. We took our 3 year old daughter with us and they were kind to her and welcoming! (That means a lot - not all hotels are welcoming to small children.) they made sure to open the doors for us each time we came in with our stroller. We will absolutely be back to the Riu in Chicago! 10/10
Reviewed on 9 Feb 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was £1,492, price is now £1,063 per person
£1,063
per person
12 Mar - 16 Mar
found 10 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Lovely room. Excellent staff.
Reviewed on 3 Feb 2026
Waldorf Astoria Chicago
Downtown Chicago
Price was £1,688, price is now £1,267 per person
£1,267
per person
4 May - 8 May
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Completely loved our stay. Probably the best hotel in all Chicago. Amenities are great and the staff are even better.
Reviewed on 26 Jan 2026
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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.
