Northwest Side Mountain Holidays
Book a Mountain Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to £750 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 Northwest Side
Price found within the past 48 hours. Click for updated prices.
Wind Creek Southland Casino and Hotel
East Hazel Crest
Price was £1,153, price is now £918 per person
£918
per person
17 Sept - 23 Sept
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (437 reviews)
First time experience was best starting with free garage parking. From there get on the elevator and checking in. Check in with shift manager Shanika she was super sweet and nice. Explained everything and showed us how to access everything. Casino was nice. Ordered breakfast was good. Casino was big and nice only thing not a gambler so lost my money lol. But would recommend nice hotel was beautiful.
Reviewed on 24 Jun 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was £1,804, price is now £1,235 per person
£1,235
per person
1 Sept - 6 Sept
found 3 hours ago
Return direct flight included
London (LGW) to Chicago (ORD)
9.4/10 Exceptional! (2,557 reviews)
The hotel and location are beautiful but there needs to be much clearer signage as to where the entrance of the hotel is and the main lobby. Extremely confusing to travellers.
Reviewed on 23 Jun 2026
Hilton Chicago
Downtown Chicago
Price was £1,352, price is now £999 per person
£999
per person
1 Sept - 6 Sept
found 3 hours ago
Return direct flight included
London (LGW) to Chicago (ORD)
8.6/10 Excellent! (2,860 reviews)
Location is ideal for sight seeing and well maintained. Friendly staff
Reviewed on 26 Jun 2026
Level Chicago Fulton Market
Downtown Chicago
Price was £1,941, price is now £1,517 per person
£1,517
per person
15 Aug - 20 Aug
found 1 day ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.2/10 Wonderful! (504 reviews)
Upscale amazing stay in trendy neighborhood in Chcago. Walking distance to coffee shops, great restaurants. The amenities were beyond what I expected/ great lap pool, hot tubs, sauna steam room and amazing gym with enough equipment to do a full strength training workout. We will stay here again!
Reviewed on 25 Jun 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was £2,538, price is now £2,028 per person
£2,028
per person
15 Aug - 20 Aug
found 1 day ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.6/10 Exceptional! (1,893 reviews)
Fantastic hotel, super clean and excellent customer service, I would recommend it to anyone going to Chicago
Reviewed on 26 Jun 2026
Don't see what you're looking for?
See all available trips from London to Northwest Side
View all trips5* Mountain holidays in Northwest Side
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was £2,538, price is now £2,028 per person
£2,028
per person
15 Aug - 20 Aug
found 1 day ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.6/10 Exceptional! (1,893 reviews)
Fantastic hotel, super clean and excellent customer service, I would recommend it to anyone going to Chicago
Reviewed on 26 Jun 2026
The Peninsula Chicago
Downtown Chicago
Price was £1,504, price is now £1,295 per person
£1,295
per person
30 Aug - 2 Sept
found 24 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.8/10 Exceptional! (1,009 reviews)
We love the Peninsula! The staff, location, room, and the Shanghai restaurant top tier.
Reviewed on 21 Jun 2026
Don't see what you're looking for?
See all available trips from Dublin to Northwest Side
View all trips3 Night Mountain holidays in Northwest Side
Price found within the past 48 hours. Click for updated prices.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was £1,136, price is now £899 per person
£899
per person
2 Sept - 5 Sept
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (2,557 reviews)
The hotel and location are beautiful but there needs to be much clearer signage as to where the entrance of the hotel is and the main lobby. Extremely confusing to travellers.
Reviewed on 23 Jun 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was £1,425, price is now £1,155 per person
£1,155
per person
30 Aug - 2 Sept
found 24 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.6/10 Exceptional! (1,893 reviews)
Fantastic hotel, super clean and excellent customer service, I would recommend it to anyone going to Chicago
Reviewed on 26 Jun 2026
Don't see what you're looking for?
See all available trips from London to Northwest Side
View all tripsThings to do
Chicago: Navy Pier Centennial Wheel Ticket
£18
per adult
88% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
£30
per adult
94% of travellers recommend
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.
