Northwest Chicago 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 Chicago
Price found within the past 48 hours. Click for updated prices.
Kimpton Gray Hotel by IHG
Downtown Chicago
Price was £898, price is now £719 per person
£719
per person
20 Jan - 24 Jan
found 23 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,005 reviews)
Not worth it for the money. Good location but nothing special.
Reviewed on 8 Nov 2026
Pendry Chicago
Downtown Chicago
Price was £1,091, price is now £818 per person
£818
per person
20 Jan - 24 Jan
found 23 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,161 reviews)
The building and hotel are gorgeous, the staff were so kind and friendly, the carbon suite was clean and had an exceptional view, and the in room dining was delicious. Amazing experience, def will be back.
Reviewed on 8 Nov 2026
Don't see what you're looking for?
See all available trips from London to Northwest Chicago
View all trips5* Mountain holidays in Northwest Chicago
Price found within the past 48 hours. Click for updated prices.
Don't see what you're looking for?
See all available trips from London to Northwest Chicago
View all trips3 Night Mountain holidays in Northwest Chicago
Price found within the past 48 hours. Click for updated prices.
Le Méridien Essex Chicago
Downtown Chicago
Price was £984, price is now £854 per person
£854
per person
21 Jan - 24 Jan
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9/10 Wonderful! (1,005 reviews)
I really loved this hotel. The rooms were clean and spacious. The staff was nice and helpful James was especially great. The restaurant staff was very helpful. When I visit again I'll stay here. And it was close to everything.
Reviewed on 3 Nov 2026
Don't see what you're looking for?
See all available trips from London to Northwest Chicago
View all trips4 Night Mountain holidays in Northwest Chicago
Price found within the past 48 hours. Click for updated prices.
Pendry Chicago
Downtown Chicago
Price was £1,091, price is now £818 per person
£818
per person
20 Jan - 24 Jan
found 23 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,161 reviews)
The building and hotel are gorgeous, the staff were so kind and friendly, the carbon suite was clean and had an exceptional view, and the in room dining was delicious. Amazing experience, def will be back.
Reviewed on 8 Nov 2026
Don't see what you're looking for?
See all available trips from London to Northwest Chicago
View all tripsThings to do
Skydeck Chicago at Willis Tower
£32
per adult
84% 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.
