
Northwest Chicago Mountain Holidays
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Top flight + Mountain hotel deals in Northwest Chicago
Price found within the past 48 hours. Click for updated prices.


Kasa Magnificent Mile Chicago
Downtown Chicago
£1,394
per person
8 Nov - 12 Nov
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (884 reviews)
Super accommodation. Big. Roomy. Clean. Close to restaurants n shops.
Despite communication being mostly via text.. the managers were VERY responsive.
I would return in a jiffy to stay here..
Thank you. Thank you
Reviewed on 24 Sept 2026

The Drake
Downtown Chicago
£1,450
per person
8 Nov - 12 Nov
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9/10 Wonderful! (1,583 reviews)
The location was THE BEST!! The view was TO DIE FOR (lake view room). AIhigher floor stay might help avoid the noise of the heavy traffic The restaurant and bar was a little different (not what I had in mind for a restaurant -it is more like a bar with tables to order food and eat. The fish and chips were great. The reuben was very good and the martini was spot on. So - it worked out. Breakfast was very good. The Magnificent Mile walk was refreshing and SO MUCH TO SHOPPING available. The weather was perfect 55-70 degrees everyday of our trip. It was hard to return to Texas after such a lovely weather experience in the windy city.
Reviewed on 25 Sept 2026

Hilton Vacation Club Hotel Blake Chicago
Downtown Chicago
£1,478
per person
8 Nov - 12 Nov
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.6/10 Exceptional! (1,255 reviews)
The hotel itself is really cute, is clean, it’s in a convenient spot. I liked how it looked at the entrance. Only issue is obviously the parking, you know, we were lucky to find a cheaper parking lot very close by, but it’s just that was a lot. And then the room is really beautiful when you get into it, has a lot of character. I loved it clean, like it’s, it’s super clean for sure. The only reason I removed a couple stars is we stayed for two nights and not once they, the housekeeping did not come in to, you know, replenish stuff or make the beds nothing, like, so it was just kind of like, I don’t know if that was an oversight, but I think that’s not how it’s supposed to be. Other than that, everything was fine. I guess it was, it was nice
Reviewed on 24 Sept 2026

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Pendry Chicago
Downtown Chicago
£1,522
per person
29 Nov - 2 Dec
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (1,146 reviews)
Property was clean. Staff was so lovely. Asked if special occasion and sent some drinks up. Overall great location and convenient. On the downside - noisy location also and difficult to get rooftop seating. It is not a bar rooftop. Flew into O’Hare and took subway and from there walked to hotel w one carry on suitcase.
Reviewed on 23 Sept 2026
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Skydeck Chicago at Willis Tower
£31
per adult
90% of travellers recommend
* 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.












