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


Pendry Chicago
Downtown Chicago
per person
25 Aug - 29 Aug
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
Nice property, very walkable. Front desk was great. Bar area nice & welcome drink nice. Concierge was not around. Got suite with 2 full baths which was awesome with teens. Great stay overall!
Reviewed on 12 Jul 2025


Trump International Hotel & Tower Chicago
Downtown Chicago
per person
25 Aug - 29 Aug
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (1,635 reviews)
I didn’t like the staff insinuating that I couldn’t afford a bottle of Dom. I didn’t like the 3 calls to my room to make sure I understood what the price was. I didn’t like how Brandy told me the reason for doubting my ability to pay for a $700 bottle of champagne was because of what my “profile” said about me. I would love to see this profile they had on me. I did not appreciate being embarrassed in front of my wife. We spent close to 10K at this place for the 7 days we spent there. We chose to stay at Trump Intl in Chicago because we can afford to do so. I understood before checking in that it would be very expensive. I did not know that a profile would be built about me and I would be judged by the staff according to it. I will never stay at a Trump hotel again. There are too many hotels to chose from to have to deal with this kind of treatment.
Reviewed on 12 Jul 2025

Virgin Hotels Chicago
Downtown Chicago
per person
25 Aug - 29 Aug
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.2/10 Wonderful! (1,334 reviews)
I love Virgin air and expected a 5-star experience. Hotel checkin was not all that welcoming, but efficientl. They had no valet service and basically told us we were on our own. Thought ok I need a drink so went to the rooftop bar. An afterthought at this hotel. Cushions were dirty and faded. Barely staffed. More like a rooftop bar in costs rica than downtown Chicago. Room was nice and stylish. The highlight of the stay tbh as was the coffee shop.
Reviewed on 13 Jul 2025
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Price found within the past 48 hours. Click for updated prices.


Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
per person
20 Sept - 27 Sept
found 20 hours ago
Return direct flight included
Leeds (LBA) to Chicago (ORD)
9.4/10 Exceptional! (1,635 reviews)
I didn’t like the staff insinuating that I couldn’t afford a bottle of Dom. I didn’t like the 3 calls to my room to make sure I understood what the price was. I didn’t like how Brandy told me the reason for doubting my ability to pay for a $700 bottle of champagne was because of what my “profile” said about me. I would love to see this profile they had on me. I did not appreciate being embarrassed in front of my wife. We spent close to 10K at this place for the 7 days we spent there. We chose to stay at Trump Intl in Chicago because we can afford to do so. I understood before checking in that it would be very expensive. I did not know that a profile would be built about me and I would be judged by the staff according to it. I will never stay at a Trump hotel again. There are too many hotels to chose from to have to deal with this kind of treatment.
Reviewed on 12 Jul 2025

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Price found within the past 48 hours. Click for updated prices.

Level Chicago - River North
Downtown Chicago
per person
5 Sept - 8 Sept
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9/10 Wonderful! (627 reviews)
This place was secure and beautiful. The amenities were top notch & I felt 100% safe while there. Will return!
Reviewed on 7 Jul 2025

Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
per person
4 Sept - 7 Sept
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,635 reviews)
I didn’t like the staff insinuating that I couldn’t afford a bottle of Dom. I didn’t like the 3 calls to my room to make sure I understood what the price was. I didn’t like how Brandy told me the reason for doubting my ability to pay for a $700 bottle of champagne was because of what my “profile” said about me. I would love to see this profile they had on me. I did not appreciate being embarrassed in front of my wife. We spent close to 10K at this place for the 7 days we spent there. We chose to stay at Trump Intl in Chicago because we can afford to do so. I understood before checking in that it would be very expensive. I did not know that a profile would be built about me and I would be judged by the staff according to it. I will never stay at a Trump hotel again. There are too many hotels to chose from to have to deal with this kind of treatment.
Reviewed on 12 Jul 2025

Pendry Chicago
Downtown Chicago
per person
4 Sept - 7 Sept
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
Nice property, very walkable. Front desk was great. Bar area nice & welcome drink nice. Concierge was not around. Got suite with 2 full baths which was awesome with teens. Great stay overall!
Reviewed on 12 Jul 2025
Don't see what you're looking for?
See all available trips from London to Northwest Side
View all trips4 Night Adventure holidays in Northwest Side
Price found within the past 48 hours. Click for updated prices.


Pendry Chicago
Downtown Chicago
per person
25 Aug - 29 Aug
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
Nice property, very walkable. Front desk was great. Bar area nice & welcome drink nice. Concierge was not around. Got suite with 2 full baths which was awesome with teens. Great stay overall!
Reviewed on 12 Jul 2025

Trump International Hotel & Tower Chicago
Downtown Chicago
per person
25 Aug - 29 Aug
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (1,635 reviews)
I didn’t like the staff insinuating that I couldn’t afford a bottle of Dom. I didn’t like the 3 calls to my room to make sure I understood what the price was. I didn’t like how Brandy told me the reason for doubting my ability to pay for a $700 bottle of champagne was because of what my “profile” said about me. I would love to see this profile they had on me. I did not appreciate being embarrassed in front of my wife. We spent close to 10K at this place for the 7 days we spent there. We chose to stay at Trump Intl in Chicago because we can afford to do so. I understood before checking in that it would be very expensive. I did not know that a profile would be built about me and I would be judged by the staff according to it. I will never stay at a Trump hotel again. There are too many hotels to chose from to have to deal with this kind of treatment.
Reviewed on 12 Jul 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.