Northwest Side Cheap Holidays
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Top flight + Cheap hotel deals in Northwest Side
Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel
Downtown Chicago
per person
5 Oct - 8 Oct
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9/10 Wonderful! (1,000 reviews)
In my opinion you are paying for the convenience. The location hotel is perfect. You pretty much can walk to shopping centers and stores. The rooftop is awesome but is hard to get into because of outside reservations.
Reviewed on 16 Jul 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
per person
5 Oct - 8 Oct
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (1,635 reviews)
Excellent stay - outstanding Director of Rooms and valet staff made my daughters wedding an amazing experience - just outstanding !!
Reviewed on 16 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
12 Sept - 15 Sept
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,635 reviews)
Excellent stay - outstanding Director of Rooms and valet staff made my daughters wedding an amazing experience - just outstanding !!
Reviewed on 16 Jul 2025
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View all trips3 Night Cheap holidays in Northwest Side
Price found within the past 48 hours. Click for updated prices.
Pendry Chicago
Downtown Chicago
per person
4 Sept - 7 Sept
found 1 hour ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
This hotel is designed well and has a great little bar downstairs along with a nice restaurant/cafe adjacent to the property. The front desk girls are mostly helpful specifically Muriel who made my stay extremely comfortable and gave me tons of recs on eats, etc. I was so thankful to have her around!
I had AC issues with a crazy rattling noise in my first room and was upgraded to another nicer room my last night there. Neither of the beds were very comfortable - I think adding a pillow top would be helpful! The rooms are cute though!
Reviewed on 14 Jul 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
per person
12 Sept - 15 Sept
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,635 reviews)
Excellent stay - outstanding Director of Rooms and valet staff made my daughters wedding an amazing experience - just outstanding !!
Reviewed on 16 Jul 2025
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View all trips4 Night Cheap holidays in Northwest Side
Price found within the past 48 hours. Click for updated prices.
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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.