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.
Hyatt Centric Chicago Magnificent Mile
Downtown Chicago
Price was £1,764, price is now £1,332 per person
£1,332
per person
17 Jun - 22 Jun
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9/10 Wonderful! (1,092 reviews)
I would have really appreciated if there were a microwave available in our room.
Reviewed on 4 May 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was £2,531, price is now £1,804 per person
£1,804
per person
14 Jun - 21 Jun
found 7 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (2,489 reviews)
If you plan on staying in this hotel by all means the view is great, but if you plan on moving your vehicle at all the hotel does not validate In-N-Out parking. You have to pay every time you want to leave and come back. Unlike the normal hotel, La Quinta downtown Chicago validate parking yes it’s $70 but you can drive in and out as many times as you want during your stay. Unlike this hotel.
Reviewed on 8 May 2026
Hotel Chicago Downtown, Autograph Collection by Marriott
Downtown Chicago
Price was £1,858, price is now £1,414 per person
£1,414
per person
17 Jun - 22 Jun
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9/10 Wonderful! (1,004 reviews)
The staff was excellent and understanding and very helpful when it came to leaving
Reviewed on 9 May 2026
Chicago Marriott Downtown Magnificent Mile
Downtown Chicago
Price was £1,959, price is now £1,506 per person
£1,506
per person
14 Jun - 21 Jun
found 7 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
8.8/10 Excellent! (1,002 reviews)
Breakfast menu was good, staff at the lounge was good. Checking in was not so good, they wanted to charge me $25 to check in 15 minutes before the time. I think it would be better to say the room is not ready yet the saying your room is ready but is not 2 and if you want it now it will be an extra $25. That I think is ridiculous, which took away from my experience.
Reviewed on 11 May 2026
DoubleTree by Hilton Chicago - Magnificent Mile
Downtown Chicago
Price was £1,974, price is now £1,536 per person
£1,536
per person
17 Jun - 22 Jun
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
8.8/10 Excellent! (2,451 reviews)
The staff was extremely polite, and the hotel was in the most convenient area for the activities we were doing. Great visit!
Reviewed on 11 May 2026
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Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was £3,722, price is now £3,165 per person
£3,165
per person
3 Aug - 8 Aug
found 11 hours ago
Return flight included
London (LCY) to Chicago (ORD)
9.4/10 Exceptional! (1,863 reviews)
The hotel is in the best location in the city. The staff is very friendly and rooms are immaculate. Terrace 16 restaurant and bar in the hotel has a great view. Overall experience was wonderful highly recommend and will definitely be back soon.
Reviewed on 11 May 2026
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Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was £2,255, price is now £1,746 per person
£1,746
per person
24 Jul - 28 Jul
found 11 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,863 reviews)
The hotel is in the best location in the city. The staff is very friendly and rooms are immaculate. Terrace 16 restaurant and bar in the hotel has a great view. Overall experience was wonderful highly recommend and will definitely be back soon.
Reviewed on 11 May 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was £1,703, price is now £1,371 per person
£1,371
per person
24 Jul - 28 Jul
found 11 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (2,489 reviews)
If you plan on staying in this hotel by all means the view is great, but if you plan on moving your vehicle at all the hotel does not validate In-N-Out parking. You have to pay every time you want to leave and come back. Unlike the normal hotel, La Quinta downtown Chicago validate parking yes it’s $70 but you can drive in and out as many times as you want during your stay. Unlike this hotel.
Reviewed on 8 May 2026
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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.
