Northwest Side Cheap Vacations
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Top Cheap vacation packages in Northwest Side
Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel
Downtown Chicago
Save 100% on your flight
Price was ￥109,282, price is now ￥73,496 per person
￥73,496
per person
Nov 22 - Nov 27
found 1 day ago
Roundtrip flight included
Memphis (MEM) to Chicago (ORD)
9/10 Wonderful! (1,011 reviews)
Our guests that are not from Chicago there should be some sort of a quick tips handout that gives an overview of the events that are taking place over the next week popular restaurants things that are within walking distance of the hotel
Reviewed on Oct 20, 2025
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was ￥163,896, price is now ￥90,382 per person
￥90,382
per person
Nov 22 - Nov 27
found 1 day ago
Roundtrip flight included
Memphis (MEM) to Chicago (ORD)
9.4/10 Exceptional! (2,602 reviews)
This is the perfect hotel centrally located in the middle of everything. The room was super clean and the breakfast was superb! This is my new favorite Chicago hotel.
Reviewed on Oct 22, 2025
Pendry Chicago
Downtown Chicago
Save 100% on your flight
Price was ￥143,510, price is now ￥86,908 per person
￥86,908
per person
Nov 22 - Nov 27
found 1 day ago
Roundtrip flight included
Memphis (MEM) to Chicago (ORD)
9.4/10 Exceptional! (1,110 reviews)
Ideal area if it’s your first time visiting Chicago. Hotel staff was very friendly.
Reviewed on Oct 16, 2025
Arlo Chicago
Downtown Chicago
Save 100% on your flight
Price was ￥121,388, price is now ￥76,961 per person
￥76,961
per person
Nov 22 - Nov 27
found 1 day ago
Roundtrip flight included
Memphis (MEM) to Chicago (ORD)
9.2/10 Wonderful! (1,852 reviews)
We had an amazing time staying at the Arlo. The staff was very friendly, the check-in/check-out process was very fast. The room was always clean. The location of the hotel is extremely convenient. Everything was awesome. I’m 100% coming back when I’m in Chicago again.
Reviewed on Oct 22, 2025
The Emily Hotel
Downtown Chicago
Save 100% on your flight
Price was ￥141,692, price is now ￥91,637 per person
￥91,637
per person
Nov 22 - Nov 27
found 1 day ago
Roundtrip flight included
Memphis (MEM) to Chicago (ORD)
9.2/10 Wonderful! (1,248 reviews)
We really like The Emily Hotel Chicago. We've stayed a few times this year because the location is very near many great restaurants and bars. The hotel itself has really good dining and lounge options. The staff treats us very well and the rooms and beds are clean and comfortable. A great hotel in a really fun part of town!
Reviewed on Oct 22, 2025
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View all trips5* Cheap vacations in Northwest Side
Price found within the past 48 hours. Click for updated prices.
The Langham, Chicago
Downtown Chicago
Save 100% on your flight
Price was ￥270,972, price is now ￥192,119 per person
￥192,119
per person
Nov 22 - Nov 27
found 1 day ago
Roundtrip flight included
Memphis (MEM) to Chicago (ORD)
9.8/10 Exceptional! (1,008 reviews)
Excellent staff, check in process and dining experiences all superb!
Reviewed on Oct 14, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥307,410, price is now ￥251,867 per person
￥251,867
per person
Jan 17 - Jan 21
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,761 reviews)
The kitchen was VERY clean and very well stocked. Our room was as nice as any room as I have ever stayed in. The Hotel Manager and Pablo, the Director of Rooms, were outstanding!!! they were truly a credit to the Trump brand. I have stayed at the Trump International and would stay there again in a heartbeat.
Reviewed on Oct 20, 2025
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View all trips3 Night Cheap vacations in Northwest Side
Price found within the past 48 hours. Click for updated prices.
Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel
Downtown Chicago
Price was ￥263,234, price is now ￥223,794 per person
￥223,794
per person
Dec 1 - Dec 4
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,042 reviews)
Our room had a smell..don’t know what it was, they tried to fix it promptly. It was in a safe area, it’s very very clean. Walkable to lots of places. Showtime, the doorman told us directions to all of the places to see. We had a good time. Everyone was extremely nice! I would stay here again! And it was safe!
Reviewed on Oct 20, 2025
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥341,982, price is now ￥254,196 per person
￥254,196
per person
Dec 1 - Dec 4
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,602 reviews)
This is the perfect hotel centrally located in the middle of everything. The room was super clean and the breakfast was superb! This is my new favorite Chicago hotel.
Reviewed on Oct 22, 2025
theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was ￥279,600, price is now ￥231,276 per person
￥231,276
per person
Dec 1 - Dec 4
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (1,011 reviews)
Our guests that are not from Chicago there should be some sort of a quick tips handout that gives an overview of the events that are taking place over the next week popular restaurants things that are within walking distance of the hotel
Reviewed on Oct 20, 2025
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See all available trips from Tokyo to Northwest Side
View all trips4 Night Cheap vacations in Northwest Side
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥225,057, price is now ￥193,089 per person
￥193,089
per person
Jan 17 - Jan 21
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,602 reviews)
This is the perfect hotel centrally located in the middle of everything. The room was super clean and the breakfast was superb! This is my new favorite Chicago hotel.
Reviewed on Oct 22, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥307,410, price is now ￥251,867 per person
￥251,867
per person
Jan 17 - Jan 21
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,761 reviews)
The kitchen was VERY clean and very well stocked. Our room was as nice as any room as I have ever stayed in. The Hotel Manager and Pablo, the Director of Rooms, were outstanding!!! they were truly a credit to the Trump brand. I have stayed at the Trump International and would stay there again in a heartbeat.
Reviewed on Oct 20, 2025
Pendry Chicago
Downtown Chicago
Price was ￥249,900, price is now ￥218,036 per person
￥218,036
per person
Jan 17 - Jan 21
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,110 reviews)
Ideal area if it’s your first time visiting Chicago. Hotel staff was very friendly.
Reviewed on Oct 16, 2025
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View all trips* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
