
West Side Cheap Vacations
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Top Cheap vacation packages in West Side
Price found within the past 48 hours. Click for updated prices.

The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Price was ¥233,615, price is now ¥189,692 per person
¥189,692
per person
Nov 21 - Nov 25
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9/10 Wonderful! (1,992 reviews)
A beautiful property with friendly staff.
Reviewed on Sep 13, 2025


Pendry Chicago
Downtown Chicago
Price was ¥256,500, price is now ¥211,142 per person
¥211,142
per person
Nov 21 - Nov 25
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (1,070 reviews)
This is an exceptional hotel. The rooms are clean. The service is impeccable, and the products!! The signature scent is to die for. It is now a part of my life. I had to buy a candle on the way out and have already visited the online store for body wash and lotion. Well done. There are a lot of choices in Chicago, but this is now my go to. Will definitely be back!
Reviewed on Sep 12, 2025

theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was ¥243,274, price is now ¥204,282 per person
¥204,282
per person
Nov 21 - Nov 25
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9/10 Wonderful! (1,014 reviews)
First time but won’t be the last. Very nice place with lots to do right around there.
Reviewed on Sep 9, 2025

The Royal Sonesta Chicago River North
Downtown Chicago
Price was ¥229,542, price is now ¥195,209 per person
¥195,209
per person
Nov 21 - Nov 25
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.2/10 Wonderful! (2,078 reviews)
The property and staff were amazing from arrival with hotel porters, Antwonne & Spiro to front desk team and Gabby. The wonderful Shaunda always there to assist and who can forget the amazing restaurant and bar staff starting with Nate, Jess, Miguel and Chef Alfonso. Truly fantastic!
Reviewed on Sep 11, 2025
4 Night Cheap vacations in West Side
Price found within the past 48 hours. Click for updated prices.

The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Price was ¥233,615, price is now ¥189,692 per person
¥189,692
per person
Nov 21 - Nov 25
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9/10 Wonderful! (1,992 reviews)
A beautiful property with friendly staff.
Reviewed on Sep 13, 2025


Pendry Chicago
Downtown Chicago
Price was ¥256,500, price is now ¥211,142 per person
¥211,142
per person
Nov 21 - Nov 25
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (1,070 reviews)
This is an exceptional hotel. The rooms are clean. The service is impeccable, and the products!! The signature scent is to die for. It is now a part of my life. I had to buy a candle on the way out and have already visited the online store for body wash and lotion. Well done. There are a lot of choices in Chicago, but this is now my go to. Will definitely be back!
Reviewed on Sep 12, 2025
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.