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

Swissotel - Chicago
Downtown Chicago
Price was ¥224,150, price is now ¥171,434 per person
¥171,434
per person
Nov 1 - Nov 4
found 5 hours ago
Roundtrip non-stop flight included
Komatsu (KMQ) to Chicago (ORD)
9/10 Wonderful! (2,765 reviews)
Stay was quiet for the short time we were in the room. We used offsite parking that was much cheaper than self parking at hotel.
Reviewed on Sep 23, 2025

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥311,050, price is now ¥219,958 per person
¥219,958
per person
Nov 1 - Nov 4
found 5 hours ago
Roundtrip non-stop flight included
Komatsu (KMQ) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
The hotel was above the expectations and river view was fabulous also staff were incredibly awesome specially the front dest employee Natalia she was helpful, smiling and welcoming.
Reviewed on Sep 24, 2025

Hotel Riu Plaza Chicago
Downtown Chicago
Price was ¥343,518, price is now ¥246,906 per person
¥246,906
per person
Nov 29 - Dec 3
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
Clean rooms and friendly staff. Centrally located. Breakfast is a feast. One of the best hotel breakfasts I have experienced. Roof top bar has a terrific view of the City and perfect for an evening cocktail. They don't have their own parking. I think this is typical for downtown so I recommend figuring that out before you arrive.
Reviewed on Sep 24, 2025

theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was ¥326,194, price is now ¥242,014 per person
¥242,014
per person
Nov 29 - Dec 3
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (1,004 reviews)
The room was perfect and the front staff were exceptional. Our stay was amazing!
Reviewed on Sep 21, 2025

The Emily Hotel
Downtown Chicago
Price was ¥227,102, price is now ¥174,422 per person
¥174,422
per person
Nov 1 - Nov 4
found 5 hours ago
Roundtrip non-stop flight included
Komatsu (KMQ) to Chicago (ORD)
9.2/10 Wonderful! (1,222 reviews)
I was so disappointed in my stay at the Emily. For almost $500/night I was expecting nice, spacious rooms. The room was so small, the sink was in the hallway, the bed was so uncomfortable, dingy design. I’ve stayed at better Aloft or Moxy rooms. The food at Fora, the hotel restaurant, is uninspired and unseasoned. The brunch chiliques were bland. Skip this hotel in west loop and stay at the hoxton instead
Reviewed on Sep 22, 2025
5* Luxury vacations in West Side
Price found within the past 48 hours. Click for updated prices.

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥311,050, price is now ¥219,958 per person
¥219,958
per person
Nov 1 - Nov 4
found 5 hours ago
Roundtrip non-stop flight included
Komatsu (KMQ) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
The hotel was above the expectations and river view was fabulous also staff were incredibly awesome specially the front dest employee Natalia she was helpful, smiling and welcoming.
Reviewed on Sep 24, 2025

Park Hyatt Chicago
Downtown Chicago
Price was ¥373,586, price is now ¥297,150 per person
¥297,150
per person
Nov 17 - Nov 20
found 14 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,002 reviews)
Got pick pocketed in the elevator. I really like this hotel. Plan to return.
Reviewed on Sep 8, 2025

3 Night Luxury vacations in West Side
Price found within the past 48 hours. Click for updated prices.

Park Hyatt Chicago
Downtown Chicago
Price was ¥373,586, price is now ¥297,150 per person
¥297,150
per person
Nov 17 - Nov 20
found 14 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,002 reviews)
Got pick pocketed in the elevator. I really like this hotel. Plan to return.
Reviewed on Sep 8, 2025


The Peninsula Chicago
Downtown Chicago
Price was ¥421,584, price is now ¥340,642 per person
¥340,642
per person
Nov 17 - Nov 20
found 14 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,006 reviews)
Clean and comfortable room, attentive staff.
Reviewed on Sep 24, 2025
4 Night Luxury vacations in West Side
Price found within the past 48 hours. Click for updated prices.

theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was ¥326,194, price is now ¥242,014 per person
¥242,014
per person
Nov 29 - Dec 3
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (1,004 reviews)
The room was perfect and the front staff were exceptional. Our stay was amazing!
Reviewed on Sep 21, 2025

Hotel Riu Plaza Chicago
Downtown Chicago
Price was ¥343,518, price is now ¥246,906 per person
¥246,906
per person
Nov 29 - Dec 3
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
Clean rooms and friendly staff. Centrally located. Breakfast is a feast. One of the best hotel breakfasts I have experienced. Roof top bar has a terrific view of the City and perfect for an evening cocktail. They don't have their own parking. I think this is typical for downtown so I recommend figuring that out before you arrive.
Reviewed on Sep 24, 2025

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥399,230, price is now ¥289,662 per person
¥289,662
per person
Nov 29 - Dec 3
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
The hotel was above the expectations and river view was fabulous also staff were incredibly awesome specially the front dest employee Natalia she was helpful, smiling and welcoming.
Reviewed on Sep 24, 2025
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.