
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.

JW Marriott Chicago
Downtown Chicago
Price was ¥145,544, price is now ¥110,028 per person
¥110,028
per person
Jul 10 - Jul 13
found 14 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,003 reviews)
Good customer service and the food in the lobby restaurants was so good! Also the service at that restaurant is amazing I believe her name was Stephanie, she went out of her way to find me caffeine free Diet Coke. Also, we forgot to tell them that we don’t eat bacon after the hamburger came. They happily to get back and started another hamburger to make sure there’s no bacon residue in it.
Reviewed on May 31, 2026

Pendry Chicago
Downtown Chicago
Save 100% on your flight
Price was ¥200,302, price is now ¥144,012 per person
¥144,012
per person
Jul 10 - Jul 13
found 14 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,121 reviews)
I absolutely loved it! I little bit noisy but close to literally everything!
Reviewed on Jun 2, 2026

Kimpton Gray Hotel by IHG
Downtown Chicago
Save 100% on your flight
Price was ¥166,326, price is now ¥122,686 per person
¥122,686
per person
Jul 10 - Jul 13
found 14 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,005 reviews)
Great hotel. Loved the lobby and our room. Would definitely stay here again.
Reviewed on May 19, 2026


The Emily Hotel
Downtown Chicago
Price was ¥420,630, price is now ¥347,626 per person
¥347,626
per person
Jul 18 - Jul 22
found 10 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,322 reviews)
Convenient location and easy building to deal with. Parking was a little expensive.
Reviewed on Jun 2, 2026
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 ¥491,550, price is now ¥406,321 per person
¥406,321
per person
Jul 18 - Jul 22
found 10 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,886 reviews)
Great room, professional staff, no complaints.
Reviewed on May 31, 2026

The Peninsula Chicago
Downtown Chicago
Price was ¥704,922, price is now ¥612,544 per person
¥612,544
per person
Aug 8 - Aug 12
found 14 hours ago
Roundtrip non-stop flight included
Nagoya (NGO) to Chicago (ORD)
9.8/10 Exceptional! (1,002 reviews)
Everyone was so helpful and friendly
Great environment.
Cleaning, room service ,breakfast A+
Reviewed on May 29, 2026

Nobu Hotel Chicago
Downtown Chicago
Price was ¥672,837, price is now ¥615,602 per person
¥615,602
per person
Aug 3 - Aug 9
found 15 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (854 reviews)
Beautiful room. Well appointed. love the ambiance. Ashley Cartagena was very helpful with reservations!! Great location. Do not eat here, food is not good especially for the price. Rooftop bar view is cute but cocktails not great, I would skip them. There are dozens of cute coffee shops, bakeries, restaurants, bars & shops all steps away. would definitely stay here again.
Reviewed on May 28, 2026
3 Night Luxury vacations in West Side
Price found within the past 48 hours. Click for updated prices.

Hotel Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was ¥159,687, price is now ¥105,567 per person
¥105,567
per person
Jul 10 - Jul 13
found 14 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very Good! (2,732 reviews)
The hotel location and room was nice. I didn’t like that you had to pay $5 per bag for storage if you wanted to check out if the room early. I thought giving the room before noon would be better for them especially since I was coming back before that checkout time. So I just brought my stuff back up to the room
Other than that the front desk and cleaning ladies was very nice.
Reviewed on May 29, 2026

Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was ¥195,854, price is now ¥124,324 per person
¥124,324
per person
Jul 10 - Jul 13
found 14 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (4,258 reviews)
Excellent location and good selection of breakfast
Reviewed on Jun 2, 2026

The Emily Hotel
Downtown Chicago
Save 100% on your flight
Price was ¥169,214, price is now ¥112,825 per person
¥112,825
per person
Jul 10 - Jul 13
found 14 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,322 reviews)
Convenient location and easy building to deal with. Parking was a little expensive.
Reviewed on Jun 2, 2026
4 Night Luxury vacations in West Side
Price found within the past 48 hours. Click for updated prices.

Hotel Riu Plaza Chicago
Downtown Chicago
Price was ¥390,516, price is now ¥317,526 per person
¥317,526
per person
Jul 18 - Jul 22
found 10 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (4,258 reviews)
Excellent location and good selection of breakfast
Reviewed on Jun 2, 2026

Omni Chicago Hotel
Downtown Chicago
Price was ¥414,300, price is now ¥338,024 per person
¥338,024
per person
Jul 18 - Jul 22
found 10 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,784 reviews)
Restaurant is excellent.
Breakfast is excellent.
Doorman & all entrance staff are terrific & helpful.
We never received the $25 food coupons as advertised.
From Exxpedia??? or from Omni???
Reviewed on Jun 2, 2026

The Emily Hotel
Downtown Chicago
Price was ¥420,630, price is now ¥347,626 per person
¥347,626
per person
Jul 18 - Jul 22
found 10 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,322 reviews)
Convenient location and easy building to deal with. Parking was a little expensive.
Reviewed on Jun 2, 2026
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
