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


Level Chicago - River North
Downtown Chicago
Price was ¥218,872, price is now ¥174,100 per person
¥174,100
per person
Nov 1 - Nov 4
found 23 hours ago
Roundtrip non-stop flight included
Komatsu (KMQ) to Chicago (ORD)
9/10 Wonderful! (698 reviews)
Close to any and everything u wanna do highly suggested place to stay
Reviewed on Sep 19, 2025

Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ¥213,660, price is now ¥174,872 per person
¥174,872
per person
Nov 1 - Nov 4
found 23 hours ago
Roundtrip non-stop flight included
Komatsu (KMQ) to Chicago (ORD)
9.4/10 Exceptional! (2,142 reviews)
parking costs $65 per day.
I was bought another $30 a day without even knowing what it was.
The place is very good but the hotel itself doesn't offer anything.
Reviewed on Sep 29, 2025

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥1,035,152, price is now ¥871,432 per person
¥871,432
per person
Nov 22 - Nov 28
found 6 hours ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
Perfect location, beautiful view, nice staffs, excellently maintained room and facility!
Reviewed on Sep 28, 2025

Level Chicago Fulton Market
Downtown Chicago
Price was ¥366,160, price is now ¥316,665 per person
¥316,665
per person
Nov 1 - Nov 5
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (294 reviews)
I had such a lovely time here. I love the extra things that come with staying here! The pool was very nice and clean. I really loved the space of the rooms and how clean it was. Will be coming here again!
Reviewed on Sep 21, 2025
5* Beach vacations in West Side
Price found within the past 48 hours. Click for updated prices.

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥1,035,152, price is now ¥871,432 per person
¥871,432
per person
Nov 22 - Nov 28
found 6 hours ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
Perfect location, beautiful view, nice staffs, excellently maintained room and facility!
Reviewed on Sep 28, 2025

Park Hyatt Chicago
Downtown Chicago
Price was ¥1,253,017, price is now ¥1,111,188 per person
¥1,111,188
per person
Nov 22 - Nov 28
found 6 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.6/10 Exceptional! (1,002 reviews)
My wife and I spent an incredibly enjoyable weekend at the hotel. It is within walking distance to many different points of interest in the heart of the Magnificent Mile. The service, amenities, and stay were memorable. We will definitely return.
Reviewed on Sep 29, 2025

The Peninsula Chicago
Downtown Chicago
Price was ¥1,300,753, price is now ¥1,173,353 per person
¥1,173,353
per person
Nov 22 - Nov 28
found 6 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.8/10 Exceptional! (1,006 reviews)
Excellent hotel, my only complaint would be the Peninsula food service.
We ate at the Shanghai Terrace our first night on site and honestly the food was only 2 stars. Specifically the appetizers were minuscule, and 90% pastry dough. Whatever filling was supposed to be inside all the dough largely wasn’t. The whole Peking duck was arranged haphazardly on the plate, the skin was not really crispy, and the taste experience was completely lackluster.
As to the main dining room the service continues, as always, to be erratic and frequently slow. Food is sometimes served hot, sometimes not.
The room service on our checkout day was absolutely abysmal. We both ordered eggs Benedict and both orders were served not a degree above room temperature. The hollandaise sauce was so cold it had solidified.
There really is no excuse for this.
And unfortunately we did not have time to return the order as we had a plane to catch and we were running a bit behind.
For an otherwise professional hotel the food service and quality is sadly lacking. It leads one to believe that the F&B manager could be a nephew, a cousin, or some other family member need of a job.
Reviewed on Sep 27, 2025
3 Night Beach vacations in West Side
Price found within the past 48 hours. Click for updated prices.

Level Chicago - River North
Downtown Chicago
Price was ¥218,872, price is now ¥174,100 per person
¥174,100
per person
Nov 1 - Nov 4
found 23 hours ago
Roundtrip non-stop flight included
Komatsu (KMQ) to Chicago (ORD)
9/10 Wonderful! (698 reviews)
Close to any and everything u wanna do highly suggested place to stay
Reviewed on Sep 19, 2025

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥313,513, price is now ¥224,654 per person
¥224,654
per person
Nov 1 - Nov 4
found 23 hours ago
Roundtrip non-stop flight included
Komatsu (KMQ) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
Perfect location, beautiful view, nice staffs, excellently maintained room and facility!
Reviewed on Sep 28, 2025

The Emily Hotel
Downtown Chicago
Price was ¥230,676, price is now ¥179,926 per person
¥179,926
per person
Nov 1 - Nov 4
found 23 hours ago
Roundtrip non-stop flight included
Komatsu (KMQ) to Chicago (ORD)
9.2/10 Wonderful! (1,222 reviews)
Beautiful hotel in great walkable area. There were major renovations going on while we were there so our actual floor was a bit messy/busy, although the common areas remained lovely. Would stay again for the good location. All staff very nice.
Reviewed on Sep 29, 2025
4 Night Beach vacations in West Side
Price found within the past 48 hours. Click for updated prices.

Courtyard by Marriott Chicago Wood Dale
Price was ¥308,604, price is now ¥291,096 per person
¥291,096
per person
Nov 1 - Nov 5
found 1 hour ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.6/10 Excellent! (1,004 reviews)
Super helpful staff and very nice clean rooms! The shuttle to the airport is a great convenience when traveling to and from the airport.
Reviewed on Sep 29, 2025

4BR Corporate Suite Central and Modern
Near North Side
Price was ¥416,678, price is now ¥387,604 per person
¥387,604
per person
Nov 1 - Nov 5
found 1 hour ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
10/10 Exceptional! (3 reviews)
Great location in Lincoln Park. Easy walk to several shops and restaurants. And about a 5 minute walk to the redline station (North/Clybourn). Very clean and quiet inside the unit. Building is very new. Room access through the Latch app is simple.
I would definitely stay here again. The overall experience was excellent and my other guests would agree.
Reviewed on Aug 18, 2025

Staybridge Suites Chicago O'Hare - Rosemont by IHG
O'Hare
Price was ¥312,792, price is now ¥293,732 per person
¥293,732
per person
Nov 1 - Nov 5
found 1 hour ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (1,005 reviews)
Temperature in the room was freezing when we entered… 62 degrees. You could save some energy by moderating the air conditioning.
Reviewed on Sep 27, 2025
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.