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



theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was ¥346,169, price is now ¥287,546 per person
¥287,546
per person
Dec 31 - Jan 6
found 6 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9/10 Wonderful! (1,004 reviews)
Clean room, friendly staff, great location and within walking distance from all shops!
Reviewed on Oct 7, 2025

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥304,531, price is now ¥253,332 per person
¥253,332
per person
Nov 28 - Nov 30
found 19 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
I stayed at the Trump International Washington DC, and this one pales in comparison to be honest. The staff was friendly/excellent, but the hotel itself was pretty standard. I expected the same level as the old Washington DC hotel. The shower was plugged up and drained as slow as frozen molasses.
Reviewed on Oct 6, 2025

Hilton Chicago O'Hare Airport
O'Hare
Price was ¥384,047, price is now ¥320,608 per person
¥320,608
per person
Dec 31 - Jan 6
found 6 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
8.2/10 Very Good! (2,123 reviews)
Very very dated room but the only game in town if you have a very early flight. Unappealing bar and extortionate prices at the carry out place for a beer. Luckily we had enough time to take the subway one stop to Rosemont for a decent meal.
Reviewed on Oct 5, 2025
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View all trips5* Adventure vacations in Northwest Side
Price found within the past 48 hours. Click for updated prices.

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥304,531, price is now ¥253,332 per person
¥253,332
per person
Nov 28 - Nov 30
found 19 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
I stayed at the Trump International Washington DC, and this one pales in comparison to be honest. The staff was friendly/excellent, but the hotel itself was pretty standard. I expected the same level as the old Washington DC hotel. The shower was plugged up and drained as slow as frozen molasses.
Reviewed on Oct 6, 2025

The Peninsula Chicago
Downtown Chicago
Price was ¥615,268, price is now ¥544,743 per person
¥544,743
per person
Dec 4 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) 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

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View all trips4 Night Adventure vacations in Northwest Side
Price found within the past 48 hours. Click for updated prices.

Congress Plaza Hotel
Downtown Chicago
Price was ¥244,142, price is now ¥220,989 per person
¥220,989
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8/10 Very Good! (9,193 reviews)
We did not use laundry service, and the front desk staff did not mention any availbale services
Reviewed on Oct 7, 2025

Wrigleyville Suites
Lakeview
Price was ¥584,363, price is now ¥510,324 per person
¥510,324
per person
Dec 4 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.6/10 Exceptional! (19 reviews)
This property is very clean and a nice place to stay, especially when attending a cubs game in wrigleyville. Everything is in walking distance and it’s a safe neighborhood.
Reviewed on Aug 23, 2025

The Peninsula Chicago
Downtown Chicago
Price was ¥615,268, price is now ¥544,743 per person
¥544,743
per person
Dec 4 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) 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
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