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

The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Price was ¥74,690, price is now ¥48,177 per person
¥48,177
per person
Dec 5 - Dec 8
found 13 hours ago
Roundtrip flight included
Washington (WAS) to Chicago (ORD)
9/10 Wonderful! (2,027 reviews)
We had an amazing stay for a weekend getaway.
Reviewed on Sep 30, 2025


Hilton Chicago O'Hare Airport
O'Hare
Save 100% on your flight
Price was ¥111,061, price is now ¥75,466 per person
¥75,466
per person
Dec 5 - Dec 8
found 13 hours ago
Roundtrip flight included
Washington (WAS) to Chicago (ORD)
8.2/10 Very Good! (2,123 reviews)
Very friendly helpful staff! Carpets in hallway and room need to be replaced.
Reviewed on Sep 30, 2025

Hilton Orrington / Evanston
Downtown Evanston
Price was ¥78,318, price is now ¥53,499 per person
¥53,499
per person
Dec 5 - Dec 8
found 13 hours ago
Roundtrip flight included
Washington (WAS) to Chicago (ORD)
7.6/10 Good! (1,007 reviews)
Two mornings received poor service at breakfast.
King bed in room. Could not open cabinet
Reviewed on Sep 15, 2025

Renaissance Chicago O'Hare Suites Hotel
O'Hare
Price was ¥90,416, price is now ¥66,236 per person
¥66,236
per person
Dec 5 - Dec 8
found 13 hours ago
Roundtrip flight included
Washington (WAS) to Chicago (ORD)
8.4/10 Very Good! (1,013 reviews)
Parking in the ramp is $40 a night but there is a big open lot to the right of the hotel that may be free. Lobby is beautiful and clean, Starbucks is a plus and opens at 6am. TV’s are huge in the rooms, the bed is very bouncy but extremely comfortable. I like how the living room is separate from bedroom. Bathroom is connected to bedroom and living room. Overall I would stay here every time I come to the O’Hare area.
Reviewed on Sep 29, 2025
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View all trips5* Luxury vacations in Far North 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 18 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 18 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 18 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
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See all available trips from Osaka to Far North Side
View all trips3 Night Luxury vacations in Far North Side
Price found within the past 48 hours. Click for updated prices.

The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Price was ¥74,690, price is now ¥48,177 per person
¥48,177
per person
Dec 5 - Dec 8
found 13 hours ago
Roundtrip flight included
Washington (WAS) to Chicago (ORD)
9/10 Wonderful! (2,027 reviews)
We had an amazing stay for a weekend getaway.
Reviewed on Sep 30, 2025


Hilton Chicago O'Hare Airport
O'Hare
Save 100% on your flight
Price was ¥111,061, price is now ¥75,466 per person
¥75,466
per person
Dec 5 - Dec 8
found 13 hours ago
Roundtrip flight included
Washington (WAS) to Chicago (ORD)
8.2/10 Very Good! (2,123 reviews)
Very friendly helpful staff! Carpets in hallway and room need to be replaced.
Reviewed on Sep 30, 2025
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View all trips4 Night Luxury vacations in Far North Side
Price found within the past 48 hours. Click for updated prices.

theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was ¥380,308, price is now ¥321,538 per person
¥321,538
per person
Nov 1 - Nov 5
found 12 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (1,004 reviews)
The WIt was everything. The Roof at the Wit, was amazing, be sure to make reservations. I love this hotel and Chicago it was safe and close to everything!!
Reviewed on Sep 26, 2025

Hotel Riu Plaza Chicago
Downtown Chicago
Price was ¥410,316, price is now ¥327,626 per person
¥327,626
per person
Nov 1 - Nov 5
found 12 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
Beautiful new hotel, gorgeous rooftop with delicious food. Hotel staff are super friendly and helpful.
Reviewed on Sep 30, 2025

The Emily Hotel
Downtown Chicago
Price was ¥409,002, price is now ¥339,849 per person
¥339,849
per person
Nov 1 - Nov 5
found 12 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) 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
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View all trips* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.