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


Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥400,778, price is now ¥333,140 per person
¥333,140
per person
Mar 14 - Mar 17
found 11 hours ago
Roundtrip non-stop flight included
Nagoya (NGO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
The staff was super friendly and accommodating. The rooms were immaculately clean, and the spa was amazing
Reviewed on Jan 13, 2026

Waldorf Astoria Chicago
Downtown Chicago
Price was ¥282,630, price is now ¥243,250 per person
¥243,250
per person
Apr 2 - Apr 4
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
When we arrived at check in time, we were informed that our room was not ready but that we could upgrade at a discounted additional cost to a suite. At first, we didn't want to do that and decided to wait. The host provided complimentary round of drinks and meal for the wait. We decided to upgrade and I'm so glad that we did. The room was incredible and the service, from concierge, staff and valets, here is top notch. We ordered the Waldorf salad and Waldorf chocolate chip cookies because you have to if you stay here. Loved this place and will definitely return.
Reviewed on Jan 5, 2026

The Emily Hotel
Downtown Chicago
Price was ¥335,613, price is now ¥299,958 per person
¥299,958
per person
Mar 14 - Mar 17
found 11 hours ago
Roundtrip non-stop flight included
Nagoya (NGO) to Chicago (ORD)
9.2/10 Wonderful! (1,264 reviews)
Nice newer hotel with lots of options. Rooms are a bit industrial but fine, nothing super luxurious but adequate.
Reviewed on Jan 16, 2026

Level Chicago – Old Town
Downtown Chicago
Price was ¥231,578, price is now ¥208,858 per person
¥208,858
per person
Apr 2 - Apr 4
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
I stayed 5 nights total, 4 nights in a two BR, 1 bath with a balcony and the last night in a one BR. The 2BR was great. It faced East, received a lot of sunlight, was clean, modern and the bed was very comfortable. The gym had what I needed too. actually liked sleeping with the sound of the el nearby because I used to live in the area. I did not give it 5 stars because the walls are super thin. Someone had a party next to me and it was impossible to sleep hearing voices straight through the walls. Being a newer building, I don’t think the best quality appliances or fixtures were chosen. My ice machine wasn’t working and the heat/fan only worked in certain areas in the 2BR. Additional lighting should be added. The 1BR shower fixtures and drain needed some attention. That said, Mihajlo and the front desk staff were very helpful and attentive and helped me with whatever I needed. The 1BR seemed more like a studio to m. I’d prefer to book directly through Level, but it was a better price with Expedia. I still thought it was pricey but I was overall happy with my stay.
Reviewed on Jan 12, 2026
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View all trips5* Ski vacations in Far North Side
Price found within the past 48 hours. Click for updated prices.

The Peninsula Chicago
Downtown Chicago
Price was ¥193,946, price is now ¥171,120 per person
¥171,120
per person
Apr 3 - Apr 5
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
The staff was great. Everybody was friendly. The room was beautifully appointed, although maybe a little too heavy on electronics. I don't think every light switch needs to be a touch pad. And there were one or two things we couldn't figure out, such as the lighted mirror on the credenza: don't know where the controls for that were hiding. These are minor issues and do not take away from the splendid funishings in the room.
Reviewed on Jan 11, 2026

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥400,778, price is now ¥333,140 per person
¥333,140
per person
Mar 14 - Mar 17
found 11 hours ago
Roundtrip non-stop flight included
Nagoya (NGO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
The staff was super friendly and accommodating. The rooms were immaculately clean, and the spa was amazing
Reviewed on Jan 13, 2026

Waldorf Astoria Chicago
Downtown Chicago
Price was ¥282,630, price is now ¥243,250 per person
¥243,250
per person
Apr 2 - Apr 4
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
When we arrived at check in time, we were informed that our room was not ready but that we could upgrade at a discounted additional cost to a suite. At first, we didn't want to do that and decided to wait. The host provided complimentary round of drinks and meal for the wait. We decided to upgrade and I'm so glad that we did. The room was incredible and the service, from concierge, staff and valets, here is top notch. We ordered the Waldorf salad and Waldorf chocolate chip cookies because you have to if you stay here. Loved this place and will definitely return.
Reviewed on Jan 5, 2026
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View all trips3 Night Ski vacations in Far North Side
Price found within the past 48 hours. Click for updated prices.


Hilton Chicago O'Hare Airport
O'Hare
Price was ¥271,808, price is now ¥246,306 per person
¥246,306
per person
Feb 20 - Feb 23
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (2,158 reviews)
Stayed prior to flight, clean, quiet room!
Reviewed on Jan 13, 2026

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥161,242, price is now ¥129,873 per person
¥129,873
per person
Apr 3 - Apr 5
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
The staff was super friendly and accommodating. The rooms were immaculately clean, and the spa was amazing
Reviewed on Jan 13, 2026
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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.
