
Northwest Side Golf Vacations
Book a Golf Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ¥45,448 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Golf vacation packages in Northwest Side
Price found within the past 48 hours. Click for updated prices.

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥265,722, price is now ¥236,814 per person
¥236,814
per person
Apr 2 - Apr 4
found 19 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) 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 ¥382,354, price is now ¥306,076 per person
¥306,076
per person
Mar 15 - Mar 19
found 1 day ago
Roundtrip 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


Viceroy Chicago
Downtown Chicago
Price was ¥286,474, price is now ¥255,829 per person
¥255,829
per person
Mar 15 - Mar 19
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,129 reviews)
Staff is always excellent. Our favorite stay in the Chicago area.
Reviewed on Jan 9, 2026

Kimpton Gray Hotel by IHG
Downtown Chicago
Price was ¥288,804, price is now ¥258,341 per person
¥258,341
per person
Mar 15 - Mar 19
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,003 reviews)
Friendly and welcoming staff, extremely helpful valet, beautiful room, comfortable beds, and a warm ambiance. We genuinely enjoyed our stay here. We were only in town for one night, but we would have easily been comfortable here for a longer stay. Walking distance to many popular places, and the hotel itself was in a safe area. (Whenever I travel without my husband, that is of particular concern, so it was appreciated.) The next time we're in town for a show, we will absolutely stay at the Kimpton Gray again.
Reviewed on Jan 11, 2026
Don't see what you're looking for?
See all available trips from Tokyo to Northwest Side
View all trips5* Golf vacations in Northwest 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 7 hours 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

Waldorf Astoria Chicago
Downtown Chicago
Price was ¥382,354, price is now ¥306,076 per person
¥306,076
per person
Mar 15 - Mar 19
found 1 day ago
Roundtrip 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

Don't see what you're looking for?
See all available trips from Vancouver to Northwest Side
View all trips3 Night Golf vacations in Northwest Side
Price found within the past 48 hours. Click for updated prices.

Level Chicago – Old Town
Downtown Chicago
Price was ¥242,985, price is now ¥219,014 per person
¥219,014
per person
Mar 8 - Mar 11
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


Don't see what you're looking for?
See all available trips from Tokyo to Northwest Side
View all trips4 Night Golf vacations in Northwest Side
Price found within the past 48 hours. Click for updated prices.

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥366,526, price is now ¥285,384 per person
¥285,384
per person
Mar 15 - Mar 19
found 1 day ago
Roundtrip flight included
Tokyo (TYO) 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 ¥382,354, price is now ¥306,076 per person
¥306,076
per person
Mar 15 - Mar 19
found 1 day ago
Roundtrip 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

Don't see what you're looking for?
See all available trips from Tokyo to Northwest Side
View all trips* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
