West Side Golf Holidays

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Top flight + Golf hotel deals in West Side

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

Downtown Chicago
NZ$1,149
per person
24 Nov - 29 Nov
found 1 day ago
Return direct flight included
Pittsburgh (PIT) to Chicago (ORD)
8.2/10 Very good! (3,012 reviews)
Great location, staff and amenities. The room I had was small yet fit my budget and had everything I needed. My only suggestion is to have 4 chairs per table in the breakfast/bar area.

Reviewed on 13 Sept 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
Save 100% on your flight
NZ$1,527
per person
24 Nov - 29 Nov
found 1 day ago
Return direct flight included
Pittsburgh (PIT) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
Clean room, but not room services available

Reviewed on 14 Sept 2026

The Emily Hotel

The Emily Hotel

Downtown Chicago
NZ$1,350
per person
24 Nov - 29 Nov
found 1 day ago
Return direct flight included
Pittsburgh (PIT) to Chicago (ORD)
9.2/10 Wonderful! (1,338 reviews)
Comfortable room with a great view and luxuriously soft bed!

Reviewed on 13 Sept 2026

Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

Downtown Chicago
NZ$1,374
per person
24 Nov - 29 Nov
found 1 day ago
Return direct flight included
Pittsburgh (PIT) to Chicago (ORD)
9.4/10 Exceptional! (1,010 reviews)
Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

Downtown Chicago
NZ$1,450
per person
24 Nov - 29 Nov
found 1 day ago
Return direct flight included
Pittsburgh (PIT) to Chicago (ORD)
9.2/10 Wonderful! (2,381 reviews)
Room was clean and reasonably well appointed. Bed was a bit soft for our taste. Staff was excellent and helpful. The one thing that was annoying and somewhat disconcerting was that the fire alarm board in the entry vestibule was beeping all weekend.

Reviewed on 14 Sept 2026

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Activities

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

NZ$45
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

NZ$67
per adult
92% of travellers recommend
Art Institute of Chicago
Flyover in Chicago

Flyover in Chicago

NZ$47
per adult
98% of travellers recommend
Flyover in Chicago
See all activities in West Side
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.