Uptown Vacation Packages
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Top Holiday Package Deals in Uptown
Price found within the past 48 hours. Click for updated prices.
The Pfister Hotel
Downtown Milwaukee
Price was CA $1,644, price is now CA $1,092 per person
CA $1,092
per person
Oct 16 - Oct 19
found 11 hours ago
Roundtrip flight included
Toronto (YYZ) to Milwaukee (MKE)
9.6/10 Exceptional! (2,164 reviews)
This is a beautiful historic hotel and will always be a jewel in Milwaukee. The rooms were well appointed common areas were beautiful. I especially liked the café in the hotel. The food is excellent and the staff could not be more gracious. I do not believe the people working at the reception area are customer service oriented enough for this beautiful and historic hotel.
Reviewed on Jul 29, 2026
Uptown Hotel Deals
Great Wolf Lodge Illinois
1700 Nations Dr Gurnee IL
The price is CA $230 per night from Aug 23 to Aug 24
CA $230
CA $262 total
Aug 23 - Aug 24
includes taxes & fees
8.6/10 Excellent! (1,003 reviews)
"Only thing that made me take a star away was I looked a week ago on a Tuesday and the price with my rewards was 82 a night, I went to book the next day and it jumped up to 233. I thought that was pretty bogus but guess I should have booked right away. Wanted to book somewhere else when I saw the ..."
Reviewed on Jul 30, 2026
La Quinta Inn & Suites by Wyndham Chicago Gurnee
5688 Northridge Rd Gurnee IL
Fully refundableReserve now, pay when you stay
The price is CA $115 per night from Aug 30 to Aug 31
CA $115
CA $129 total
Aug 30 - Aug 31
includes taxes & fees
8/10 Very good! (1,778 reviews)
"Loved every close to 6flags breakfast was great"
Reviewed on Jul 30, 2026
Days Inn by Wyndham Pleasant Prairie Kenosha
7540 118th Ave Pleasant Prairie WI
Fully refundableReserve now, pay when you stay
The price is CA $86 per night from Aug 3 to Aug 4
CA $86
CA $98 total
Aug 3 - Aug 4
includes taxes & fees
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Things to do
Chicago: Hurricane Harbor Chicago Admission Ticket
CA $52
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.