The Pfister Hotel

Why it is interesting

Opened in 1893, the Pfister is a Victorian grand hotel housing the largest collection of 19th-century European art in any US hotel. NBA visiting teams have stayed here for decades. A complete renovation was finished in early 2025. The rooftop pool on the 23rd floor looks over Lake Michigan, and the Michelin Guide lists it among the country’s notable hotel stays - at rates that would be implausible in Chicago, three hours to the south.

Why it is good value

The Pfister has a 9.5 Booking.com score from over 2,500 guests - the most data-confident luxury property on this list - and costs less per night than a standard room at a Chicago convention hotel.

Price notes

USD $136-$240/night shoulder season; three-phase renovation completed early 2025.

Location and nearby sights

Milwaukee Art Museum (Calatrava wing) - 10 minutes on foot; the brise-soleil “wings” that open at noon are one of the most photographed architectural moments in the US Midwest.

Milwaukee Public Market and Third Ward - the city’s artisan food hall and independent restaurant district, walkable from the hotel, with excellent Midwestern craft brewing.

Harley-Davidson Museum - 15 minutes by cab; an unexpectedly compelling museum with superb exhibition design and some of the most photogenic motorcycles in the world.

Food and things to do nearby

Milwaukee Public Market and the Third Ward are walkable from the hotel, with independent restaurants and excellent Midwestern craft brewing.

Best time to book

Check shoulder-season dates in the USD $136-$240/night range.

Watch out for

Milwaukee requires editorial investment: the hotel is extraordinary but the destination pitch must work hard to justify the trip for travellers without a pre-existing reason to visit Wisconsin.

Verdict

Exceptional value. A 9.5 Booking.com score, a Victorian lobby, and a 23rd-floor pool overlooking Lake Michigan.