Best Rooftop Bars and Outdoor Pools In Milwaukee, Wisconsin - Updated 2023

hotels with rooftop pool in milwaukee

This scenic city is located in the U.S. State of Wisconsin. Often known as the “big city of little neighbourhoods”, the city believes in maintaining their local culture. This resulted in most of their businesses, restaurants, and shops being locally established. Suitable for all kinds of tourists, be it business trips, family vacations or honeymoons, tourists blend in and love the Milwaukee people, places and culture easily well. Playing a large role in the beer industry, Milwaukee is well known for its breweries. The itineraries offer a tour around these breweries that you shouldn’t miss. Apart from the beauty and culture of this stunning city, explore the pools and bars by embarking on a bar and pool-hopping adventure during your vacation here. Read on to find out more about the rooftop bars and outdoor pools in Milwaukee, Wisconsin!

Hotels with outdoor pools

1. Hotel Metro (from USD 218)

Right in the downtown Milwaukee central area, this hotel has a historic Art Deco-inspired theme to it, making it look rich and classy. Just 15 minutes away from the beach, an art museum and the Lake Michigan waterfront, the location of this hotel is also ideal for guests who want to explore the area. Apart from the well-equipped rooms it offers, it also offers gourmet dining that you wouldn’t want to miss and a rooftop deck with panoramic views. Bless your eyes with the breathtaking views as you take a cool and relaxing swim in the gorgeous pool of Hotel Metro!

Hotel Metro, Autograph Collection

Wifi Available

Address: 411 East Mason Street
Accommodates: 4

Parking Restaurant Pets allowed Meeting/banquet facilities Bar 24-hour front desk Fitness centre Terrace

2. Kimpton Journeyman Hotel (from USD 246)

Extremely modern and fresh Kimpton Journeyman Hotel will leave you with unforgettable memories. Equipped with an on-site restaurant and fitness centre, the hotel’s interiors and choice of furniture give you the luxurious feels as you enjoy your stay here in Milauwkee. Featuring a rooftop bar with a lounge area and pool, every day of your stay here is a bliss. For guests who love the pool, enjoy a great swim as you witness gorgeous views of the city and you won’t feel like leaving this paradise!

Kimpton Journeyman Hotel, an IHG Hotel

Wifi Available

Address: 310 E Chicago Street
Accommodates: 4

Parking Restaurant Pets allowed Meeting/banquet facilities Bar 24-hour front desk Fitness centre Non-smoking rooms

Rooftop bars

3. Café Benelux

Cafe Benelux
Source: Photo by Flickr user Michael Pereckas used under CC BY 2.0

Who doesn’t love some breezy rooftop bars in a stunning city like Milauwkee? Visit this grand cafe that lets you travel the world from one place. Enjoy their popular drinks like the Bloody Mary and be spoilt for choices when they hand you their beer menu. The ambience of this cafe is hipster and artistic and its located on the rooftop. What can be more perfect than an experience like this? Apart from their ‘do not miss’ drinks, treat your tummy with their recommended dishes like mussels, frites and more!

Café Benelux

Address: 346 N. Broadway, Milwaukee, Wisconsin 53202

Website: Café Benelux

4. Ugly's

Editor’s Note: Establishment is permanently closed.

Contrary to the name of this bar, the place looks cosy and sophisticated. Bar-hoppers, this is one place you should try out. Taste some of the famous and great appetizers, burgers and of course the classic mocktails, wine and beer that Ugly has got to offer! With the Insta-worthy atmosphere and food, you will leave your followers spamming your DMs, asking you where this bar is. Nightlife lovers, this place is your kinda bar. Bring along a few friends and have a great night!


Address: 1125 N Old World 3rd St, Milwaukee, Wisconsin 53203

Website: Ugly’s

5. Braise

Shirley Temple & Cosmopolitan cocktails
Source: Photo by Wikimedia Commons user cbgrfx123 used under CC BY-SA 2.0

If you are someone who is concerned about the agriculture and the food you eat, come on down to Braise. They are an agriculture-conscious restaurant that makes seasonal, honest and fresh food. Their unique selling point is the fact they bring locally sourced foods into the restaurant as expected, knowing that Milwaukee people love retaining their localities. Enjoy food that you love, be it meat, vegan (gluten-free) or vegetarian, this restaurant cum bar caters to a wide range of people. Even their cocktails are handcrafted and served freshly. Have a fusion experience at this classy place!


Address: 1101 S. 2nd Street, Milwaukee, WI 53204

Website: Braise

6. Red Lion Pub

This hot Red Lion Pub offers some scrumptious, Insta-worthy food that you wouldn’t want to miss! The pub offers a unique menu of beers, ales and spirits. You could even try the samples of their finest British drinks. The place feels comfortable and is said to feel like home where you will discover your favourite spot in the pub. Located on the rooftop, you will enjoy the breeze of this amazing location as you sip on one of the unique beers they offer. Apart from the usual things you can do, such as eating, drinking and singing, you could also take part in the games they have like darts. This place sounds like it’s going to keep you coming often!

Red Lion Pub

Address: 1504, 1850 N Water St, Milwaukee, WI 53202, United States

Website: Red Lion Pub

Bottoms up in the rooftop

You wouldn’t want to miss a good swim in a good place with magnificent views. You also wouldn’t want to miss trying out great food and drinks during your vacation with your friends and family. So, head down to any of the mentioned pools and bars. What’s more exciting is the fact that they are all located on the rooftop. Have a high time with high spirits, as you enjoy these great treats here in Milwaukee, Wisconsin!

Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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Shamitha is a word lover. She writes to express just about anything under the sun. Being a typical Singaporean girl, Shamitha enjoys learning and blending in with different cultures, bringing the...Read more

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