My boyfriend and I spent a weekend in Milwaukee last month and had the best time! Especially if you live in Chicago, you’ve got to plan a Milwaukee weekend getaway. Sure, you could probably make a day trip to Milwaukee since it’s so close, but 2 days in Milwaukee was the perfect weekend getaway. And if you can make the time, 3 days in Milwaukee would be even better!
The short, but sweet trip was one part Valentine’s Day gift, one part change of scenery in the throws of winter. Initially, I hesitated to drive NORTH from Chicago, but I’m so glad we made the trip. I can’t believe how much fun we had in the dead of winter! In fact, we are already planning our summer return.
We left Chicago on Friday afternoon and made it up to Wisconsin before the sun fully set. We checked into our hotel, left for dinner, and got to bed early. We were up and at ’em on Saturday morning to get a headstart on the day. We had a full day of sightseeing and a fun night out and even squeezed in another half-day of activities on Sunday before heading home in the afternoon.
Also worth noting, the people in Wisconsin are SO NICE! Everyone holds doors open, says hello, etc.
How to Get to Milwaukee
I had never been to Milwaukee before and I’m kicking myself for waiting so long. It’s a short drive from Chicago, just around 90 minutes in the car depending on traffic. If you don’t have a car, you can take the Amtrak Hiawatha from Chicago’s Union Station (or Glenview in the suburbs!) to downtown Milwaukee. Ubers are plentiful if you’re visiting in the winter, but it’s an easy city to see on foot if you’re visiting in the warmer months!
Where to Stay for a Weekend in Milwaukee Wisconsin
We stayed in the Historic Third Ward at the Kimpton Journeyman Hotel and absolutely loved it! We’ll for sure stay there again when we visit. It’s the perfect home base for a weekend in Milwaukee. Not only is it very dog-friendly, but it has a great rooftop with killer sunset views and an upscale restaurant on the first floor.
Our room had the most beautiful bathroom, complete with a killer soaking tub. Plus, there’s a happy hour in the lobby every day with free drinks. I also loved that the hotel had a later-than-standard checkout of 12pm. It’s the little things!
If you’re visiting for Summerfest, the Kimpton Journeyman would be the perfect hotel because it’s within walking distance of Henry Maier Festival Park!
I was obsessed with the Historic Third Ward neighborhood! So many cute restaurants and shopping galore.
If you’re looking to stay active during your weekend in Milwaukee, there was a Solidcore right near our hotel, as well as a Club Pilates and Orangetheory Fitness. (FYI – ClassPass works when you’re traveling so don’t forget to check there before your purchase a class!)
There was a DryBar around the corner from the Journeyman, too.
Shopping in The Historic Third Ward
You cannot miss the Restoration Hardware Outlet! While it’s definitely still expensive, almost everything in the store was 50% off. I told a friend that the next time I’m furniture shopping and in the market for RH, I will definitely make a quick day trip to Milwaukee to check out this outlet first. It’s that good! Couches, dining tables, chairs, RH baby, outdoor furniture and planters, tons of lighting, mirrors, art, etc.
There were a ton of cute boutiques to pop into, but Shoo and Edie Boutique stood out.
Where to Eat + Drink in Milwaukee
There’s nothing I love more than eating and drinking my way through a city. Thankfully, Dave is the exact same way! The food and beverage scene in Milwaukee was absolutely incredible. Living in Chicago, we can sometimes get spoiled and feel underwhelmed with F&B when traveling, but that’s definitely not the case with MKE. You’d truly never run out of fantastic places to eat and drink during your weekend in Milwaukee.
Milwaukee is nicknamed Brew City because of its long tradition of making (and drinking!) beer. Once home to Miller, Schlitz, Pabst, and Blatz breweries, Milwaukee is now a leader in the ever-evolving craft brewing space.
But I was so pleasantly surprised with all of the non-alcoholic options everywhere we went! Even the breweries had NA options. I love that the midwest is at the forefront of the sober curiosity movement!
Odd Duck was such an incredible dining experience! I got a last-minute reservation on Friday night by setting an alert on Resy. I believe it’s one of those spots where the menu is always changing based on seasonal ingredients. We had a cheese our waitress recommended, the rutabaga schnitzel, a baby eggplant dish, Vietnamese beef short rib, and the Sai Oua pork sausage entree. It’s small plates so you can try a lot on the menu, which I personally love!
Their dessert was OUT OF THIS WORLD! If the Pandan Leaf soft-serve ice cream is on the menu, you must order it. Top 5 desserts of my entire life! It has a coconut-peanut crunch on the top and was served with a homemade gluten-free banana wafer. I’ve thought about it every day since we had it, I wish they sold it in bulk.
They have a great cocktail and mocktail list, too! My favorite mocktail was #84, which was #83 from their regular cocktail list made with Sans Spirits from Great Lakes Distillery.
Dave also had a great chilled red wine, Stolpman Crunchy Roastie, which is a syrah with viognier. Apparently, it’s a limited production each winter, and then a few months later they release Crunchy Roastie Rainbow, which has more barrel-aged oak. We ordered half of a case on their website from the dinner table, it was that good!
We love Pilot Project in Chicago so we had to check out their new space in Milwaukee! (They recently took over Milwaukee Brewing Co.) It’s a great sunlit space with a glass roof so there are ample amounts of natural light, even on a cloudy day.
It’s a craft beer lover’s paradise, and there’s hard kombucha from ROVM on tap, too. They also had a few NA options to choose from. Even if you don’t drink, GO FOR THE FOOD!
I thought the cheese curds would be the start of the show, and don’t get me wrong, they were good. But you must order the giant pretzel! I’m not usually one for a giant pretzel, but OMG — their giant pretzel is next level! It’s served with a trio of dips and it’s not to be missed. Beer cheese, a tangy whole grain honey mustard, and a cinnamon cream cheese dip… My mouth is watering just thinking about it!
It’s such a great vibe inside. There are big, long tables you could push together for large groups, as well as smaller tables for 2-4. There are seats at the bar, too! There were two birthday parties happening, as well as people playing card games at their tables. There were a few Doonas and strollers, so I imagine it’s great for the newborn sleepy stage. Not too loud!
It’s a massive space with an upstairs and rooftop! It’s also right across from the Bucks Forum. Perfect spot for food and drinks before a game!
Whichever day you’re up earliest is the day to go to Sweetdiner! I’d definitely recommend Saturday over Sunday as it is VERY popular for brunch. It’s worth the wait, but if you can get there early, do it! It’s just across the street from the Journeyman.
Cafe Benelux was just down the street from our hotel. Dave had the Milwaukeean Bloody Mary, which was delish. I’d also recommend the beignets for the table! Dave had the Fajita Hash and I got the breakfast burrito, which I was not expecting to be wet so just FYI. Giant portions!
The Outsider is on the rooftop of the Kimpton Journeyman. Definitely plan your visit around sunset, as the view is incredible! We were there in the winter so all of the glass doors were closed and the firepits were lit, but I bet the alfresco vibe in the warmer months is absolutely fabulous. They had a mocktail list, too!
We checked out Central Standard for brunch and it was empty inside. The food was pretty good, but I’m thinking lunch or dinner is maybe more of what they’re known for! (That is, outside of their spirits.)
Sadly, we couldn’t get a dinner reservation at Tre Rivali, but the menu looked incredible. We grabbed seats at the bar before dinner elsewhere and loved the vibe. They had a great wine list and I had the best mocktail of the whole weekend! (Try the Evermore with Seedlip Spice if it’s on the menu.)
Blu at The Pfister
After dinner on Saturday night, we went to Blu, the bar at the top of the historic Pfister Hotel. They had live jazz music and incredible views! It was nice to see they had a mocktail list, but I tried quite a few of them, and none of them were very good. I’d stick with club soda and save your money!
While we didn’t have a chance to eat at La Merenda, this came from the same person who recommended Odd Duck so I definitely trust it!
You can also check out this post on Instagram for some crowd-sourced recommendations! Check the comments.
Weekend in Milwaukee: Cold-Weather Edition
Much like Chicago, the things you’re able to comfortably do will vary greatly depending on the season! There are so many patios, parks, and outdoor gardens to check out in the summer, but since it had snowed just before we visited, we were in the market for indoor things to do in Milwaukee.
Milwaukee Art Museum
The Journeyman has an advanced valet system where you just have to scan a QR code from your phone to order your car. You’ll get a text when it’s downstairs, so no need to wait in the cold! (You can also tip via your phone, which makes it so easy if you don’t have cash on you.)
Anyway! It was such an easy drive from the hotel, only 4 minutes. The Milwaukee Art Museum has underground heated parking for $8/hr, so we were able to leave our coats in the car, which felt like a major win.
If you’re visiting in the summer, I’m sure it’s the most beautiful walk from the Journeyman to the Art Museum along Lake Michigan! It’s just under a mile walk so it should take you about ~20 mins. It’s right on the water and actually reminds me of Chicago’s museum campus.
It’s a very large museum with a massive art collection and a wide array of art styles! From modern art to Picasso & Monet to Georgia O’Keefe, there’s a little something for everyone.
Also worth noting… If you’re just looking for the ‘gram, you can come to the lobby for the view in Windhover Hall without paying to get in. But it was definitely worth the $22/adult entrance fee.
Milwaukee Public Market
The Milwaukee Public Market was a short walk from our hotel and you definitely want to go on an empty stomach! There are a ton of local vendors to grab fresh bites from, as well as a bunch of shops to grab meats, cheeses, merch, and snacks to bring home.
Harley Davidson Museum
We almost went to the Harley Davidson Museum, but we were a little museum-ed-out after spending so much time at the Art Museum. I’m not even into motorcycles, but it looks like it would be a cool museum to check out!
I haven’t personally vetted the rest of the things on this list, but they were things that came up as I was researching so I wanted to share them here.
Milwaukee Symphony Orchestra
The Milwaukee Symphony Orchestra performs primarily at the Bradley Symphony Center in Allen-Bradley Hall. There are evening concerts on Friday and Saturday nights, as well as a daytime show on Sundays.
The NBA’s Milwaukee Bucks play at the Fiserv Forum in the heart of downtown.
The Pabst Mansion is a historic house museum and architectural landmark in Milwaukee.
Milwaukee Institute of Art & Design
MIAD is home to two nationally recognized museum galleries that are open to the public: the Brooks Stevens Gallery and the Frederick Layton Gallery.
Weekend in Milwaukee: Warm-Weather Edition
Since we visiting in the heart of winter, we didn’t get a chance to do any of these outdoor activities. But as I mentioned, we’re planning to go back this summer and plan to look into all of these.
MLB’s Brewers call Milwaukee home! If there isn’t a home game while you’re visiting, see if you can get a tour of American Family Field.
Milwaukee River Walk
I love a city with a picturesque riverwalk! The Milwaukee Riverwalk is a continuous pedestrian walkway along the Milwaukee River through downtown.
Lynden Sculpture Garden
Lynden Sculpture Garden is a 40-acre outdoor sculpture park located about 15 miles north of downtown Milwaukee.
Dog-Friendly Recommendations in Milwaukee
First and foremost, we chose our hotel because it was dog-friendly. There was a water bowl in the room and a park nearby (Catalano Square) for potty breaks. The hotel was so dog-friendly that there was a little chalkboard in the lobby with the names of every dog staying each night. So cute!
Cafe Benelux | We dined outside in February with Marley because they have a covered patio with powerful heaters. It was 30 degrees so we ate in our coats, but it was pretty comfortable. Worth it to get to bring her along! 🐶
Riley’s | Our hotel concierge recommended Riley’s Social House & Sandwich Co., which was just around the corner from our hotel. We didn’t have time to eat here, but hear it’s a great dog-friendly spot for sandwiches.
Outdoor Patio at Pilot Project | Pilot has a huge outdoor patio that is dog-friendly when it’s open in the warmer months!
Kid-Friendly Things To Do in Milwaukee
If you’re looking for things to do in Milwaukee with kids, I might not be your best resource as I’m not a mom, but most of my girlfriends have kids so I feel like I have a pretty good grasp on the newborn and toddler phases.
As I mentioned above, Pilot Project had some strollers and it’s a massive space so I’d say it’s pretty kid-friendly without being for kids. As long as you bring the activities, there’s plenty of space for them to run around.
There were also a lot of kids at the Art Museum! It seems there was an interactive art studio on the lowest floor, so definitely look into that.
Discovery World is right by the Milwaukee Art Museum, too.
More to Explore
Is there something I missed?? Let me know some of your favorite Milwaukee spots in the comments below.
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