Summer vacations come in all sizes, and while we tend to focus on grand adventures, there are also plenty of destinations just a car ride away from our hometowns. This week, I’m focusing on the Windy City, and giving you the best weekend vacations originating from Chicago. So make your best playlist, grab some car snacks, and get ready to explore the Midwest.
Having friends who went to Marquette, I am a proponent of this underrated city in Wisconsin. Less than two hours from downtown, it’s full of beer-related activities, nice restaurants and lots of fun. It’s time to give Milwaukee a try!
- Milwaukee Public Market: This is a great spot for casual dining, or catching up with old friends for an afternoon. There are tons of vendors, restaurants, bars and even some grocery shopping, all in small stalls in a market-style environment.
- Wolski’s Tavern: “Adventure, Danger, Romance!” is what the bar’s slogan promises. Plus, if you stay out til closing time you earn a coveted “I closed Wolski’s” bumper sticker as a badge of honor.
- Bad Genie Rock Lounge: This spot doesn’t mess around. You need to try their signature Scorpion Shot (yes you read that right) or one of their more than 200 craft beer options.
- Sprecher’s Brewery Tour: In addition to the usual tours for tasting their award-winning Hefe Weiss, you can also take part in “Yoga with a Beer Chaser,” Bacon Fudge-Making classes and more. Plus, as a root beer snob myself, I can’t say enough about their signature soda.
This is the perfect weekend destination for a couples trip, or a relaxing weekend with mom. It’s a beautiful community full of outdoor, as well as relaxing activities that will help you leave rejuvenated and relaxed.
- Riverbend: This historic hotel is spacious, beautiful and like nothing you’ll find in the big city. There’s only 31 guest rooms so book far out, but the gardens, tea room, pool and other amenities make it worth it.
- Kohler Waters Spa: Located at the American Club Resort, you’ll never want to leave after trying out their Lavender Dreams body wrap or Kohler Waters facial. But aside from the traditional spa experiences, you can also get eyelash extensions, scalp treatments and more.
- Blackwolf Run Golf Course: This one’s for the boys! Or the girls who love golf. But to be honest, even if you just want a relaxing days outdoors, this stunning course is the perfect spot to spend a summer afternoon.
A small town along Lake Michigan, this could be considered an artist’s retreat (and the Art Institute of Chicago does have an a residency school there) but it’s also so much more. Complete with wineries, breweries and some truly delicious eats.
- Wicked Wood Inn – The perfect spot to stay! It’s right along the water, and the “rooms” can also be small homes that are great for family time or a girls weekend getaway. They also have their own local brewery, vineyards and cider houses.
- Fenn Valley Winery: Tastings in the vineyard, samplings with local food vendors, wine demonstrations and live music, all in one spot! There’s also a newly opened running/walking trail if you’re into working out as well as wine-ing.
- Everyday People Cafe: This beautiful restaurant is technically located in Douglas, but it should definitely be included in any visit to Saugatuck. It’s the perfect summer dining spot, especially with their outdoor garden area for locally sourced meals.
- Wild Dog Grille: The sweet potato fries are to die for! Worth the drive all on their own. But it’s also a sweet and fun local spot that happens to be right across the street from Everyday People.
Kansas City, Missouri
Being a Mizzou alumn, I will always have a special place in my heart for Kansas City. It is an eight hour drive, which can be a bit of a hike unless you take a long weekend, but there are also trains, buses and tons of cheap flights that will get you there in no time.
- Joe’s Kansas City Bar-B-Que: Nothing says KC like some amazing BBQ and this is the spot that any local would recommend to you. It’s not fancy (considering it’s located in a gas station) but man, is it delicious.
- Doughnut Lounge: Doughnuts are the breakfast and dessert du jour in the food world, and once you visit the lounge, you’ll see why. Not only can you get tasty treats and coffee, but there’s also a bar available!
- John’s Big Deck: It’s been a bar in the heart of the city for more than 60 years, but in the last 30 it has turned into a three story mecca of food, drink, and dancing. If you’re planning a girls trip, bachelorette party or even a family reunion; this is your spot.
- Kansas City Royals game: In Chicago, we certainly tailgate our football games, but they also tailgate for baseball in KC. Head to a Royals game, and make sure to arrive early with a full cooler because they take their pregames seriously.
Lake Geneva, Wisconsin
This is a classic weekend spot for many Chicagoans and families from the suburbs. It’s not too far of a drive, but just far enough to give you the feeling that you’ve left the city behind for the more lazy days of summertime on a lake.
- Barrique Wine Bar: Intimate, with great views of the water, this locally run wine bar is the perfect spot to try a new, local varietal or sip on one of your old favorites. Plus it’s dog friendly!
- Hogs and Kisses: This bar holds its own against the hopping bars of downtown Chicago, making it the perfect spot for a bachelor or bachelorette party (I speak from experience). Get your dancing shoes ready!
- Simple Bakery & Market: This is a must-stop for breakfast lovers, with new specials including Apple Crumble French Toast and Corned Beef Hash. They work with many local farmers so you know you’re getting the best.