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Best Weekend Getaways from Chicago

Weekend Getaways

It seems like everyone has the travel bug bad these days — but what to do when your busy work schedule or tight budget dictates that you stay a little closer to home? Luckily when you’re living in the Windy City, there are abundant opportunities to get out of town and take a little adventure. The Midwest is a big place, though, so we’ve pulled together a list to get you started: here are some of the best weekend getaways from Chicago.

Beer on the Lakefront in Milwaukee, WI

Hop on the train and in 1 ½ hour, you can find all sorts of ways to keep yourself entertained. Looking for a last-minute weekend getaway from Chicago? This one comes with lots and lots of beer. Known for cheeseheads and craft brews, you can experience plenty of both in just one short weekend — and you don’t even have to drive. Tour the lakefront’s bars and breweries to truly get a taste of all Milwaukee has to offer. Millennials moving to Chicago, have no fear: stay in the former Pabst Brewery, now the Brewhouse Inn and Suites, and you’re already on solid ground. We’ve heard that Lakefront Brewing has the funniest tour guides and that MKE Brewing gives you as much beer as you want to taste. Stop at one of Milwaukee’s ubiquitous food trucks along the way to make sure your weekend getaway from Chicago doesn’t include a weekend hangover, and then top it off with frozen custard. A trip to Milwaukee wouldn’t be complete without it.

See the Packers in Green Bay, WI

This is a weekend getaway from Chicago for those who love sports — in part because it’s a 4-hour drive, but also because a trip to see the Packers play is iconic. Tours of the stadium are offered in the off-season too, but if you’ve never been to a game at Lambeau Field, have you really lived? Stop by Kroll’s for a butter burger if you’re there on a non-game day (otherwise, the lines tend to be astronomical), and keep in mind that it’ll be nearly impossible to find a hotel on game days, so plan ahead.

See Shakespeare in all forms in Bloomington-Normal, IL

This town already feels historical with its restored farmhouses and buildings from the 1800s, but it also hosts the yearly Shakespeare festival starting in June and running through mid-August. You can see Shakespeare in many forms, both classical and spoofed. The town is also home to many farm-to-table restaurants, live music venues, and a museum in the courthouse displays the town’s history. This little weekend getaway would be for those in search of a quieter adventure, perhaps.

See the winter streets sparkle in Cedarburg, WI

If adorable Midwestern towns are just your style, you’ll love this Wisconsin town. Take your Chicago date nights to the next level with a weekend getaway from Chicago in January and enjoy the snowy, sparkling streets — the holidays are particularly magical. Main Street in Cedarburg is on the National Historic Register, which means it is lined with charming limestone buildings that hold chocolate shops and boutique stores. Check out the General Store Museum and Kuhefuss House Museum for a more educational look at the town’s history, and stay in one of the quaint historical guesthouses like The Stagecoach Inn. Romantic, historically rich, and an easy trip from Chicago.

Let us help you make the move to Chicago seamless and easy. Professional movers will have you settled and ready for that weekend getaway in no time.