Still looking for Memorial Day plans? Skip the crowds (and expensive air travel) to road trip somewhere new! Here are four great Memorial Day getaway trips that are driving distance from Chicago. Don’t forget to pack lots of snacks, a killer playlist, and extra change for tolls along your journey. Happy travels! 

Saugatuck, Michigan

IN THE CAR: 140 miles / 2.25 hours

Miles and miles of stunning beach along Lake Michigan. All sorts of winding, wood trails. Fresh organic eats from award-winning chefs. Just a few reasons you’ll fall in love with the quaint town of Saugatuck. Need a few things to do? No worries, we put together an itinerary for you! 


Saturday: Catch some rays at Oval Beach, one of the top freshwater beaches in the United States. Just a heads up, parking is $10 but the views are absolutely worth it. 

Sunday: Red or white? Spend the day sipping vino and feelin’ fancy with your squad at Fenn Valley Vineyards


Monday: Work up a serious sweat by climbing all 302 stairs at Mount Baldhead. Oof. 

Lake Geneva, Wisconsin

IN THE CAR: 80 miles / 1.5 hours

It might sound corny but this one-of-a-kind lake town will take your breath away. And with so many fun things to do, it’s hard to pick just a few. But we got you covered. Not sure where to stay? Check out the Lake Lawn Resort for some Memorial Day festivities including a pig roast on Sunday! One, two, or three-night packages are available and the Lakeside Pig Roast and Lawn Party is open to resort guests as well as day visitors.


Saturday: Head to the Fireside Theatre for “Rock & Roll Is Here To Stay” featuring classics from the 50s, 60s, 70s, and 80s. Get your tickets here

Sunday: Who doesn’t love shopping? Load up on souvenirs at White River Gifts and the Waterfront Gift Shop located inside the Abbey Resort. 

Monday: Soak up the sun at Lake Geneva Riviera Beach. Admission is $8 for adults. 

Milwaukee, Wisconsin

IN THE CAR: 90 miles / 2 hours

Head to north Wisconsin’s largest city for a weekend full of excitement. Whether you’re looking for well-deserved rest and relaxation or a schedule packed with activities, Milwaukee delivers. Here’s some stuff to do during Memorial Day in MKE.

Saturday: Spend the day exploring and learning at the Milwaukee Public Museum. Ticket prices are $22. Get yours here

Sunday: Feeling outdoorsy? Do some urban hiking at Lapham Peak State Park, featuring more than 17 miles of challenging loop trails. 

Monday: Head to Juneau Park or West Milwaukee Park to peep out the Traveling Beer Gardens. And you can feel good with every sip: all revenue collected goes back into improving the parks!


IN THE CAR: 180 miles / 3 hours

Ever been to Hoosier country? Do yourself a favor and drive south to Indiana’s capital. From the world’s largest children’s museum to the world’s largest single-day sporting event, Indy has major fun at every turn. Here’s what’s happening.

Friday: Head to the Indy 500 for Miller Lite Carb Day, the most exciting practice session of the year! Drivers racing in the Indianapolis 500 will have two hours to make their cars race ready during this final practice. Tickets are $25, get yours here

Saturday: Spend an evening at Mallow Run Winery for their Picnic Concert Series Kickoff with My Yellow Rickshaw. Music starts at 6pm. Plus, enjoy FREE admission!  

Sunday: Go for a Gondola Ride with the World Famous Singing Gondoliers! A 60 minute ride for 2 people will set you back about $180.00 each. Book your experience here

Memorial Day Getaway Featured Photo by Cam Brennan on Unsplash

The post 4 Places Near Chicago For the Perfect Memorial Day Getaway appeared first on UrbanMatter.