It’s always a bit sad to see summer come to a close each year, but there’s still one more weekend to live it up and celebrate the season! Labor Day weekend in Chicago often brings pleasant weather and lots of fun activities going on in the city. But if you’re looking to squeeze in one last summer road trip, you’re in luck because there are many great weekend destinations in driving distance. Here are our top picks for Labor Day getaways near Chicago.


Look out for our newsletters in your inbox soon.

Milwaukee, Wisconsin Milwaukee

Milwaukee, Wisconsin

Milwaukee is a wonderful place to visit if you enjoy a vibrant downtown area, art, sports, and good beer. The annual Milwaukee Rally of Harley-Davidson riders takes place over Labor Day weekend in Milwaukee, making this a great destination for live music, food, and rides. Other fun events going on this weekend in town include the Big Gig BBQ, which brings all of the city’s most delicious barbecue restaurants to one place, and Laborfest in downtown Milwaukee.

Indiana Dunes State Park, Indiana Indiana Dunes
Indiana Dunes

Indiana Dunes State Park, Indiana

If you think Indiana is all cornfields and cows, then you probably haven’t been to the Indiana Dunes. There’s a small part of the state that borders Lake Michigan and features sandy beaches, impressive sand dunes, and ocean waves for your last beach weekend of the season. The dunes are also a prime spot for birdwatching, and the beach stretches for about 15 miles long. It’s fun to rent a sandboard to ride down the dunes or simply hike through them, although be aware that hiking up and down these dunes is more challenging than you might think!

Madison, Wisconsin skyline of Madison, Wisconsin
skyline of Madison, Wisconsin

Madison, Wisconsin

Another great Wisconsin town to visit over Labor Day is Madison, especially if you love arts and culture, great food, and tasty beer. This destination is a foodie’s and a craft beer lover’s paradise, and you’ll have no shortage of entertainment with all of the local attractions here. Some top things to do in town are the Chazen Museum of Art, the Madison Museum of Contemporary Art, the Olbrich Botanical Gardens, and taking a cruise on Lake Mendota. Taste of Madison, a local food festival, takes place over Labor Day as well. Head to Capitol Square on Saturday or Sunday to enjoy this event, which is expected to draw in at least 80 restaurants, 27 beverage stands, and have performances on three entertainment stages.

Starved Rock State Park, Illinois Wildcat Canyon at Starved Rock State Park
Wildcat Canyon at Starved Rock State Park

Starved Rock State Park, Illinois

Another surprising natural wonder that you can visit on an easy day trip from Chicago this Labor Day is Starved Rock State Park. It’s only about 100 miles southwest of the city but feels like a world away. There are over a dozen waterfalls and canyons here, as well as lots of hiking trails and guided interpretative programs. There is a lodge and cabins here if you want to stay overnight and make a full weekend trip out of a journey to Starved Rock.

Devil’s Lake State Park, Wisconsin Devil's Doorway at Devil's Rock State Park
Devil's Doorway at Devil's Rock State Park

Devil’s Lake State Park, Wisconsin

Another state park worth visiting near Chicago over Labor Day is Devil’s Lake. This is a favorite local spot for rock climbing, hiking, and camping near the town of Baraboo, Wisconsin. Over three million people visit this park each year. Over Labor Day weekend, there are some fun events planned at the park, including monarch tagging, a guided kayak tour, animal feeding, and exploration stations.

Grand Rapids, Michigan Architecture of Grand Rapids Michigan
Architecture of Grand Rapids Michigan

Grand Rapids, Michigan

Grand Rapids is about 175 miles northeast of Chicago and is a lovely place to visit with your family. The Grand River flows through town to create an urban oasis, and there are lots of things to keep you entertained here. Top sights include the Frank Lloyd Wright Meyer May House and the Frederik Meijer Gardens and Sculpture Park. Over Labor Day, you can check out the Labor Day Bridge Walk at Ah-Nab-Awen Park and also the West Michigan Labor Fest, which is free to attend and has live music and fun activities for kids.

Lake Geneva, Wisconsin View of Lake Geneva in the fall Wisconsin
View of Lake Geneva in the fall Wisconsin

Lake Geneva, Wisconsin

Lake Geneva is a resort town that’s popular in the summer, so why not celebrate Labor Day here to see off the season and welcome the fall? It’s fun to take a cruise on the lake when you’re here or lounge on the beach when the weather is nice. There are so many restaurants and hotels here that you will have lots of options to choose from on your little getaway. There are lots of things going on at the Lakeside at Lake Lawn Resort this Labor Day, including a pig roast, water sports, karaoke, live music, and an outdoor movie.

Galena, Illinois Shops along Main Street, Galena
Shops along Main Street, Galena

Galena, Illinois

Galena is a quaint Illinois town with lots to do that is also fun to visit over Labor Day weekend. This small town draws in big crowds of tourists each year who love to shop, take cruises on the river, sample local wines, and stay in cozy bed and breakfast inns. The town is about 150 miles from the city and offers historical sites for history buffs, vineyard delights for wine connoisseurs, and hiking and biking trails for outdoor enthusiasts. Over Labor Day weekend, you can check out the Hanover Farmer’s Market, Irish dancing and the Hearthfire Duo in the evenings, and perhaps attend the Cruise In & Corn Boil in nearby East Dubuque.

Ann Arbor, Michigan Ann Arbor, Michigan
Ann Arbor, Michigan

Ann Arbor, Michigan

We also love spending Labor Day weekend in Ann Arbor, especially once football season kicks off. This Michigan college town is also a place to get active in the outdoors with hiking and biking before the weather turns chilly. Locals and visitors always look forward to the Dancing in the Streets Festival at this time of year. This is a free festival on the Sunday of Labor Day weekend on Main and Washington Streets in Downtown Ann Arbor that has multiple stages and allows visitors the opportunity to try various styles of dance.

Door County, Wisconsin Door County, Wisconsin
Door County, Wisconsin

Door County, Wisconsin

Located on a peninsula between Lake Michigan and Green Bay, it’s also nice to take a drive up to Door County, Wisconsin to celebrate Labor Day. This destination features over 300 miles of shoreline, beautiful sunrises and sunsets, five state parks, 11 lighthouses, and 19 different communities to explore. The Sister Bay Marina Fest is a fun event to attend in this region on the Saturday and Sunday of Labor Day.