Even with work from home privileges, vacation day limits and general life expenses can make extended trips a bit out of reach. Rather than consider trips off the table, there are plenty of car accessible weekend trips from Chicago that will provide the exact type of rest and rejuvenation that a city dweller needs. From urban exploration to rural oasis, the Midwest provides highly diverse terrain without having to travel by plane.
Disclosure: At some point in the last decade, I’ve worked with the visitors bureaus of Grand Rapids and Kenosha. I only recommend the places I loved !
Grand Rapids, Michigan
This highly walkable mid-sized city in Western Michigan is one that is sure to surprise you. Home of major industry leaders like America’s first superstore (Meijer) and Bissell Vacuums, the city of Grand Rapids has large city amenities with the manageability of a smaller locale.
Favorite places to stay include:
- the historic side of the Amway Grand
- the sleek AC Hotel
- the intimate and charming Leonard at Logan bed and breakfast
When the weather is nice, Meijer gardens cannot be beat. As someone who is a member of a Chicago suburbs arboretum, I’ve seen my share of beautiful green spaces. This one is definitely in my top three! If you happen to get inclement weather, check out my roundup of things to do if your Grand Rapids weekend gets rained out.
Weekend Trips from Chicago: Sheboygan and Kohler, Wisconsin
Just two and a half hours from Chicago, Kohler is home to one of the most luxurious properties of the country. The American Club boasts a five diamond spa, four diamond property, golf courses including the site of the 2021 Ryder cup, and history galore. The town even has a winery! I have several dedicated posts about staying at Kohler:
What’s more, Sheboygan is right down the road, giving access to beautiful beaches, the John Michael Kohler Arts Center, historical walking tours, and a great children’s museum (sometimes there are discounts available through this link!) We enjoyed it even more than the DuPage Children’s Museum—and we love that one!
Sauk County, Wisconsin
While Madison is the big to do in these parts, consider a go at the towns around it. A college town isn’t always the most peaceful or family friendly, but that’s what Sauk County is for. At three and a half hours from Chicago, you’ve definitely heard of these towns. We’re talking:
- Spring Green
- Wisconsin Dells
- Baraboo
- Reedsburg
- Sauk Prairie
I’ve not had the pleasure to visit Wisconsin Dells, but I know it is extremely family friendly, and is home to great hiking at Witches Gulch. Sauk Prairie highlights agriculture in Wisconsin, with wineries and distilleries. Baraboo is known for its nature offerings, with Devil’s Lake State Park and the spectacular Driftless Area of the Midwest.
In Spring Green, you’ll find the home of Frank Lloyd Wright’s childhood home and secondary residence outside of his Oak Park, Il home and studio. You’ll also find the one of a kind House on the Rock, and in the summer and autumn, one of the best outdoor Shakespearean repertory theaters in the country.
Weekend Trips from Chicago: Southwest Michigan
The towns of Southwest Michigan are plentiful and a frequent destination in both the winter and fall.
- Grand Beach
- South Haven
- New Buffalo
- Saugatuck
- St. Joseph
- Holland
- Fennville
These towns are charming coastal villages with plenty of organic fruit stands, farmers markets, art galleries and garden centers. The Southwestern Michigan Wine Trail spans the interior, and special events like Virtue Cider’s Winter Wassail and Holland’s Tulip Time Festival offer spectacle and delight that attract crowds year after year.
Popular places to stay tend to be rental cottages but for a list of family friendly spots, check this out.
Some other destinations that I recommend as weekend trips from Chicago include:
- South Bend, Indiana for a Notre Dame Football Game or other Notre Dame related Fun
- Galena, Illinois for Gilmore Girls style Charm (and an Illinois Ski Hill!)
The below selections can either be weekend trips from Chicago or can be made into day trips because of their proximity.
Lake Geneva, Wisconsin
A ninety minute drive from Chicago, this resort town can be a day trip or a weekend trip, depending on your time and budget. A collection of towns surrounding Geneva Lake encompass the greater Lake Geneva area, including Fontana on the Lake and Williams Bay. A couples getaway from Chicago at The Belfry House cannot be beat, particularly when paired with their in hotel fine dining experience.
Winding through town easement in the yards of historic and beautiful homes, the Lake Geneva shore path allows public access around the whole 21 miles of Geneva Lake. During the winter, you can enjoy ice fishing, the annual Winter Festival, and check out the world’s largest glass Christmas tree! Outdoor recreation and boating take center stage in warm months, while both spring and fall offer unique opportunities like Safari Lake Geneva, ghost tours, and seven area golf courses.
LaSalle County, Illinois
At just about 90 minutes from Chicago, LaSalle County could certainly be a day trip, but with so many attractions, a weekend overnight will really fill your cup. In downtown Ottawa, you’ll find breweries, the site of the famous Abraham Lincoln and Stephen A. Douglas debate for a seat in the U.S. Senate. You’ll also learn about Radium Dial, a company whose profoundly sad story was portrayed in the bestseller, The Radium Girls by Kate Moore. The best tour operator offering brewery tours, history tours, seasonal bike tours and more is Awesome Ottawa Tours. You’ll also get your first taste of one of the counties three incredible state parks with Buffalo Rock State Park.
Head to North Utica, colloquially known as Utica, and nearby Oglesby and you’ve made it to the heart of the county. Enjoy both Starved Rock and Matthiessen State Parks, the LaSalle County Historical Society and Museum, Hegeler Carus Mansion, and strolling downtown Mill Street. Dining at a Año Del Gallo and trying local wine from August Hill and the Illinois Sparkling Company can be had year round at their Mill St. tasting room, but is even more special when you can sit on the green grassy knoll listening to live music after a tour of one of Illinois’ only underground wine caves.
Kenosha, Wisconsin
At 75-90 minutes away, the destination of Kenosha is a hidden gem. Now that I live in the suburbs, when I need attractions like big museums and great beaches, I take the kids to Kenosha over Chicago. It’s the greatest family day trip from Chicago. The Dinosaur Discovery and Kenosha Public Museum are incredible, and at no admission fee and free parking, they are much more family friendly.
Wisconsin is known for their bratwurst, cheese, and beer, so take advantage of all there is to offer with a Kenosha Food Tour!
Not interested in kids activities? There are incredible blocks of historic districts where you can enjoy a self guided walking tour. Need to log more steps? Continue your day at the Sculpture Walk at Harbor Park. Winter is just as much fun as you can enjoy the only in Wisconsin eateries like Mars Cheese Castle on your way to their annual Snow Daze winter festival.
If you’re staying overnight, consider :
Weekend Trips from Chicago: Milwaukee, Wisconsin
How fortunate it is to have another world class city only 90 minutes drive from Chicago. While Milwaukee often lives in Chicago’s shadow, a weekend in Milwaukee allows it to shine on its own. I love perusing the Milwaukee Public Market, walking along the Riverfront and historic Third Ward, and visiting the incredible Calatrava designed Milwaukee Art Museum. Beer lovers can enjoy an official Miller Brewery tour, but the smaller scale tours of other microbreweries and cheese shops (!) have a bit more local charm.
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There are certainly more weekend trip destinations that I hope to share with you as I visit them. Make sure you don’t miss anything by subscribing to my blog and following me on instagram @Jaimesays.
- North Farm: A Luxury Farm Stay Near Traverse City - October 5
- Championing Wine and Wellness in Temecula - June 22
- 9 Best and Unique Things to do in Leelanau County Michigan - June 16
- Kenosha: The Greatest Family Day Trip from Chicago - April 27
- A Unique and Luxurious Couples Getaway from Chicago near Lake Geneva - April 19
- I’m A Nationally Published Writer and Other Updates - March 28
- Celebrating Women in Wine on International Women’s Day - March 7
- Eight of the Best Weekend Trips from Chicago - January 27
- Unexpected (and Mostly Free!) Chicagoland Indoor Activities in Winter - December 31
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