4 Best Michigan Day Trips From Chicago To Escape the Windy City This Summer

Ashley Pichea

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Road trip

Escape the Windy City this summer and explore one of these Michigan day trips from Chicago. Whether you're looking for outdoor adventures, a chance to stroll a small town street, or immersive historical museums, steal our itinerary for a full-day getaway near Chicago.

South Haven

  • Driving Time: 2 Hours

One of the shorter day trips from Chicago, a visit to the Lake Michigan beach town of South Haven is a quick two-hour drive along the coastline with ample opportunity for exploring this walkable historic town's many attractions and activities – perfect for a day trip close to home.

Catch a Wave & Soak Up the Sun

South Haven is best known for its sandy beaches on Lake Michigan, making them a must-add to any summer day trip. South Haven boasts seven public beaches, but we recommend visiting the quieter Oak Street Beach for a less-crowded experience. This is a great place to enjoy kayaking on Lake Michigan.

Enjoy Lunch at Phoenix Street on Broadway

While there are many South Haven restaurants, we recommend grabbing a mid-morning or early-afternoon bite from Phoenix Street on Broadway. This cafe is open daily (check for seasonal hours) for breakfast, brunch, and lunch, and it serves some of our favorite entrees: B.(E.)L.T.s, apple pecan salads, Reuben sandwiches, and more!

Ride the (Former) Rails on the Kal-Haven Trail

After a morning at the beach, it's time to be adventurous! Grab your bike if you brought it along (or rent one from a local outfitter – we recommend Rock ‘n' Road Cycle), and hit the Kal-Haven Trail for a few dozen miles. This former railway once connected South Haven's lumber industry to the metropolis of Kalamazoo, and it is now a state park with a history of its own.

Not a fan of biking? No worries. As a multi-use trail, Kal-Haven Trail is one of the best walking and hiking trails in the area, too!

Sneak in a Sweet Treat at Sherman's Dairy Bar

After you've pedaled your hearts out, aim your wheels for Sherman's Dairy Bar for a refreshing sweet treat. No trip to South Haven is complete without an ice cream cone or another frozen dessert from Sherman's. For a true Michigan experience, we recommend indulging in a scoop or two of Superman ice cream!

Explore Maritime History at the Michigan Maritime Museum

If you're looking for an indoor activity on your day trip from Chicago, don't miss exploring the Michigan Maritime Museum. This historical museum in Michigan will take you into the heritage of boating on the Great Lakes and includes hands-on exhibits to immersive historical onboard experiences for everyone to discover and enjoy.

Savor Supper at Clementine's

Enjoy a leisurely evening meal before you head back into the city at the end of the day. A South Haven institution since 1981, Clementine's has a casual atmosphere and serves home-cooked entrees crafted with quality ingredients. Our favorite menu items include Roscoe Ribeye, Tin Pan Walleye, Clem's O-Ring Burger, and Thai Chicken Linguine.


  • Driving Time: 2 Hours and 30 Minutes

One of the best perks about a day trip from Chicago to Kalamazoo, Michigan, is that you don't need a vehicle! Just jump on the Amtrack commuter train for a two-hour ride into the heart of downtown Kalamazoo.

Kalamazoo's downtown offers all the energy of a big city without sacrificing the beauty of a small town. Everyone will find something to enjoy in Kalamazoo, from the tasty craft beer to the entertaining events at the local history museum.

Connect with History

Just a few blocks from the Kalamazoo Amtrak station, the Kalamazoo Valley Museum has science and history exhibits that will capture the imaginations of every member of your traveling party. Or, if you'd rather spend the morning outdoors, take a self-guided walking tour of Historic Downtown Kalamazoo with Lynn Houghton and Richard Piet.

Drink, Shop, and Stroll Downtown

Kalamazoo's Downtown Social District has a Central Commons Refreshment Area where you can purchase a beverage from a participating establishment and sip it while exploring and shopping downtown. Some of our favorite stores in Downtown Kalamazoo include Kzoo in the Mitten, Great Lakes Thrift Co., and The Spirit of Kalamazoo.

Linger Over Lunch at the Crow's Nest

Open every day except Tuesday, the Crow's Nest is a quaint, second-story restaurant with flair that serves three meals daily. We're big fans of The Rooster's Melt, Captain Kokey's Club, and the Kzoo Stir Fry on its mouth-watering menu. 

Reach for the Skies at the Air Zoo

The Air Zoo Aerospace & Science Museum in Kalamazoo appeals to visitors of all ages and is regarded as one of Kalamazoo's best day trip amusements. With interactive exhibits focused on science, space, aviation, and flight, the museum has more than 100 aircraft and space artifacts on display.

Dine In or Carry Out Dinner from Bell's Eccentric Cafe

The original location of Bell's Brewery, Bell's Eccentric Cafe, is a must-visit restaurant during your day trip from Chicago. Sample one of the 20+ Bell's beers on tap while you wait for your meal. Pull up a seat at the bar or grab your grub to go and picnic at Mayors Riverfront Park.


  • Driving Time: 2 Hours and 30 Minutes

While it might be best known for its Dutch roots and culture, there is so much more to do in Holland than just attending its annual Tulip Time Festival. This Lake Michigan beach town is full of activities and attractions, making it one of the best day trip ideas when you're looking to escape the Windy City.

Hike the Dunes

One of our favorite things about Michigan is its many state parks, and Holland State Park is one of the best. The Holland Dune Trail is a stunning out-and-back hike that offers breathtaking views of Lake Michigan, Big Red, and Lake Macatawa from the top of Mount Pisgah.

Pro Tip: Return just before dusk to catch one of the most spectacular sunsets over Lake Michigan!

Eat Breakfast Any Time

As odd as it might seem to eat breakfast in the middle of the day, that's precisely what we recommend when visiting Holland, Michigan. Holland's iconic Windmill Restaurant is a destination in and of itself, and you won't want to miss ordering its famous Windmill Hashbrown Omelette when you stop in for a mid-day meal!

Dive into Dutch Culture

A day trip from Chicago to Holland won't allow you to experience all the Dutch culture here, but you should have plenty of time to try on a pair of wooden shoes at the De Klomp Wooden Shoe and Delft Factory, explore a working windmill at Windmill Island Gardens, or stroll through an interactive history lesson at Nelis' Dutch Village.

Embrace Your Pirate Side

You might not think about pirates when you think about Holland, but a visit to Holland isn't complete without a visit to Captain Sundae and Pirates Landing Mini Golf. Challenge your mateys to a round of 18 holes and celebrate with a Salty Dog or Mint Munity sundae.

Dine In & Drink Up

Established by two native Michiganders in 1996, New Holland Brewing Company is one of the best places for dinner and drinks in Holland. Stop in at its family-friendly downtown location for dinner and drinks before you hit the road and head back to Chicago – just be sure to imbibe responsibly and designate a driver!

Grand Rapids

  • Driving Time: 3 Hours

Just three hours from downtown Chicago (depending on traffic and construction) and only 25 miles from Lake Michigan, Grand Rapids is a day trip destination worth exploring. An early morning commute out of the city will leave you with more than enough time to sample some of the best things to do in Grand Rapids this summer.

Visit John Ball Zoo

A favorite Michigan zoo, John Ball Zoo, is one of our favorite family fun things to do in the city. With plenty of shaded pathways, active animals, and special events scheduled throughout the summer, you could easily explore for a half day or more.

Explore Downtown Grand Rapids

After spending the morning at the zoo, find your way to Downtown Grand Rapids for a bite to eat at one of the local restaurants, Brick and Porter. After your meal, stroll along the Grand River and discover why Grand Rapids is called “River City.”

Stroll Through History at the Grand Rapids Public Museum

While downtown enjoying the river views, stop at the Grand Rapids Public Museum for a stroll through the city's past. This multi-level history museum is engaging and informative, making it an ideal destination for all ages. Kids (and kids at heart) won't want to miss riding the carousel that overlooks the Grand River.

Catch a Game at LMCU Ballpark

A summer day trip from Chicago to Grand Rapids isn't complete without enjoying America's Pastime at LMCU Ballpark. Catching a West Michigan Whitecaps minor league baseball game is a great way to end your day in Grand Rapids before you head back to the Windy City.

Experience Other Grand Rapids Attractions

Of course, you can't fully experience towns like Grand Rapids in just one day. You'll want to plan another day trip or an extended stay to check out other Grand Rapids attractions like the Frederik Meijer Gardens and Sculpture Park, the Blandford Nature Center, and, of course, the city's many breweries (after all, it's not called Beer City USA for nothing!).

More Michigan Day Trips from Chicago to Explore

These best destinations from the Chicago area are just the tip of the iceberg for potential adventures when you want to escape the Windy City for a day. Whether you want to enjoy outdoor activities, a small-town shopping experience, or a relaxing getaway, Michigan has no shortage of road trip destinations to explore, just a short trip away from home.

With natural wonders like waterfalls and scenic views to coastline classics like lighthouses and pristine beaches, Michigan is the perfect destination to unwind with its many hidden gems and great day trip getaway ideas!

This article originally appeared on Savoteur

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