Chicago is an incredible city with so many neighborhoods, festivals, events, and activities to explore. It’s practically impossible to be bored in Chicago with its long list of top attractions, even if you’ve called it home for many years. But even with all that going on, Chicagoans sometimes need a break from the pace of the city and a change of scenery to break up their routines.
Since Chicago is so centrally located in the Midwest, there are lots of unique places to visit that can be reached within a few hours and are totally doable over a weekend. Wisconsin, Michigan, Missouri, and Wisconsin are all nearby and just waiting to be explored by city-dwellers in need of a city break. Whether you’re looking for nature, relaxation, history, or charm, these are some of our favorite weekend getaways from Chicago.
Galena, Illinois
Galena is a top weekend getaway spot for Chicagoans because it combines the best of small-town charm, outdoor adventure, shopping, wineries, and top-notch restaurants. This is a tiny town that really packs a punch with lots of bed & breakfasts and locally owned boutiques. It’s only about 165 miles west of Chicago and easy to squeeze in over a Saturday and Sunday if you get a jump on the traffic leaving the city.
Indiana Dunes State Park
You’ll only need to travel about 55 miles southeast of Chicago to reach Indiana Dunes State Park, which is unlike anywhere else in the Greater Chicago area. These sandy dunes are along the coast of Lake Michigan and are perfect for a challenging hike or trying out the sport of sandboarding. Rent a sandboard from a local shop nearby to try coasting down some of the dunes for yourself! The town of Chesterton, Indiana is nearby and a great place to grab dinner after a day at the dunes. If you have a little more time, there’s lots more to see and do in Northwest Indiana, and you can even take the CTA to the Millennium Park South Shore Station to get here.
Milwaukee, Wisconsin
Milwaukee is so close to Chicago that it’d be a shame to not spend some weekends here if you live in Chicago. It’s only about 90 minutes north of the city and a mecca for beer lovers and cheese fans. There are lots of food, music, and art festivals scheduled during the summer months that are definitely worth making the drive. Some other top attractions and things to do include catching a baseball game at Miller Park, touring the Pabst Mansion, visit the Harley-Davidson Museum. If you have your own kayak or rent one at a local shop, you can kayak down the river that runs through town and get a “backside peek” at all the waterfront businesses. Bring an anchor and a rope because there are docks along the way where you can pull over and hop out to grab a snack or a beer! It’s easy to catch an Amtrak train at Union Station to reach Milwaukee if you don’t have a car or want a break from the traffic.
Madison, Wisconsin
The city of Madison lies just about 150 miles northwest of Chicago and has everything you need for a culturally rich weekend away with far fewer crowds and a different take on art. There’s plenty of family-friendly activities to choose from, as there’s a great culinary scene here for foodies, as well as a farmer’s market and lots of diverse restaurants. Top attractions include the University of Wisconsin Arboretum, the Chazen Museum of Art, the Madison Museum of Contemporary Art, and the Olbrich Botanical Gardens.
Starved Rock State Park
If you think all of downstate Illinois is farm fields and Amish country, then head 100 miles southwest of Chicago until you reach Starved Rock State Park. This amazingly scene park has over a dozen sandstone canyons and waterfall and is the perfect way to get in touch with nature when you live in an urban environment. Keep an eye out for wildlife and birds because there are lots of them here. You can go for a hike, take a paddleboat ride, and snap some amazing photos that your friends back home will never believe were taken in Illinois. In the winter, local guide companies take adventurous souls ice climbing here for a cold-weather thrill! The Starved Rock Lodge has rooms for an overnight stay and a restaurant too.
Ann Arbor, Michigan
Ann Arbor is best known for being the home of the University of Michigan, but it’s also a mecca for beer lovers. You’ll need to drive about four hours to reach Ann Arbor from Chicago, so this is a great trip for a three-day weekend next time one of those rolls around. Breweries not to be missed include the Arbor Brewing Company, Jolly Pumpkin Café and Brewery, and the Grizzly Peak Brewing Company. Recommended restaurants to check out during your weekend getaway include Zingerman’s Deli for sandwiches and Ferita Batidos for Cuban street food.
Lake Geneva, Wisconsin
A big resort area near Chicago is Lake Geneva, which about 80 miles northwest of the city. There are lots of hotels, resorts, and restaurants in this family-friendly destination. But the big draws here are the beach and the boat cruises. Summer is the most popular season to visit Lake Geneva, but you can also check out Winterfest in February if you need a post-holiday getaway.
New Buffalo/Three Oaks, Michigan
Three Oaks and New Buffalo are nearby towns in Michigan that are ideal for foodies in Chicago. To get here, you’ll only need to drive about two hours, and a stop for local meats and jam at P&G Mullins Local is a must. This is another Michigan destination that’s favored by craft beer lovers because there are several amazing breweries to check out. Make sure to stop by New Holland Brewery and Bell’s Brewing while you’re in the area, and Journeyman Distillery is a great place for local spirits.
Door County, Wisconsin
Door County is the place to be for crafts, antiques, shops, and hearty restaurants. Door County also has 300 miles of shoreline, which makes it a lovely place to slow down the pace of life and watch the sun rise and set. Here you’ll also find 11 historic lighthouses, five state parks, lakes to paddle in, art galleries to browse, wineries to sample, and some of the best cherry pie anywhere in America.
Saugatuck, Michigan
Saugatuck and the neighboring town of Douglas have been helping Chicagoans leave their stressful schedules and busy lives behind for generations. These towns are bordered by the sand dunes and the Kalamazoo River, providing waterways with beaches for swimmers and sunbathers. The Saugatuck Dunes State Park has hiking trails for the warm seasons and cross country ski trails for the winter. The beaches to check out here are Oval Beach, Douglas Beach, Pier Cove Beach, and Laketown Beach. Other popular activities here include taking a boat charter, visiting the Fenn Valley Vineyards & Winery, and renting kayaks to explore the natural beauty of Michigan on your own.
St. Louis, Missouri
Although many Chicagoans think of heading north for weekend getaways, you can also head southwest to spend the weekend in the awesome city of St. Louis. This is a riverfront city that has lots of things to do for families, including the St. Louis Zoo, Forest Park, and Grant’s Farm. Beer lovers can take a free tour of the Anheuser-Busch Brewery, and a trip up to the top of the iconic arch is a must when you’re in St. Louis.
Traverse City, Michgian
For a winter getaway not too far from Chicago, keep the name Traverse City in the back of your mind. This Michigan city transforms itself into a winter wonderland with Nordic skiing, snowshoe trails, and snowmobile rides. There’s a charming downtown district here that’s great for holiday shopping too. Traverse City is also the cherry capital of northern Michigan, and its cherry festival takes place in July each year. Other top events around town include the Traverse City Film Festival, the Northwestern Michigan Fair, Taste of Traverse City, Blossom Days, and the Traverse City Wine & Art Festival. This is also a great destination for golfers because there are championship courses here. Take some time to visit some of the many wineries the Leelanau Peninsula with tours and tastings as well!
