10 effortless weekend getaways from Chicago – no flight required

Despite crying about the winter weather, Chicago is undoubtedly blessed with what we like to call it location, location, location: With prime real estate on Lake Michigan, the Midwestern city is about as far by car from Minneapolis (six hours) as Toronto (eight hours) and Nashville (seven hours). In this sense, it is an ideal starting point for a road trip. There are several weekend trips from Chicago, whether you want to put a lot of miles in the car or settle in a fresh place before the kids finish watching Cars. Read on for ten ideas for effortless weekend getaways from Chicago.

What cities are less than a three-hour drive from Chicago?

• Milwaukee, Wisconsin (1 hour 30 minutes)
• Madison, Wisconsin (2 hours 25 minutes)
• Grand Rapids, Michigan (2 hours 47 minutes)
• Peoria, Illinois (2 hours 41 minutes)
• South Bend, Indiana (1 hour 39 minutes)
• Indianapolis, Indiana (2 hours 56 minutes)

Geneva, Illinois

• Distance: An hour’s drive
• Best for: Unique art and great shopping

OK OK. Geneva is technically in the suburbs of Chicago, but with its small-town charm it feels like a completely different world. Leave your bags at the boutique Herrington Inn & Spa, located on the Fox River, and take a walking tour of the city’s walkable downtown. There is no shortage of public art, independent shops and restaurants (over 150 in total in the historic district).

Michigan City, Indiana

• Distance: An hour and a quarter by car
• Best for: Hiking (and swimming for the brave ones)

On a clear day, from Michigan City you can see the Chicago skyline across the water. Enjoy towering sand dunes, the cold waters of Lake Michigan, and nearly 80 miles of trails Indiana Dunes National Park; in Michigan City itself, attractions include the 19th century Barker Manor– listed on the National Register of Historic Places – and family affable Washington Park Zoo.

Michigan’s port country

• Distance: An hour and a quarter by car
• Best for: A combined beach and wine trip

It includes the eight cities of Michiana, Grand Beach, New Buffalo, Three Oaks, Union Pier, Lakeside, Harbert and Sawyer. Harbert Country is a favorite place for a weekend escape from the Windy City thanks to the beach AND rural offers. The area is also home to many world-class wineries and breweries, including popular ones Lehman’s farm AND Dablon Vineyards and Wineryin nearby Baroda.

Milwaukee, Wisconsin

• Distance: One and a half hours by car
• Best for: Brothers and breweries

Milwaukee has a opulent German heritage, which means the city is full of places to enjoy good beer and brats (and more beer, if that’s your thing). Both Pabst Blue Ribbon and Miller are based here, but don’t sleep on the smaller guys, including Milwaukee Brewery AND By the lake.

South Bend, Indiana

• Distance: One hour and forty minutes by car
• Best for: Mountain rafting

There’s more to South Bend than Irish football, although we absolutely love the idea of ​​walking around Notre Dame’s picturesque campus. Hit the rapids Race Eastern WaterwayNorth America’s first artificial waterway that cuts through the city, or visit the historic Robinson Department Store and throw your own pottery into the pottery Pigeon and hen. Play arcade games – for free! – In Garage arcade and barwhich includes all the classics including Galaga and Ms. Pac-Man.

Grand Rapids, Michigan

• Distance: About three hours by car
• Best for: Beer, of course, but also outdoor sculptures

Voted “Beer City in the USA” in several national surveys, Grand Rapids is known for its foam: Check Beer City Beer Trail, a map showing all the options in the city. When it comes to eating, we prefer walking Śródmieście Market Square, which counts more than 20 vendors in a hall just south of Heartside Park (a perfect spot for a picnic, if you ask us). If you’re looking for an outdoor experience that requires a little more activity, head to the 58-acre grounds Frederik Meijer Gardens and Sculpture Park: here you will find works by Auguste Rodin, as well as a room dedicated exclusively to carnivorous plants.

Indianapolis, Indiana

• Distance: Three hours by car
• Best for: Museums, both time-honored and unusual

Indianapolis is an amazing city of museums. Although two of its most popular attractions are the Children’s Museum and its extensive indoor and outdoor areas Indianapolis Museum of Artdon’t miss the city’s most bizarre options: Indiana Museum of Medical History (not for the subdued of heart) i Kurt Vonnegut Museum and Library. Visit the eminent Indy’s City Square sample over 25 local restaurants; Once you’ve had your fill, go underground on a public catacomb tour, held on select Saturdays from May to October, from 10 a.m. to 3:15 p.m. (private tours can be booked through Indiana Landmarks.)

Ann Arbor, MI

• Distance: About three hours and 45 minutes by car
• Best for: Adventures on the river

Activities abound at any time of year in Ann Arbor, best known as the home of the University of Michigan. Take a subway, kayak, SUP or canoe ride along a tranquil stretch of the Huron River – accessible from the 69-acre Gallup Park – or stroll the eminent U of M’s Matthew Botanical Garden and Nichols Arboretum. Be sure to make time for the city Kerrytown market and shops, a picturesque area full of independent boutiques and restaurants. (Zingerman’s Delicatessenone of the best sandwich places in Ann Arbor is here.)

Door County, Wisconsin

• Distance: Four and a half hours by car
• Best for: Exploring the rugged coastline

Door County, a 70-mile-long peninsula, is often called “Cape Cod in the Midwest”— and rightly so. Just 80 miles northeast of Green Bay, Door County has stunning coves, cherry orchards, harbors, lighthouses, wineries and approximately 500 miles of coastline. Newport State Park is a 900-acre International Dark Sky Preserve Rock Island State Park there are no cars; if you’re looking for a dose of small-town charm, stop in Ephraim, a Scandinavian-style village.

Traverse City, Michigan

• Distance: Five hours by car
• Best for: Explore the shops and galleries in a rightfully popular diminutive town

It’s no wonder Traverse City was voted one of the nicest diminutive towns to visit in the summer: lovely on the lake with Art Deco architecture, a town beloved by many Chicagoans (including Oprah herself). One of Traverse City’s most popular attractions is the Village at Grand Traverse Commons: a 19th-century hospital convoluted that has since been reborn into a mixed-use space with shops, restaurants, walking trails and art galleries. Northwest of Traverse City is the Leelanau Peninsula, home to the strikers Sleeping Bear Dunes National Shore.

Where can I take the train from Chicago?

Without a car? No problem. You can get almost anywhere by train from Chicago: Memphis is a 10-hour train ride away; Seattle is 46 years aged. But for a weekend getaway we prefer these types:

• Indiana Dunes National Park (South Shore line from Chicago Millennium Station stops at four stations in the park)
• Milwaukee, Wisconsin (approximately 90 minutes on Amtrak from Chicago’s Union Station)
• Kalamazoo, Michigan (about two hours on Amtrak from Union Station in Chicago)
• Grand Rapids, Michigan (about four hours on Amtrak from Union Station in Chicago)

Of course, there’s plenty to do in Chicago itself before you head out; after all, it was ranked No. 2 in the 2023 Best Cities in the U.S. thanks to its best restaurants, world-class museums, and extensive hotel offerings. On the other hand, if you feel Really If you’re looking for adventure, you can always take the epic journey: 2,448 miles all the way to Santa Monica, California.

Have a nice weekend.

This article originally appeared online in 2020; it was last updated on August 31, 2023 to include current information.