Top Weekend Getaways from Chicago, Illinois

Nicknames as the “Windy City”, Chicago is often referred to as the greatest American city of recent times by travelers. The home of the Chicago Bulls and the Blackhawks, the city is a mecca for sports lovers. However, sports are not the only thing that makes Chicago stand out. In fact, the city is also known for its bold architecture and a skyline that is dotted with several world-famous skyscrapers including but not limited to the neo-Gothic Tribune Tower, the legendary John Hancock Center, and the gigantic Willis Tower (a.k.a Sears Tower).

If you are planning on taking a weekend break in and around the city, the list below will offer you the top 7 weekend getaways from Chicago to enjoy with your friends and family.

List of Top Weekend Getaways from Chicago

1. Indianapolis, Indiana

Indiana Dunes, Indiana
Indianapolis, Indiana

Nestled on the banks of the White River, Indianapolis, popularly known as Indy or Circle City, is popular globally as the home of the biggest single-day sporting event in the world, the Indianapolis 500, the annual car racing tournament. If you are traveling with kids, the city is home to the largest children’s museum – the Children Museum of Indianapolis. Other places of interest in the city include the Indianapolis Museum of Art, Central Canal, and Benjamin Harrison Presidential Site.

Best Time to Visit: Although summer is the peak travel season here, it is best to visit during the fall months to avoid the high temperatures and heavy footfall.

How to Reach: To travel from Chicago to Indianapolis, you can take a flight, a train, a bus, or even a car. The cheapest is the bus for $16 and four hours, however, the fastest is the flight for 45 mins and $200 round-trip.

2. Saugatuck, Michigan

Saugatuck, Michigan
Saugatuck, Michigan

A peaceful beach town on the west coast of Michigan, Saugatuck enjoys a stunning coastline and plenty of outdoor activities to keep you occupied. Along with the neighboring village of Douglas, the town is famed as the state’s Art Coast as art lovers will find plenty of studios, art classes, as well galleries scattered around. When here, do spend some time at what is known as one of the best freshwater beaches in America, Oval Beach.

Best Time to Visit: Spring and Summer are the best seasons to visit Saugatuck. However, if you want to indulge in Apple Picking, go during the harvest season between September and November.

How to Reach: The fastest and the cheapest way to get here from Chicago is by car. However, a train is a second-best option which takes under four hours and costs between $65 to $95.

3. Lake Geneva

Lake Geneva
Lake Geneva

A perfect summer getaway, Lake Geneva is among the most liked road-trip attractions from the Windy City. A bustling resort town, the place is home to the 26-mile-long Lake Geneva Shore Town that has been a popular native American walking trail for several years. Stay at the historic Baker House, a magnificent lakefront mansion built-in 1885 with staffs dressed in period-accurate clothes. While there are quite a few fancy cocktail lounges scattered around the town, you must head to one of the dive bars here to experience the local culture. And, if you are feeling rather adventurous, try ziplining, hiking, and biking in the 100-acre forest surroundings.

Best Time to Visit: The summer months of June to August are the most preferred time to visit Lake Geneva.

How to Reach: You can take a train, a taxi, or drive to Lake Geneva from Chicago. The fastest, of course, is to drive.

4. Milwaukee, Wisconsin

Milwaukee, Wisconsin
Milwaukee, Wisconsin

The largest city in Wisconsin, Milwaukee is blessed with a picturesque landscape that you experience as you stroll down the stunning Riverwalk pedestrian path. However, the city’s biggest claim to fame is perhaps its identity as the home of the legendary motorcycle brand, Harley-Davidson. As you walk through the waterfront, don’t miss out on the War Memorial Center dedicated to the Korean War and WWII. Other places of interest here are the Milwaukee Art Museum, Pabst Theatre, and Mitchell Park Horticultural Conservatory.

Best Time to Visit: The months between June and September are the best to visit here.

How to Reach: The cheapest option to travel between the two cities is to get on a Greyhound. It costs between $8 to $23 and takes less than a couple of hours. Alternatively, you can take a train that takes about one and a half hours and costs between $27 to $40.

5. Madison, Wisconsin

Madison, Wisconsin
Madison, Wisconsin

Known for its cheerful cultural scene, Madison plays host to several events and festivals throughout the year. While summer month activities include biking along the wonderful city’s trail and sailing on the popular lakes of Mendota, Waubesa, and Monona. Architect lovers should not miss a chance of paying homage to one of the greatest architects, Frank Llyod Wright, at the Taliesin East. Other places of interest here include the Olbrich Botanical Gardens and Memorial Union Terrace.

Best Time to Visit: Although the city can be visited throughout the year, the most suitable months to visit here are from May to August and September to November.

How to Reach: The most convenient way to get from Chicago to Madison is by bus that takes around three hours and costs approximately $15.

6. Holland, Michigan

Holland, Michigan
Holland, Michigan

Holland is one of those evergreen cities that can be visited around the year. However, to make the most out of your weekend getaway from Chicago, you must plan your visit around the Tulip Time Festival so you can see the parks, gardens and the Dutch attractions lighten up with the bright colors of the namesake flower. Cycle along the paved paths around the city, visit the Aquatic Center, enjoy yourself at some of the best award-winning breweries and brewpubs in the country, and get some photos at the iconic Big Red Lighthouse.

Best Time to Visit: The best time to visit Holland is around the Tulip Time festival when the whole city comes alive with a festive spirit. Late April or Early May is highly recommended.

How to Reach: There are two preferred options to get from Chicago to Holland – a train that takes three hours and costs between $30 to $50 and a car drive that takes two and a half hours and costs between $14 to $22.

7. Indiana Dunes, Indiana

Indiana Dunes, Indiana
Indiana Dunes, Indiana

Towering dunes, calming waves, and well-defined hiking trails are some of the things you can enjoy during your visit to Indiana Dunes on the weekend. Home to a massive National Park that is spread across 15,000 acres of mind-blowing wilderness which is packed with beaches, wetlands, bogs, rivers, and prairies. Camping, Sailing, and Swimming are some of the popular activities to be enjoyed here.

Best Time to Visit: Spring and Fall are the best seasons to visit the area as these months are less crowded.

How to Reach: You could either take a bus or a train to get to the closest point to the National Lakeshore and get a taxi from there. Alternatively, you can drive to the site in under an hour.

Scroll to Top