Weekend Trips from Chicago

Although the entertainment available in the Windy City is endless, the area around Chicago is just as worthy of exploration.  Due to the city’s central location, there are plenty of exciting destinations just a quick trip away. When you’re ready for a weekend adventure, hit the road!


Indiana Dunes National Park

In just one hour, you can trade in the cement sidewalks of Chicago for the sandy shores of this preserved land. According to the National Park Service site, “hikers will enjoy 50 miles of trails over rugged dunes, mysterious wetlands, sunny prairies, meandering rivers and peaceful forests.” For first time visitors, it is recommended that you start your day in nature at the Visitor Center, where rangers can help plan your adventure depending on your interests.

Escape to Mackinac Island, MI

For those who are feeling ambitious (and might have a vacation days to bookend a weekend), make a 7 hour playlist for your journey from Chicago to the charismatic Mackinac Island. This trip involves a 6.5 hour drive and 30 minute ferry ride to the island, but you will truly feel like you have been transported. The best way to get around the island is via bike….and don’t forget a swimsuit!


Check off a State Capital in Madison, WI

The home of the University of Wisconsin is an energetic destination, easily reached in under three hours from Chicago. Madison regularly makes appearances at the top of “happiest cities in the world” lists, and its easy to see why. No matter the season, there is plenty to pack into a weekend during your visit. Some favorites include the zoo (it’s free!), botanical gardens, and the State Capitol building.


Enjoy a Winter Retreat in Galena, IL

In three hours, you can be transported from one of the biggest cities in the USA to picturesque “small-town USA” Galena. Pack your gloves in the winter months; you won’t want to miss out on the skiing the scenic peaks. Relax at a winery, play 18 holes, or pop in the shops in the center of town. Galena is also home to interesting historically significant places, museums with guided tours, and artist studios that offer behind-the-scenes glimpses.


Starved Rock State Park, IL

Plan a forest retreat in this green oasis on the Illinois River. After a two hour drive from Chicago, drop your bags in the Lodge and change into your hiking boots to hit the trails. The breathtaking canyons and waterfalls are home to native wildlife, which changes throughout the seasons. There are also historical and cultural sights, wineries and breweries, and plenty of restaurants around the area.


Midwest Charm in Milwaukee, WI

Like Chicago, Milwaukee is perched on the shores of Lake Michigan. This city is a great option if you are looking for a shorter drive (it is just under two hours north of Chicago). Milwaukee is composed of many neighborhoods that each have a unique feel and signature attractions. Visitors to the city enjoy brewery tours at the Pabst Blue Ribbon brewery, the Harley-Davidson museum, and the historically enlightening Milwaukee Public Museum.


Visit Amish Country in Arthur, IL

More than 2,000 Amish residents call Arthur home. Spend a weekend learning about the Amish way of life after heading three hours south from Chicago. Tour electricity-free homes and linger over rich classic meals during your visit. It won’t be hard to find handmade treats to bring back to share with friends!


It is easy to fall in love with Chicago and spend all your free time checking things off your “to-see” list, but there are also many destinations waiting to be discovered just a short trip from your doorstep.