7 Day Trips from Chicago IL – 2024 Ultimate Guide

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Are you looking to escape the hustle and bustle of Chicago for a day? Explore the beauty and charm of the surrounding areas with exciting day trips from Chicago IL. From picturesque lakeside towns to historic landmarks and outdoor adventures, there is no shortage of options for a memorable day trip. Whether you’re craving a peaceful retreat in nature or a cultural experience in a nearby city, these day trips from Chicago IL offer something for every traveler. So pack your bags, hit the road, and embark on a new adventure just a short drive away from the Windy City.

Milwaukee, Wisconsin

Travel tips

  • Distance from Chicago IL: Approximately 92 miles
  • Time to get there: Around 1.5 to 2 hours by car
  • How to get there: You can take the Amtrak train from Chicago Union Station to Milwaukee Intermodal Station. Alternatively, you can also take a Greyhound bus from Chicago to Milwaukee.
  • Click for Google maps directions: Milwaukee, Wisconsin

Exploring Milwaukee, Wisconsin: Things to do

Milwaukee, Wisconsin, is a vibrant city known for its rich brewing history, stunning lakefront views, and diverse cultural attractions. A must-see place for any traveler looking to experience the Midwest charm combined with urban sophistication.

One of the top things to do in Milwaukee is to visit the iconic Harley-Davidson Museum, where you can learn about the legendary motorcycle brand’s history and see a collection of classic bikes. For art enthusiasts, the Milwaukee Art Museum is a must-visit, with its striking architecture and impressive collection of over 30,000 works spanning from antiquity to the present day.

Nature lovers will appreciate a visit to the Milwaukee County Zoo, home to over 2,000 animals from around the world. Stroll through the beautiful Mitchell Park Horticultural Conservatory, also known as “The Domes,” and immerse yourself in a tropical oasis right in the heart of the city.

Don’t miss the opportunity to explore the historic Third Ward neighborhood, filled with boutique shops, art galleries, and trendy restaurants. Grab a bite to eat at one of the local eateries and savor the flavors of the city, from classic Wisconsin cheese curds to innovative farm-to-table cuisine.

Whether you’re interested in history, art, nature, or simply soaking in the local culture, Milwaukee offers a diverse range of experiences that are sure to captivate any visitor. Plan your day trip from Chicago to Milwaukee and discover all that this dynamic city has to offer.

Starved Rock State Park, Illinois

Travel tips

  • Distance from Chicago IL: Approximately 90 miles
  • Time to get there: Around 1.5 to 2 hours drive
  • How to get there: You can reach Starved Rock State Park by car via I-55 S and I-80 W. Alternatively, you can take a bus from Chicago to Ottawa, IL, and then arrange for a taxi or ride-sharing service to the park. There are no direct train stations near the park.
  • Click for Google maps directions: Starved Rock State Park, Illinois

Exploring Starved Rock State Park, Illinois: Things to do

Starved Rock State Park in Illinois is a must-see destination for nature lovers and outdoor enthusiasts alike. The park is renowned for its stunning canyons, towering waterfalls, and breathtaking views of the Illinois River. Visitors can enjoy a variety of activities, from hiking along the scenic trails to birdwatching and picnicking in the picturesque surroundings.

One of the top things to do at Starved Rock State Park is to hike to the iconic Starved Rock, a sandstone butte that offers panoramic views of the surrounding landscape. The park boasts over 13 miles of well-maintained trails, ranging from easy walks to more challenging hikes, providing opportunities for visitors of all fitness levels to explore the natural beauty of the area.

In addition to hiking, visitors can also indulge in fishing, boating, and wildlife observation at Starved Rock State Park. The park is home to a diverse range of flora and fauna, making it a paradise for nature enthusiasts. Be sure to bring your camera to capture the stunning scenery and wildlife encounters during your visit.

Whether you’re looking for a peaceful retreat in nature or an adventurous day out, Starved Rock State Park offers something for everyone. Plan your day trip from Chicago to this scenic gem and immerse yourself in the beauty of Illinois’ outdoors.

Lake Geneva, Wisconsin

Travel tips

  • Distance from Chicago IL: Approximately 80 miles
  • Time to get there: Around 1.5 to 2 hours drive
  • How to get there from Chicago IL: You can take a bus from Chicago to Lake Geneva or drive via I-94 W. The nearest train station is in Harvard, IL.
  • Click for Google maps directions: Lake Geneva, Wisconsin

Exploring Lake Geneva, Wisconsin: Things to do

Lake Geneva, Wisconsin, is a charming destination that offers a perfect escape from the hustle and bustle of city life. Known for its picturesque lakeside setting and a variety of outdoor activities, Lake Geneva is a must-see place for nature lovers and adventure seekers alike.

One of the top things to do in Lake Geneva is to explore the beautiful Geneva Lake. You can take a leisurely boat tour around the lake, enjoying stunning views of the surrounding landscape. For those seeking more adventure, water sports such as kayaking, paddleboarding, and jet skiing are popular options.

If you prefer land-based activities, Lake Geneva has plenty to offer. You can hike or bike along the scenic trails, taking in the fresh air and natural beauty of the area. Golf enthusiasts will appreciate the world-class golf courses in the vicinity, providing a challenging and enjoyable experience.

For a taste of history and culture, visit the Black Point Estate and Gardens, a historic mansion that offers guided tours showcasing the opulent lifestyle of the past. The downtown area of Lake Geneva is also worth exploring, with its quaint shops, galleries, and restaurants offering a mix of local flavors and unique finds.

Whether you are looking for a relaxing getaway or an active outdoor adventure, Lake Geneva, Wisconsin, has something for everyone. Plan your day trip from Chicago and immerse yourself in the natural beauty and charm of this delightful destination.

Galena, Illinois

Travel tips

  • Distance from Chicago IL: Approximately 164 miles
  • Time to get there: Around 3 hours by car
  • How to get there from Chicago IL: You can drive to Galena, Illinois via I-90 W and US-20 W. Alternatively, you can take a bus from Chicago to Galena with Greyhound Lines or Burlington Trailways. There are no direct train routes to Galena.
  • Click for Google maps directions: Galena, Illinois

Exploring Galena, Illinois: Things to do

Galena, Illinois, a charming town with a rich history, is a must-see destination for those seeking a blend of culture, outdoor adventures, and small-town charm. One of the top attractions in Galena is the Ulysses S. Grant Home State Historic Site, where visitors can explore the former residence of the Civil War general and 18th President of the United States.

For outdoor enthusiasts, Galena offers scenic hiking trails at the Casper Bluff Land & Water Reserve and the Galena River Trail. The town is also known for its golf courses, such as Eagle Ridge Resort & Spa, providing a picturesque backdrop for a relaxing day on the greens.

History buffs will appreciate a visit to the Old Market House State Historic Site, a Greek Revival building that once served as a marketplace in the 19th century. The Dowling House, one of the oldest homes in Galena, offers a glimpse into the town’s early days with its preserved period furnishings.

In addition to its historical sites, Galena boasts a vibrant arts scene, with numerous galleries showcasing local artists’ works. Visitors can browse unique shops along Main Street, known for its quaint boutiques and antique stores.

Whether you’re interested in history, outdoor activities, or simply strolling through a picturesque town, Galena, Illinois, offers a diverse range of attractions that make it a memorable day trip from Chicago.

Indiana Dunes National Park, Indiana

Travel tips

  • Distance from Chicago IL: Approximately 50 miles
  • Time to get there: Around 1 hour drive
  • How to get there: You can take the South Shore Line train from Millennium Station in Chicago to the Dune Park Station. From there, you can transfer to a bus that will take you directly to Indiana Dunes National Park.
  • Click for Google maps directions: Indiana Dunes National Park, Indiana

Exploring Indiana Dunes National Park, Indiana: Things to do

Indiana Dunes National Park in Indiana is a must-see destination for nature lovers and outdoor enthusiasts alike. The park boasts stunning sandy beaches along the shores of Lake Michigan, offering visitors a perfect blend of sun, sand, and water.

One of the top activities at Indiana Dunes National Park is hiking. With over 50 miles of trails winding through diverse landscapes including dunes, wetlands, forests, and prairies, hikers can enjoy breathtaking views and encounter a variety of flora and fauna along the way. Be sure to check out the iconic 3 Dune Challenge for a more challenging trek.

For those looking to relax by the water, the park’s beaches provide a serene escape. Whether you prefer swimming, sunbathing, or simply taking a leisurely stroll along the shoreline, the sandy beaches offer a peaceful retreat for visitors of all ages.

Birdwatching is another popular pastime at Indiana Dunes National Park, as the park is home to a wide array of bird species. Bring your binoculars and keep an eye out for migratory birds, waterfowl, and raptors soaring overhead.

If you’re interested in history, don’t miss the Chellberg Farm and Bailly Homestead, where you can step back in time and learn about the area’s early settlers and farming practices.

Whether you’re seeking adventure, relaxation, or a bit of both, Indiana Dunes National Park offers something for everyone. Plan your day trip from Chicago and immerse yourself in the natural beauty of this unique Midwestern gem.

Saugatuck, Michigan

Travel tips

  • Distance from Chicago IL: Approximately 140 miles
  • Time to get there: Around 2.5 to 3 hours by car
  • How to get there: You can drive from Chicago to Saugatuck, taking I-94 E and I-196 N. Alternatively, you can take a Greyhound bus from Chicago to Holland, MI, and then a taxi or Uber to Saugatuck. There is no direct train service to Saugatuck.
  • Click for Google maps directions: Saugatuck, Michigan

Exploring Saugatuck, Michigan: Things to do

Saugatuck, Michigan, is a charming coastal town known for its artistic community, beautiful beaches, and vibrant downtown area. One of the top attractions in Saugatuck is Oval Beach, a pristine stretch of sand along Lake Michigan perfect for sunbathing and swimming. For art enthusiasts, a visit to the Saugatuck Center for the Arts is a must, showcasing local and regional talent through exhibitions and workshops.

Outdoor enthusiasts will appreciate the opportunities for hiking and biking at Saugatuck Dunes State Park, offering stunning views of the lake and dunes. The nearby Mount Baldhead Park provides a challenging climb to the top for panoramic vistas of the surrounding area. Visitors can also explore the Kalamazoo River by renting kayaks or paddleboards for a leisurely paddle through the scenic waterways.

In downtown Saugatuck, you’ll find a variety of boutique shops, art galleries, and restaurants to explore. Don’t miss the chance to sample fresh seafood at one of the waterfront eateries or indulge in homemade ice cream from a local creamery. The Saugatuck Chain Ferry, one of the last hand-cranked chain ferries in the country, offers a unique way to cross the river and experience a piece of local history.

Whether you’re seeking relaxation on the beach, outdoor adventures in nature, or cultural experiences in the arts, Saugatuck, Michigan, offers a diverse range of activities that make it a must-see destination for a day trip from Chicago.

Door County, Wisconsin

Travel tips

  • Distance from Chicago IL to Door County, Wisconsin: Approximately 250 miles
  • Time to get there: Around 4-5 hours by car
  • How to get there from Chicago IL: Take I-94 N and I-43 N to WI-42 N in Algoma. Take exit 54 from WI-57 N. Continue on WI-42 N. Drive to County Rd A in Baileys Harbor.
  • Click for Google maps directions: Door County, Wisconsin

Exploring Door County, Wisconsin: Things to do

Door County, Wisconsin is a charming destination that offers a perfect blend of natural beauty and cultural experiences. Known for its picturesque landscapes and quaint villages, Door County is a must-see place for nature lovers and outdoor enthusiasts alike.

One of the top attractions in Door County is Peninsula State Park, which boasts stunning views of Lake Michigan and offers a variety of outdoor activities such as hiking, biking, and kayaking. Visitors can also explore the charming towns of Fish Creek and Ephraim, known for their historic buildings and local shops.

For those interested in history, a visit to the Door County Maritime Museum is a must. This museum showcases the rich maritime heritage of the region and features exhibits on shipwrecks, lighthouses, and the area’s fishing industry.

Foodies will delight in the local culinary scene, with Door County being famous for its cherry orchards and delicious cherry pies. Be sure to stop by one of the many orchards or farm stands to sample fresh cherries and other local produce.

Overall, Door County, Wisconsin offers a perfect escape from the hustle and bustle of city life, with its serene natural beauty and welcoming small-town charm. Whether you’re looking to relax on the beach, explore scenic trails, or indulge in local cuisine, Door County has something for everyone.

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