15 Best Road Trips from Chicago Within a Few Hours Drive

Craving a quick escape from Chicago? Here are the best road trips from Chicago that offer everything from nature and history to charming beach towns.

We've organized the best destinations from closest to furthest to help you plan your perfect trip.

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1. Milwaukee, Wisconsin (92 miles, 1.5 hours)

A vibrant city perfect for cultural exploration, with museums, breweries, and a lively arts scene. Milwaukee is an ideal spot for a quick city escape with plenty to see and do.

Must-See Attractions:

• Harley-Davidson Museum: Delve into the history of an American icon. Cost: $$.
• Milwaukee Art Museum: Admire its architecture and impressive collections. Cost: $$.
• Lakefront Brewery: Take a tour and enjoy a brew by the river. Cost: $.

Best Places to Eat:

• Sanford: A high-end dining experience with innovative dishes. Cost: $$$$.
• Glorioso's Italian Market: Great for deli sandwiches and Italian specialties. Cost: $$.
• Lakefront Brewery Beer Hall: Enjoy traditional pub fare with your beer. Cost: $$.

2. Lake Geneva, Wisconsin (83 miles, 1.5 hours)

An excellent destination for relaxation and outdoor activities, offering beautiful lakeside views and charming historic estates. Perfect for a weekend getaway with scenic walks and water sports.

Must-See Attractions:

• Geneva Lake Shore Path: A scenic walk offering views of historic estates. Cost: Free.
• Yerkes Observatory: Visit the historic observatory with beautiful architecture. Cost: $.
• Riviera Beach: Perfect for a relaxing day by the water. Cost: $.

Best Places to Eat:

• Simple Café: A cozy spot known for its fresh, locally-sourced breakfasts. Cost: $$.
• Sopra Bistro: Offers creative American cuisine with a focus on seasonal ingredients. Cost: $$$.
• Popeye’s on Lake Geneva: Famous for its rotisserie chicken and lake views. Cost: $$.

3. South Bend, Indiana (96 miles, 2 hours)

Home to the prestigious University of Notre Dame, South Bend blends rich history with family-friendly attractions like the Potawatomi Zoo. Ideal for those interested in history and education.

Must-See Attractions:

• University of Notre Dame: Explore the beautiful campus and its historic buildings. Cost: Free.
• Studebaker National Museum: Learn about the history of Studebaker automobiles. Cost: $$.
• Potawatomi Zoo: Indiana’s oldest zoo, offering a variety of animal exhibits. Cost: $.

Best Places to Eat:

• Tippecanoe Place Restaurant: Set in a historic mansion, offering American cuisine. Cost: $$$.
• The Carriage House: A charming spot with French-American fare. Cost: $$$.
• Evil Czech Brewery: Great for craft beer and creative pub food. Cost: $$.

4. New Buffalo, Michigan (70 miles, 1.5 hours)

A quaint beach town offering serene shores and scenic parks, making it perfect for a relaxing day trip or weekend escape. Great for families and those seeking a peaceful retreat.

Must-See Attractions:

• New Buffalo Beach: Relax on the sandy shores of Lake Michigan. Cost: Free.
• Galien River County Park: Enjoy a scenic walk through the marshlands. Cost: Free.
• Hesston Steam Museum: Experience steam-powered trains and vintage machinery. Cost: $.

Best Places to Eat:

• The Stray Dog Bar & Grill: Popular for its casual American fare and lake views. Cost: $$.
• Brewster’s Italian Café: Offers authentic Italian dishes in a cozy setting. Cost: $$.
• Oink’s Dutch Treat: Known for its homemade ice cream and fun, family-friendly atmosphere. Cost: $.

5. Starved Rock State Park, Illinois (93 miles, 2 hours)

A nature lover’s paradise with stunning canyons, waterfalls, and endless hiking opportunities. Ideal for outdoor enthusiasts looking for a rugged adventure.

Must-See Attractions:

• Hiking Trails: Discover canyons and seasonal waterfalls on the park’s trails. Cost: Free.
• Starved Rock Lodge: Visit the historic lodge with great views and dining. Cost: Free.
• Eagle Watching: In winter, spot bald eagles along the Illinois River. Cost: Free.

Best Places to Eat:

• Starved Rock Lodge Restaurant: Enjoy hearty meals with a view of the park. Cost: $$.
• Duffy’s Tavern: A casual spot in nearby Utica, known for its burgers. Cost: $.
• Nonie’s Bakery & Café: Perfect for breakfast or grabbing a quick bite before exploring. Cost: $$.

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6. Elkhart Lake, Wisconsin (150 miles, 2.5 hours)

Known for its clear, serene waters and thrilling auto racing experiences, Elkhart Lake is perfect for both relaxation and excitement. A great spot for water sports and racing fans.

Must-See Attractions:

• Ice Age National Scenic Trail: Perfect for hiking and taking in the scenery. Cost: Free.
• Road America: Experience the thrill of auto racing or take part in a driving course. Cost: $$.
• Elkhart Lake Beaches: Relax and enjoy water activities at these serene beaches. Cost: Free.

Best Places to Eat:

• Paddock Club: Farm-to-table cuisine with a focus on local ingredients. Cost: $$$.
• Off the Rail: A popular spot for breakfast and sandwiches. Cost: $$.
• Lake Street Café: Known for its wood-fired pizzas and eclectic menu. Cost: $$.

7. Madison, Wisconsin (150 miles, 3 hours)

A charming college town with a mix of historical attractions and outdoor activities, offering something for everyone. Perfect for a quick getaway that combines education and adventure.

Must-See Attractions:

• Wisconsin State Capitol: Take a free tour of this beautiful building. Cost: Free.
• Olbrich Botanical Gardens: Explore stunning gardens and conservatory. Cost: Free.
• Henry Vilas Zoo: A popular family destination with free admission. Cost: Free.

Best Places to Eat:

• L’Etoile: A high-end dining experience focused on seasonal, local cuisine. Cost: $$$$.
• The Old Fashioned: A Madison favorite for Wisconsin-style comfort food. Cost: $$.
• Graze: Offers creative farm-to-table dishes in a casual setting. Cost: $$$.

8. Indianapolis, Indiana (185 miles, 3 hours)

The best spot for sports and museum lovers, with the iconic Indianapolis Motor Speedway and the largest children's museum in the world. Ideal for a family weekend filled with fun and learning.

Must-See Attractions:

• Indianapolis Motor Speedway: Home of the Indy 500, with a museum and tours. Cost: $$.
• The Children’s Museum of Indianapolis: The largest children’s museum in the world. Cost: $$.
• White River State Park: A green oasis in the city with trails and attractions. Cost: Free-$.

Best Places to Eat:

• St. Elmo Steak House: Famous for its spicy shrimp cocktail and steaks. Cost: $$$$.
• Milktooth: A trendy spot for brunch with unique dishes. Cost: $$.
• Bluebeard: Offers innovative New American cuisine in a cool, industrial setting. Cost: $$$.

9. South Haven, Michigan (124 miles, 2.5 hours)

A picturesque beach town known for its beautiful lighthouses and maritime history. Perfect for a romantic getaway or a family beach day.

Must-See Attractions:

• South Beach: Enjoy the sun, sand, and picturesque views of Lake Michigan. Cost: Free.
• Michigan Maritime Museum: Learn about the region’s maritime history. Cost: $$.
• South Haven Lighthouse: A perfect spot for a scenic walk and photos. Cost: Free.

Best Places to Eat:

• Clementine’s: A local favorite for American fare in a historic building. Cost: $$.
• Captain Lou’s: Casual seafood spot with a laid-back vibe by the river. Cost: $$.
• Phoenix Street Café: Known for its delicious breakfast and brunch. Cost: $$.

10. Galena, Illinois (164 miles, 3 hours)

A historic town with well-preserved 19th-century architecture and rich Civil War history. Ideal for history buffs and those who appreciate a charming, small-town atmosphere.

Must-See Attractions:

• Downtown Galena: Explore the charming streets lined with 19th-century architecture. Cost: Free.
• Ulysses S. Grant Home: Visit the home of the 18th U.S. president. Cost: $.
• Galena Cellars Vineyard & Winery: Enjoy wine tasting with beautiful views. Cost: $$.

Best Places to Eat:

• Fried Green Tomatoes: A popular Italian-American restaurant in the heart of Galena. Cost: $$$.
• Log Cabin Steakhouse: Known for its steaks and historic setting. Cost: $$$.
• Otto’s Place: Great for breakfast or brunch with a cozy atmosphere. Cost: $$.

11. Holland, Michigan (154 miles, 3 hours)

Famous for its Dutch heritage and stunning tulip displays in the spring, Holland is perfect for cultural exploration and scenic beauty. Ideal for those interested in unique cultural experiences.

Must-See Attractions:

• Windmill Island Gardens: Visit the only working Dutch windmill in the U.S. Cost: $$.
• Tulip Time Festival: Visit in spring for a stunning display of tulips. Cost: Free.
• Holland State Park: Enjoy the beach and a view of Big Red Lighthouse. Cost: $.

Best Places to Eat:

• Butch’s Dry Dock: A fine dining experience with a great wine selection. Cost: $$$$.
• Deboer Bakkerij: A Dutch bakery offering excellent breakfasts and pastries. Cost: $$.
• Boatwerks Waterfront Restaurant: Holland’s only waterfront dining spot. Cost: $$$.

12. Door County, Wisconsin (280 miles, 4.5 hours)

A nature lover’s dream with stunning parks, orchards, and waterfront views, offering a mix of outdoor adventure and relaxation. Perfect for a longer road trip with diverse activities.

Must-See Attractions:

• Peninsula State Park: Perfect for hiking, camping, and enjoying nature. Cost: $$.
• Washington Island: Take a ferry to explore this serene island. Cost: $$.
• Cave Point County Park: Known for its stunning limestone cliffs. Cost: Free.

Best Places to Eat:

• Wild Tomato Wood-Fired Pizza and Grille: Delicious pizzas with fresh ingredients. Cost: $$.
• Al Johnson’s Swedish Restaurant: Famous for its grass-covered roof with grazing goats. Cost: $$.
• Whistling Swan Inn: A historic inn with fine dining. Cost: $$$$.

13. St. Louis, Missouri (300 miles, 5 hours)

A dynamic city known for its iconic Gateway Arch, rich history, and thriving food scene. Ideal for those seeking a blend of urban exploration and outdoor adventures.

Must-See Attractions:

• Gateway Arch: Ride to the top for breathtaking views of the city. Cost: $$.
• City Museum: A unique, interactive museum perfect for all ages. Cost: $$.
• Forest Park: Home to several free attractions, including the St. Louis Zoo, St. Louis Art Museum, and more. Cost: Free.

Best Places to Eat:

• Pappy’s Smokehouse: Renowned for its Memphis-style barbecue. Cost: $$.
• Tony’s: A St. Louis institution offering upscale Italian cuisine. Cost: $$$$.
• Schlafly Tap Room: Enjoy craft beers and pub fare in a relaxed atmosphere. Cost: $$.

14. Shawnee National Forest, Illinois (335 miles, 5.5 hours)

A must-visit for hikers and nature enthusiasts, offering breathtaking rock formations and serene forest trails. Perfect for a peaceful retreat into nature.

Must-See Attractions:

• Garden of the Gods: Marvel at the iconic rock formations and panoramic views. Cost: Free.
• Rim Rock Recreation Trail: Explore this scenic trail known for its stunning rock formations. Cost: Free.
• Cave-in-Rock State Park: Visit the historic cave along the Ohio River and enjoy the peaceful surroundings. Cost: Free.

Best Places to Eat:

• The Red Onion: A local favorite in nearby Equality, known for its steaks and seafood. Cost: $$$.
• E-town River Restaurant: Enjoy casual dining with beautiful river views in Elizabethtown. Cost: $$.
• Trails End Restaurant: A cozy spot in Harrisburg offering comfort food and friendly service. Cost: $$.

15. Traverse City, Michigan (315 miles, 5-7 hours)

A top destination for outdoor activities and scenic drives, especially known for the Sleeping Bear Dunes and local wineries. Ideal for a nature-filled vacation with a touch of luxury.

Must-See Attractions:

• Sleeping Bear Dunes National Lakeshore: Hike the dunes and enjoy stunning views of Lake Michigan. Cost: $$.
• Old Mission Peninsula: Drive through picturesque vineyards and visit local wineries. Cost: $$-$$$.
• The Village at Grand Traverse Commons: Explore shops, restaurants, and trails in this historic former asylum. Cost: Free-$.

Best Places to Eat:

• Trattoria Stella: Located in the historic Grand Traverse Commons, offering Italian cuisine with local ingredients. Cost: $$$.
• The Cooks’ House: A farm-to-table restaurant known for its creative, seasonal dishes. Cost: $$$$.
• Apache Trout Grill: Enjoy seafood and steaks with beautiful views of West Bay. Cost: $$$.

Frequently Asked Questions (FAQ)

1. What are the best road trips from Chicago for nature lovers?

Nature enthusiasts should consider visiting Starved Rock State Park for its stunning canyons and waterfalls, Shawnee National Forest for breathtaking rock formations, or Sleeping Bear Dunes National Lakeshore for scenic hikes and views of Lake Michigan.

2. Which road trip destinations near Chicago are ideal for a family getaway?

New Buffalo, Michigan and South Haven, Michigan are great for family-friendly beach outings, while Indianapolis, Indiana offers attractions like the Children’s Museum and the Indianapolis Zoo, perfect for a fun-filled family weekend.

3. Where can I find historical attractions on a road trip from Chicago?

Galena, Illinois is a top choice for history buffs, with its well-preserved 19th-century architecture and Ulysses S. Grant Home. St. Louis, Missouri also offers rich history with attractions like the Gateway Arch and the Missouri History Museum.

4. What are the best destinations for foodies on a road trip from Chicago?

Milwaukee, Wisconsin is known for its vibrant food scene, including brewery tours and farm-to-table restaurants. Traverse City, Michigan offers excellent dining options with a focus on local, seasonal ingredients, and Indianapolis, Indiana is famous for its diverse culinary experiences, from steakhouses to innovative brunch spots.

5. Which road trip destinations offer the best outdoor activities?

For outdoor adventure, Door County, Wisconsin offers a mix of hiking, kayaking, and cherry-picking, while Elkhart Lake, Wisconsin is ideal for water sports and auto racing fans. Shawnee National Forest is perfect for hiking and exploring scenic trails.

6. What are some quick weekend getaway options from Chicago?

For a quick weekend escape, consider Lake Geneva, Wisconsin for its lakeside charm and outdoor activities, Milwaukee, Wisconsin for its cultural attractions and breweries, or New Buffalo, Michigan for a peaceful beach retreat.

7. Which destinations are best for a romantic road trip from Chicago?

South Haven, Michigan is perfect for a romantic beach getaway, while Door County, Wisconsin offers tranquil lakeside views and cozy accommodations. Holland, Michigan is also a great choice, especially during the Tulip Time Festival for a romantic spring escape.