Best One-Day Getaways from Chicago Within 150 Miles for Families and Couples

Why Choose a One-Day Getaway from Chicago?

Chicago’s vibrant energy is infectious, but sometimes you need a break from the urban grind. A one-day getaway offers the perfect balance of adventure and relaxation, allowing you to explore new destinations and return home refreshed—all in a single day. Within a 150-mile radius, you’ll find diverse attractions, including serene parks, historic towns, and lakeside retreats, all accessible by a short drive or train ride.

These trips are budget-friendly, time-efficient, and versatile enough to suit different interests. Families can enjoy interactive museums and outdoor fun, while couples can savor romantic dining and scenic strolls. Ready to hit the road? Let’s dive into the top destinations for your next day trip from Chicago.

Top One-Day Getaways from Chicago Within 150 Miles

Below, we’ve curated a list of the best day trips from Chicago, each offering unique experiences for families and couples. We’ve included travel details, activity highlights, and insider tips to ensure your getaway is a success.

1. Starved Rock State Park, Illinois (94 miles from Chicago)

Nestled along the Illinois River, Starved Rock State Park is a haven for outdoor enthusiasts. With 13 miles of hiking trails, 18 canyons, and seasonal waterfalls, it’s a top pick for nature lovers. Families will find plenty of kid-friendly activities, while couples can enjoy secluded trails and romantic dining options.

Family-Friendly Activities

The park’s easy trails, like the 0.7-mile Lover’s Leap Overlook, are perfect for kids. The visitor center offers interactive exhibits about the park’s history and wildlife, keeping young explorers engaged. Families can also join guided trolley tours for a fun, educational ride through the park.

Romantic Highlights

Couples can hike to the serene French Canyon for a private picnic or enjoy a cozy meal at the Starved Rock Lodge’s restaurant, known for its rustic charm and hearty dishes. The park’s scenic overlooks, like Eagle Cliff, provide stunning views for a romantic photo op.

Travel Details

• Distance: 94 miles from Chicago, about a 1.5-hour drive via I-80.
• Cost: Free entry and parking.
• Best Time to Visit: Spring and fall for vibrant scenery and fewer crowds.

Insider Tip

Arrive early to snag a parking spot, especially on weekends. Bring sturdy shoes for hiking and a reusable water bottle to stay hydrated.

Waterfalls and hiking trails at Starved Rock State Park, a top one-day getaway from Chicago

2. Lake Geneva, Wisconsin (80 miles from Chicago)

Lake Geneva is a gem of a destination, blending lakeside beauty with small-town charm. Known for its crystal-clear lake and historic mansions, it’s a versatile spot for families and couples seeking a mix of relaxation and adventure.

Family-Friendly Activities

Kids will love the Lake Geneva Cruise Line’s narrated boat tours, which offer a glimpse into the area’s history and stunning estates. The Tristan Crist Magic Theatre provides family-friendly entertainment with jaw-dropping illusions. For outdoor fun, head to Big Foot Beach State Park for swimming and picnicking.

Romantic Highlights

Couples can stroll the 21-mile Geneva Lake Shore Path, offering breathtaking views and quiet moments. For a romantic evening, dine at the Grand Geneva Resort’s steakhouse or sip cocktails at The Baker House, a historic lakeside mansion with a cozy ambiance.

Travel Details

• Distance: 80 miles from Chicago, about a 1.5-hour drive via US-12.
• Cost: Free parking in downtown Lake Geneva; some activities have fees.
• Best Time to Visit: Summer for water activities, winter for holiday charm.

Insider Tip

Book boat tours or dining reservations in advance, especially during summer weekends. Wear comfortable shoes for the shore path, as some sections are uneven.

Scenic Lake Geneva, a perfect one-day getaway from Chicago for families and couples

3. Indiana Dunes National Park, Indiana (50 miles from Chicago)

Just an hour from Chicago, Indiana Dunes National Park is a treasure trove of sandy beaches, towering dunes, and scenic trails along Lake Michigan. It’s an ideal spot for a quick nature escape that appeals to both families and couples.

Family-Friendly Activities

Families can build sandcastles on West Beach or hike the easy 1.5-mile Dune Succession Trail, which offers educational signs about the park’s ecosystem. The Dunewood Campground area has picnic spots perfect for a family lunch. Kids will also enjoy birdwatching, as the park is a hotspot for migratory birds.

Romantic Highlights

Couples can watch the sunset from Mount Baldy, the park’s tallest dune, or enjoy a quiet picnic at Kemil Beach. For a romantic twist, pack a blanket and stargaze on the beach after dusk. Nearby Chesterton offers charming cafes for a cozy coffee date.

Travel Details

• Distance: 50 miles from Chicago, about a 1-hour drive via I-94 or a 1.5-hour ride on the South Shore Line train.
• Cost: $6-$12 parking fee; train fares vary.
• Best Time to Visit: Summer for beach activities, fall for hiking.

Insider Tip

Arrive before 10 AM to secure parking during peak season. Bring sunscreen and beach towels for a relaxing day by the lake.

Sandy beaches at Indiana Dunes National Park, a top Chicago day trip destination

4. Galena, Illinois (150 miles from Chicago)

Galena, a historic gem in northwest Illinois, offers rolling hills, charming streets, and a rich history. It’s perfect for those seeking a blend of culture, shopping, and outdoor activities, making it a great fit for both families and couples.

Family-Friendly Activities

Visit the Ulysses S. Grant Home, a historic site with guided tours that fascinate kids and adults alike. The Galena Trolley Tours offer a fun way to explore the town’s history. For outdoor fun, head to Horseshoe Mound Preserve for easy trails and panoramic views.

Romantic Highlights

Couples can wander Main Street’s boutiques, filled with antiques and artisanal goods, or enjoy a wine tasting at Galena Cellars Vineyard. For a romantic dinner, try Fried Green Tomatoes, known for its intimate atmosphere and Italian-inspired cuisine.

Travel Details

• Distance: 150 miles from Chicago, about a 2.5-hour drive via US-20.
• Cost: Free street parking; some attractions have small fees.
• Best Time to Visit: Fall for stunning foliage and festive events.

Insider Tip

Visit midweek to avoid crowds, especially in fall. Bring a light jacket for cooler evenings in the hills.

Historic Main Street in Galena, a charming day trip from Chicago

5. Milwaukee, Wisconsin (92 miles from Chicago)

Milwaukee offers a vibrant mix of urban attractions and lakeside relaxation, making it a fantastic day trip destination. From world-class museums to craft breweries, there’s something for everyone.

Family-Friendly Activities

The Milwaukee Public Museum is a hit with kids, featuring immersive exhibits on dinosaurs and ancient cultures. Discovery World, a science and technology center, offers hands-on activities perfect for curious minds. Families can also stroll the Milwaukee Riverwalk for a scenic outing.

Romantic Highlights

Couples can tour Lakefront Brewery, sampling craft beers in a lively setting, or dine at Sanford Restaurant, a fine-dining spot known for its seasonal menu. For a romantic evening, visit the Milwaukee Art Museum, where the stunning architecture is as captivating as the art.

Travel Details

• Distance: 92 miles from Chicago, about a 1.5-hour drive via I-94 or a 1.5-hour Amtrak Hiawatha train ride.
• Cost: Parking varies by attraction; train fares start at $25 round-trip.
• Best Time to Visit: Summer for festivals like Summerfest, winter for indoor attractions.

Insider Tip

Check Milwaukee’s event calendar for festivals or markets, which add extra flair to your visit. Book brewery tours early for the best times.

Milwaukee’s vibrant downtown, a great one-day getaway from Chicago

6. New Glarus, Wisconsin (130 miles from Chicago)

Known as “America’s Little Switzerland,” New Glarus is a charming village with Swiss-inspired architecture, local breweries, and rolling countryside. It’s a unique getaway for those seeking culture and relaxation.

Family-Friendly Activities

The Swiss Historical Village Museum offers a fun, educational look at the area’s heritage, with kid-friendly exhibits. Families can explore New Glarus Woods State Park for easy hiking or biking. Stop by the New Glarus Bakery for Swiss pastries that kids will love.

Romantic Highlights

Couples can tour the New Glarus Brewing Company, famous for its Spotted Cow beer, or enjoy a romantic dinner at Glarner Stube, serving authentic Swiss cuisine. The town’s quaint streets are perfect for a leisurely hand-in-hand stroll.

Travel Details

• Distance: 130 miles from Chicago, about a 2.5-hour drive via I-90.
• Cost: Free parking; brewery tours and museums have small fees.
• Best Time to Visit: Summer for festivals, fall for scenic drives.

Insider Tip

Visit during the annual Swiss Volksfest in August for cultural immersion. Bring cash for small shops that may not accept cards.

Swiss-inspired New Glarus, a unique day trip from Chicago

7. Saugatuck, Michigan (140 miles from Chicago)

Saugatuck is a vibrant lakeside town known for its art galleries, beaches, and laid-back vibe. It’s a perfect blend of culture and nature for a memorable day trip.

Family-Friendly Activities

Families can visit Oval Beach for swimming and sandcastle-building or take a ride on the Star of Saugatuck, a paddleboat cruise along the Kalamazoo River. The Express Yourself Art Barn offers creative workshops for kids.

Romantic Highlights

Couples can browse Saugatuck’s art galleries or take a scenic hike at Saugatuck Dunes State Park. For a romantic dinner, try The Southerner, known for its Southern-inspired dishes and cozy ambiance.

Travel Details

• Distance: 140 miles from Chicago, about a 2.5-hour drive via I-94.
• Cost: Beach parking fees apply; other activities vary.
• Best Time to Visit: Summer for beach fun, fall for vibrant colors.

Insider Tip

Book paddleboat cruises in advance during peak season. Pack a light sweater for cooler lake breezes.

Oval Beach in Saugatuck, a vibrant day trip from Chicago

Why These Getaways Stand Out

These destinations were chosen for their diversity, accessibility, and appeal to both families and couples. Whether you’re hiking through Starved Rock’s canyons, sipping wine in Galena, or relaxing on Lake Geneva’s shores, each spot offers a unique experience. They’re all within a short drive or train ride, making them ideal for spontaneous adventures. Plus, they cater to a range of interests, from outdoor exploration to cultural immersion, ensuring everyone leaves with lasting memories.

Conclusion

Chicago’s proximity to diverse destinations makes it a perfect launching pad for unforgettable one-day getaways. Whether you’re exploring the rugged beauty of Starved Rock, soaking up the Swiss charm of New Glarus, or relaxing on Saugatuck’s beaches, these trips offer something for every family and couple. Pack your bags, plan your route, and embark on one of the best one-day getaways from Chicago within 150 miles.