Weekend Getaways From Chicago

15 Best Weekend Getaways from Chicago in 2025 (Quick & Scenic Escapes)

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Chicago is a vibrant city with a society, food, and countless activities. However, every once in a while, even the most dedicated Chicago ans require a break. What better way to recharge than trading the high-rise buildings for scenic vistas, cozy towns, or peaceful lakes? Fortunately, Chicago prime location offers plenty of places for weekend getaways, all within a couple of hours drive.

Whether you’re a nature enthusiast, a history aficionado, or a person seeking a relaxing retreat, this guide covers you. Continue reading to uncover handpicked destinations that are best for your next weekend getaways break experience.

Retreat to the City

Often, all you require is an adjustment of landscapes. Within three hours of the Windy City, you’ll find lovely small towns, beautiful state parks, and lively urban hubs waiting to welcome you. A brief drive can bring you to an entirely new world, using peace, fresh points of view, and experiences you won’t soon forget.

Why Consider a Quick Escape?

  • Ease: Say goodbye to airport lines; pack, get in the car, and go.
  • Inexpensive Enjoyable: Cut take-a-trip prices without sacrificing adventure.
  • Reenergize instantly: Even a 48-hour trip can leave you feeling invigorated.

Lake Geneva, Wisconsin

Nestled along Geneva Lake’s carbonated water, this captivating community is a place for those who yearn for relaxation with a side of activity.

Top Things to Do

  • Stroll along the Geneva Lake Shore Course, a beautiful walkway that loops around the lake.
  • Shop to your heart’s content at shops housed in brought-back historic structures.
  • Relax on the Riviera Coastline or treat yourself to a boat tour.

Where to Stay Chicago

  • You will not fail to stay at The Abbey Resort, supplying high-end and lakefront sights.

Best Places to Eat

For a memorable eating experience, try Sopra Bistro, known for its modern-day American recipes.

Lake Geneva, Wisconsin
Lake Geneva

Starved Rock State Park, Illinois

Starved Rock State Park is a dream come true for the outdoor fanatic. It is recognized for lush routes, canyons, and waterfalls and provides a banquet for the eyes and the spirit.

What to Do

  • Hiking tracks like the French Canyon offer spectacular sights, especially after rainfall.
  • Check out throughout springtime or succumb to the most dazzling surroundings.
  • Don’t avoid the concealed treasures like the Enthusiast’s Jump Overlook.

Where to Stay

Keep right at the heart of the park at Starved Rock Lodge, supplying rustic convenience with contemporary amenities.

Starved Rock State Park, Illinois
Starved Rock State Park

Door County, Wisconsin Chicago

Commonly described as the “Cape Cod of the Midwest,” Door Region integrates coastal beauty with picturesque elegance and sectarian heat.

Don’t Miss

  • Stray through Peninsula State Park for spectacular water sights.
  • Relish neighborhood red wines at Door Peninsula Vineyard.
  • Check out historical lighthouses and enjoy a traditional fish boil.

Best Places to Stay

Remain in a charming cabin or publish an area at Harbor Residence Inn for unrivaled comfort.

Door County, Wisconsin
Door County, Wisconsin

Galena, Illinois.

History, charm, and high-end integration in Galena, Illinois. This stunning town is best for those who delight in abundant cultural experiences with a sprinkle of extravagance.

Points to Do.

  • Stroll via Key Road, which is loaded with historic architecture and specialty stores.
  • Soar to the skies with a hot-air balloon experience over the rolling countryside.
  • Discover gastronomic thrills with red wine samplings at Galena Cellars Winery.

Where to Remain.

Ruin on your own with a stay at Goldmoor Inn, a luxury retreat overlooking the Mississippi River.

Galena, Illinois.
Galena, Illinois.

Milwaukee, Wisconsin.

Wisconsin’s biggest city supplies culture, food, and home entertainment making it an ideal area for a fast city escape.

Leading Attractions.

  • Step into the future at the magnificent Milwaukee Art Museum.
  • Tour regional staples like Lakefront Brewery.
  • For motorbike lovers, the Harley-Davidson Museum is a must-visit.

Where to Eat.

Get a bite at Blue Egg, a breakfast sanctuary that locals and site visitors love.

Milwaukee, Wisconsin.
Milwaukee, Wisconsin.

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Saugatuck, Michigan.

Perfect for artists, beachgoers, and white wine enthusiasts, this lovely community on Lake Michigan will make you feel miles away from stressful city life.

Highlights.

  • Relax at Oval Beach, among the best weekend getaways beaches in Michigan.
  • Explore Mount Baldhead Park for breathtaking sights.
  • Look at regional art galleries or enjoy a glass of wine sampling at Modales Wines.
Saugatuck, Michigan.
Saugatuck, Michigan.

Holland, Michigan.

Missing out on Europe? This destination is a wonderful Dutch-inspired getaway without leaving the Midwest.

What to See.

  • During the Tulip Time Event, Windmill Island Gardens showcases genuine Dutch design and tulip areas.
  • Do not neglect to visit Big Red Lighthouse for spectacular photos.
Holland, Michigan.
Holland, Michigan.

Mackinac Island, Michigan.

Return to this car-free island, where horse-drawn carriages and Victorian-era charm define the landscape.

Must-Do Activities.

  • Bike around the island’s perimeter for beautiful sights of the lake.
  • Enjoy world-famous fudge shops.
  • Stay at the opulent Grand Resort, an experience in itself.
Mackinac Island, Michigan.
Mackinac Island, Michigan.

Final Notes for Planning Your Escape 

With all these choices, there’s something for everybody within a few hours of Chicago. Whether you wish to feel the sand between your toes, check out trekking tracks, or submerge yourself in history or art, a weekend getaways vacation is simply a trip away.

Start planning your trip, load your bags, and hit the trail to discover the best of the Midwest’s edges.

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