Home Destinations 15 Best Weekend Getaways from Chicago 2024 That Are Award-Winning

15 Best Weekend Getaways from Chicago 2024 That Are Award-Winning

by Ethan
15 Best Weekend Getaways from Chicago 2024 That Are Award-Winning

Need to shake off the noise and non-stop pace of Chicago? If you’re from Chi-Town, you’ve got loads of weekend escapes perfect for unwinding, heading off on an adventure, or just seeing different places. All of these spots are just a quick drive or hop on a plane away. Whether you want to sink into nature’s quiet or dive into a bustling city vibe, these 15 spots will fill you up with new energy and leave you with amazing stories.

### 1. Starved Rock State Park: Nature’s Majesty

Just a bit southwest of Chicago, Starved Rock State Park awaits as an outdoor lover’s dream. Its awesome canyons, tumbling waterfalls, and winding trails are famous. Wander by the Illinois River or take on the forest paths for some show-stopping views. With 13 miles of trails, nature’s beauty is just a stone’s throw from your doorstep.

### 2. Door County, Wisconsin: The Cape Cod of the Midwest

Take a little trip to Door County, and you’ll see why it’s a gem with its cute lighthouses, cherry trees, and peaceful lake edges. Sticking out into Lake Michigan, this pretty spot shows off a cozy slice of American small-town life. Fill your day with wine tasting, paddling along the shore, or checking out local art spots. Door County mixes country vibes with a touch of grace, perfect for a weekend away.

### 3. Galena, Illinois: Historically Rich Retreat

Drop into Galena and it’s like you’ve time-traveled! It’s under three hours from Chicago and charms visitors with its 1800s architecture and stories. Check out historic houses like President Grant’s, wander the lively Main Street, and gaze from the Horseshoe Mound. Whether you’re into history or just want to chill in a sweet little town, Galena won’t disappoint.

### 4. Saugatuck, Michigan: Artistic Haven

Hop across Lake Michigan to hit Saugatuck, a spot known for both its creative side and stunning beaches. Find some art treasures, enjoy tasty bites, or just chill on Oval Beach. Saugatuck is where natural beauty meets artsy vibes, offering the perfect spot to refresh and inspire.

### 5. Lake Geneva, Wisconsin: Lakeside Luxury

For over 100 years, Lake Geneva has been where Chicago’s well-to-do folks escape. When you see its posh resorts, golf links, and bustling downtown, you’ll get it. Cruise the lake, sunbathe on soft sands, or walk by the water’s edge, checking out grand old homes. Lake Geneva brings a dash of luxury in a drop-dead gorgeous setting.

### 6. Holland, Michigan: Tulip Time Festival

Come spring, Holland, Michigan turns into a scene from the Netherlands. The Tulip Time Festival shows off oceans of tulips, plus parades, dances, and markets. And even when the tulips aren’t out, Holland’s Dutch roots are all around with windmills and old-timey buildings – ideal for a weekend packed with charm.

### 7. Madison, Wisconsin: A Blend of Urban and Natural

Madison, Wisconsin’s capital, nails the mix of city cool and the great outdoors. Sitting by two lakes, it offers top-notch biking paths, green parks, and a buzzing arts scene. Dig into the famous State Capitol, taste the city’s foodie side, or join in one of the many fests. Madison is a slice of city fun wrapped in a nature hug.

### 8. Traverse City, Michigan: A Gourmet’s Delight

Food lovers, heads up! Traverse City doesn’t just wow with its bay views – it’s a treasure trove for your taste buds. Jump on a food tour with local wines and cherries, pop into farm shops, or dine at some fab restaurants. Wine buffs should hit the Old Mission Peninsula for a taste tour to remember.

### 9. Milwaukee, Wisconsin: Brew City Excursion

Not far from Chicago, Milwaukee shines with beer houses aplenty, but there’s heaps more. Plunge into the city’s seaside past at the Milwaukee Art Museum, meander the old Third Ward, or catch some action at American Family Field. Milwaukee knows how to pair its working-class roots with a fresh and fun edge.

### 10. Shawnee National Forest, Illinois: Wilderness Weekend

Head for the southern part of Illinois to find Shawnee National Forest. This big, wild place is dotted with hills, woods, and craggy rock shapes. Hike the Garden of the Gods or the Rim Rock Trail for some real get-away-from-it-all time.

### 11. Cedarburg, Wisconsin: Quaint and Cozy

Cedarburg’s old town is snug with its unique stores, cafes, and inns. Just a hop from Milwaukee, this peaceful Wisconsin slice is great for those who love old treasures and a slower pace. Cedarburg’s wineries and festivals add a spice of fun to a calm weekend.

### 12. The Indiana Dunes: Nature’s Playground

A weekend at the Indiana Dunes is a huge hug from Mother Nature. Right on the south tip of Lake Michigan, the park has 15 miles of beach and lots for hikers and bird fans. You can climb the dunes or wade through the marshes for a peaceful city break.

### 13. Springfield, Illinois: Land of Lincoln

If history’s your thing, check out Springfield, the core of the Lincoln story. Visit Lincoln’s house, his tomb, and the Lincoln museum. Springfield’s got a cozy downtown and tasty food spots, too, making it a sweet spot to visit.

### 14. Ottawa, Illinois: A Gateway to Adventure

Sitting where the Fox and Illinois rivers meet, Ottawa’s your launchpad for outdoorsy fun. It’s the doorway to Starved Rock adventures with rafting, fishing, and more. Explore Ottawa’s past, browse the shops, and try local food spots after your day out.

### 15. Kalamazoo, Michigan: Craft Beer and Culture

Kalamazoo’s buzzing with craft beer action, but it’s also cool and cultural. Visit the arts institute, watch a show at the State Theatre, or stroll the nature trails. Kalamazoo blends brews with a cultural kick.


What are some budget-friendly weekend getaways from Chicago?
Check out Starved Rock State Park, the Indiana Dunes, and Springfield, Illinois. These spots wave bye to high costs with free or cheap things like walks, history, and beach time.

Are there any family-friendly weekend getaways near Chicago?
Door County, Wisconsin, is sweet for family fun outdoors, and Madison, Wisconsin, mixes learning and playtime perfectly.

What are the best romantic weekend getaways from Chicago?
When it comes to romance, Lake Geneva, Wisconsin, and Galena, Illinois, top the list with gorgeous views, fine dining, and cozy B&Bs.

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