7 Underrated Weekend Getaways Near Chicago

Living in Chicago has its perks world-class food, stunning skyline views, endless festivals, and vibrant neighbourhoods. But the traffic, packed trains, long winters, and nonstop pace can leave you craving a break.

Sometimes you don’t need a full vacation you just need a change of scenery within just a few hours of Chicago, you’ll find charming historic towns, quiet lakeside escapes, dramatic hiking trails, art-filled villages, and cozy waterfront hideaways that feel worlds apart from city life. Whether you’re dreaming of a romantic weekend, a peaceful solo retreat, or a spontaneous road trip with friends, these underrated destinations deliver the reset you’ve been craving without the airport stress.

Here are 7 underrated weekend getaways near Chicago that deserve a spot on your travel list.

1. Galena

Why It’s Underrated

Galena often gets labelled as just a “historic town,” but that barely scratches the surface. Tucked into rolling hills near the Mississippi River, it feels more like a New England escape than a Midwest destination. Many Chicagoans assume it’s quiet and sleepy, yet it offers a surprisingly romantic atmosphere with wineries, scenic overlooks, boutique shopping, and cozy inns. The town’s preserved 19th-century architecture makes it feel timeless, and its slower pace provides the perfect mental reset. It’s close enough for a weekend but far enough to feel like a true getaway.

Best Time to Visit

Fall is arguably Galena’s most magical season. The surrounding hills explode into shades of red, orange, and gold, making it ideal for scenic drives and winery hopping. Spring brings blooming landscapes and fewer crowds, perfect for relaxed exploration. Summer offers river activities and lively downtown events, while winter transforms the town into a charming holiday postcard with festive lights and snowy rooftops. No matter the season, Galena delivers cozy, small-town charm.

Top 3 Things to Do

1. Stroll Main Street – Lined with historic buildings, boutiques, art galleries, and locally owned restaurants, it’s easy to spend hours wandering.

2. Visit the Ulysses S. Grant Home – A beautifully preserved home that offers insight into Civil War history and the town’s legacy.

3. Go Wine Tasting – The surrounding countryside features scenic vineyards where you can sip local wines with panoramic views.

Where to Stay

Galena is known for its charming bed-and-breakfasts, many located in historic mansions. These properties often include fireplaces, clawfoot tubs, and homemade breakfasts that elevate the weekend experience. If you prefer modern luxury, there are upscale inns and countryside resorts offering spa services and golf. For a more private escape, cabin rentals in the hills provide quiet seclusion with beautiful sunset views. No matter your style, accommodations here add to the romantic atmosphere.

2. Saugatuck

Why It’s Underrated

While many travellers head to larger Michigan beach towns, Saugatuck remains quietly charming and artsy. It combines Lake Michigan’s soft sandy beaches with a creative, small-town atmosphere that feels both relaxed and refined. The art scene is vibrant but not overwhelming, and the town has a welcoming, inclusive energy that makes visitors feel at home. Because it’s less commercialized than some bigger resort towns, it feels more authentic and intimate perfect for a peaceful weekend away.

Best Time to Visit

Summer is peak season, with beach days, boat rides, and vibrant sunsets over Lake Michigan. However, early fall is a hidden gem time to visit — the crowds thin out, the weather remains mild, and the lakeshore becomes incredibly peaceful. Spring offers blooming dunes and quieter streets, ideal for a romantic trip. Even winter has its appeal, with cozy inns and dramatic frozen shoreline views that feel almost cinematic.

Top 3 Things to Do

1. Relax at Oval Beach – Consistently ranked among the best beaches in the Midwest, it offers wide sandy shores and stunning sunsets.

2. Explore the Art Scene – The town is packed with galleries featuring local and national artists.

3. Ride the Dunes – Adventurous visitors can explore towering sand dunes with guided rides or hiking trails.

Where to Stay

Saugatuck has a strong boutique hotel and inn culture, with charming waterfront properties offering harbour views. Many stays include wraparound porches and cozy fireplaces, perfect for unwinding. There are also stylish vacation rentals near the dunes for groups or families. Couples often opt for romantic inns tucked into quiet streets just steps from downtown dining. Whether modern or classic, accommodations here emphasize relaxation.

3. Starved Rock State Park

Why It’s Underrated

Many Chicago residents have heard of Starved Rock, but surprisingly few explore it fully. The park’s dramatic canyons, seasonal waterfalls, and scenic overlooks feel far more rugged than most expect from Illinois. Because it’s so close to the city, it’s often dismissed as a simple day trip — yet staying overnight allows you to experience sunrise hikes and peaceful moments after day visitors leave. It’s one of the Midwest’s most accessible nature escapes, offering real adventure without a long drive.

Best Time to Visit

Spring brings roaring waterfalls thanks to melting snow and rainfall, making it one of the most photogenic seasons. Fall offers colourful foliage and crisp hiking weather. Winter is uniquely beautiful waterfalls freeze into icy sculptures, attracting photographers and adventurers alike. Summer can be busy but provides lush greenery and longer daylight hours for exploring multiple trails. Each season completely transforms the landscape.

Top 3 Things to Do

1. Hike the Canyon Trails – Trails lead through sandstone canyons and to scenic river overlooks.

2. Chase Waterfalls – Several waterfalls flow after rain, creating magical photo opportunities.

3. Stay for Sunset Views – Overlooks above the Illinois River provide sweeping, peaceful vistas.

Where to Stay

The historic lodge inside the park offers rustic charm and convenience, allowing early access to trails. Nearby cabins provide more privacy for couples or families. In surrounding towns, you’ll find cozy inns and vacation rentals ideal for a weekend base. Staying overnight makes a huge difference — the park feels quieter and more immersive once day-trippers head home.

4. New Buffalo

Why It’s Underrated

New Buffalo is often overshadowed by larger Michigan lake towns, which makes it one of the best-kept secrets near Chicago. Just about an hour and a half away, it offers that dreamy Lake Michigan shoreline experience without the overwhelming crowds. The town blends relaxed beach vibes with upscale touches — think boutique shops, waterfront dining, and quiet marina views. Because it’s smaller and less commercial than some popular destinations, it feels more intimate and refined. It’s perfect for a spontaneous weekend when you want luxury lake energy without driving too far.

Best Time to Visit

Summer is ideal for beach days, boating, and sunset dinners along the water. The lake breeze keeps temperatures comfortable, making it perfect for outdoor relaxation. Early fall is especially beautiful — warm days, fewer visitors, and stunning golden sunsets over Lake Michigan. Spring offers peaceful shoreline walks and blooming landscapes, while winter brings a quiet, cozy atmosphere ideal for couples looking for a serene escape. Each season offers a slightly different version of lakeside charm.

Top 3 Things to Do

1. Spend the Day at the Beach – Wide sandy beaches make it easy to unwind, swim, or simply relax with a book.

2. Explore the Marina – Sunset walks along the harbour feel calming and picturesque, especially as boats return for the evening.

3. Visit Local Wineries & Breweries – The surrounding Harbour Country area features excellent tasting rooms perfect for a laid-back afternoon.

Where to Stay

New Buffalo offers stylish boutique hotels with rooftop decks and lake views, ideal for romantic getaways. Many vacation rentals sit just steps from the beach, perfect for families or friend groups. There are also cozy inns tucked into quiet neighbourhoods that provide privacy and comfort. For a more upscale stay, you’ll find waterfront resorts with spa services and fine dining options. No matter your preference, accommodations here lean toward relaxed luxury.

5. Door County

Why It’s Underrated

While Door County is well-known, most visitors stick to a few popular towns and miss its quieter corners. Stretching between Green Bay and Lake Michigan, the peninsula offers dramatic coastal views, charming fishing villages, hidden lighthouses, and peaceful countryside roads. Venture beyond the busiest spots and you’ll find tranquil beaches, scenic bluffs, and even islands that feel untouched. Its mix of maritime history and natural beauty makes it feel like a Midwest version of coastal New England — without the airfare.

Best Time to Visit

Summer is vibrant with cherry picking, boating, and waterfront dining. However, early fall is a hidden treasure, as colourful foliage reflects beautifully off the water. Late spring brings blooming orchards and fewer tourists, offering a quieter experience. Winter transforms the peninsula into a peaceful snowy escape, perfect for cross-country skiing and cozy cabin stays. The shoulder seasons are especially ideal if you want scenic beauty without heavy crowds.

Top 3 Things to Do

1. Explore Peninsula State Park – Hike scenic trails with sweeping views of the water and limestone cliffs.

2. Visit Washington Island – A short ferry ride leads to a slower-paced island filled with beaches and Nordic charm.

3. Tour the Lighthouses – Historic lighthouses dot the coastline and offer incredible photo opportunities.

Where to Stay

Door County is known for waterfront inns, charming cottages, and lakeside resorts. Many properties offer private beach access and sunset views over the bay. Cabin rentals provide a secluded, nature-focused experience ideal for families. Boutique hotels in smaller towns deliver cozy, small-community vibes with walkable access to shops and cafes. Whether rustic or refined, lodging here embraces the peaceful coastal atmosphere.

6. Lake Geneva

Why It’s Underrated

Lake Geneva has a reputation as a summer hotspot, but it’s surprisingly magical in the off-season. Once the peak crowds leave, the town reveals a quieter, more intimate charm. The lakefront mansions, scenic shoreline path, and cozy downtown feel far more relaxing in fall and winter. Many visitors only think of it as a boating destination, yet it offers year-round appeal with spa retreats, holiday markets, and scenic lake walks. Visiting during the quieter months feels like discovering a hidden side of a classic Midwest escape.

Best Time to Visit

Fall is one of the best times to go, as vibrant foliage surrounds the lake and crisp air makes shoreline walks refreshing. Winter offers snow-covered views and festive charm, especially around the holidays. Spring brings blooming trees and comfortable temperatures for exploring the lake path. While summer is lively and fun, the true underrated magic appears in the cooler months when the town feels calmer and more romantic.

Top 3 Things to Do

1. Walk the Shore Path – A scenic path wraps around the lake, offering views of historic mansions and sparkling water.

2. Take a Boat Tour – Even in cooler months, guided tours provide fascinating stories about the area’s history.

3. Explore Downtown – Browse boutiques, grab coffee, and enjoy lakeside dining with beautiful views.

Where to Stay

Lake Geneva offers historic grand resorts with lakefront views and spa services, perfect for a romantic retreat. There are also charming inns within walking distance of downtown shops. Cozy cabin-style rentals provide privacy for couples or small groups. During winter, many accommodations create a warm, festive atmosphere with fireplaces and lake views. No matter the season, the lodging scene enhances the relaxing experience.

7. Holland

Why It’s Underrated

Holland is often associated only with its famous tulip festival, but it offers far more than spring blooms. This lakeside town blends Dutch heritage, beautiful beaches, and a charming downtown filled with locally owned shops. Its iconic windmill and red lighthouse give it a European feel, making it feel like an international escape without leaving the Midwest. Because many travellers only visit during peak festival season, the rest of the year remains pleasantly uncrowded and peaceful.

Best Time to Visit

Spring is stunning during tulip season, when colourful flowers line the streets. Summer offers beach days at Holland State Park and lively outdoor events. Fall is quieter and filled with crisp air and golden lake sunsets. Even winter has charm, as snow transforms the lighthouse and shoreline into dramatic, photogenic scenes. Each season brings a different personality to the town.

Top 3 Things to Do

1. Visit Holland State Park – Relax on the beach and capture photos of the iconic “Big Red” lighthouse.

2. Explore Downtown – Enjoy boutique shopping, local cafes, and Dutch-inspired architecture.

3. Tour the Windmill & Gardens – Learn about the town’s heritage while strolling through beautifully maintained grounds.

Where to Stay

Holland offers cozy lakeside cottages and boutique inns near downtown. Many accommodations are within walking distance of shops and restaurants, making weekend exploring easy. Beachfront vacation rentals are perfect for families wanting direct access to Lake Michigan. For couples, charming bed-and-breakfasts provide a romantic and quiet setting. The town’s lodging options reflect its welcoming and relaxed atmosphere.