Best Weekend Getaways From Chicago

Living in or near Chicago means you’re in the perfect spot to explore a wide variety of weekend destinations. From charming small towns to scenic lakefront escapes, the Midwest offers some incredible options for quick and refreshing short trips from Chicago. Whether you’re planning a romantic getaway, a family outing, or just a break from city life, these weekend road trips from Chicago promise relaxation, fun, and memorable experiences all just a few hours away.

Here are 10 of the best weekend getaways from Chicago you should definitely add to your travel list.

1. Lake Geneva, Wisconsin

Travel Time: About 1.5 hours

Lake Geneva is a long-time favorite for weekend getaways from Chicago and for good reason. This lakeside resort town is packed with things to do, from boating and hiking to shopping and dining. In the summer, enjoy water sports and scenic lake cruises. During winter, cozy up in a lakeside cabin or go snowshoeing through nearby trails. Lake Geneva also offers luxury resorts and romantic B&Bs, making it ideal for couples looking for a peaceful retreat.

Best For: Couples, outdoor lovers, spa-goers

2. Galena, Illinois

Travel Time: About 3 hours

Galena is one of Illinois’ most picturesque small towns, with historic architecture, boutique shopping, and a rich Civil War-era past. Take a stroll down Main Street, enjoy wine tastings at local vineyards, or explore nature with a hike along the Galena River Trail. In winter, Chestnut Mountain Resort offers skiing and snowboarding.

Best For: History buffs, antique lovers, romantic getaways near Chicago

3. Starved Rock State Park, Illinois

Travel Time: About 1.5–2 hours

For nature lovers, Starved Rock State Park is a must-visit. Known for its dramatic canyons, waterfalls, and wooded trails, it’s one of the best places to visit near Chicago if you want to disconnect and explore the outdoors. In spring, the waterfalls are at their peak. In fall, the foliage is absolutely stunning.

Best For: Hikers, families, photographers

4. Saugatuck, Michigan

Travel Time: About 2.5 hours

Saugatuck is a charming coastal town on Lake Michigan, known for its art galleries, craft breweries, and sandy beaches. Oval Beach is one of the best in the region, and the downtown area is perfect for browsing local shops and enjoying fresh seafood. If you’re looking for a relaxing escape, this is one of the most peaceful short trips from Chicago.

Best For: Beach lovers, art enthusiasts, romantic weekends

5. Milwaukee, Wisconsin

Travel Time: About 1.5 hours

Milwaukee might not be the first city that comes to mind for a weekend getaway, but it has a lot to offer especially for foodies and beer lovers. Tour iconic breweries like Lakefront Brewery or explore the Milwaukee Public Market. Museums like the Milwaukee Art Museum and the Harley-Davidson Museum provide a cultural fix.

Best For: Foodies, beer lovers, city explorers

6. Indiana Dunes National Park, Indiana

Travel Time: About 1 hour

Just a short drive from the city, Indiana Dunes offers over 15 miles of sandy beaches along Lake Michigan, plus miles of hiking and biking trails. This national park is a perfect escape during warmer months, with options for swimming, picnicking, birdwatching, and even camping. It’s one of the best weekend road trips from Chicago if you’re craving sun and sand.

Best For: Families, nature seekers, beachgoers

7. Madison, Wisconsin

Travel Time: About 2.5 hours

The capital of Wisconsin, Madison offers a mix of small-town charm and big-city attractions. Visit the Capitol building, rent bikes to ride around Lake Monona, or explore the lively farmers market. With its college-town vibe and eclectic food scene, Madison is a laid-back but energizing getaway.

Best For: Food lovers, bikers, culture seekers

8. Door County, Wisconsin

Travel Time: About 4.5 hours

If you have a full weekend to spare, Door County is worth the drive. This peninsula between Green Bay and Lake Michigan is dotted with quaint villages, orchards, lighthouses, and state parks. It’s a favorite for fall foliage tours, cherry-picking in summer, and cozy winter retreats.

Best For: Scenic drives, nature lovers, romantic getaways near Chicago

9. New Buffalo, Michigan

Travel Time: About 1.5 hours

This Lake Michigan beach town offers stunning lake views, delicious food, and boutique shopping. It’s also home to wineries, breweries, and luxurious inns. Whether you’re up for paddleboarding or sipping wine on a patio, New Buffalo is one of the best places to visit near Chicago for a quick, peaceful weekend.

Best For: Couples, wine lovers, beach trips

10. Holland, Michigan

Travel Time: About 2.5 hours

Famous for its Dutch heritage and tulip festival, Holland is a unique weekend destination. Explore Windmill Island Gardens, enjoy the sandy beaches of Lake Michigan, and take a stroll through the charming downtown. It’s especially magical in spring, but worth visiting year-round.

Best For: Spring trips, families, cultural escapes

Final Thoughts

With so many incredible weekend getaways from Chicago, there’s no need to go far for a memorable escape. Whether you’re in the mood for a beachside break, an outdoor adventure, or a cultural experience, the Midwest offers something for every kind of traveler. These short trips from Chicago are perfect for recharging and discovering something new without the stress of long travel.