15 Easy Weekend Getaways Within 3 Hours of Chicago (That You Probably Haven't Heard Of)
Can you believe there are only a few weeks of summer left? (And for those with kids—less than a month before school is back in session!) If you’re anything like me, you’re probably looking to squeeze in every last bit of sunshine, adventure, and family time before the routines of fall take over.
That’s why I’ve pulled together a list of 15 easy, family-friendly weekend trips that are just a short drive from Chicago—and best of all, these are under-the-radar spots. You won’t find the usual tourist crowds here, but you will find charming towns, quiet beaches, hiking trails, and unique attractions perfect for a quick escape.
And yes, these have all been curated and road-tested by yours truly (and often, my family!). If one of these places steals your heart? Let me know. I have trusted referral partners in each of these areas who would be happy to help you explore your real estate options there.
Illinois Hidden Gems
1. Ottawa, IL
Basecamp for Starved Rock, but head to Matthiessen and Buffalo Rock State Parks for less crowded hiking and waterfall views. Ottawa itself has a charming walkable downtown and historic murals kids love.
2. Utica & Oglesby, IL
Close to Starved Rock but slower-paced. Enjoy horseback riding, canoeing on the Vermillion River, and local farm stands.
3. Galena Territory / Elizabeth, IL
Skip bustling Galena and head 20 minutes east. Apple River Canyon State Park offers peaceful hikes and picnicking. You’ll also find horseback riding and family-friendly farms.
4. Rockford, IL
Often overlooked, but the Discovery Center Museum is amazing for kids, and Anderson Japanese Gardens is a serene surprise.
5. Kankakee River State Park, IL
An easy drive south with great fishing, swimming, and family-friendly hiking. Pack a picnic and spend the whole day.
Wisconsin Wonders
6. Delavan, WI
Just minutes from Lake Geneva but way less busy. Lake Lawn Resort is great for families, and the town has cute shops and lakeside parks.
7. New Glarus, WI
Switzerland in the Midwest! Known for beer, but also family-friendly with hiking, cheese tasting, and a very walkable downtown.
8. Baraboo, WI
A quirky, retro town with the Circus World Museum and proximity to Devil’s Lake State Park for swimming, hiking, and rock climbing.
9. Elkhart Lake, WI
Clear water, less commercial than the Dells, and great for paddleboarding, beach time, and family-friendly resorts.
10. Kettle Moraine State Forest – Southern Unit
Quiet, beautiful, and packed with trails, campgrounds, and biking routes. Bring your bug spray and your sense of adventure.
Indiana & Michigan Escapes
11. Chesterton, IN
Offers easy access to Indiana Dunes without the chaos. Visit Coffee Creek Preserve and the European Market downtown.
12. Beverly Shores, IN
A hidden beach town with mid-century architecture, dunes trails, and quiet shoreline.
13. Union Pier & Lakeside, MI
Smaller, quainter alternatives to New Buffalo with bikeable neighborhoods and peaceful beaches.
14. St. Joseph River Area – Niles, MI
Kayaking, fruit farms, and a quieter riverside setting than nearby tourist hubs.
15. Three Oaks, MI
An artsy little town with a big personality—the Journeyman Distillery is surprisingly family-friendly, and you can pop over to Warren Dunes for an afternoon adventure.
If you’re planning one last summer hurrah, consider trying somewhere new. Each of these destinations offers something unique and refreshing without the hassle of long travel days or airport delays.
Need help picking the right fit? Reach out! I’m always happy to share insider tips—and if you fall in love with one of these spots (it happens!), I can connect you with a trusted real estate expert who knows the area inside and out.
Here’s to making the most of the final stretch of summer!
