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Amazing Day Trips from Chicago

Destinations for all styles and seasons.

a waterfall at Matthiessen State Park

Have you been around Chicago’s blocks a few times? Ready to see all the amazing local treasures that you can find just outside the city? All these locations are within a few hours drive of Chicago, most of them much closer! You’ll see the natural beauty of the Midwest, and visit some amazing local gems. 

Ready? Let’s go!

Starved Rock State Park and Matthiessen State Park

a waterfall at Matthiessen State Park

These two state parks are neighbors, with their entrances just steps away from each other, and they feel like an entirely different world from Chicago. Both Starved Rock and Matthiessen are full of iconic rock formations, rivers, and waterfalls. The natural beauty is truly astounding, and not at all what people picture when they imagine Illinois!

Both parks are open year round, with Starved Rock in particular being a haven for ice climbers in the winter, but the best times to visit these parks are in the warmer months. In spring, the waterfalls are extra vivacious. In summer, the whole forest comes alive. And in the autumn, the trees turn their spectacular colors!

Word to the wise: the parking lots at these amazing state parks fill up early in the peak season (read: summer, holiday weekends, etc…) so if you plan to make the drive from Chicago, make sure you get an early start!

Lightscape at the Chicago Botanic Garden

Chicago Botanic Garden

Just a short trek north of Chicago proper, you’ll find the Chicago Botanic Garden. This gorgeous place is made up of acres upon acres of manicured beauty. They have everything from local produce trees and pollinator gardens, to a classic Japanese Garden and a Rose Garden. You could spend hours in this place and not see everything there is to see.

Spring and Summer are the best times to visit the Garden for the natural foliage, but their seasonal special events also draw huge crowds every year. Most iconic are the Night of 1,000 Jack-o-Lanterns every October, and the Lightscape display that graces the grounds every holiday season. Tickets for these always sell out, so be sure to plan well in advance if you want to attend one of these iconic events!

Jonamac Orchard

a redhead picking apples at an orchard

As someone who grew up with several apple orchards within spitting distance of their childhood home, I’m very picky when it comes to my autumn apple orchard trip. And my favorite place near Chicago is Jonamac Orchard in Malta, IL.

Jonamac offers everything your inner child could possibly want. Endless rows of trees for pick-your-own apples, amazing apple cider donuts, food trucks, a cider house for the grown ups, a petting zoo, and a plethora of county-faire-style games and attractions, including a corn maze and apple cannons! It’s the perfect place to bask in all the traditional activities of fall, and to take home way too many apples.

Casting Whimsey Teashop

Casting Whimsey Tea is a local gem of a tea shop up in Woodstock, IL. This family-run shop makes unique, flavorful tea blends and amazing baked treats. They have a whole wall of tea blends to smell and sample, and you can order tea by the glass or by the tin to take home. Best of all, the blends and their names are inspired by all your favorite nerdy fandoms!

afternoon tea service at Casting Whimsey Teahouse

Best of all, this shop regularly hosts special events like Tea & D, (the mashup of D&D and teatime you never knew you needed), or weekend Afternoon Tea services, complete with meal items and sweet treats, for under $25! It’s a deal you absolutely cannot miss. Just make sure to book well in advance as the dates tend to fill up quickly! The towers of Casting Whimsy tea blend tins in my kitchen cupboard salute you.

Indiana Dunes State Park

For lakefront tranquility, it doesn’t get much better than Indiana Dunes State Park. Just a short drive around the south end of Lake Michigan (or you can take the Metra!) you’ll find beautiful beaches and cozy campgrounds. It’s the perfect place for a refreshing swim (the Great Lakes never really get warm), or a luxurious beachside walk. On a clear day, you can see all the way back to the Chicago skyline across the water!

Bristol Renaissance Faire

If you happen to be visiting Chicago in the summer months, the Bristol Renaissance Faire is just about the best day trip out there! Running Saturdays and Sundays from July to Labor Day, the Bristol Ren Faire is located just across the border into Wisconsin, about a 90-minute drive from Chicago’s center. If you’re a ren faire aficionado, Bristol is consistently voted among the best in the country, and will blow you away! If you’re unfamiliar with ren faires, Bristol will absolutely ruin you for other ren faires in the best possible way! 

It’s miles of magic, consisting of amazing attractions, delicious food, unique shopping experiences, period-appropriate entertainment (up to and including live jousting!), and the best damn people watching you’ve ever experienced in your life! Don a costume and step back in time! It’ll be the time of your life.

Pick one of these amazing day trips from Chicago and go on an adventure!

Chicago offers endless treats, and has even more to offer just a short distance away. Branch out on your next visit and find something new and spectacular!

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Love and Shenanigans,


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