10 Great Road Trips from Chicago

May 15, 2023

Road trip season is officially here! Here is a list of 10 great Chicago road trips you can do a day or weekend with or without the kids. Many of these make family trips and a weekend couples trip, all 3 hours or less from Chicago.

Galena, IL

One of our most favorite getaways is Galena! It’s great for families, a romantic getaway, or a relaxing girls weekend. This charming southwestern Illinois city is an easy drive – just a little over 3 hours from Chicago. Grab a coffee at Trolley Depot Coffee & Tea and take the trolley on a scenic, historic tour of Galena where you’ll see many of the original early nineteenth century buildings. You can do yoga with or take a walk with goats, and then shop the small boutiques & cafes that line the main streets. I love Bread and Vine for breakfast, brunch, or lunch, Durty Gurt’s for lunch or dinner, Isabella Ltd for gifts and home decor, and Poopsies for toys and gifts. If you’re a golfer and/or want to get away from the hustle and bustle, I recommend staying at the sprawling Eagle Ridge Resort & Spa. It is a bit of a drive to Main Street, so if the majority of your plans center around shopping and dining, I would suggest staying closer to town! The Irish Cottage Inn & Suites is a boutique hotel about 3 minutes from downtown with friendly staff, onsite dining, and has been recently renovated. There are also plenty of AirBnb’s to choose from right on the main strip.

Sheboygan, WI

Sheboygan, Wisconsin is a lake resort town, where a summer stay is the star but with an indoor water park at Blue Harbor Resort, it’s a the perfect all-season getaway! The resort also has mini golf, an arcade, outdoor swimming, nightly campfires, and beaches. Stay in the hotel for easy access to the amenties and restaurants, or get a villa down the beachside with your own kitchen, living room, and multiple bedrooms. Sheboygan is great for families, girls getaways, and couple trips. If you’re traveling with younger children, Bookworm Gardens is a must-see. And, definitely make sure you eat at Field to Fork Cafe!

Blue Harbor Resort, Sheyboygan

Milwaukee, WI

Black Cat Alley, Milwaukee

Milwaukee, Wisconsin is SO close to Chicago which makes it such an easy day trip! MKE serves up great restaurants with lots of shopping! You can brewery hop or walk around downtown. Visit Broadway Paper (paper and gift store) and MOD GEN (gorgeous plants), and then brunch at the popular and delicious Sweetdiner! This can be done in a day or stay for the weekend! I’ve taken the Amtrak there and it’s such an easy ride!

Starved Rock, IL

I just recently went to Starved Rock, Illinois and had the best time! It is about 2 hours away from Chicago and a pretty easy road trip! It’s great for hiking with or without the kids. I would recommend taking older kids though, because part of the trail is pretty difficult. It took about one hour each way to complete one hike. Then, there is a restaurant we grabbed lunch at on the top of Starved Rock. It was pretty good and had pretty views of the canyon!


Oregon, IL

We took a family road trip to Oregon, Illinois two years ago and stayed at @pinecreekescape cabins. cabins. These are log cabins across from White Pines State Park. Check out the Bison at Nachusa Grasslands where you can see Bison roam free. It’s pretty cool! Or hike the White Pines State Park, which has beautiful hiking paths and a playground for the kids.

White Pines State Park hiking trails map
Map of White Pines State Park hiking trails

Rockford, IL

Rockford, Illinois is just about under 100 miles northwest from Chicago. We love to stroll through and see the 12 acres of gardens, waterfalls, ponds, and tea house at the Anderson Japanese Gardens. When you’re ready to fill your belly, head over to The Norwegian, which is only a 3 minute drive from the Gardens. They serve delicious drinks, brunch, and dinner in the summer. Don’t skip the Danish pancake balls and house-made jam! Walk off your meal and shop next door at the cutest mid-century modern shop, Rooted, for gifts and home decor.  If the weather is good and you’re there on a weekend, check out The Top Rooftop Bar & Lounge at Embassy Suites for views of historical downtown, drinks, and apps! If you’re visiting with kids, make sure to check out Discovery Center Museum for a totally fun, interactive experience.

Lake Geneva, IL

Lake Geneva is a popular lake town with so much to do! There’s magic shows for tweens+, a historical museum, boat and jet ski rentals, boat tours (the mailboat is particular cool), a skate park, disc golf course, a safari(!) and golfing galore. The water park at Timber Ridge, @timberridgelodge, part of @grand_geneva, is great for littles! You can also take a walk or bike ride by the lake and then grab something yummy at one of the downtown restaurants.

Saugatuck, MI

One of my favorite road trips is to Saugatuck, Michigan! It’s about 3 hours away from Chicago and there is so much to do! Dune rides, beaches, lots of great restaurants, ferry ride shops, & art galleries! I have two full blog posts here- for families or a couples trip to the area!

New Buffalo, MI

Roughly 90 minutes from Chicago, New Buffalo, Michigan is a super fast drive and you can stay the day or the weekend. Public beach, small shops, wine trail, check out a some breweries in the area, hike the dunes, etc. There’s a full blog post here.

Holland, MI

Holland, MI

Lastly, is Holland, Michigan. It’s just the cutest little town! There’s so much to see and do between the dunes, the beach, the tulips and the windmills! Downtown Holland has many great restaurants and shops. Don’t miss Lemonjello’s for college shop vibes, coffee and pastries, The Holland Peanut Store, an old school candy shop, Neli’s Dutch Village, a Netherlands theme park with a great gift shop, and Deboer Bakery for amazing cronuts. For dinner, we love New Holland Brewery, Boatwerks (the only waterfront restaurant in town), and Beechwood Grill.

Hopefully some of these road trip ideas from Chicago will be helpful this summer or even in the fall!


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