Chicago is an amazing city, but sometimes you need to escape the hustle and bustle for a refreshing road trip. In 2025, my family and I embarked on some unforgettable journeys to nearby destinations, each offering unique experiences and cherished memories. Whether you’re planning a family getaway trip from Chicago, a foodie adventure, or a relaxing retreat, these road trips will inspire your next adventure. Here are my personal experiences with four fantastic road trips from Chicago: Sheboygan, Milwaukee, Wauwatosa, and Champaign.
Sheboygan, Wisconsin: A Lakeside Retreat
Sheboygan, affectionately known as “The Malibu of the Midwest,” was the perfect first stop for a family-friendly adventure. The town’s stunning lakeside views and welcoming atmosphere immediately set the tone for our trip from Chicago.
We Stayed at Blue Harbor Resort
Blue Harbor Resort is a delightful escape situated right on the shores of Lake Michigan. Our family suite was spacious, with comfortable beds and breathtaking views of the lake. The kids adored the indoor waterpark, featuring slides, a lazy river, and a splash pad. The resort’s amenities also included an on-site spa and cozy fire pits, perfect for relaxing evenings.
Things We Did in Sheboygan, Wisconsin
- Mini Golf at Blue Harbor Resort: After breakfast, we enjoyed a round of mini-golf right on the resort grounds. It was a fun and relaxing activity for the whole family.
- Indoor Waterpark at Blue Harbor Resort: My family spent a half day to experience all the games in this waterpark. It was so much fun and unforgettable.
Exploring Sheboygan’s Culinary Gems:
- Parker John’s BBQ & Pizza: For lunch, we indulged in delicious barbecue and pizza. The smoky flavors of the brisket and the cheesy goodness of their pizza were unforgettable. The rustic decor and friendly staff added to the charm.
- Pier Ice Cream Shop: A visit to this quaint shop was a highlight. The kids loved the variety of unique ice cream flavors, while I enjoyed a classic scoop of vanilla bean. The lakefront seating was an added bonus.
- Sunday Dough Donut Shop: We couldn’t resist trying the donuts here. The maple bacon and lemon-filled varieties were the perfect sweet treat to end our Sheboygan experience. The shop’s cozy atmosphere made it even more enjoyable.
Milwaukee and Wauwatosa, Wisconsin: Art and Flavor
Milwaukee and nearby Wauwatosa are just a short drive from Chicago, but they felt like a world away. These vibrant towns combined rich culture, fantastic food, and cozy accommodations for an unforgettable stay.
We love Renaissance Hotel
The Renaissance Hotel in Wauwatosa exceeded our expectations. The sleek, modern design of the lobby and rooms was impressive, but it was the small touches that stood out. The beds were incredibly comfortable, and the rainfall shower in the bathroom felt luxurious. The staff’s attentiveness and recommendations for local attractions made our stay even better.
Dining and Cider Tasting at Pomona
Our first stop was Pomona, a cider-focused eatery where we sampled flights of local ciders paired with delicious small plates. The tangy apple cider and the savory cheese platter were standouts. The atmosphere was rustic yet trendy, making it a great place to unwind after the drive.
Immersed in Art at Art 64 Wauwatosa
Wauwatosa’s Art 64 event was a creative feast. Local artists showcased their talent, and we even participated in a painting workshop. It was a unique and enriching experience that left us inspired.
Dinner at Crafty Cow Food Restaurant
This restaurant was a hit for dinner. Known for its creative burgers and comfort food, the Crafty Cow did not disappoint. I’d highly recommend the “Mac Attack Burger,” which features a mouthwatering layer of mac and cheese. Their selection of local craft beers perfectly complemented the meal.
Ice Cream at Joy Ice Cream Wauwatosa
Before leaving, we treated ourselves to dessert at Joy Ice Cream. The locally sourced ingredients and creative flavors, like honey lavender, were absolutely divine. The shop’s cheerful decor and friendly service made it a delightful experience.
Champaign, Illinois: A Blend of History, Food, and Fun
Champaign was our final road trip destination, and it offered a delightful mix of history, culinary exploration, and unique activities.
I Hotel we chose to stay in Champaign
The I Hotel was an exceptional choice for our stay. From the moment we arrived, the staff made us feel welcome. Our room was spacious, featuring plush bedding and modern amenities like a Nespresso machine. The on-site restaurant served a delicious breakfast and the hotel’s proximity to local attractions made getting around easy. The hotel also had a lovely outdoor patio, which was perfect for unwinding in the evening.
Historical Adventures at Heritage Trail Destinations
We started our Champaign experience by visiting Heritage Trail Destinations like Illinois Central Railroad African Trail, J.C. Penney Boycott and Picketing Site, Skelton Park, Richmond Alumni Gallery, Black Joy Project, North First Street Corridor, African Americans in the Civil War & African American Elected Officials, Black Businesses in Urbana which offered a fascinating glimpse into the area’s rich history. The guided tours were informative and engaging, making it a highlight of our trip.
Culinary Delights in Champaign
- Pekara Breakfast: Our mornings began with breakfast at Pekara, where freshly baked pastries and aromatic coffee provided the perfect start to the day. The croissants were flaky and buttery, and the lattes were perfectly brewed.
- Maize Mexican Restaurant: For lunch, we enjoyed authentic Mexican cuisine at Maize. Their handmade tortillas and flavorful enchiladas were incredible. The vibrant decor and lively ambiance added to the experience.
- Collective Pour Restaurant: Dinner at Collective Pour was a treat for the senses. This restaurant offered an impressive selection of craft beers and a menu full of delicious pairings. The pork belly sliders were a standout.
- Neil Street Brunch: On our last morning, we had brunch at Neil Street Brunch, where the fluffy pancakes and hearty omelets left us feeling satisfied and ready for the day. The staff’s friendliness made us feel right at home.
Unique Experiences in Champaign
- Basketball Game Night: Watching a live basketball game was a thrilling experience at 1700 S. Fourth Street, Champaign. The energy of the crowd and the excitement of the game made for unforgettable memories.
- Goat Hike Tour and Cheese Tasting at Caprae Restaurant: This was hands down one of the most unique activities we’ve ever done. Hiking with friendly goats and sampling artisan cheeses at Caprae Restaurant was both fun and delicious. The goats were charming, and the cheese tasting was a culinary delight.
- Exploring Historical Murals: Champaign’s murals were a feast for the eyes, like the North First Street Barbershop Mural, Mural: Each One Teach One, and the KOFENA Mural. Each one told a story, and we enjoyed learning about the history and culture they represented.
What to Pack for a Weekend Getaway Trip from Chicago
Packing efficiently can make or break your weekend road trips. Here are some essentials to ensure a stress-free journey:
- Clothing: Pack versatile layers like sweaters, t-shirts, and comfortable jeans or leggings. Don’t forget pajamas and weather-appropriate outerwear.
- Shoes: Comfortable walking shoes for exploring and a pair of casual shoes for dinners or events.
- Toiletries: Travel-sized essentials like toothpaste, shampoo, and sunscreen. Bring a small first-aid kit just in case.
- Snacks and Drinks: Keep energy bars, nuts, and bottled water handy for the drive.
- Entertainment: Download podcasts, playlists, or audiobooks for the road. Bring games or activities for kids.
- Tech Gear: Chargers, power banks, and a camera or smartphone for capturing memories.
- Day Bag: A lightweight backpack for carrying essentials during outings.
- Miscellaneous: A reusable water bottle, travel pillow, and any specific items like hiking gear or swimsuits.
Tips for a Weekend Getaway Trips from Chicago
Planning can make your trips from Chicago smoother and more enjoyable. Here are my top tips:
- Start Early: Leave early in the morning to maximize your time at the destination and avoid traffic.
- Plan Your Stops: Research pit stops or attractions along the way to break up the drive.
- Make Reservations: Book accommodations, restaurants, and activities in advance to secure your spots.
- Check the Weather: Be prepared for changing weather conditions by packing accordingly.
- Travel Light: Stick to the essentials to avoid overpacking. Use a small suitcase or duffel bag.
- Stay Flexible: While planning is important, leave room for spontaneity. Some of the best memories come from unplanned adventures.
- Use Apps: Download travel apps for navigation, dining recommendations, and finding local attractions.
- Budget Wisely: Set a budget for accommodations, meals, and activities to avoid overspending.
Final Thoughts
These road trips provided everything we were looking for: relaxation, adventure, great food, and family-friendly fun. Whether you’re staying by the lake in Sheboygan, soaking up the art and flavors of Milwaukee and Wauwatosa, or diving into history and unique experiences in Champaign, each destination offers something special. Pack your bags and hit the road—these Midwest gems are waiting to be explored!
Remember to tag @travelwiththerussells on social media to share your adventures and connect with other travelers.
Enjoy your weekend getaway trip from Chicago, and I’m waiting for you to tag me to share your experience!
