Need a getaway from the hustle and bustle of the Windy City? Grab our top tips, tricks, and ideas on some of the best weekend trips from Chicago. From outdoor adventures to bucket list sports trips to small town charm, there is something for everyone!
Ready for a Weekend Getaway from Chicago?
Look no further as we have handpicked the best weekend trips that promise to leave you refreshed and rejuvenated. Whether you are a traveler who is visiting Chicago or a resident, you’ll find our list filled with options that are within driving distance to help you plan an exciting weekend road trip.
These destinations were selected by a Chicagoan who has visited these cities several times for family weekend getaways. You can be assured that, with this post, you will be in the know about the best outdoor activities, food, and cultural experiences.
These top recommendations for weekend trips that are just a short drive or train ride away from the Windy City. So pack your bags and get ready for an unforgettable weekend adventure!
This post contains affiliate links which means I could earn a small commission, if you make a purchase, at no additional cost to you. As an Amazon Associate, I earn from qualifying purchases. For more information, read my full Disclosure HERE.
There are so many fun things to do in Chicago. But there’s so much more to explore! Check out our top picks for the best weekend trips from Chicago:
St. Joseph, Michigan
Travel Time from Chicago: 1.5 Hours | 95 Miles
Love beach getaways? Similar to Union Pier, St. Joseph is one of the best beach towns near the Great Lakes and it’s much closer to Chicago than other well-known coastal towns in Michigan.
The best time to visit for warmer weather is May through August. During the fall, the town is much less crowded, but water temperatures will be much cooler, perhaps too cool, for a swim.
Start your day with a stroll through downtown where you will find many quaint boutiques and stores. Most of the retail stores are on Broad Street and State Street.
Don’t miss the G&M Variety store, it is like a throw-back five-and-dime store with nostalgic vibes that sell affordable items that you may have forgotten to pack. The boutique clothing stores are small, and the purchase almost guarantees a one-of-a-kind garment because they are so different than what is found in chain retailers.
Walk down Broad Street towards Silverbeach to spend the afternoon at Compass Fountain (kids will love playing here). Across the street on the other side is the historic Silver Beach Carousel. There are plenty of cafes and ice cream parlors, like Kilwins Ice Cream Parlor, that are less than a five-minute walk away for refreshments. Wind down the evening with a fantastic burger at Buck Burgers and Brew or stop at Schu’s Grill & Bar.
Insider Tip: From Chicago, you can skip the drive and take a relaxing train ride to St. Joseph via Amtrak. The ride is just under two hours and stops downtown near the beach at Broad and Vine Streets.
Trying to decide where to stay in St. Joseph? Check out current rates and availability at The Springhill Suites St Joseph Benton Harbor or an area VRBO.
Love a beach vacation? Check out these amazing beaches on the east coast that are perfect for your next family vacation!
Galena, Illinois
Travel Time from Chicago: 3 Hours | 170 Miles
Looking for a fun road trip from Chicago? Head west to Galena for a bit of nostalgia, history, and water fun.
Historically, this city was a rapidly growing town for the rich ore deposits and during the Civil War, Galena made its mark in Illinois as the hometown of President Ulysses S. Grant.
Today, it is a favorite destination in the Midwest for a weekend getaway. The town of Galena is historic and charming. The peak months for visiting are May through August for summer activities like canoeing, hiking, biking, and golfing.
In addition to festivals, parks, boutique shops, and art galleries, you can enjoy wineries from local vineyards. There are plenty of activities that will keep you entertained and engaged during your visit.
Insider Tip: For a fun and unique experience, make a reservation in a heated igloo at Galena Vineyards.
During winter, the holiday vibes are magical, and the streets are bustling with holiday shoppers for unique gifts. Year-round, you can explore historic sites like the Ulysses S. Grant Home, Dowling House, and Old Market House.
Trying to decide where to stay? Check out current rates and availability at area hotels in Galena.
Even a weekend getaway requires some planning! Grab our free travel planning worksheet and road trip essentials checklist for a worry free vacay!
And be sure to share all your epic adventures on Instagram with these fun road trip captions and quotes!
Milwaukee, Wisconsin
Travel Time from Chicago: 1.5 Hours | 93 Miles
Milwaukee’s unique blend of urban charm and natural beauty makes it a great weekend getaway for families and couples. The city is on the shore of Lake Michigan and has several must-see attractions. We highly recommend:
- The Milwaukee Art Museum
- The Harley-Davidson Art Museum
- The Milwaukee Public Market
- The Milwaukee Riverwalk
Milwaukee is a great destination year-round for music festivals, celebrity performances, and seasonal activities.
And since Wisconsin is famous for dairy products, particularly cheese, no visit would be complete without sampling the cheese. The Wisconsin Cheese Market has an incredible selection of cheeses — some varieties can be sampled in the store. The West Allis Cheese & Sausage Shoppe at the Public Market is not to be missed, they have the best deep-fried cheese curds!
Insider Tip: If you are looking for an evening of family fun, we highly recommend the Safe House. The interior is whimsically decorated in a spy theme with secret codes hidden throughout the restaurant. They serve great comfort food in generous portions.
Milwaukee is definitely one of the most underrated and best weekend trips from Chicago!
Trying to decide where to stay in Milwaukee? Check out current rates and availability at Hotel Metro (We love The Autograph Collection Hotels!)
Love an adrenaline rush? Add a stop at Six Flags Great America Amusement Park on your way to Milwaukee from Chicago!
Oglesby, Illinois
Travel Time from Chicago: 1.5 Hours | 100 Miles
Starved Rock State Park is a haven for outdoor enthusiasts and nature lovers. There are towering sandstone canyons, cascading waterfalls, and lush forests. The landscape is a perfect backdrop for hiking, biking, walking, and rock climbing in Spring and Summer.
Designated areas have tables and grills for a picnic or an extended family gathering. You can also explore the Illinois River by kayak or canoe (rentals are available at the Lone Point Shelter). It is also a popular destination for fishing because the river is known for its abundant catch of catfish, bass, and walleye.
During Fall, you will be surrounded by jewel-toned leaves as the foliage turns. Plan a weekend getaway to Starved Rock in October and November; It is the perfect time of year to watch the brilliant colors of nature in the Midwest.
If you are seeking a getaway to relax, have an adventure, or connect with nature, Starved Rock is a must-visit destination that promises memorable outdoor experiences.
Trying to decide where to stay near Starved Rock State Park? Check out current rates and availability at these adorable cabins!
Have more than a weekend to getaway? Check out these fun Midwest road trips for your next vacation!
Madison, Wisconsin
Travel Time from Chicago: 2.5 Hours | 147 Miles
Looking for a fun-filled weekend getaway in Madison, Wisconsin? You’re in for a treat!
Start your adventure by exploring the lively State Street, where you can shop for unique treasures, indulge in delicious local cuisine, and soak up the vibrant atmosphere. Don’t miss the opportunity to visit the iconic State Capitol building, with its stunning architecture and panoramic views of the city.
For a dose of natural beauty, take a leisurely walk around Olbrich Botanical Gardens, where you can slow down and immerse yourself in the serene surroundings.
If you’re a sports enthusiast, catch a Badgers game at the University of Wisconsin-Madison and feel the electric atmosphere as the crowd cheers on their beloved team. (We personally love attending local sporting events when we travel!)
And no visit to Madison is complete without a visit to the renowned Dane County Farmers’ Market, where you can sample fresh produce, artisanal cheeses, and other local treats.
Insider Tip: Grab a burger and cheese curds at local institution Dotty Dumpling’s Dowry. Seriously yummy!
Whether you’re seeking outdoor adventures, cultural experiences, or simply a warm Midwestern welcome, Madison is one of the most fun weekend trips from Chicago.
Trying to decide where to stay in Madison? Check out current rates and availability at The Graduate Madison or The AC Hotel Madison Downtown.
Keep the whole family entertained while traveling with these fun road trip questions and games.
Kohler, Wisconsin
Travel Time from Chicago: 2.25 Hours | 145 Miles
Want a truly unique getaway from Chicago?
Then you might want to check out Kohler, Wisconsin!
Kohler, Wisconsin (yes, named for the well known pluming company) is a small village in Sheboygan County on the shores of Lake Michigan that offers visitors a little something different. From world class golf to luxurious accommodations and small town charm, Kohler is sure to surprise you.
Golf enthusiasts will be thrilled to experience Kohler’s championship-level golf courses, including the acclaimed Whistling Straits and Blackwolf Run, where you can tee off amidst breathtaking landscapes. Pro Tip: Make sure to check the weather forecast, as conditions can vary drastically day to day.
Outdoor enthusiasts can also venture to the nearby Kohler-Andrae State Park, boasting picturesque trails and sandy beaches, perfect for picnics and sunset views. There are also several you-pick farms in the area for picking fruit depending on the season.
If you’re looking for a weekend full of rest, relaxation and luxury, treat yourself to the world-renowned Kohler Waters Spa and stay at the five star, five diamond American Club Resort Hotel. For a taste of culinary excellence, indulge in exquisite dining experiences at Kohler’s award-winning restaurants, where skilled chefs showcase locally sourced ingredients.
For something a little fun and different, check out the incredible signature Kohler Store and Showroom. Finish up your weekend strolling the quaint streets of Kohler and exploring the fabulous boutiques and galleries before heading back home.
Check out current rates and availability at The American Club Resort Hotel in Kohler, Wisconsin for a true five star experience!
We love a good road trip! For more ideas all over the country, check out our top picks for the best USA road trips for an adventure.
Green Bay, Wisconsin
Travel Time from Chicago: 3.25 Hours | 207 Miles
Are you a sports fanatic? The you need to add Green Bay, Wisconsin to your bucket list.
Why? The Green Bay Packers, of course!
We aren’t even die hard Packers fans. But anyone in the sports world will tell you that a game at Lambeau Field is definitely a bucket list experience for any sports enthusiast. And my husband is a HUGE sports fantatic.
So, start your weekend out by catching an exciting Packers game at the iconic Lambeau Field, where the atmosphere is electric and the cheeseheads are always out in full force.
Not into football? No worries, there’s more to Green Bay than just football! Green Bay has so much to offer visitors from arts and cultural experiences to breathtaking natural beauty.
Explore the city’s charming downtown area, filled with cozy cafes, trendy shops, and delicious local eateries. If you’re a nature lover, be sure to check out the stunning Green Bay Botanical Garden or embark on a scenic hike along the picturesque shores of Lake Michigan.
And of course, no trip to Green Bay would be complete without indulging in some mouthwatering cheese curds – a local specialty. So pack your bags, bring your sense of adventure, and get ready for an unforgettable weekend in Green Bay, Wisconsin!
Trying to decide where to stay in Green Bay? Check out current rates and availability at The Hotel Northland (another Autograph Collection pick!) or The Springhill Suites Green Bay to be within walking distance of Lambeau Field. Be sure to book early if you’re planning to catch a game!
We love a bucket list! Get even more ideas and inspo from our huge USA bucket list!
Final Thoughts on Weekend Trips from Chicago
A weekend getaway from Chicago offers the perfect opportunity to escape the bustling city and discover new adventures. Whether you seek outdoor thrills, cultural experiences, or simply a tranquil retreat, there are endless options within a short distance from the Windy City.
From the breathtaking landscapes of Starved Rock and the charming coastal towns along Lake Michigan to the vibrant cityscapes of Milwaukee and the historic allure of Galena, each destination has its unique charm and attractions.
So pack your bags, embark on a short drive, and enjoy one of these memorable weekend trips from Chicago. You’re sure to find the weekend will leave you refreshed, inspired, and eagerly planning your next adventure.
About The Author
Thank you to Tanya from Travels and Treasures for contributing to this post. Be sure to check out her site for all things Chicago!
And be sure to save these best weekend trips from Chicago for you future travels! Happy adventuring!
