20 Best Weekend Getaways Near Chicago by Car
{{This post might contain affiliate links. If you use any of these links to buy a product, I will earn a small commission at no additional cost to you}}. Read my full disclosure for more details.
Sometimes we all need to escape from the city we live in and go somewhere to relax, to think about our lives far from the people, or have a short vacation to fill out our energy. The last-minute trip from Chicago can be made quickly as there are 20 best weekend getaways near Chicago by car within 8 hours.
Even a short weekend getaway to a new place can make a big difference in our lifestyle and help us to recharge.
If you live in Chicago, you have many options, from just going on a day trip or the whole weekend, which can take from a minimum of 1.5 hours drive to an 8-hour drive.
Here is the list of 20 short weekend getaways near Chicago
20 Best Weekend Getaways Near Chicago by Car
Wisconsin
There are so many places to visit in Wisconsin, such as Milwaukee, Wisconsin Dells, Madison, and Lake Geneva, and this list can go on and on.
1. Milwaukee, WI
Milwaukee is a city in Wisconsin located just 90 miles from Chicago. Approximately 1.5 hours drive. The best time to visit Milwaukee is the summer. From visiting the Milwaukee Art Museum, Veterans Park, Summerfest, Harley Davidson museum, exploring Brady street or farmer’s market, and more.
There are lots and lots of things to do in the summer and most of the things you can do for FREE.
Want to know all things to do in Milwaukee? checkCheckthis article.
Book Now and Save at Hotels.com
2. Wisconsin Dells, WI
The distance between Chicago and Wisconsin Dells is 164 miles (about 3 hour’s drive). Wisconsin Dells is the most popular city in Wisconsin, especially for young people, as it offers a lot of attractions to explore. To be more exact, the number of attractions is close to 100. You can expect to find a lot of outdoor and indoor Waterparks, museums and exhibits, live entertainment, amusement parks, and many more.
This can be the best getaway with kids, loved ones, or with friends. It doesn’t matter who you are going with as there are so many good things to do for anybody and any age.
Best things to do in Wisconsin Dells
Best hotels to stay in Wisconsin Dells
1. Hilton Garden Inn Wisconsin Dells
2. Home2 Suites by Hilton Milwaukee Brookfield
3. Tamarack Wisconsin Dells a Ramada by Wyndham
3. Madison, WI
Madison is Wisconsin’s capital city and is just 147 miles from Chicago (about 2.14 hours drive). The best time to visit Madison is the summer (if you want to take advantage of all activities early fall, and spring if you just want to explore around.
Madison’s five lakes cover more than 15,000 acres, and there are so many water activities in the summertime.
Capitol Square is a must historical building to visit.
Are you a live music fan? No problem, catch one at the outdoor square, rooftop, or park concert on one of the beautiful summer days.
Want to visit with a family? Then, they offer kids entertainment as well.
From my personal experience, I can say that I couldn’t take advantage of the activities this city offers as I visited it in the fall when it was already chilly and super windy.
Madison should always be on your list of places to visit near Chicago though. It can be fun. There are so many things to do in Madison for FREE. Definitely take advantage of that on your visit.
Here are the best tips on how to plan the best micro trip
4. Door County, WI
Door County is a county in Wisconsin, which is on a peninsula between Green Bay and Lake Michigan. It is known for its long shoreline and many beautiful parks.
Door County is 244.7 miles from Chicago (3h 43m drive). Whether you are looking for a place to relax, to have a romantic or family getaway, or simply to have a friend’s short vacation together, this is a place to go.
It has so much to offer, from nature preserves, to cultural entertainment, adventure sports, and more.
Best things to do in Door County, WI
Save up to 25% on hotel exclusive offers
5. Lake Geneva, WI
Lake Geneva is the best place to enjoy the beautiful landscape and relax. Lake Geneva is 83.5 miles from Chicago (just a 1.25-hour drive).
Lake Geneva can be a perfect getaway any time of the year, but summer is at the top of the list. From water activities, hiking, horse riding, and visiting parks to outdoor activities, and more.
One of the famous and unique attractions in Lake Geneva is the 26-mile Lake Geneva Shore Path. This old Native American walking trail crosses right over the front yards of private waterfront properties and continues along the entire length of the lake.
Check out more things to do in Lake Geneva here.
Best hotels and vacation rentals to stay in Lake Geneva
2. Harbor Shores on Lake Geneva
3. Find your private vacation rental in Lake Geneva with VRBO
6. Apostle Islands, WI
This is the longest trip from Chicago, which can take up to 8 hours, but it is worth visiting. This place is the best for avid hikers, water sports enthusiasts, and campers. The only way to get to the island is by water. There is a ferry that can take cars to Madeline Island.
Stockton Island is home to one of the greatest species of black bears in North America, though you can find bears on any of the Apostle Islands.
Looking for a vacation rental? Check out the VRBO listing with many nice places in the Apostle Islands, WI.
Or stay in one of the hotels offered by hotels.com where you can find a big choice of hotels based on your budget, location, or preferences. Free cancellations in most hotels when you book now and stay later. Book your room now!
Kentucky
7. Louisville, KY
Louisville is the #7 destination on the list of 20 best weekend getaways near Chicago by car
Louisville is the biggest city in Kentucky, based on the Ohio River along the Indiana border, and is 298.5 miles away from Chicago (and a 4.39h drive).
Louisville is a fun place to be, to be honest. If you are a baseball fan, the Louisville Slugger Museum & Factory is your must-do. Or if you are into boxing, I would suggest visiting Muhammad Ali Center.
When you visit Louisville, you will find plenty of things to do. From visiting museums, trying great food, taking riverboat tours, or simply exploring around. This city has so much to offer its visitors at any time of the year.
To see the full list of activities in Louisville, check out this post.
Looking for a hotel in Louisville, KY? Don’t miss these last-minute deals! Book today with Hotels.com!
Or find flexible cancellation vacation rentals from VRBO.
8. Mammoth Cave National Park, KY
Mammoth Cave National park is a must-do for everybody who loves to explore beautiful natural caves. The park is less than a 1.5 h drive from Louisville and 383.0 miles away from Chicago (5h51m drive).
I had been there 5 years ago, and the mistake I made was that I didn’t book the tours online when we came there, there was only one tour available that day. This was sad, but I am glad I had an opportunity to explore at least one cave. OMG! That was so cool and terrifying at the same time. In some places, we had to crawl the cave tunnel, and there was no way to go back.
Once that was over, we got into the room where they just turned off the light, and we couldn’t see anything. That was scary. It felt like we were dead. Oh:). But it was so much fun.
Mammoth Cave is the longest cave system in the world, and it is very popular among tourists every year.
TIP: Make sure before you go there, you make an online reservation. Do not repeat my mistake and try to book as many tours as you can last minute. As I am sure, they are all worth your time. Tickets can also be bought in person, but you might experience long lines. It depends on what time of the year you will be there.
Get more details on what you need once you are there, here.
Save big on hotels while you explore the beauty of America’s parks and caves!
Search VRBO to find the perfect property for your stay in Mammoth Cave National Park, KY
Missouri
9. St Louis, MI
St. Louis is a major city in Missouri, along with the Mississippi River. It is 296.5 mi from Chicago (which is a 4h38m drive).
The main sight of the city is the iconic, 630-ft. Gateway Arch. The arch can be explored outside (for free) and inside for a fee.
I should admit that I was surprised by how nice St. Louis downtown is. Despite how small it is, there are so many things to explore.
Are you a nature lover? Then definitely visit the botanical garden. For live music lovers, there is a good opportunity to visit festivals in the summer. Along with parks, the zoo, taking food tours, and many more. You will find something you love or are interested in.
Check out this list of 25 things to do in St.Louis on your visit.
Find the Best Deals at hotels.com!
Find the best vacation rentals with VRBO!
Ohio
10. Cleveland, OH
Cleveland is a major city in Ohio and 344.4 miles from Chicago (about a 5h 19m drive).
The state itself doesn’t sound like too much fun, at least to me :), but Cleveland is a nice place to go. I’ve been there in the early wintertime and still enjoyed it.
The most famous sightseeing to see is the Rock & Roll Hall of Fame. They offer an impressive collection of memorable pieces — from John Lennon’s guitar to hip-hop pioneer Jam Master Jay’s gold chains. There is so much more to see.
If you visit in the summer, don’t skip visiting the Botanical garden, parks, or zoo. There are lots of attractions that can be done inside, but if you have a chance to do an outside activity, don’t skip that. Every city is beautiful in the summer and worth to be explored around.
Check out the great choice of hotels in Cleveland,OH
1.Homestead House Bed and Breakfast
2. Cleveland Marriott Downtown at Key Tower
Or book a private apartment with VRBO.
Illinois
11. Starved Rock State Park, IL
Starved Rock is a national park located on the Illinois River. It is known for its drastic canyons formed by glacial meltwater. Some of them have waterfalls. The downside of this park is if you go at the wrong time when the canyons dry out, you won’t see their waterfalls. So a little tip is always to call to confirm if there are waterfalls unless it won’t be so exciting to observe dried canyons.
Starved Rock Park is located just 80 miles from Chicago (which is less than a 2-hour drive). The park is open daily from 7 am to 8:30 pm and requires some rules. To make sure you are aware of everything you need to know, check the link above to prepare for your park adventure.
Find more info about Starved Rock State Park here.
You might consider these places to stay in Starved Rock Park:
3. Holiday Inn Express Hotel & Suites Peru – Lasalle Area, an IHG Hotel
Book a private place with VRBO here.
12. Galena, IL
Galena is an old small town in Illinois located on the north side. We know this city for its well-preserved 19th-century buildings. Galen is just 163.5 miles from Chicago (2h 50m drive).
There are 2 main seasons: summer and winter. Summer is the best to explore the city from all angles, and wintertime is the best for ski lovers.
If you want to escape Chicago and change the big city vibe for a while, Galena is the perfect place to do that. Galena, like many cities I mentioned above, offers so many activities to do. From biking around, taking wine tours, paddling down on the Galena River, visiting historical places, simply enjoying the city views, and more.
There is never a shortage of things to do in Galena, and you will be surprised how busy you can get there :).
You might be interested in the best travel accessories you need to have to make your travel easier.
Book your accommodation in Galena here and take advantage of free amenities and free-of-charge cancellations in most hotels.
Want to have a different experience? Choose a private apartment with VRBO.
13. Shawnee National Forest, IL
Shawnee National Forest can be easily described as terrain that spans woodlands, hills, and lakes. It is 337.4 miles from Chicago (5h 7m drive).
Great place for hiking and enjoying amazing views. Once you get there, you will be surrounded by natural beauty everywhere.
There are beautiful forests, lands, and lakes. Any season is good for visiting. Make sure to explore the Grand Canyon, Garden of the Gods Rim Rock, Giant City, and Fern Clyffe. Be prepared to drive a lot as these spots are very spread apart.
Save up to 55% on top bookings here.
Or find your vacation rental on VRBO.
Check out special places to visit in Shawnee National Forest
14. Rockford, IL
Rockford is a city in northern Illinois and is located 88.6 mi (1.25h drive). The best thing to do in Rockford, in my opinion, is to visit Anderson Japanese Garden. The garden is so beautiful with wild fishes, beautiful rare flowers, and more.
The city is not big, but I can assure you that you won’t be bored as there are so many other things to explore outside and inside besides visiting the Japanese garden. There are parks, museums, water cruises, and more.
Check out these hotels in Rockford, IL
1. Riverview Inn & Suites, Ascend Hotel Collection
2. Home2 Suites by Hilton Loves Park Rockford
3. Staybridge Suites Rockford, an IHG Hotel
Want a private space instead? Look for great deals on VRBO.
15 best things to do in Rockford,IL.
Michigan
15. Traverse City, MI
Traverse City is 323.0 mi from Chicago (4h 54m drive). This green city is a beautiful place to relax, clear your mind, and explore around. The views this city offers are breathtaking and mesmerizing.
Once in the city, you will enjoy exploring Sleeping Bear Dunes National Lakeshore (a 64-mile curve of beaches), tasting the best wines in the country, sailing the tall ships, visiting lighthouses, and doing vintage shopping, or something else. This place is incredible, especially for nature mother lovers.
Check out this article on the 25 best things to do in Traverse City, Michigan.
Book your accommodation now and save on hotels.
Or get the best deal for a private accommodation with VRBO.
16. Kalamazoo, MI
This city with a funny name is a southern city in Michigan. Which is 145.9 miles from Chicago (2h 23m drive).
Kalamazoo is best known for Gibson guitars, Bell’s Brewery, Checker Motors, and Stryker Corporation. You can enjoy live music, drink locally brewed beer, visit museums, eat, and do shopping once you are there.
Summer is a beautiful time to go. Discover famous fishing spots, find the perfect biking trail, hike, or paddle on the Kalamazoo River on a kayak, canoe, or stand-up paddleboard. As you can see, there are plenty of things to do when it is warm outside.
Here is the list of the 25 best things to do in Kalamazoo, Mi.
Looking for a perfect place to stay in Kalamazoo, IL? Check various properties on VRBO.
Or find a good deal based on your budget and preference with Hotels.com. Book now and save.
17. New Buffalo, MI
New Buffalo is a nice small beach town in Michigan, just 70 miles from Chicago (1h16m drive). I am suggesting getting a chance to explore all the wonderful things in this city.
Anything from bike riding, hiking, wine tasting, or shopping. This amazing place with a special vibe awaits you.
Here is the list of events and attractions in New Buffalo, Mi you might be interested in.
Book your perfect private stay in New Buffalo, MI, here
Not comfortable staying by yourself in q whole apartment? Check out booking options on Hotels.com
18. Three Oaks, MI
Three Oaks is a tiny village in Michigan with famous massive oaks that grow near a town rail crossing. Three Oaks is 74.6 miles from Chicago (just a 1h 21m drive).
When you visit this village, you will find many things to do in Three Oaks, Mi. From eating excellent food, shopping for antique pieces, visiting parks, seasonal events, and more.
Places to stay in Three Oaks, MI
1.SpringHill Suites by Marriott Mishawaka-University Area
2. The Brick House near Notre Dame 1stFloor/stylish apt
3. Courtyard by Marriott South Bend Downtown
Or search VRBO to find the perfect property in Three Oaks, MI
19. Grand Rapids, MI
Grand Rapids is one more city in Michigan worth visiting. It is 181.3 mi from Chicago (which is a 2.50h drive).
Grand Rapids was a mecca for art creators and admirers. It is also the place for beer lovers, as there are so many breweries that, most likely, you won’t be able to visit them all at once.
The interesting fact about Grand Rapids is that back in the old days (1945), the city was known as being the first U.S. city to add fluoride to its drinking water.
Check out this perfect Grand Rapids guide for first-time travelers.
Book now and save on the good hotel deals on Hotels.com
Check VRBO private apartments here.
20. Harbor Country, MI
Harbor Country is known as an upscale weekend getaway destination. It is located 71.6 miles from Chicago and can be considered a 1h 12m drive.
You will find many interesting things to do and see in Harbor Country. From antique shops, national wineries, various outdoor activities, museums, and more.
Best places to stay in Harbour Country, MI
1. Cozy Cottage Near Union Pier with Private Beach Access
2. Downtown Cottage w/ Firepit, Fireplace, Wi-Fi, & Yard
Or book a private place with VRBO.
Final thoughts
Traveling could never be easier. Nowadays, you do not even have to have days off to travel as so many places are located just near where you live.
Weekend getaways from Chicago are an ideal plan for what to do on the weekend. Whether it is just a day tour or 2-3 days, you will get the best feelings and emotions to discover the beauty near you.
Have you traveled to any place from these 20 best weekend getaways near Chicago yet? If so, share your experience :).
Pin it for later
I’ve been surfing on-line more than 3 hours lately, but I by no means discovered any interesting article like yours. It is lovely price sufficient for me. Personally, if all web owners and bloggers made excellent content as you did, the web shall be much more useful than ever before.
I am glad you found it useful, Iwan. Thank you for stopping by :).
Thank you for sharing your complete reviews surrounding Chicago, it’s help me to make my dreams list to go.