10 Long Weekend Drivable Getaways From Chicagoland

With Labor Day weekend around the corner, I wanted to share a few long weekend getaway ideas for you to take advantage of, if you’re in the Chicagoland. But hurry, and make sure to make your plans asap, as accommodations will most likely sell out, if they haven’t already. I wanted to make sure the destinations are just a few hours away, and offer options for dining, shopping, outdoor activities, maybe some water fun, and more. They are listed in no particular order, and I made sure information is short but to the point, so you can do your own research on the details of each place.

Let me know where you’re heading this Labor Day Weekend! And if you need help with planning your Labor Day Weekend getaway, make sure to check out details at the bottom of this post.

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1. Bowling Green, KY

Approx. 415 miles from South Suburbs - 6 - 7 hr drive each way

While this destination requires a bit of a longer drive, it sure has lots to offer.

Top 10 things to do in and around Bowling Green, KY:

1. The Historic RailPark & Train Museum and L&N Depot

2. National Corvette Museum

3. Aviation Heritage Park

4. Baker Arboretum & Downing Museum

5. Mammoth Cave National Park (Advanced reservations for cave tours are recommended.)

6. Beech Bend Raceway & Motorsports Park (lots of events for car enthusiasts)

7. Beech Bend Amusement Park & Splash Lagoon

8. Bowling Green Hot Rods Baseball

9. Lost River Cave

10. NCM Kartplex

2. Hannibal, MO

Approx. 290 miles from South Suburbs - 4.5 - 5 hr drive each way

Top 10 things to do in and around Hannibal, MO:

1. Historic Downtown Hannibal (Trolley City Tours available)

2. Farmer’s Market

3. Mark Twain Memorial Lighthouse

4. Mark Twain Boyhood Home & Museum

5. Mark Twain Cave

6. Mississippi River Cruise on the Mark Twain Riverboat

7. Galleries & Antique Shopping

8. Haunted Hannibal Tours

9. Hike or Bike the Riverview Park

10. Boating on Mark Twain Lake (approx. 35 miles from Hannibal)

3. French Lick, IN

Approx. 280 miles from South Suburbs - 5 hr drive

Top 10 things to do in and around French Lick, IN:

1. French Lick Scenic Railway

2. West Baden Museum

3. French Lick Winery

4. Marengo Cave U.S. National Landmark (approx. 27 miles from French Lick)

5. Blue Spring Caverns (approx. 25 miles from French Lick)

6. Go on a horseback ride at Stables at French Lick

7. Golfing

8. Drive-through safari at Wilstem Wildlife Park

9. Enjoy a beach or boating day at Patoka Lake

10. Hike Hoosier National Forest

4. Frankenmuth, MI

Approx. 300 miles form South Suburbs - 5 hr drive

Top 10 things to do in and around Frankenmuth, MI:

1. Bavarian Blacksmith Experience

2. Pretzel Rolling Workshop

3. Bronner’s Christmas Wonderland

4. Cheese Haus (& Figurinespiel Tower)

5. Frankenmuth Aerial Park

6. Pedal-powered Trolley Ride

7. Weiss Centennial Farm

8. Carriage Ride

9. Beer Tour

10. The Cass River River Cruise

5. Door County, WI

Approx. 290 miles from South Suburbs - 4.5 - 5 hr drive

Top 10 things to do in and around Door County, WI:

1. Cave Point State Park

2. Admire 11 Area Lighthouses (from land or water)

3. Enjoy a Beach Day at one of many beautiful beaches

4. Rent a kayak or a boat and admire the Niagara Escarpment from the water

5. Hike in Potawatomi State Park

6. Visit Rock Island

7. The Stavkirke - Norwegian Church on Washington Island

8. Enjoy a bike ride on one of many bike trails

9. Birdwatch (can you find the Bald Eagles?)

10. Shipwreck Diving

6. Springfield, IL

Approx. 190 miles from South Suburbs - 3 hr drive

Top 10 things to do in and around Springfield, IL:

1. Lincoln Home National Historic Site

2. Oak Ridge Cemetery & Lincoln’s Tomb

3. Abraham Lincoln Presidential Museum & Library

4. Air Combat Museum

5. Illinois State Museum and Military Museum

6. Route 66 Motorheads Museum

7. Historic Illinois Fairgrounds (with Slide Down 66! and mini Illinois Route 66 Corridor)

8. See a movie at Route 66 Drive In Theater

9. Ace Sign Co. Sign Museum

10. Stop at multiple sites along the way to/from Springfield for historic Route 66 experience (Dwight, Pontiac, Atlanta, Lincoln)

7. Sandusky, OH

Approx. 295 miles from South Suburbs - 5 hr drive

Top 10 things to do in and around Sandusky, OH:

1. Cedar Point Amusement Park

2. African Safari Wildlife Park

3. Marblehead Lighthouse State Park

4. Enjoy the many beautiful beaches on the shores of Lake Erie

5. Explore one of many trails ex. Barn Quilt Trail, or Sandusky’s Mini-lighthouse Trail

6. Thomas Edison Birthplace

7. Rent a boat or a kayak for a day on the water

8. Spend a day at an indoor/outdoor waterpark

9. Butterfly House at Put-in-Bay

10. Common Ground Zipline Canopy Tours

8. Traverse City, MI

Approx. 320 miles from South Suburbs - 5 hr drive

Top 10 things to do in and around Traverse City, MI:

1. Rent an ATV and go for a trail ride

2. Rainbow Valley Family Farms (Alpaca farm!)

3. Enjoy a Wine or Brew Tour

4. Go on a Sailing Tour

5. Explore Downtown Traverse City for dining, shopping, antiquing, galleries, and more

6. Cycle Pub Tour

7. Go on a bike tour

8. Rent a kayak or jetski and enjoy a day on the water or spend a day at the beach

9. Wheels on Rails

10. Sleeping Bear Dunes

9. Indianapolis, IN

Approx. 190 miles from South Suburbs - 3 hr drive

Top 10 things to do in and around Indianapolis, IN:

1. Gondola Ride on the Central Canal

2. The Children’s Museum of Indianapolis

3. Indianapolis Zoo

4. Conner Prairie

5. White River State Park

6. Visit Bottleworks District & Fountain Square District

7. Bike the Cultural Trail

8. Indy 500 Motors Speedway Museum & Track Tour (Museum is currently closed until April 2025, but track tours are available)

9. Visit City Market

10. Make Your Own Bouquet at the Flower Boys

10. Dubuque, IA

Approx. 200 miles from South Suburbs - 3.5 hr drive

Top 10 things to do in and around Dubuque, IA:

1. National Mississippi River Museum & Aquarium

2. Anamosa Penitentiary Museum

3. Hike in Backbone State Park

4. Berning Acres Dairy Farm (between Dubuque and Galena, IL)

5. Fenelon Place Elevator

6. Enjoy a River Cruise

7. Crystal Lake Cave

8. Eagle Point Park

9. Enjoy dining, shopping, breweries, galleries and more

10. Julien Dubuque Monument at Mines of Spain

Last Few Words…

So, there you have it. Ideas for 10 long weekend getaways from the Chicago area. Each offers unique activities and sights, and while I only listed 10 in each destination, there are many more possibilities for things to do in each one of these places.

If you’d like help planning your weekend getaway, I would love to assist. I can prepare a very detailed itinerary options for each of these (and other places), so you don’t have to spend hours and hours researching and putting together a fun getaway. I can do it all for you, so all you need to do is pack. If you’d like to chat about putting together a weekend trip like this, schedule a free consult so we can discuss your plans in more details, and you can decide if you’d like to hire me to plan your getaway.

Make sure to check out details of this planning service and download the planning guide here:

Schedule your free consultation here:

Or head straight to a Request Form, and let’s get to work on your Long Weekend Getaway here:

I can’t wait to plan your weekend getaway!

Please make sure to check opening hours and days for each of the above attractions, as they are subject to change, may be closed seasonally, and I cannot guarantee they will be available for your chosen travel dates.