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The Best Of The Midwest Road Trip Through Indiana, Illinois, and Kentucky

In this whirlwind road trip, you'll traverse three states in four days to experience the best nature, food, breweries, and wineries that this corner of the Midwest has to offer. 

Destinations Explored

1

Indianapolis, IN

2

Louisville, OH

3

Mammoth Cave National Park, KY

4

Shawnee National Forest, IL

Escape the buzz of Chicago with a road trip south of the city. Along the way, you'll experience local gems (including an old-fashioned soda shop and candy museum) as well as nationally-recognized landmarks. You'll pick berries at a family farm in Indianapolis, sip brandy in Louisville, go cave-hopping in a national park, and so much more. Whether you're in it for the food, drinks, history, or folklore, this getaway will have you covered. 

Key Highlights

Hike to and through the abandoned amusement park of Rose Island

Explore the caves and 53,000 acres of beautiful forest at Mammoth Cave National Park

Hike one of the most picturesque parts of Midwest at the Garden of the Gods

Best Times to Visit

April - October

Sample Trip Itinerary

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Indianapolis

3 hour and 30 minute drive from Chicago

Accommodation in Indianapolis

Suggested options (actual bookings will vary based on pricing and availability)

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Louisville

2-hour drive from Indianapolis to Louisville

Accommodation in Louisville

Suggested options (actual bookings will vary based on pricing and availability)

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Mammoth Cave National Park

2-hour drive from Louisville to Mammoth Cave National Park

Accommodation in Mammoth Cave National Park

Suggested options (actual bookings will vary based on pricing and availability)

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Shawnee National Forest Area

3-hour drive from Mammoth Cave National Park to Shawnee National Forest

Accommodation in Shawnee National Forest Area

Suggested options (actual bookings will vary based on pricing and availability)

Ready to plan?

Fill out the form below and we’ll get in touch within 24 hrs to craft your perfect trip

South of Chicago

Indianapolis, IN, Louisville, OH, Mammoth Cave National Park, KY, Shawnee National Forest, IL

Prices start from $740 per person.

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How Journy Works

Share Preferences

1

Share your travel preferences.

Chat with trip designer

2

Get paired with an expert trip designer within 24 hours.

Use App on your trip

3

Get your custom trip plan so you can take off stress-free.

Plan My Trip
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Travel planning for current times

Itching to hop on a plane and get back to exploring? We've got you covered.

Comprehensive vetting of restaurant/hotel sanitary measures

Including employee mask mandates and no-contact check-in.

Flexible, refundable rates

We’ll only book select hotels and rental properties with flexible cancellation policies and refundable rates.

Up-to-date guidance on COVID-related travel policies

From health certificate requirements to airport testing, we’ll stay on top of changes that may impact your travel plans so you don’t have to.

Detailed daily travel plans

With lodging, restaurants, activities, tours, and transfers all logistically optimized to help you efficiently get from point A to point B.

100% customized to you

With recommendations sourced from our network of local experts.

Testimonials

Journy helps thousands of travelers a year plan their dream trips to 75+ destinations around the world.

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Carol’s Family Trip to Japan

“The experience was out of this world! Anything that we requested or that we were interested in, Sarah was able to accommodate it for us.”

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Omar’s London & Paris Family Vacation with Kids

“We really enjoyed the mix of cultural, food and shopping experiences. Most of all, it was great to hit the ground with a plan for each day, but also improvise depending on how our kids were feeling.”

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Deborah & Lew’s 25th Wedding Anniversary in Italy

“Couldn’t be happier with how it turned out. I had some specific ideas about what to see—what art, what part of the countryside, etc. Elena (our trip designer) was very patient with me as we worked out just the right itinerary.”

Testimonial Profile Image

Carol’s Family Trip to Japan

“The experience was out of this world! Anything that we requested or that we were interested in, Sarah was able to accommodate it for us.”

Testimonial Profile Image

Omar’s London & Paris Family Vacation with Kids

“We really enjoyed the mix of cultural, food and shopping experiences. Most of all, it was great to hit the ground with a plan for each day, but also improvise depending on how our kids were feeling.”

Testimonial Profile Image

Deborah & Lew’s 25th Wedding Anniversary in Italy

“Couldn’t be happier with how it turned out. I had some specific ideas about what to see—what art, what part of the countryside, etc. Elena (our trip designer) was very patient with me as we worked out just the right itinerary.”

Testimonial Profile Image

Carol’s Family Trip to Japan

“The experience was out of this world! Anything that we requested or that we were interested in, Sarah was able to accommodate it for us.”

Testimonial Profile Image

Omar’s London & Paris Family Vacation with Kids

“We really enjoyed the mix of cultural, food and shopping experiences. Most of all, it was great to hit the ground with a plan for each day, but also improvise depending on how our kids were feeling.”

Testimonial Profile Image

Deborah & Lew’s 25th Wedding Anniversary in Italy

“Couldn’t be happier with how it turned out. I had some specific ideas about what to see—what art, what part of the countryside, etc. Elena (our trip designer) was very patient with me as we worked out just the right itinerary.”