savvy road trips from chicago

savvy road trips from chicago

Driving through an old fashioned local fast food joint... or driving to a nearby state for a change of scenery... when you take a road trip you can feel like you're thousands of miles away!


So with the long Columbus Day weekend coming up, or just because it’s fall… consider these car trips from Chicago. We explored these and then decided to hit the road to northern Michigan. Here are our findings of safe alternatives nearby.


It’s a 1 ½ hour drive 50 miles northwest of Chicago and it’s famous for the filming of Bill Murray’s Groundhog Day.

It’s beautiful in the fall with cobblestone streets and a historic downtown.

Starved Rock State Park

It’s in Oglesby, Illinois, 95 miles southwest, a 2-hour drive.

The tall bluffs and canyon waterfalls are gorgeous, especially with fall foliage. You can drive along the river from Ottawa to Peru and enjoy the small-town culture.


If you’ve never been to Galena, you’re in for a surprise. It’s not flat like most of the midwest!  Drive along the Great River Road 170 miles west from Chicago, a 3-hour drive.

It’s a charming town and you can also visit the nearby Apple River Canyon State Park. Fish in the river or just check out the wildlife.

Grand Rapids, MI

It’s 178 miles northeast of Chicago, a 3-hour drive.

It’s the number 8 city in the country for beer because of all the breweries. But in COVID times call first to make sure they’re open. 

Sawyer and Three Oaks, Michigan

You don’t have to go far to go to a vineyard!

Sawyer and Three Oaks, Michigan are right off the Red Arrow Highway, just 80 miles away, a 1 ½ hour drive. They are the cutest towns with plenty of unique mom and pop restaurants with outdoor seating.

Let me know if you've been to these places and what you thought!

Comments 4

Kathy Johnson on

The Upper Peninsula – The UP as we say up here, specifically the Keweenaw starting now is spectacular !!

Donba on

Thanks so very much for the little
“escape” and walk down memory lane. Beautiful pictures!

Theretha Annette Lewis Reid on

Where and when to go on a trip to see pretty fall foliage close to Chicago?

Cindy on

Hi I was born and raised in Grand Rapids, the town has Changed very much, We spent summer trips to Mackinac City and the Island so if you have more time go further and explore Charlevoix, Petoskey and Mackinaw city …You can also bike around the island which I did ….

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