Driving Trips from Chicago

We all spend too much time trapped behind the wheels of our cars, stuck in traffic. And while a 100 mile circle around Chicago does not offer the same scenic variation and beauty that one might find surrounding San Francisco; there are still many great day drives. This is particularly true in the Fall as the changing leaves paint the views with fiery reds, oranges and bright yellows.

Fortunately for Chicagoans we are much closer to natures fireworks show than many of us realize. I have listed a few suggested drives that will provide you, your friends and family a great way to celebrate the beauty and the last nice weather of the year.

Starved Rock   

This is is one of the state’s most popular attractions. It has miles of trails, and something unusual for Illinois- Hills. The drive down the highway, would give you no indication that hills, valley and high bluffs await. There is a lodge and cabins if you choose to spend the night; but the park in close enough that a day trip works well. Bring good shoes, some of the trails can be a bit steep, and depending on weather, a bit slick.

Route 178 & Route 71, Utica, IL 61373

Starved Rock Trail Map Overview 

Lake Geneva

This time you are pointing your car north and headed up to Wisconsin. Again this is a destination that you can reach in 2 hours from the cities center.  Lake Geneva, from which the town take it’s name, is one of several lakes in the area, each with it’s own town, willed with fudge shops, bars and restaurants and shopping. There are also several fine golf courses and resorts.

The drive from Lake Geneva to Lake Delevan is among one of the most beautiful in the region, but a word of caution, there always seems to be police just waiting for a visitor to hit 5 miles over the speed limit.

Wisconsin Dells:

OK, if your like me the first thing that crosses your mind when you hear “The Dells” is Tourist-trap. And yes, the Dells can be a bit tacky, or as many refer to it, “Las Vegas for kids”, and not Bellagio’s Vegas either. But if you step away from that side of the town, The Wisconsin Dells contain miles of carved sandstone cliffs cut by the Wisconsin river, forests and many sources of beauty worth visiting.

Keep in mind this IS a bit longer of a trip, and therefore it is best to figure a weekend stay.


This is a collection of many small towns, including Union Pier, New Buffalo Michiana and others. This has been referred to as Chicago’s answer to the Hampton’s, only far move affordable and “Low-Key.”   Sitting on Lake Michigan, a body of water so large, that the area rightfully gets the name ”The Third Coast.” There are a multitude of restaurants, clubs, places to rent bikes and even a few world-class wineries.  Just 90 minutes from downtown (OK let’s assume the traffic is not too heavy) it feels a world away and offers a great way to kick back and relax.

Traverse City / Petoskey:

This is another designation that is too far for a day trip, but can make for a lovely weekend get-away. Traverse City, owing in part to Michael Moore’s yearly Film Festival, is town that has the look and pace of a small midwestern town, yet also maintains many upscale restaurants and shopping.

Located in the northwest corner of Michigan’s Lower Peninsula, the region is complete astonishing views and miles of trails. Petoskey, just a short drive away, is famous for the natural polished glass found of their beaches that are called Petoskey stones.

These are just a few of the many scenic opportunities that await Chicagoans that are looking for a quick break from the city.

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