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11 Cities Within 100 Miles Of Chicago, IL (With Directions)

Chicago is the 3rd largest city in the United States and is often known as the City that Works. Despite the fact that Chicago can have some tough weather in the winter, there are lot of people in this town that bicycle to and from work. As it lies along the shore of Lake Michigan, summer and spring can be quite lovely here.

Here are 11 cities within 100 miles of Chicago.

1) Cherry Valley, IL – 77 miles
2) DeKalb, IL – 64 miles
3) Kenosha, WI – 66 miles
4) La Porte, IN – 70 miles
5) Milwaukee, WI – 92 miles
6) Oregon, IL – 100 miles
7) Ottawa, IL – 83 miles
8) Pontiac, IL – 100 miles
9) Valparaiso, IN – 57 miles
10) Wanatah, IN – 64 miles
11) Woodstock, IL – 61 miles

Chicago tourist sign

1) Cherry Valley, IL – 77 miles

To get to Cherry Valley from Chicago, just take 90 west out of the city. Once you arrive, you will find many things to do, whether it’s cold or hot during your visit.

In the summer months, you can enjoy a trip to the water park in nearby Rockford or enjoy a day of golf on one of the many local courses.

This region was settled permanently in the 1830s. The local library offers a number of interesting photos of school classes from the late 19th and early 20th century.

While a separate village, Cherry Valley is a bedroom community of Rockford, IL.

2) DeKalb, IL – 64 miles

Take Interstate 290 west to interstate 88 west to reach DeKalb. The city of DeKalb is named after a revolutionary war hero and is rich in history and justifiably proud of local architecture.

If you enjoy museums, you will love the city of DeKalb. In addition to the Ellwood House and the Blackwood History of Education Museum, you can find excellent food and many parks where you can stretch your legs and get some air.

Illinois state road map with Interstates and U.S. Highways.

3) Kenosha, WI – 66 miles

Interstate 94 west to 294 north will get you to Kenosha. You can also take a slower route closer to the shore of the lake, but it will require you to pay a great deal of attention to traffic lights.

If you’re traveling with children (or anyone with an interest in fossils) you will find interesting fun at the Dinosaur Discover Museum. If you sail, there’s plenty of waterfront. If you don’t yet, you can take lessons!

4) La Porte, IN – 70 miles

Follow Interstate 90 east to interstate 94 east to get to La Porte, Indiana. This name translates to “the door” in French and was the home of many lumber and sawmills in the 1830s.

Fans of shopping and architecture will love their time in La Porte. The historic downtown is a wonderful spot to stroll and enjoy the fresh air, and many of the local shops feature one-of-a-kind artisan pieces for your enjoyment.

La Porte also offers advanced internet options, so surf away!

5) Milwaukee, WI – 92 miles

By following interstate 94 west to interstate 41 north, you can quickly get to Milwaukee from Chicago. If possible, treat yourself to this drive in the fall and stop at every outlook along the way.

For a trip between 2 very large cities, this drive is surprisingly scenic and the fall colors are lovely. Of course, if you enjoy beer, you’ll find fun in Milwaukee.

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Do keep an eye out for construction; this very welcoming city offers plenty of diversity and is enjoying a population and construction boom!

city of Milwaukee, WI

6) Oregon, IL – 100 miles

If you take Interstate 88 west to Illinois state highway 64, you will reach Oregon, Illinois. Like many cities in this region, Oregon was established by folks in the timber industry.

Oregon is a small town with a lot of wilderness to offer. Bring your hiking shoes and your kayaks as well as your binoculars to study the wildlife of the region.

Don’t miss the statues created by Lorado Taft, including the Blackhawk Statue.

7) Ottawa, IL – 83 miles

By following interstate 55 south to interstate 80 west, you will come to Ottawa, Illinois. This city has a long history as a shipping port as it sits at the convergence of the Illinois River and Fox River, or at least the parts of the rivers that are deep enough for barge traffic.

Bring your favorite water toys to Ottawa. Canoes, kayaks, and boats are all welcome, as are fishermen.

Those who love history and old buildings will have a grand time in the historic downtown and there are many pubs with terrific locally brewed beer and great food.

interstate 55 south highway sign

8) Pontiac, IL – 100 miles

Take Interstate 55 south for 100 miles and you’ll be in Pontiac, IL. It’s pretty much a straight shot southwest out of the windy city. If you like road trips, check out the Route 66 Museum.

Pontiac was once known as a hub for manufacturing shoes and was visited repeatedly by Abraham Lincoln. There is a Museum of the Gilding Arts and a number of historical buildings that you can enjoy as you stroll through this charming town.

9) Valparaiso, IN – 57 miles

Follow Interstate 90 east to Indiana state highway 49 for a fun visit to Valparaiso, Indiana. If you’ve never been to an old-fashioned harvest festival, this city carries that spirit well.

It’s no surprise that this region is farm country. However, it’s also loaded with artists and other creators. Do come and have fun in Scarecrow Square, but also make sure you check out the galleries in the downtown area.

interstate 90 east highway sign

10) Wanatah, IN – 64 miles

If you take Interstate 90 each to Indiana state highway 49, you can quickly get to Wanatah, Indiana.

There’s some discussion about the name; while there was a Chief Wanatah of the Potawatomie tribe, the name is also assigned to a beautiful Indian maiden.

For those who have longed to learn to ride a horse, this may be the vacation spot you’ve longed for. There are numerous trails in the area that are open to horses. If you can’t get to a dude ranch, visit Wanatah.

11) Woodstock, IL – 61 miles

Take 90 west to Illinois state highway 47 for your trip to Woodstock, Illinois. Bring your camera. There are multiple historic buildings that you will love to see, including the historic Opera House.

Woodstock is loaded with artists and entrepreneurs. If you have always longed for a one-of-a-kind piece of jewelry or a bowl like no other, a shopping trip in Woodstock will send you home happy.

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