The central location of Chicago and its proximity to several other states make it a goldmine for road trip options. Whether you want to spend some time in nature, lay on the beach along Lake Michigan, or visit an authentic Japanese garden, our 5 day trip options have something for everyone. If you want to visit one of the places on our list in the winter, be sure to check if it’s open when you plan to go.
Starved Rock State Park
The Starved Rock State Park, near Oglesby in north-central Illinois, is a popular day-trip destination from Chicago. You can get there in roughly 1.5 hours from downtown, and there are ample opportunities for hiking. Those looking for something more low impact can take a guided boat cruise on the Illinois River, or a trolley tour.
Milwaukee, Wisconsin
Drive north about 1.5 hours on I-94 W and you’ll hit Milwaukee, which also sits on Lake Michigan. The home of Harley-Davidson also has several breweries both old and new for you to explore. If you have kids along, you can visit 2 lakefront museums, Discovery World and the Milwaukee Art Museum with its eye-catching building.
Indiana Dunes National Lakeshore
Just an hour from Chicago, across the border in Indiana, you can bask in the sun on the beach at the Indiana Dunes National Lakeshore. You can also go hiking in the Indiana Dunes State Park, visit the 126-foot-tall Mount Baldy, or visit one of the several towns in the area that contain historic houses and museums. One of the most interesting is the transplanted Century of Progress homes from the 1933 Chicago World’s Fair that sit near the lakeshore by the town of Beverly Shores.
Lake Geneva, Wisconsin
This summer resort destination for the rich and famous of Chicago is a 1.5-hour drive northwest the city. Go to Riviera Beach or Big Foot Beach State Park to go swimming or kayaking. Or walk or run around the lake on the Lake Geneva Shore Path. On the southern shore of the lake is Black Point Estate and Gardens, one of the old Victorian homes that the wealthy built here. In the winter, you can go skiing at the nearby Mountain Top Ski & Adventure Center or Wilmot Mountain Ski Resort.
Rockford, Illinois
The main reason you will want to come to this city 1.5 hours west of Chicago is the Anderson Japanese Gardens. Covering 12 acres, the gardens have waterfalls, and authentic intricate designs done by a master Japanese landscaper. If you need yet more plants in your visit to Rockford, just down the river is the Nicholas Conservatory & Gardens.
SIXT Rent a Car in Chicago
There is so much to see and do in Chicago that you will definitely want your own transportation. SIXT has convenient locations to meet your needs, whether you need a rental car in Chicago airport or in the city center. Our fleet has something for everyone, including luxury sedans to get around the city, and SUVs to handle the snow of a Chicago winter.
