Road Trips Around Chicago

Leave behind the skyscrapers and city traffic and enjoy the great outdoors around the Midwest, where you can experience great lakes and sandy dunes, weather permitting, of course. Route 66 begins in downtown Chicago, just please don’t take it all the way to Santa Monica. For now, we’re focusing on road trips that are a bit more manageable, so you’ve got more time to enjoy the adventure and not spend the whole time behind the wheel!

Indiana State Dunes, IN

1 hour drive from Chicago

With over 2,000 acres of sand and shore, this is a great escape from the city to get outside and enjoy the day. Since 1925, the Indiana Dunes have provided 70 miles of hiking, and 15 miles of swimming along Lake Michigan’s coast. If bird watching is your thing (we don’t judge), there’s over 350 bird species flying around the dunes to admire. It’s a quick trip, just an hour drive from the city, and is sure to impress with its endless views, challenging climbs up sand dunes, and plenty of coastline for boating, fishing, or laying out to soak up the sun.

Lake Geneva, WI

1 hour, 30 minute drive from Chicago

Who doesn’t love a day on the lake? Whether you’re looking for a relaxing (or bougie) getaway or full day on the water, Lake Geneva has options for everyone. It’s another quick trip from Chicago, with many Instagram-able views, good eats, and endless activities including boat rentals and ziplining.

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Saugatuck, MI

2 hour, 30 minute drive from Chicago

Six beaches, miles of Lake Michigan shoreline, a bustling arts scene, and plenty of hiking trails make Saugatuck a great getaway from Chicago. There are year-round activities to keep the whole family (or whoever your travel buddies are) entertained. Practice your golf swing, go fishing, or antique at one of the many unique shops.

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