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My Urban Family

Practical guides for raising a family in Chicago

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Five Easy Road Trips From Chicago With Kids

Dunes, canyons, lake towns and a historic main street, all within a few hours’ drive of downtown.

Five Easy Road Trips From Chicago With Kids

Photo: aparlette / Flickr, CC BY 2.0

One of the best things about living in Chicago is how much is within a couple of hours’ drive. You don’t need a week off or a plane ticket to give the kids a change of scene. These five trips all work as long day trips or easy overnights. Drive times are rough estimates from downtown without heavy traffic, which on a summer Friday is a big “without.”

Indiana Dunes National Park

About an hour. Beaches, big sand dunes to climb and trails through woods and wetland, all on the southern shore of Lake Michigan. You can also get there by train on the South Shore Line, which many kids will count as part of the fun. Go early on summer weekends, as the beach parking fills up.

Fallen leaves along a canyon trail and creek at Starved Rock State Park
Photo: danxoneil / Flickr, CC BY 2.0

Starved Rock State Park

About an hour and a half to two hours. Canyons, bluffs above the Illinois River and seasonal waterfalls after rain or snowmelt. Some trails have a lot of stairs, so choose shorter routes with little ones and bring a carrier for toddlers. Spring and fall are the best seasons. The waterfalls are at their best after wet weather, and the leaves are spectacular in October.

Milwaukee

About an hour and a half. A city trip that feels different from Chicago without being far. The lakefront, the public museum and the children’s museum keep kids busy, and there’s plenty of space to run around by the water. It’s an easy first overnight with young kids.

Lake Geneva, Wisconsin

About an hour and a half to two hours. A classic summer lake town. Walk part of the shore path, take a boat tour, get ice cream and call it a day. It’s popular and busy in peak summer, so a weekday or the shoulder season is calmer.

Galena

About three hours. A historic town in the hills of north-west Illinois, with old brick buildings, a long main street and countryside that surprises people who think Illinois is flat. It’s better as an overnight than a day trip. Older kids will appreciate the history, and younger ones will be happy with the river and the hills.

Making road trips work with kids

  • Leave early. Getting out of the city before traffic builds makes the whole day better.
  • Plan one stop on the way. A playground or a snack break halfway beats three unplanned stops.
  • Pack the car the night before. Snacks, water, wipes, a change of clothes and something to do for each child.
  • Keep the day loose. One main activity is plenty. The best part is often the thing you didn’t plan.
  • Check before you go. Parks and attractions change hours and fees by season, and some state parks need reservations or parking passes at busy times.

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