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Fabulous Weekend Getaways from Chicago

Updated on May 30, 2016
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Melanie loves to write about her adventures in traveling and continues to explore new places.

If you're looking to get away from Chicago for the weekend, there are a number of wonderful places to visit located just outside the city.

Whether you want to relax and work on your tan, browse through unique shops, rough it at a campsite, go wine tasting, or pick berries (or apples) in an orchard, the midwest is jam-packed with fun places to visit.

The following list contains some of midwest best vacation spots (each located only a few hours away from Chicago), and, of course, a number of fun activities in each area. Be careful, though! Chances are that once you spend a weekend at any of these places, you might never want to come back to the city!

Sailboats on Lake Mendota in Madison, Wisconsin
Sailboats on Lake Mendota in Madison, Wisconsin | Source

Harbor Country, Michigan (Wine Country)

The Harbor Country area of Michigan has a lot to offer Chicagoans. This area is particularly popular for its beautiful Lake Michigan coastline. While boating, swimming, laying out in the sun, and other beach activities are the main draw, Harbor Country is also known for its specialty shops and its fantastic restaurants.

Saint Joe and New Buffalo are two particularly popular towns. Each offers a beautiful harbor, great shopping, and awesome food. New Buffalo is home to Four Winds Casino which makes it a great places to visit year-round.

The area offers a quiet environment that allows you to get away from it all. A number of fruit orchards operate in the area. These are usually open during the Summer and end their season in the fall. Many orchards allow you to pick apples, blueberries, strawberries, raspberries, tomatoes, cherries, and pumpkins.

If you enjoy bicycling, the Apple Cider Century happen in late September. This ride will allow you to see the colorful leaves of the area's maple, beech, birch, ash, and oak trees.

The area is home to a large number of vineyards and wineries (Tabor Hill and St. Julien to name a few.) Wine tasting tours are a great way to explore southwest Michigan and get a fabulous bottle of wine on the cheap.

Madison, Wisconsin

With nearby Middleton ranking as the number one place to live in the United States, it's easy to guess that Madison is fantastic. Madison, Wisconsin is home to the University of Wisconsin, miles upon miles of bicycle trails, and, of course, the state's capital building.

The city is full of small specialty shops (especially near the campus.) Aside from the shops you'd expect in a college town, there are bicycle shops, beer supply stores, comic book shops, and more!

Madison is sandwiched between Lake Mendota and Monona which offer beautiful views and places to swim. Don't miss bicycling along the lakes! If you're not a cyclist, everything is in walking distance (and there are a number of parking garages if you're driving.)

The city hosts a fabulous outdoor market near the capital building (not to be missed) as well as a number of world class restaurants. Everything is in walking distance, so this is definitely a place to enjoy on foot!

Indiana Dunes National Lakeshore

Indiana Dune National Lakeshore is located just a hop, skip, and a jump from Harbor Country. Here you can climb Mount Baldy, one of the tallest sand dunes on Lake Michigan's south shore. Of course, once you get to the top, you'll want to run all the way down to the lake below. The beach at Mount Baldy is quiet, so it's an amazing place to swim or lay out in the sun.

Camping at the National Lakeshore is a popular activity. There are a number of campsites throughout Northwest Indiana where you can rough it while enjoying beautiful scenery.

National Lakeshore is especially known for its beautiful wetlands, where you can catch a glimpse of heron and other wildlife.


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    • ktrapp profile image

      Kristin Trapp 5 years ago from Illinois

      I've always planned on going to the Indiana Dunes as a day-trip, but just have never gotten around to it. Thanks for reminding me.

    • andreaknightly profile image

      andreaknightly 5 years ago from Los Angeles, California

      Chicago is indeed a beautiful place. Wish someday, I could go there too.

    • Suhail and my dog profile image

      Suhail Zubaid aka Clark Kent 5 years ago from Mississauga, ON

      I love Chicago and the state of Illinois. You listed some nice destinations. In addition to Indiana Dunes, there are few other State Parks in northern Illinois that are a pleasure to visit with a family.

    • RealHousewife profile image

      Kelly Umphenour 5 years ago from St. Louis, MO

      I love Chicago - I am close enough to hop on a train for 20 bucks to get there! I went not too long ago with the kids for their first train ride:0 It was fun!

    • randomcreative profile image

      Rose Clearfield 5 years ago from Milwaukee, Wisconsin

      Great suggestions! The Indiana dunes is one of my all-time favorite places.