3 Great Chicago Weekend Getaway Ideas

While you can always stay in and mope on the couch while staring at the wall in a catatonic state for a weekend, you would do well to switch things up from time to time, keeping things fresh and interesting by visiting someplace unfamiliar.

Whether or not you simply sit and mope on the couches there while drooling is up to you, but here you can get some ideas about other things to keep you busy on a Chicago weekend getaway.

1. Louisville, KY

Located about 300 miles away from Chicago, there’s no shortage of things to do in Hunter S. Thompson’s home turf. If you want to focus on food, you can pay a visit to either Highland Morning for a perfect breakfast, or The Comfy Cow for some sweet dairy goodness in the form of excellent ice cream.

For all you drinkers out there, you can try the Highland Coffee Company for some non-alcoholic coffee, or The Silver Dollar if you’re into some authentic Kentucky bourbon.

2. St. Louis, MO

This city is also around 300 miles outside of Chicago, with a drive of about four hours, but the Megabus can cost you as little as $5.

st louis arch

For good eating, try Pastaria for some excellent pasta and gelato, along with everything else you could ever want from an Italian restaurant, or you can check out the Crown Candy Kitchen for some sweetness.

Get your fill of cocktails or other varieties of booze when you visit either the Three Sixty for a killer rooftop view, or Ballpark Village if you’re in the mood for a sports bar.

3. Madison, WI

This city sits about 150 miles from Chicago and about the same distance from hotels in Willowbrook, IL, and is easy to get to with a car within three hours, or you can take the Megabus. If food is your goal, consider the Babcock Hall Dairy Store for some delicious ice cream on the University of Wisconsin campus, or Smoky’s Club for some of the best steaks and relish trays (which do somehow exist) you’ll find anywhere.

madison wisconsin

If you’d rather imbibe your time away from home, simply head over to Essen Haus for a solid beer selection with a German atmosphere, or try the Hilton Madison Monona Terrace for some beers in a location that’s within walking distance of most of the sights worth seeing.

Just remember that hotel staff will think you’re a sad individual if you drink alone at a hotel bar more than twice.

Obviously, these are only a few of the many places worth checking out while you’re out of town.

For more ideas about what to do at these locations, you can always ask the locals when you’re there, but don’t be obnoxious about it or you may find yourself quickly made unwelcome, if you’re not too careful.

However, chances are you’ll simply be another tourist just trying to escape from Chicago’s miserable winter for some more interesting sights.


Some of the areas around those cities are also great for backpacking. Be sure to check out this backpacking guide for the best tips if you need any guidance or are new to backpacking.

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