3 Weekend Getaways Within 3 Hours of Chicago

You work hard all week. When Friday rolls around, you are ready for a well-deserved escape.

You want to blow this town, but not blow a lot of dough. You also don’t want to spend the whole weekend in your truck or car getting there and back. For your next weekend getaway, kick off your boots in one of these not-too-distant destinations.

1. Galena, Illinois

Flickr/ John C Hansen

Drive three hours west of Chicago (and a bit north,) and you will find yourself in this quaint small town that provides a great getaway any time of year. Built into the hillside of the Galena River shores, it offers a picturesque setting for your escape.

What to do:

The charming downtown is filled with stores, eateries, and fudge and ice cream shops. Historic buildings create a beautiful strip to stroll, shop, and snack. While it may be a bit touristy, it offers enough treasures that is doesn’t feel like a trap.

For those who want to take in a little history, Ulysses S. Grant’s home can be toured.

Those more interested in movie history will be delighted to walk the setting of Field of Dreams. Several scenes were filmed here. (When watching the movie, look for the parts set in a cute town nestled into a hillside, where the old doctor lives.)

The surrounding nature offers plenty to do in any season. The nearby Mississippi River can be cruised on a summer boat tour. In the winter, the slopes at the Chestnut Mountain Resort are a choice skiing locale.


Where to stay:

Located a few miles outside of Galena, overlooking the Mississippi River, The Chestnut Mountain Resort offers ski runs, a snowboard park, a mega slide, and every amenity you would expect at a resort. Best-known for their skiing, the resort offers on-site activities year-round.  It also provides a variety of lodging options for romantic getaways or family escapes.

For an in-town location, visitors can rest their heads at the DeSoto House. Located on the main strip, it’s the oldest operating hotel in Illinois, dating from 1855. With Victorian-style rooms, this places oozes with historic charm.

2. Lake Geneva, Wisconsin

Flickr/ Michael Lucas
Flickr/ Michael Lucas

A two-hour drive northwest of Chicago will take you just over the cheeseland border and get you to Lake Geneva.

What to do:

This is THE spot for water play. Bring your boat, or rent one. Get out on the lake for a weekend of floating, skiing, swimming, and sun-soaking.

There’s also plenty of options for bikers. Circle the entire lake if you’re feeling adventurous, or find a nice short strip of trail for beginners.

Shopping is in no short supply either. Just up from the lake is a plethora of options for spending that hard-earned paycheck that’s burning a hole in your digital wallet. Then, after you’ve worked up an appetite shopping, the area offers great dining options from seafood to down-home cooking.


Where to stay:

The Grand Geneva Resort and Spa is a top destination. With a spa, an indoor water park, a ski hill, trails, and two championship golf courses, it has something for everyone. That indoor water park makes it especially appealing if you’re looking for a winter getaway with the cabin-fevered kids.

If you like to wear fancy duds occasionally, the Baker House will suit you just fine. Luxury suites take you back to the aristocratic living of 1885. Butlers and maids pamper guests as they are surrounded by artifacts, ornate décor, and beautiful lake views from every room. This can provide a great romantic getaway setting.

SEE ALSO: The 20 Best Small Towns to Visit, According to the Smithsonian

3. Michigan City, Indiana

Flickr/ Russell Sekeet

An hour-and-a-half drive east of Chicago, around the southern coast of Lake Michigan, gets you to Michigan City, Indiana. Despite its odd name, it offers a great spot for a weekend of live entertainment, natural wonders, or both.

What to do:

If the gambling bug has bit you, drop in at the Blue Chip Casino. One of the region’s largest casinos, you’re sure to find a slot that fits you.

If you win big, the Lighthouse Place Premium Outlets offers great shopping.

Feel like kickin’ up your heels? The Blue Chip also offers live entertainment, with bands, a dance floor, and everything from country to rock ‘n roll. A dueling piano bar at the Blue Chip’s It’s Vegas Baby restaurant is another great option for a music-filled evening.

If you prefer picturesque over poker, there’s plenty of nature to see. Long stretches of sandy beach offer great places for strolling, volleyball, swimming, and even a trek out to the end of the pier to climb around a little lighthouse. The city zoo is also surprisingly enjoyable. Though fairly small, and fairly inexpensive to see, the animal enclosures are designed so that you can almost feel the tiger’s breath through the nearby bars and can go face to face with a monkey against the glass.

Of course, the Indiana Dunes are just a skip away, so you can head there for a day of sand climbing, swimming, hiking, and picnicking.

SEE ALSO: 14 Best Places to Take Your RV This Summer

Where to stay:

The Blue Chip Casino not only offers all the fun mentioned above, but you can sleep there, too! The hotel offers luxury suites for the big spenders or big winners, and affordable rooms for the simple getaway weekenders.

If you’re looking for down-to-earth prices and simple but charming surroundings, the Best Western Plus LaPorte Hotel and Conference Center is a good bet. It’s actually in LaPorte, nearby Michigan City. The three floors of rooms open up to a central area designed to look like an adobe village. That’s unique. This area includes a mini golf course, shuffleboard, a hot tub, and a pool that’s half indoors and half out. (The kids will love swimming under the wall.) That’s fun.

Next: 11 Hidden Gems of the Great Lakes Region 

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3 Weekend Getaways Within 3 Hours of Chicago