After your first few weeks of living in Chicago, you might start feeling the itch to get away for the weekend. Have no fear; Chicago is surrounded by plenty of great destinations within a two-hour drive. Whether you’re single or traveling with a significant other or group of friends, these are all weekend getaways from Chicago that you won’t want to miss.


1. Lake Geneva, WI

Lake Geneva in Wisconsin

Distance from Chicago: 1.5 hours

This fantastic first weekend getaway from Chicago is at the top of the list for a reason! Lake Geneva is the most fashionable place for Chicagoans to own a vacation home, and they flock here by the thousands during the summer months. There are plenty of hotels and resorts to choose from, such as the historic Grand Geneva, and the walkable downtown is filled with cute shops and incredible restaurants. Blueground offers fully-furnished, equipped and serviced apartments in some of the world's most sought after cities. Of course, you can’t visit Lake Geneva without paying your respects to the lake, which is surrounded by a 26-mile walking path. There are also plenty of activities to keep you entertained, such as boat rides, golfing, and even zip line courses. Try to schedule your trip during the Venetian Festival in August, a five-day carnival with entertainment, music, and fireworks.


2. Cedarburg, WI

Old mill house in the countryside at Cedarburg, Wisconsin

Distance from Chicago: 2 hours

Cedarburg is an idyllic small town that has yet to be discovered by throngs of Chicago tourists. Twenty miles north of Milwaukee, it’s conveniently located yet far enough from the city that you’ll almost forget what rush hour traffic feels like. There are plenty of historic inns to choose from, such as the 1886-built Stagecoach Inn. Nearby you’ll find an old mill that’s been converted into artisan shops, two wineries, and even a vintage store. The latter of which sells clothing and accessories from the last century.

The best time to visit Cedarburg is for the annual Strawberry Festival, a nationally recognized event that attracts 100,000 visitors each June. Highlights include live music, local vendors, and of course, plenty of strawberries.


3. Starved Rock State Park, IL

two natural waterfalls at state park in Illinois state

Distance from Chicago: 1.5 hours

If you’re an avid hiker, this is the weekend getaway from Chicago for you. Starved Rock State Park is the top-rated attraction in the entire state of Illinois, and for good reason. Thirteen miles of trails will take you over cliffs, through caves, and past breathtaking waterfalls. Once you’ve tackled that, pay a visit to neighboring Matthiessen State Park for an additional five miles of equally gorgeous hiking.

Starved Rock also has its own lodge for multi-day stays with an assortment of rooms and lodges, some of which are pet-friendly. The lodge is complete with multiple dining options, including Sunday brunch, as well as a souvenir shop and event space.


4. Milwaukee, WI

City view of Milwaukee

Distance from Chicago: 1.5 hours

Milwaukee is the nearest major city to Chicago and it’s certainly worth a weekend visit. You’ll have plenty of choices for hotels and restaurants, so try to stay downtown where you’ll be close to all the action. There are several museums at your disposal, most notably the Milwaukee Art Museum, but also the Harley-Davidson Museum, Milwaukee Public Museum, and Discovery World. Make sure to take advantage of immersive experiences with some of Wisconsin’s signature items, such as the Miller Brewing Tour and Cheese Head Factory.

There is also a robust lineup of annual events in Milwaukee that will keep you coming back for repeat visits. Summerfest is a two-week event packed with concerts from major headliners that have included Florida Georgia Line, James Taylor, and Jason Derulo. Bastille Days is a French-themed festival each July that comes complete with a Mardi Gras parade. The Air and Water Show, also in July, is certainly not one to miss; stunt pilots come out to put on back-to-back jaw-dropping aerial shows that are free to watch from anywhere along the shore.


5. Woodstock, IL

Front view of the Woodstock Opera House

Distance from Chicago: 1 hour

You might not know it, but if you’ve watched the movie Groundhog Day, you’re already familiar with Woodstock. Walk through the town square and you might just hear Sonny and Cher’s “I Got You Babe” playing over the speakers. Take a stroll through downtown to see plaques commemorating the exact locations where scenes from the movie were filmed.

Woodstock is a short drive for a weekend getaway from Chicago, but it’s also easily accessible by Metra commuter train. Ideal if you haven’t sorted out a car or driver’s license after relocating to Chicago. It’s a small town with quite a bit to offer in terms of entertainment, like the Woodstock Opera House and Illinois Railway Museum. Take your pick from a bountiful selection of restaurants and shops. In October, check out the Woodstock Ale Fest, which brings local breweries from the surrounding area to one place.



Chicago might not be close to any major cities, but it’s got plenty of options for weekend getaways. These destinations are all within two hours by car, but many are also accessible by train, adding yet another reason to look for an apartment in Chicago’s downtown neighborhoods where the train station is nearby. Companies such as Blueground cater to professionals looking for centrally located apartments to make it easy to get into work and out of the city.

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