Chicago Weekend trips

Chicago is a vibrant and busy city that has a lot to offer. Still, sometimes it’s nice to escape the hustle and bustle of The Windy City and go somewhere new for the weekend. If you don’t have plans this upcoming weekend, consider booking a weekend getaway to one of these five spots that are all within driving distance from Chicago.

1. Lake Geneva, Wisconsin

One-Way Driving Time: 1 hour, 28 minutes

One-Way Driving Distance: 83 miles

Lake Geneva is a romantic resort-city that is home to a small population of about 8,000 residents. Tourists from nearby states often come to Lake Geneva for a relaxing escape or a fun-filled adventure weekend. There’s always something to do, including booze cruises, ziplining, and hot air balloon rides. 

For anyone looking for a more quiet weekend, you can relax by the lake, go on one of the many hikes in the area, or visit a spa. Between the great weather, the fantastic waterfront views, and the proximity to Chicago, Lake Geneva is a top contender for a weekend getaway. 

2. Boyne, Michigan

One-Way Driving Time: 5 hours, 42 minutes

One-Way Driving Distance: 352.6 miles

This destination is a long drive, so you’ll either want to leave first thing in the morning or save this trip for a long weekend. Either way, we guarantee you won’t regret visiting Boyne, Michigan, for your weekend getaway. 

Boyne, Michigan is a small city known for its beautiful mountain resorts. While most people come here in the winter for skiing, you can also visit in the summer for golfing, spas, and more. 

We recommend staying at Boyne Mountain Resort for excellent accommodation that is central to everything. When visiting Boyne in the warmer months, you can go ziplining, biking, hiking, or horseback riding. And in the winter, you can spend your weekend skiing, snowshoeing, or tubing. 

Skiing in Boyne, Michigan

For a unique experience that you could never do in Chicago, go on a Mushroom House Tour. These tours take around the city’s 28 stone homes built by Earl Young. This tour is perfect for people who love history and architecture. And, it’s a chance to see some of the most interesting homes in Michigan (and possibly, the United States)! 

3. Saugatuck, Michigan

One-Way Driving Time: 2 hours, 19 minutes

One-Way Driving Distance: 140.7 miles

Saugatuck is mainly known as a “small beach-town” and is the opposite of busy Chicago in many ways. The town runs a little more slowly, with the famous Oval Beach being the primary weekend hotspot for both locals and tourists. 

Along with lying by the beach and enjoying the views, you can also kayak, cruise, or take a paddleboat ride down the 10 miles of coastline. 

Saugatuck beach- a great road trip from Chicago

This small city has earned itself the title of “the art coast of the Midwest.” The town currently has 30 art studios and is named one of America’s top five art towns. You have to spend some time exploring all the galleries and, possibly, finding a piece to take home with you! 

Saugatuck has quite an impressive craft brewery scene for such a small town. Take a little tasting tour around the city by visiting the Saugatuck Brewery Company, Mitten Brewing, Guardian Brewing Company, and Virtue Cider all in one day. 

When it comes to lodging, there are plenty of charming small hotels and B&Bs to choose from. The cozy Wickwood Inn Boutique Hotel has great reviews and is a popular choice among tourists. 

4. Door County, Wisconsin

One-Way Driving Time: 3 hours, 46 minutes

One-Way Driving Distance: 234.7 miles

They say good things come to those who wait. Well, good things come to those who are also willing to drive a bit further from Chicago for a great weekend in Door County. Door County refers to the region of more than 12 small towns that run along a 75-mile peninsula located on Lake Michigan and Green Bay’s waters.

Ultimately, what you do in Door County depends on which of these many small towns you end up in. In total, you’ll have over 300 miles of shoreline to explore, 53 beaches, eight wineries, and five state parks. You can spend the weekend visiting the farmer’s market, local cafes, or the many lighthouses. 

If you love history, Door County also has several known shipwreck sites you can explore. There are currently over 240 known shipwrecks in the waters around Door County. Unfortunately, they’re not all accessible, but you can access 25 sites by diving, clear-bottom kayaking, and boat tours. 

Shipwreck diving in Door County

5. Indianapolis, Indiana

One-Way Driving Time: 2 hours, 55 minutes

One-Way Driving Distance: 185.3 miles

A weekend getaway doesn’t always have to be to a small town. Sometime’s it’s fun to leave your city and explore a nearby city. So, it’s time to leave Chicago and find out all that Indy has to offer. 

First, a trip to Indianapolis wouldn’t be complete without visiting the famous Indianapolis Motor Speedway. Even if you’re not a Nascar enthusiast, there’s something thrilling about seeing the racing circuit in person! 

Other popular attractions include the Indianapolis Zoo and the Indianapolis School of Art. 

But, what we love most about this fun city is its food and drink scene. Go to Union 50 for local beers, Livery for a modern take on Latin-American cuisine, and end your evening at Vida for some fantastic cocktails and a fun ambiance. 


Chicago might be home but don’t forget there’s so much to explore nearby! Take a weekend to drive someone new and you just might find your new favorite getaway spot.