Plan an Unforgettable Road Trip from Chicago to Galena, IL

Living in a big city like Chicago is exciting and has countless advantages. But sometimes, you just need to get away, right? Galena, Illinois, has become a favorite destination for those who need a break from the norm. We’re just 3 hours outside of the city. So grab your favorite tunes, pack your bags, and hit the road for an unforgettable road trip from Chicago to Galena this weekend! 

Step 1: Book a Bed and Breakfast

With your sights set on our charming town, you’ll want to book the best place to stay in Galena. The Farmers Guest House bed and breakfast is a historic landmark in and of itself. Select one of our nine rooms and enjoy comfy bedding, tons of privacy, and a delicious if not decadent breakfast each morning. If you haven’t stayed at a B&B before, you’re in for an amazing experience. We’re also within walking distance of some of the area’s best restaurants, galleries, and shops!

Step 2: Plan Your Route from Chicago to Galena

If you’d like to make the most of your road trip, we recommend taking I-90 west to Highway 20 West. You’ll encounter beautiful rolling hills, farmlands, and a few places you’ll have to stop that will prolong your journey slightly but it will be worth it! 

Lena, Il: If you’ve worked up an appetite and a thirst on your drive, consider stopping at Lena Brewing Co. for a cold brew and a bite to eat. (Please drink responsibly!). Grab a seat on their deck or porch and try the Lena Pog Irish Ale, the Lena Hefeweizen Ale, the Caramel Pecan Coffee Stout, or one of their other craft beverages. 

Stockton, Il: Don’t miss the “larger than life” murals that have been painted along Main Street and Front Avenue. The size is impressive, the details are incredible, and they make a striking backdrop for a selfie! You’ll also want to check out the architecture around town, most of which carries distinctive elements of the Queen Anne style. Be sure to stop at the Apple River Canyon State Park, too. 

Elizabeth, Il: While there is a tasting room in Galena, you don’t want to miss a chance to visit the Massbach Ridge Vineyard and Winery in Elizabeth, Il. The vineyard is gorgeous, and they are offering tastings outside. Watermelon, Velvet Hour, and Massbach Reserve are just a few of the wines they offer. Try them and let us know what you think!

Step 3: Explore Things to Do in Galena, Illinois

Once you arrive in Galena, there are plenty of fun things to do: 

History: Did you know that 85% of Galena’s buildings are in the historic district? Walk down Main Street and learn about Galena’s history during the 19th century. You can also take one of the many tours available—whether it is a walking tour, self-guided, or on a trolley, you’ll gain a unique insight into Galena’s past.

Shops: Pick up a souvenir from Poopsie’s on Main Street, which has toys and gifts for kids of all ages, or maybe something from the Galena Canning Co. This store has interesting (and award-winning) sauces, seasonings, and dressings. You’ll be taking a taste of Galena home with you! 

Food & Drink: While you’re here, try out some of the delicious restaurants around town, including Log Cabin Steakhouse. There’s also Root Beer Revelry, which is a fantastic place to quench your thirst with a mug of frothy root beer. And then, there’s the Great American Popcorn Company, which has some of the tastiest snacks in Illinois. Be sure to check out the flavor of the month club. 

Stay at Farmers Guest House in Galena