How to Plan the Perfect Chicago Getaway

Are you in need of a weekend away to slow down and hit the “reset” button? Just a three-hour drive from the windy city, Galena, Illinois, is the perfect place for a relaxing and romantic weekend getaway near Chicago. Enjoy world-class vineyards, scenic hiking trails, an idyllic downtown, and a small-town charm that will make you feel at home. Below, discover how to plan the ultimate weekend trip. For more things to do in Galena, access our free Vacation Guide!

How to Plan the Ultimate Weekend Getaway Near Chicago

Visit a Vineyard

Most people think of Napa Valley when they hear “wine country,” but Illinois has a notable wine scene of its own! In Galena, our local wineries and vineyards are some of the town’s best-kept secrets.

One of our favorites, the Galena Cellars Vineyard and Winery might be the highlight of your trip. Located just 15 minutes outside of downtown, this premier winery offers delicious wine, incredible sunset views, and fantastic tours like a couple’s wine tasting tour. This spectacular wine lover’s paradise was named the “Best Winery in Illinois” by Yahoo! Travel because of their award-winning wines. While you’re downtown, be sure to swing by their tasting room on Main Street.

Enjoy Delicious Cuisine

Galena, Illinois, is full of incredible restaurants. Our vacation guide (link above) is packed with suggestions, but one of our favorites is Log Cabin Steakhouse. This dining establishment is Galena’s oldest and longest running eatery, and its been serving delicious food since 1937. You’re sure to be delighted by the friendly service and smiles as soon as you walk in the door! Choose from a selection of thoughtfully prepared dishes and exceptional side options. We suggest pairing your sumptuous meal with a glass of local wine. For a more intimate dining experience, ask about the private dining option!

Explore the Local Hiking Trails

Nothing helps you restore your mind and body quite like an afternoon in nature! Our Galena getaway guide provides a number of fabulous hiking trails to explore. Another wonderful outdoor space in town is Grant Park. Located right downtown, Grant Park is a great place to relax on a picnic bench after an afternoon of shopping.  

Indulge with a Massage

Pamper yourselves at the relaxing spa at Farmers Guest House. Our on-site spa offers the perfect rejuvenating treatments to unwind and destress. For a romantic treat, enjoy a Couples Massage together! This 60-minute experience will have you feeling refreshed, relaxed, and closer than ever. When you place your reservation with us, order your massage, and it’ll be scheduled for the following morning. Escape your everyday routine and delight in the company of your partner this weekend!