Updated September 2026 by Colin Tate
Colin writes for Farmers Guest House, helping travelers plan unforgettable trips and discover the best of Galena, IL.
Sometimes the best girls’ trips don’t require a flight, a packed itinerary, or an entire week away. They only need a few good friends, a change of scenery, and plenty of opportunities to catch up. If you’re looking for a girls’ getaway near Chicago, Galena checks all the boxes, with wine tasting, spa days, charming shops, and incredible scenic drives all within easy reach. Here’s how to turn a visit to Galena into a memorable escape your entire crew will be talking about long after you get home.
Looking for more things to do in Galena? Check out our free travel guide for more info on local attractions, activities, and events!
Sip, Sample, and Stay a While
A girls’ weekend and a winery visit go hand in hand, and Galena Cellars Vineyard and Winery can be an incredibly easy add to your itinerary. Pop in for a tasting to sample wines made from Illinois grapes. Then, take some time to tour the winery and take in the beautiful surrounding scenery. It’s the kind of outing where you won’t feel a need to rush. Just pull up a chair, order a bottle, and enjoy the conversations with your group.
Pamper Yourself & Dine Downtown
Plan for some downtime at Indulge Day Spa, where a little pampering can easily become the centerpiece of your weekend. Book a massage, facial, or other spa treatment. Then, head to Main Street to spend the rest of the afternoon browsing boutique shops. If your group’s been waiting for an excuse to really treat yourselves, this is the perfect opportunity.
You’ll also be in an excellent location to grab dinner and drinks. Fried Green Tomatoes is a great pick for quality steaks and comfort food, while Vinny Vanucchi’s “Little Italy” offers Italian favorites and a casual, old-school setting.
Take the Party on the Road
Have some extra time? You can also turn your girls’ getaway into a mini road trip. The Galena area is surrounded by scenic countryside and small towns, making it easy to spend an afternoon cruising the roads, antiquing, or simply finding a pretty overlook for an unforgettable group photo.
Enjoy Local Events
For an extra excuse to get everyone together, consider timing your girls’ trip around Spaless Weekend. This annual spring event brings women from all over the country to Galena for a fun-filled weekend of dining, shopping, dancing, and all sorts of shenanigans.
Galena is also home to several other festivals, seasonal celebrations, and live entertainment throughout the year. Be sure to check the upcoming events before your visit to see what else might be happening during your stay.
Treasure These Moments with Farmers Guest House
After a day of laughing, relaxing, and exploring everything the Galena area has to offer, you’ll want to keep the quality time going at an ideal home base. Farmers Guest House offers a brilliant location within walking distance of downtown, plus fresh complimentary breakfast, on-site spa services, and a regular evening WineTime. Browse our available units now to find the perfect accommodations for an unforgettable girls’ trip.
Frequently Asked Questions: Girls’ Getaway in Galena, Illinois
Is Galena a good destination for a girls’ getaway near Chicago?
Yes! Galena offers plenty to do on a girls’ trip, including wine tasting, spa days, shopping, seasonal events, and plenty of scenic road trips nearby.
What are some things to do on a girls’ trip to Galena?
Popular activities include wine tastings, spa visits, downtown shopping and dining, and attending local events like Spaless Weekend.
Where can you go wine tasting in Galena?
Galena Cellars Vineyard & Winery is a popular choice for wine tasting, offering local Illinois wines in a relaxed setting that’s perfect for a weekend with friends.