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The Perfect Girlfriend Weekend Getaway Near Chicago

When the harried pace and overscheduling of your life start to feel overwhelming, why not gather your best gal pals and head off for an exciting weekend getaway together? If you’re looking for a fun, relaxed escape, there’s no better girlfriend weekend getaway near Chicago than our Galena Bed and Breakfast. Jail Hill Inn, rated as the top Bed and Breakfast in the country in recent years, offers the perfect counterbalance to the busy every day! 

Escape from the bustling pace of city life in Chicago or other major Midwestern cities, and enjoy an enchanting retreat to Galena. This town effortlessly combines historic charm with modern comfort. Galena’s well-preserved 19th-century architecture creates a nostalgic and inviting ambiance. Time seems to slow here, and the rolling hills and scenic vistas provide the perfect backdrop for a rejuvenating getaway with your girlfriends.

Whether you’re exploring the boutique shops, enjoying a leisurely meal at a local restaurant, partaking in fun activities like Goat Yoga, or simply strolling through local parks and trails, Galena offers a unique blend of charm and sophistication – perfect for an ideal girlfriend weekend getaway! But as charming as Galena is as a destination, it’s nothing compared to the luxury you’ll find at Jail Hill Inn.

For the ultimate in luxury when it comes to a girlfriend weekend getaway near Chicago, it’s hard to beat a stay at the nation’s top-rated bed and breakfast. This exquisite haven promises a level of pampering and elegance that will make your weekend getaway with your girlfriends truly unforgettable. From gourmet breakfasts to personalized spa treatments, every detail is designed to ensure you and your girlfriends feel thoroughly spoiled. Treat yourselves to the best, and let Galena’s charm and sophistication enhance your perfect girls’ escape. Book your stay today! 

Two women enjoying a breakfast at our Galena Bed and Breakfast during their Girlfriend Weekend Getaway near Chicago

Best Girlfriend Weekend Getaway Near Chicago

While our Galena Bed and Breakfast is considered one of the most romantic getaways in the Midwest and a fantastic place for couples to enjoy special occasions like birthdays or anniversaries, it’s also an exceptional place for solo adventures and a girlfriend weekend getaway! Our Inn is an easy getaway from Chicago and other major Midwest cities, meaning there are no significant logistics to figure out to gather with your best friends. 

Galena is the state’s second most visited tourist destination, and our Galena Bed and Breakfast has been rated as the #1 Bed and Breakfast in the Country. It is an inviting destination filled with abundant charm and plenty of things to do, and it easily ranks as the best girlfriend weekend getaway near Chicago. Below, we’ll offer a few suggestions on how to enjoy your time together in Galena, but first, we’d like to share what makes our Inn such a special place to gather with some of your favorite people. 

No one thing stands out above the rest. What makes Jail Hill Inn the perfect girlfriend weekend getaway near Chicago is the entirety of what we offer: Elegance, history, a welcoming, upscale ambiance, high-value amenities, and consistent dedication to our guests’ experience. Each aspect of your stay with us works in concert to create a lodging experience like no other. If your goal is to leave behind your busy life and long lists of responsibilities and enjoy some dedicated time with the friends who are there for you through it all, this is the place. 

There are six guest rooms at our Galena Bed and Breakfast. Even if you don’t fill out all six rooms, you’ll feel you have the Inn entirely to yourselves. There’s ample space to spread out and enjoy, including a third-floor deck out back, a side patio, and seating areas out front by the fountain. Of course, if you truly want the entire experience to yourselves, we’d be more than happy to help you find some dates for a whole-house rental!

Each guest room is spacious, offering plenty of room to spread out. We also provide an array of fantastic amenities, including custom-designed and super-plush Frette Spa Robes and towels, Aveda personal care products, a customizable Bluetooth sound system, and Samsung Smart TVs. Your guest room can even be transformed into your own private spa for an indulgent massage that leaves you relaxed and refreshed! 

In the morning, we’ll treat you to a sensational, three-course breakfast that you didn’t have to prepare and that will fill and satisfy you for a fun day ahead. In the afternoon, we’ll bring you a house-made tray of appetizers and locally sourced charcuterie, plus a home-baked sweet treat and a bottle of your preferred beverage. It’s the perfect bite between meals – and even for those late-night cravings! We’ve thought of everything and have curated a thoughtful experience for our guests. This attention to detail sets us apart as one of the top destinations near Chicago for girlfriend getaways. 

People enjoying Goat Yoga - one of the more fun things to do in Galena during your Girlfriend weekend getaway!

Things to Do With Your Girlfriends in Galena!

Though we’ve created what we think is the perfect guest experience, allowing you to spend the entirety of your weekend getting cozy and enjoying some R&R together, there are also plenty of things to do in Galena – many things that are so much more fun with your best girlfriends in tow! 

Whether you love tasting new releases of wine, beer, or spirits or would prefer to work off your breakfast calories by doing something active during the day, you’ll find no shortage of great things to do – and it’s this range of activities that makes Galena a great candidate for an exciting girlfriend weekend getaway near Chicago. It really does offer something for everyone and has been awarded for being one of the best small towns in America. We’ve included a list of some of our fun local favorites below!

  1. Gather your friends for a fun morning of shopping, hopping from one boutique to the next in downtown Galena. Perusing the unique shops downtown is one of the most popular things to do in Galena – it’s easy to see why, too, as Main Street is home to 100+ unique shops! There is also some great antiquing nearby. 
  2. How about an afternoon of wine tasting? There are plenty of options for wine tasting in downtown Galena, including Galena Cellars WineryMassbach Ridge WineryJamie’s Wine StudioThe Grape Escape, and Champagne on Main. Of course, you can also head out into the countryside for a winery tour!
  3. Work up a sweat and enjoy some time together during your girlfriend’s getaway. There are plenty of outdoorsy things to do in Galena. From biking the Galena River Trail to paddling on the Galena River, our town is anything but boring! You can also enjoy hiking at Mississippi Palisades State ParkApple Canyon River State ParkHorseshoe Mound Preserve, and one of the other incredible Jo Daviess County Conservation properties.
  4. For something truly unusual but fantastic, take a goat walk with Hoof It Galena. Their goat treks are full of fun and offer just the right blend of time in nature and a little animal therapy. 
  5. Speaking of animal therapy, you might also want to enjoy a little goat yoga during your weekend away! Galena Goat Yoga offers regular classes at their farm for a fun, refreshing, and relaxing experience with your friends.
  6. When the sun goes down, there’s plenty of fun to be had in Galena! From visiting local bars and enjoying live music to watching a riveting magic show or maybe even taking a haunting ghost tour of town, there are plenty of ways to enjoy Galena after dark
  7. What better way to make memories together than by making something you can take home with you? Stop at local business Board and Brush and enjoy a fun little DIY session together!
  8. You can also make a signature scent for perfume or candles at Galena’s Scent Workshop.

Of course – all of these things make a really fun addition to any girlfriend weekend getaway near Chicago – but don’t forget to leave yourself plenty of time to relax, unwind, and enjoy every aspect of the Jail Hill Inn experience. It’s truly second to none. Book your stay at one of the country’s best Bed and Breakfasts today! 

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