Where to Go For Romantic Getaways Near Chicago
Are you searching for one of the most romantic getaways near Chicago? Just under three hours from the city, Galena offers the perfect destination for couples looking to relax, recharge, and reconnect. At the heart of it all is Jail Hill Inn, a luxury bed and breakfast that has earned a reputation as one of the most romantic places to stay in the Midwest. With elegant suites, exceptional hospitality, and a rich historic setting, it is the kind of couples getaway that lingers with you long after you’ve left.
Whether you are planning a quick escape for the weekend, celebrating a special anniversary, or looking for the perfect spot to unwind together, our Bed and Breakfast delivers an experience unlike any other. Couples can enjoy spacious honeymoon-style suites with jetted tubs for two and fireplaces, indulge in gourmet breakfasts each morning, and explore all the charm that Galena has to offer. From wine tasting and shopping downtown to outdoor adventures in the rolling hills, there is no shortage of things to do in Galena, IL.
At our Galena Bed and Breakfast, every detail is designed with romance in mind. The atmosphere seamlessly blends historic character with modern luxury, providing couples with a sophisticated yet comfortable retreat. Give yourself permission to dream, plan your next adventure, and discover why Jail Hill Inn is one of the top destinations for weekend getaways for couples near Chicago. Book your stay today!
Where to Spend Romantic Getaways Near Chicago
There are plenty of wonderful places to stay in Chicago, but sometimes the best way to recharge is to escape the city altogether. If you are looking for romantic getaways near Chicago, you will find that Galena, Illinois, offers something truly special. Just under three hours away, this charming small town is known for its historic character, vibrant downtown, and breathtaking scenery, making it the perfect destination for a romantic couples getaway.
The drive from Chicago to Galena is an enjoyable part of the experience, with scenic landscapes and plenty of opportunities to stop at interesting towns along the way. Once you arrive, the real magic begins. Galena is filled with things to see and do, from boutique shopping and wine tasting to historic tours and outdoor adventures. At the center of it all is Jail Hill Inn, a luxury bed and breakfast that has been named the #1 Bed and Breakfast in the country and the #2 in the world. It is safe to say this inn has earned its place as one of the best romantic weekend getaways in the Midwest.
From the moment you walk through the doors, you will be welcomed with thoughtful touches that set the tone for your stay. Chocolates and champagne await in your suite, giving you an unexpected welcome as you sink into one of the most romantic getaways near Chicago. Each guest room is spacious and designed with indulgence in mind. Inside every guest room, you’ll find a comfortable living area, a kitchenette, a spa-inspired bathroom, and a sleeping area with a generous king-sized bed. All rooms have gas fireplaces and elegant decor, and many have jetted tubs for two and/or generous steam showers.
Every morning begins with a multi-course gourmet breakfast. You can join us in the morning for your three-course treat, or you can elevate your romantic getaways near Chicago even further and have us bring you breakfast to be enjoyed in your private suite. In the afternoon, we’ll also bring you a sumptuous tray of goodies, featuring housemade appetizers, locally procured charcuteries, and freshly baked cookies, alongside your selection of wine or non-alcoholic beverages. It’s the perfect snack before heading out on the town for the evening, and some of our guests even save it for a midnight treat.
Do you want to take your romantic getaways near Chicago to the next level? We have an on-site spa room for just that! Let us know in advance if you’d like to pamper yourself or your partner. We work with local massage therapists to offer 60 or 90-minute single and couples massages, right here at our Galena Bed and Breakfast. You can freely move about the property without having to leave the cozy comfort of your Jail Hill Inn robe or drive to an appointment, allowing you to fully relax and unwind after that massage. Your tub or steam shower will be screaming your name when you’re done!
At Jail Hill Inn, no detail is overlooked during your romantic getaways. From personalized concierge service to unmatched hospitality, it is more than just a stay. It is an unforgettable experience that turns a simple trip into the ultimate romantic getaway near Chicago.
What To Do on Your Romantic Couple’s Getaway
From the moment you arrive in Galena, you’ll be drawn in by its historic charm and welcoming atmosphere. As Illinois’ second most visited destination, this small town has earned its reputation for offering unforgettable experiences in a picturesque setting. Despite its size, Galena is packed with attractions, and that’s what makes it one of the best romantic getaways near Chicago. Even better, Downtown Galena’s award-winning Main Street is just a short walk from our Bed and Breakfast, giving guests effortless access to the heart of the city.
Downtown Galena is home to more than 100 unique storefronts, including locally owned restaurants, boutique shops, and art galleries. Recognized as the “Best Main Street in the Midwest” by Midwest Living Magazine, it’s the kind of place where you can easily spend hours exploring. The preserved 19th-century architecture adds to the experience, creating a setting that feels timeless and inherently romantic.
Of course, there are so many more things to do in Galena than shopping and dining. Visitors can explore historic attractions like the Ulysses S. Grant Home, take part in wine tastings and brewery tours, soar above the landscape in a hot air balloon, or dive into the town’s haunted history on a ghost tour. Outdoor enthusiasts will find plenty of parks, hiking trails, and the scenic Galena River Trail for biking, walking, or paddling.
With so many ways to enjoy the area, Galena is a destination that delivers something for everyone. When you are ready to experience one of the most memorable romantic weekend getaways for couples, Jail Hill Inn is here to welcome you with luxury, history, and unmatched hospitality. Book your stay at our Galena Bed and Breakfast today!
