319 Meeker St. Galena, IL 61036

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An Exclusive Dinner & Lodging Package at Jail Hill Inn

Dinner and Lodging package at Jail Hill Inn in Galena2019 was a great year. We watched business soar and got to know so many more of you! This year, we want to try something new and exciting. We’ve been working hard behind the scenes not just to improve your stay at the Inn itself, but to make your overall experience in Galena even more amazing. We think we have found the answer!

We’ve taken the guest experience at Jail Hill Inn one step further, and partnered with our friends over at Brazen, a nationally recognized and highly acclaimed restaurant located near Galena, in Dubuque, Iowa. The Chef at Brazen Open Kitchen and Bar, once featured on Top Chef, is going to treat 6 lucky couples to an exclusive 6-course wine pairing dinner, right here at our Inn!

We’ll be hosting the event on May 6 and 7, 2020. The package will be available for booking on March 15.  More details are offered below, but start clearing your calendars. Rooms will go fast!

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Looking For the Best Weekend Getaway Near Chicago?

The Best Weekend Getaway Near Chicago is our Galena IL Bed and BreakfastIf you’re looking for the best weekend getaway near Chicago, you’ve come to the right place!  Galena has long been considered to be a top getaway destination for those in Chicago and other major cities in the Midwest, including Milwaukee, Madison, and even Minneapolis/St. Paul.  From Chicago, Galena is considered to only be a one-tank getaway, as it takes just under 3 hours to get here.

If you haven’t yet made the trek from Chicago to Galena, you’re missing out on a truly extraordinary little town, and, as it happens, the Best Galena IL Bed and Breakfast. With plenty of awards and accolades and an incredible number of 5-star reviews standing behind our name, you’ll soon see why the Jail Hill Inn is the best weekend getaway near Chicago. Book a room, and come explore this romantic piece of Illinois with us! Continue reading

Galena IL Upcoming Events to Plan For in 2020

Plan Ahead for these Galena IL Upcoming Events in 2020If you’re ever visited us in Galena, you probably know that Galena hosts a variety of fun events and activities throughout the year. In fact, there are so many great Galena IL upcoming events, that we thought we’d help you do a little advanced planning. It probably comes as no surprise that we book up quickly for the most popular of Galena’s events, which include the Wine Lovers Weekend, Corkless in Galena, Halloween, Nouveau Weekend, and the Night of the Luminaria & Living Windows around the holidays.

We always encourage our guests to book early and book often. It’s no different in 2020 when we’re already seeing plenty of advanced bookings for events and weekends our previous guests simply don’t want to miss.  So, if you have your heart on attending one of these Galena IL upcoming events, head on over to our website and book your room today! Continue reading

A New Year, a New Getaway to our Galena Bed and Breakfast

Stay at the Best Galena Bed and BreakfastA New Year is upon us, and while we’re all busy making New Year’s resolutions, we have one more you should add to your list:  getting away to our sensational Galena Bed and Breakfast!  That’s right!  In this new year full of hopes, dreams, and promises, we think you should carve out some extra time this year to take care of yourself.  Even better, come stay with us, and let us take care of you! After all, pampering our guests is what we do best.

It won’t take you long to get here, and you’ll be forever glad you did. Book your room at our luxury Galena Bed and Breakfast today! Continue reading

10 Things You Simply Must do in Galena This Winter

10 Things to do in Galena This WinterHave you ever visited Galena during the winter? It’s a wonderful place to visit, even when there’s snow on the ground!  There are plenty of delightful things to do this winter, and we have a great guide for you. Head out on a cross country skiing adventure, explore our vibrant and historic downtown, or sit back and savor the luxurious accommodations found at our Galena Bed and Breakfast.

Galena has long-been a popular getaway destination for those living in or around the Chicago area, and these winter months should be no different. Even if you don’t love spending time outside during the winter, the chance to stay at our romantic Inn is more than worth the time it takes to get here. Your day will start with a delicious breakfast, but that definitely isn’t the end of our award-winning hospitality.  In the afternoon, join us for a delicious wine and cheese hour, along with some delicious fresh cookies, hot from the oven. Come see it for yourself, and book a room at our Galena Bed and Breakfast today. Continue reading

10 Reasons Why We’re the Best Galena Bed and Breakfast

Stay at the Best Galena Bed and Breakfast this WinterIt’s bold to assert that we are the Best Bed and Breakfast in Galena, but it’s a statement we can firmly stand behind.  In fact, not only is Jail Hill Inn the best Galena Bed and Breakfast, but we’re the best Bed and Breakfast in the entire country, according to TripAdvisor. After 4 incredible years in business, we’re thrilled to have seen the successes we’ve had in 2019, and are looking forward to an incredible 2020 with our guests, friends, and family.

If you’re looking for a beautiful and fun getaway destination this winter, consider staying at the Jail Hill Inn so you can see what all the hype is about for yourself. Book your room at Galena’s Best Bed and Breakfast today! Continue reading

5 Reasons to Try Goat Yoga in Galena This Fall!

Goat Yoga in GalenaHave you heard of goat yoga? Yes, it’s a thing, and it’s catching on in Galena!  Of all the things to do this fall in Galena–and there are plenty of things to choose from!–goat yoga might be one of our new favorites. We think this fall is the perfect time to get out and meet these adorable animals and participate in this exciting new adventure in Galena.

All the traditional fun is still here, too, including shopping along Main Street, wine tasting, dining out at our delicious restaurants, enjoying a performance at P.T. Murphy’s Magic Theatre, and staying in and getting cozy at the Jail Hill Inn.  Consider this just one more thing to add to your lengthy itinerary the next time you visit us at Jail Hill Inn! Are you ready to give it a try? Book your room at our Galena Bed and Breakfast today! Continue reading

5 Intriguing Things to Do in Galena Il At Night

5 Things to do in Galena At NightHave you ever wondered what there is to do in Galena after you’ve enjoyed dinner and the shops along Main Street have mostly closed up for the night? There’s actually a surprising amount of things to do in Galena at night. From hitting up live music venues or catching a local magic show to exploring the dark (and haunted!) side of Galena, there’s plenty of fun things to do in Galena at night.  You can also dine in and enjoy the many amenities and extras available to you at Jail Hill Inn.  Whatever it is you want to do, our Inn is conveniently located within walking distance to all of it. Book your stay at our luxury Galena Bed and Breakfast today! Continue reading

10 Instagram Photos to Take of Galena This Fall

Instagram Worthy Photos to Take When you Visit our Bed and Breakfast in GalenaThough many of us may not want to admit it, we love to capure picture-perfect moments of our vacations to share on Instagram. It helps when you have an exceptionally beautiful place to photograph! If you’ve ever visited Galena in the fall, then you know just how extraordinarily beautiful this historic little town is. If this will be your first time, you’re in for a treat. The hillsides around Galena light up in their fiery shades of fall each September and October, making for a breathtaking display that must be experienced to be believed.  Galena, located within easy driving distance from Chicago, Minneapolis, Des Moines, and St. Louis, is the perfect getaway destination this fall. Between hiking through the beautiful fall colors and soaking up the small-town charm of downtown Galena, there are a number of Instagram worthy destinations to show off during your stay in picturesque Galena.  Book your room at the Jail Hill Inn, and enjoy another spectacular fall at the country’s #1-rated Bed and Breakfast. Continue reading

Traveling from Chicago to Galena? Here are 11 Things to Do on the Way!

Road Trip from Chicago to Galena This FallWe love a good road trip. Are you ready to make the road trip from Chicago to Galena? We have the perfect guide for you!

Summers in Galena are filled with plenty of fun and adventure, and this summer has been no exception. There’s still plenty of time to get here and enjoy the best of Galena with us this summer, whether it’s biking down the Galena River Trail, kayaking on the river itself, shopping along Galena’s Main Street, or relaxing and enjoying the warm weather on our private patio.  But really, now is the perfect time to plan your fall getaway to the beautiful, rural town of Galena. Galena is only a one-tank road trip from Chicago, and there’s plenty to see and do as you make your way from Chicago to Galena.  Getting here is half the fun. Get started on your adventure, and book a room at our luxury Bed and Breakfast in Galena today. Continue reading

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