319 Meeker St. Galena, IL 61036

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Is the Trip From Chicago to Galena Worth It?

Enjoy the Trip from Chicago to GalenaChicago is the nearest big city to Galena, and it only takes about 3 hours to get from Chicago to Galena.  Even so, you might be asking yourself if it’s worth making the trek from Chicago to Galena.  The answer to that is a resounding yes.  Of course, we think the opportunity to visit our Galena Bed and Breakfast is more than worth the effort, but visiting us is about so much more than the luxury accommodations you’ll find once you’re here; it’s also about this incredible, historic town that you’ll get to enjoy once here.

Galena is steeped in history, and it’s hard to get a sense of appreciation for it from afar. Dating back to its earliest days as a mining town, and later as the home of famed U.S President Ulysses S. Grant, there is much to see, do, and experience once here.  And, just as with any great road trip, the journey to get from Chicago to Galena is a beautiful one and is filled with plenty of small towns and picturesque vistas to enjoy along the way. What are you waiting for? Hop in the car, and head on out to Galena. Just make sure you have reservations at the incredible Jail Hill Inn before you go!

How to Get From Chicago to Galena

Galena is located just over 2.5 hours west of Chicago.  The easiest way to get from Chicago to Galena is to head west on I-90, and then continue on Highway 20 towards Galena & Dubuque. An interesting fact:  Highway 20 is one of the longest stretches of highway in the country! Once you’re on Highway 20 near Rockford, the drive becomes not just quieter, but much more scenic as well. And the scenery just gets better the closer you get to Galena, with many wonderful overlooks and worthwhile stops along the way.

As you drive along Highway 20, take note of the small communities you travel through, for visiting these charming towns is one of the many reasons to come to Galena in the first place. In Stockton, you’ll find some incredible public art, including some great murals around town. It’s a great place to add a little color to your Instagram account if you’re so inclined.

Another charming town worth exploring is Elizabeth, home to some charming antique stores and other shops, along with some great restaurants and coffee shops. Like Galena, it’s also filled with history and is home to the Apple River Fort State Historical Site, the Chicago Great Western Railway Depot Museum, and the 1876 Banwarth House and Museum. We love to send our guests to Three Sisters Sweet Shoppe, E-Town Coffee shop, Common Cents Resale Shop, and Elizabeth Grand Antique Mall.

Enjoy the Trip from Chicago to Galena

As you continue on your journey from Chicago to Galena, make sure you take the time to enjoy the views – literally! The gently rolling hills dotted with small farms and cows and the densely wooded areas make for a truly beautiful drive. If you feel like stopping and stretching your legs, you won’t want to miss the Long Hollow Scenic Overlook. Soon enough, the charming and historic town of Galena will come into view, and before you will unfold the magic of this little town, where you’ll be spending the next few days! You’ll find Jail Hill Inn at the far end of Main Street, sitting on a hill and overlooking downtown Galena.

The Best Things to do in Galena

We wouldn’t recommend making the trip from Chicago to Galena just for the scenic drive. The journey to get here is great, but the destination once you’re here is absolutely fantastic! There isn’t a shortage of things to do in Galena, no matter the time of year you visit.  Truly, Galena is a 4-season destination, fit for adventuring travelers or those who just want to relax and enjoy a change of scenery.

But, since it’s winter, we’ll focus on our favorite things to do over these next couple of months! Of course, with all of the wonderful amenities and cozy spaces found indoors at our Inn, you may not feel the need to leave.  However, if you are up for some adventure, there’s plenty to choose from. And, while winter may look a bit different in 2020 when compared to other years – especially with some of our bigger events canceled for the time being – we can ensure you that this small, historic town still packs a punch when it comes to fun things to do.

  1.  Take a walk, bike ride, or maybe even snowshoe (conditions pending) on the Galena River Trail, enjoying the country scenery as you go. You can also enjoy some beautiful wintry views of the Mississippi River from one of the Jo Daviess Conservation Foundation’s properties, like the Casper Bluff Preserve.
  2. Get in some skiing at Chesnut Mountain Ski Resort. Space will be limited on the mountain this year for the health and wellbeing of everyone, so it’s in your best interest to plan and buy tickets early.
  3. Cross Country skiers love the trails at the Nordic Center at Eagle Ridge Resort & Spa. This is also a great place for sledding, snowshoeing, and ice skating!
  4. There’s plenty of Shopping in downtown Galena – which is just a short walk from our Galena Bed and Breakfast – where there are more than 125 independently-owned shops are waiting.
  5. Sit back, relax, and enjoy some drinks at a variety of bars and venues downtown, including Galena Cellars, Galena Brewing Company to Blaum Bros Distillery.
  6. Order takeout from any of our Galena Restaurants or even our friends Brazen Open Kitchen and Bar in Dubuque (they offer Friday night delivery to Jail Hill Inn), and enjoy it at the Inn!
  7. Get to know the history of Galena!  Popular places to visit include the US Grant Home, the Belvedere Mansion, and The Dowling House.

Enjoy the Trip from Chicago to Galena

The Best Place to Stay in Galena

At the heart of any great getaway are your accommodations.  If you want a truly wonderful getaway – one that makes that 3 hour trip from Chicago to Galena worth every second of your time – then you need to book a room at the stunning and award-winning Jail Hill Inn.  Jail Hill Inn is easily the best Bed and Breakfast in Galena, having earned the recognition of being the #1 Bed and Breakfast in the country in 2019, and the #3 Bed and Breakfast in 2020.

Apart from these incredible honors, Jail Hill Inn has more than 500 reviews, all of which are 5-star reviews – all of which have been earned in our 5 short years of being open!  From the moment you enter our Inn, you’ll see the difference between Jail Hill Inn and other Galena Bed and Breakfasts.  Each of our six suites offers 800 square feet of luxuriously decorated space, which includes a fireplace, comfortable seating areas, a luxuriously appointed king bed with silky soft Comphy Brand sheets, and Kohler bathrooms with steam showers.

Each morning of your stay will start off with our gourmet, 3-course breakfast, which can be enjoyed either in our socially distanced dining room or delivered to you in the privacy and comfort of your suite.  Each afternoon, we’ll ply you with more yummy treats, as we bring you a custom charcuterie and appetizer tray, complete with your selection of wine or other beverage.  We go the extra mile to make sure you enjoy every second of your time here and are happy to recommend activities and things to do in Galena.  Come get a taste of luxury, and book your room at the best Galena Bed and Breakfast today!


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Now Offering Dinner from Brazen!

We’ve partnered with our friends at the sensational Brazen Open Kitchen in Dubuque to bring you a new Friday night food delivery option!