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The Best of the Best in Galena

How To Get from Chicago to Galena & Where to Stay!

If you’re looking for a fantastic place to enjoy a couple’s getaway this winter, it’s time to hop in the car and make the trek from Chicago to Galena.  The drive is easy, at just around 3 hours and only one gas tank away, and at the end, you’ll find not just the best place to stay in Galena but one of the most romantic getaways in Illinois!

If you’re wondering if the 3-hour drive from Chicago to Galena is worth it, the simple answer is yes! Galena itself is a charming, historic destination filled with great shops, gorgeous scenery, and plenty of things to do. But, more importantly, Galena is where you’ll find Jail Hill Inn. It’s not enough to say we’re the top-ranked Galena Bed and Breakfast or even the best place to stay in Galena. Our Galena, IL Bed and Breakfast has been ranked the #1 Bed and Breakfast in the entire country and the #2 best Bed and Breakfast in the world!

Add those accolades to our 600+ all 5-star reviews, and you can easily start to see why the drive from Chicago to Galena is more than worth the time and effort. Of course, visiting us is about so much more than the luxury accommodations you’ll find once you’re here; it’s also about this charming, historic little town that you’ll get to enjoy once here.

It doesn’t get much better than a winter getaway to our unbeatable Galena Bed and Breakfast. Book your room at the best place to stay in Galena today!

A couple driving from Chicago to Galena in winter, where they stayed at the best place to stay in Galena

Enjoy the Trip From Chicago to Galena

The drive from Chicago to Galena is anything but challenging – the worst part about it will be getting out of (or back into) the city. From there, the trip from Chicago to Galena will take just under 3 hours, and there are a few fun things you can stop and see or do along the way if you’re interested.

The easiest way to get from Chicago to Galena is to head west on I-90. You’ll continue on that for a while before eventually taking the turn-off to Highway 20 near Rockford towards Galena and Dubuque, Iowa. If you like roadside trivia, then you might be interested to learn that Highway 20 is one o the longest stretches of highway in the country – and it goes through our charming town of Galena!

Once you’ve reached Highway 20, you’ll feel the fast-pace of the city you left behind fade from your rearview mirror. The road certainly gets quieter (and smaller!), but it also gets infinitely more scenic as you drive. This is especially true as you get closer to Galena, which is in part of what’s known as the Driftless Area – an unusually hilly part of the Midwest that was left untouched by the last receding glaciers that otherwise flatted much of the Midwest.

One of our favorite things about this drive from Chicago to Galena is the small communities you’ll drive through on Highway 20. These include the towns of Stockton and Elizabeth, the closest neighbors to Galena. If you’re on track to reach our Galena Bed and Breakfast before check-in time, you may want to stop off in one or more of these small communities.  Here are a few things to consider visiting along the way as you drive from Chicago to Galena.

  1. The murals in Stockton, which are interesting and very Instagram-friendly!
  2. The antique shops of Elizabeth, including the Elizabeth Grand Antique Mall.
  3. Grab a sweet treat at Three Sisters Sweet Shoppe
  4. If you need a caffeine boost, pick up an afternoon coffee at E-Town Coffee shop

Soon enough, the charming and historic town of Galena will come into view, and your drive from Chicago to Galena will be over. Let the charms of this historic town unfold as you drive along Main Street. At the end of town, turn left and pull up in front of Jail Hill Inn – where you’ll find the best place to stay in Galena sitting on a hill overlooking downtown Galena.

How To Get from Chicago to Galena & Where to Stay! 7

The Best Place to Stay in Galena Illinois

You’ve committed to making the trip from Chicago to Galena to experience the historic charms of this destination for yourself. Now, where are you going to stay? For us, the answer is simple. Why stay anywhere else when you can choose one of the top-rated Bed and Breakfasts in the country? There’s truly no better place to stay in Galena, and it won’t take you long to see why so many guests have said the very same thing in our seven years of being open.

Not only is Jail Hill Inn the best place to stay in Galena, but it’s one of the most romantic getaways near Chicago. Our Galena Bed and Breakfast offers just six spacious and well-appointed guest rooms and has everything you want in a romantic couple’s getaway – and so much more! Chilling in your room upon arrival you’ll find chocolates and champagne. It’s just a small touch to welcome you to our Galena Bed and Breakfast, and one of many small details that transform your stay from an ordinary getaway to an unforgettable retreat.

Each morning of your stay, join us for a multi-course gourmet breakfast – a true feast for the senses. For many of our guests, breakfast is their favorite time of day – but it’s certainly not the only time we ply you with delicious food!  Each afternoon of your stay, we’ll serve a curated selection of house-made appetizers and cookies, and charcuterie from our friends at Galena River Wine and Cheese, on a custom-made tray that features a bottle of wine or sparkling beverage of your choice. You really won’t go hungry here!

We pride ourselves on setting the perfect stage for romantic getaways near Chicago, and we think our attention to detail is what keeps our guests making the trek from Chicago to Galena time and time again. There’s not a doubt in our mind why so many consider us the best place to stay in Galena. We love what we do! Book your room at our Galena Bed and Breakfast, and discover the best place to stay in Galena today!

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Give The Gift of Jail Hill Inn This Christmas

Give your loved one a very special gift of a stay at Jail Hill Inn .  We offer gift certificates in many amounts.