Bed & Breakfast Escapes from Chicago

Bed and Breakfasts are some of my favorite places to stay. They have their own character, and for that matter, far more character than a hotel. The hosts offer local knowledge, and provide amazing homecooked breakfasts. Really, what’s not to like about a B&B? So, here’s a few ‘best of’ bed & breakfast escapes from Chicago!

I’ve stayed at dozens across both the US and internationally. Trust me, bed and breakfasts are not all lace doilies and Grandma’s furniture. They range in style, tastes and price. I decided to write about some of my favorites within a weekend’s trip from Chicago. As I did, I sadly discovered one of my ‘bests’ has forever closed its doors due to COVID-19. Now more than ever is a great time to stay at a B&B. You’re supporting the local economy, and the hosts have a far greater interest in keeping their homes clean a hotel staffer would. Plus, with generally only a few rooms at a bed and breakfast, you’ll come in contact with less people.

These are great escapes for most anytime of year, but fall is perfect for a weekend getaway. Get on the road and explore before it’s too cold to step outside! And please know, I do not receive any compensation or benefits from recommending these B&Bs- I just really enjoyed them!

Best In Town (and Best Historic!)

Steamboat House, Galena, IL

The Steamboat House is the perfect location from which to explore downtown Galena! It’s just steps from the main street, and no wonder, considering its history. A Gothic Revival mansion, built in 1855 by one of Galena’s leading citizens, it’s been an integral part of town history. It played host to countless guests, including General Ulysses S. Grant, future president (as an aside, you can visit his former home a few blocks away!). Meanwhile, the owners of Steamboat House had their own political involvement, running a station of the Underground Railroad! There is a still a tunnel under the house.

Today, it’s a fantastic B&B. All the rooms have fireplaces, and downstairs you’ll find a billiards table and plenty of shared living space. All the décor and furnishings are rich and dark, throwing back to a bygone era. Breakfasts are a formal occasion with top notch food. Afterwards, it’s easy to stroll into town for window browsing and more delicious dining!

Best Retreat

Whispering Waters, Traverse City MI

If you’re looking for a retreat- romantic, relaxing or just off grid- this is the spot for you. At this time, they don’t even have a website, but you’ll find great reviews on TripAdvisor. They offer some bookings through AirBnB, or you can do it the old fashioned way- over the phone.

Whispering Waters is about 7 miles outside of downtown Traverse City, down a dirt road and over a wooden bridge. The main house has several rooms, some with private baths, others shared. There are also separate cabins for a more private experience. We stayed in the main house with a shared bathroom, but were the only ones on that floor, so the shared bath was our own. We could hear the creek from our room, it was so peaceful.

The house is lovely, and even has a ‘secret’ room up a ladder! It’s replete with woven branch railings, almost feeling like a treehouse. Outside, enjoy the creekside hot tub or the sauna. For a bit more activity, hike the trails that snake through the back acres behind the house, or walk to the river. If you sit quietly, you’ll likely see a muskrat! The resident horse and alpaca will watch you head down, and might even come to the fence to greet you.

The hosts can arrange meditation or yoga sessions, or onsite massages. This would be the perfect place for a holistic retreat. Every morning, Brian fixes a fantastic breakfast! He was very welcoming, and provided some great info on the area.

Best Nature

Siskiwit Bay Lodge, Cornucopia, WI

So, this is a bit farther afield than my other recommendations, but I couldn’t pass it up. Siskiwit Bay Lodge is a nature lovers’ paradise! Sitting on the shores of Lake Superior, scenery changes from early morning eerie fog, to stunning sunsets. Winter visits will offer a different view of nature, with a frozen lakeshore, easily accessible ice caves, and if you’re lucky- the Northern Lights. Being so close to the Apostle Islands National Lakeshore, there’s plenty of outdoor activities any season.

During our August visit, flowers bloomed across the property and evening bonfires closed out the days. We enjoyed just being on the property- dozens of birds, chipmunks and jack rabbits were everywhere! At night, the stars were amazing. Driving towards the property, you’ll pass a small waterfall worth stopping for. When we did, we discovered a set of large animal tracks- later identified as cougar! While rare, they do venture into Wisconsin, particularly in the northern area. You may also encounter bears.

The lodge is a few miles from Cornucopia, which has the claim of Wisconsin’s northernmost town. It’s about 30 minutes to Bayfield, where the majority of the action lies, but you can grab a bite to eat and even join a kayak tour from Cornucopia.

Best Romantic- and All Around Favorite

Hidden Serenity, West Bend, WI

Just a couple hours from Chicago, Hidden Serenity is the perfect combination for a romantic getaway. We even celebrated our engagement here. Let me start by telling you how amazing the hosts are! We booked for our engagement, but then due to a medical emergency, couldn’t make it. They don’t allow last minute cancellations, and were booked for the following several months. However, they allowed us to come over Easter weekend, despite their being gone and the B&B officially closed. Their adult daughter hosted us, and provided a great experience, including breakfast, each day. I’m so grateful to all three of them for accommodating us, and making our engagement getaway so special.

Each of the rooms are luxurious, but I loved ours. It had a fireplace, a mirror TV and the most amazing bathroom! The heated pebbled floor, the dual head two person shower, and all the nature inspired touches were just perfect. It really couldn’t be any more romantic! For a little more socialization, the public areas have a billiards table and old school arcade system.

The property has a few trails, and plenty of nature. We saw deer and wild turkeys in the front while eating breakfast each morning! The hosts also produce their own maple syrup. During winter, you’ll see the sap bags on the trees. The Shalom Animal Sanctuary is just down the street, and it’s just a few miles to Kettle Moraine State Forest, if you’re looking to venture beyond the comforts of the B&B.

Most Unique

Tall Ship Manitou, Traverse City, MI

Without a doubt, my most unique B&B experience was aboard the Tall Ship Manitou, sailing out of Traverse City, MI. The ship is a replica 19th century schooner, such as frequently crossed the Great Lakes. Part of our 4th of July getaway last year, we spent one night aboard. The B&B package included a group sail in the late afternoon, but after most passengers departed, 4 couples stayed aboard. The ship stayed docked, but we were able to watch the fireworks all around Grand Traverse Bay. After an evening on deck, we retired to our small- very small- bunkroom. Now, this is a unique experience, not necessarily a romantic one! The bunkbeds are tight and sharing isn’t much of an option. Aside from the bunk, the rooms have a small table with a wash basin, but there’s a sink in the shared space. A full, modern (and clean!) showerhouse is available across the street.

Now, the best part was waking up to a calm, quiet bay. I could hear the loons call across the water, as I sipped my coffee and enjoyed the most out of this world morning glory muffins. The chef gave us the recipe, but I swear, they just didn’t taste the same at home. A full breakfast was served below deck in the galley, which was complete with a giant cast iron stove.

The Traverse City Tall Ship Company indicated they may not offer this package in 2021, due to COVID, but check their site for updates. In the meantime, you can always book their sailing yacht Scout for an overnight experience, all to yourself. If they have the same chef, it would be worth it for that alone!

Most Unique #2- Just can’t get enough of boats!

Sea Suites, Douglas, MI

I couldn’t exclude this very unique B&B from the list! Dubbed a ‘boat and breakfast’, it’s one of only a handful in the country. It does not sail, but you can still feel the slight motion of the waves. It’s essentially an enormous pontoon boat. The rooms are large and comfortable, each with a private bathroom.

Most of the communal space is overhead, on the open 105′ deck. It’s a big space, but was a bit cold for use during our early May visit. This B&B operates April- November. It’s walking distance to downtown Douglas, and just a bit farther to Saugatuck. It was perfect for our visit to the Tulip Time Festival.

Pin it for Later!