Bed & Breakfast Escapes from Chicago

by Shannon

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!

Steamboat House bed and breakfast
Photos courtesy of The Steamboat House
Bedroom at Steamboat House Bed and Breakfast
Viola Room- where we stayed!

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.

Siskiwit Bay Lodge Bed and Breakfast

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.

Hidden Serenity Bed and Breakfast

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.

Sea Suites Bed and Breakfast
Sea Suites Bed and Breakfast room

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Taylor October 23, 2020 - 8:40 pm

These bed and breakfasts look so quaint and cozy! I’ve been getting into B&Bs more. I love how the owners make you feel like you’re part of their family. 🙂

Shannon October 24, 2020 - 4:45 pm

Yes, some of my best experiences have been at B&Bs.

Karen October 23, 2020 - 8:42 pm

These are all so beautiful. There is nothing like pampering yourself in a B&B. I lived in Traverse City many years ago when I did my student teaching. It was a magical place. Fun to see the B&Bs from there.

Shannon October 24, 2020 - 4:44 pm

How cool! I’d love to live in Traverse City, just not in winter!

Sharyn October 23, 2020 - 9:29 pm

Great post. I like your photos – I didn’t know that is how you collect maple syrup?

Shannon October 24, 2020 - 4:44 pm

Thank you! The maple syrup process is pretty intensive, from what I heard. Interesting to learn about though!

Katie October 23, 2020 - 10:15 pm

Beautiful places – I want to visit them all! I love the Tall Ship or Sea Suites, I can imagine my husband would love staying here. The lodge also looks really pretty too – thanks for sharing, I have bookmarked for future travels.

Shannon October 24, 2020 - 4:43 pm

Any of these would make great couples getaways!

Albí October 24, 2020 - 4:49 am

Love the nature escape with alpaca and horses, the nature around looks amazing

Shannon October 24, 2020 - 4:42 pm

It was a wonderful place! Aside from the horse and alpaca, there were plenty of cats running around too!

Charlotte October 24, 2020 - 5:16 am

All of these look so cozy! Some of my best travel memories are from staying in B&Bs. I love how calm and relaxing it often is and, of course, the local knowledge of the hosts 🙂

Shannon October 24, 2020 - 4:41 pm

Yes, the hosts’ area expertise is so helpful! It can also be fun chatting with other guests at breakfast, seeing what they’ve done or plan to do.

April October 24, 2020 - 5:40 am

Such wonderful places and what a great idea since normal travel isn’t really possible these days, but a mini escape! Thanks for sharing.

Shannon October 24, 2020 - 4:40 pm

I know, local escapes are all I’ve been able to do this year.

Carley October 24, 2020 - 8:58 am

So fun! I love these ideas. I would NEVER think of a boat on my own but thats actually such an awesome idea. I’ll have to keep that in the back of my mind for the future.

Shannon October 24, 2020 - 4:40 pm

I’d never stayed on a boat- minus a cruise ship, but that’s a totally different ballgame- until these two.

Catherine October 24, 2020 - 11:10 am

When people think of traveling to Illinois, they think of Chicago and nothing else. Thanks for the inspiration for nearby day trips and overnight stays near Chicago!

Shannon October 24, 2020 - 4:39 pm

You’re so right! There’s alot to see outside of the city, whether in Illinois, Indiana, Michigan or Wisconsin.

Michele October 24, 2020 - 12:45 pm

I LOVE a bed and breakfast and how fun that you got to stay in all of these around Chicago. It would be so hard to just pick one as you’ve made them all sound fun and unique in their own ways. And I have always wondered how they collected maple syrup – that would be so cool to see in person!

Shannon October 24, 2020 - 4:38 pm

My hubby and I have made many a weekend trip from Chicago, so I’ve loved collecting these experiences!

Cosette October 24, 2020 - 2:05 pm

Love a good Bed & Breakfast. We have a few favorites in our area as well. When I’ll get to do a road trip around Chicago, I will keep these in mind.

Shannon October 24, 2020 - 4:38 pm

Definitely! Whether you’re escaping Chicago or roadtripping here, these make great stops.

Nichole the Nomad October 24, 2020 - 2:36 pm

All of these look so cozy and perfect for a weekend away! Whispering Waters looks SO stunning, and I’m adding it to my bucket list because who doesn’t love a good B&B?!

Shannon October 24, 2020 - 4:37 pm

Awesome, I hope you can visit soon!

Teresa October 24, 2020 - 4:24 pm

What a great post! Such a good selection of places to stay. I’d love to stay on that boat. It looks fab!

Shannon October 24, 2020 - 4:36 pm

Thank you! Both the boat stays were cool, each in their own way.

Katie October 24, 2020 - 7:16 pm

Some great choices here Shannon! I especially like the boat options because I used to live on a houseboat.

Shannon October 25, 2020 - 2:11 pm

Wow, that’s so cool- living on a houseboat!

Gian October 24, 2020 - 11:23 pm

Gosh, all of these would be such a great break from the city. Such a good idea

Shannon October 25, 2020 - 2:12 pm

Thanks! Hoping we’ll be escaping again soon ourselves! 🙂

Sally October 25, 2020 - 3:58 pm

Thank you Shannon, for including our Boat & Breakfast in your selections. Our Guests; as well as their reviews are the best!

Shannon October 26, 2020 - 10:47 am

Sally, thank you for a great stay!


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