Skip to content
  • Guides To The Midwest
    • Midwest Travel Blog
    • Illinois
    • Indiana
    • Iowa
    • Minnesota
    • Nebraska
    • Ohio
    • Wisconsin
  • Places To Stay
    • Check Availability
    • View By State
    • View By City
    • View By Alphabetical List
    • Search By Amenity
  • Experiences
    • View All Tours & Activities
    • Illinois
    • Iowa
    • Minnesota
    • Nebraska
    • Wisconsin
  • About
    • About Our Association
    • Why B&B It
    • Gift Certificates
  • Innkeepers Corner
    • Join Our Association
    • Vendor Directory
    • Conference & Learning
      • Overview
      • MWInns Conference & Trade Show
      • Aspiring Innkeeper Seminar
      • Conference Exhibitor Information
    • Inns & B&B’s For Sale
    • Inn & Potential Inn For Sale Listing
    • Room Remittance Form
  • Guides To The Midwest
    • Midwest Travel Blog
    • Illinois
    • Indiana
    • Iowa
    • Minnesota
    • Nebraska
    • Ohio
    • Wisconsin
  • Places To Stay
    • Check Availability
    • View By State
    • View By City
    • View By Alphabetical List
    • Search By Amenity
  • Experiences
    • View All Tours & Activities
    • Illinois
    • Iowa
    • Minnesota
    • Nebraska
    • Wisconsin
  • About
    • About Our Association
    • Why B&B It
    • Gift Certificates
  • Innkeepers Corner
    • Join Our Association
    • Vendor Directory
    • Conference & Learning
      • Overview
      • MWInns Conference & Trade Show
      • Aspiring Innkeeper Seminar
      • Conference Exhibitor Information
    • Inns & B&B’s For Sale
    • Inn & Potential Inn For Sale Listing
    • Room Remittance Form

These are The Best Weekend Getaways From Chicago

June 2025
SMTWTFS
June 2025
SMTWTFS

For some travelers in the Midwest, Chicago is the destination. With its stunning architecture, bustling attractions, and next-level restaurant scene, it’s easy to see why. However, for others, planning weekend getaways from Chicago is necessary. If you find yourself looking for charming small towns in the Midwest and great getaway destinations, there’s certainly no shortage of places to look. From the historic town of Galena, Illinois, to the quiet charms of Cedarburg, Wisconsin, we have plenty of ideas about where to spend your weekend getaways from Chicago. 

But before we get to the destinations, we must first talk about the experience. Where you stay for your couple’s getaway can make or break your experience. Hotels might offer convenience, and maybe even brand recognition, but they often lack the personalized warmth and attention to detail that can make a romantic getaway feel truly special. For those looking to slow down, reconnect, or simply break away from the fast pace of the city, a Bed and Breakfast or Boutique Inn, like those you’ll find among our Midwest Inns Association, offers the kind of intimate setting and thoughtful details that elevate a quick trip into something memorable.

Finding a place that feels authentic and tailored to your personality can make all the difference, especially for couples. Weekend getaways from Chicago for couples are about more than a change of scenery; they’re about shared moments, quiet conversations, and exploring something new together. A historic Bed and Breakfast filled with curated antiques, a cabin tucked in the woods with a roaring fireplace, or a cozy lakeside retreat with gourmet breakfasts—all offer a sense of place you simply won’t find at a chain hotel. That’s the beauty of boutique stays: they reflect the passion and style of their owners, offering you not just a room, but an experience crafted with intention.

The Midwest Association of Independent Inns features Bed and Breakfasts that represent some of the best weekend getaways from Chicago, offering an impressive range of options across Wisconsin, Minnesota, Iowa, and Illinois. From wine country escapes to historic small towns and nature-focused cabin trips near Chicago, there’s a diverse mix of destinations ready to welcome you with genuine hospitality. Book your stay today!

These are The Best Weekend Getaways From Chicago 1
Find By
State
These are The Best Weekend Getaways From Chicago 2
Find By
City
These are The Best Weekend Getaways From Chicago 3
Find By
Amenities
These are The Best Weekend Getaways From Chicago 4
View
Alphabeticaly
These are The Best Weekend Getaways From Chicago 5
Search By
Availability
Historic buildings in downtown Galena, one of the best weekend getaways from Chicago

The Best Cities & Towns for Weekend Getaways From Chicago

When it comes to planning the best weekend getaways from Chicago, the Midwest is packed with charming towns and scenic cities that feel worlds away from the fast, noisy pace of the city. The best part about these weekend getaways from Chicago? You don’t have to mess with the hassle of air travel – they are within an easy drive of the Windy City.

The key to finding the perfect couples getaway near Chicago is finding something that matches your style. We put all the best Bed and Breakfasts and Boutique Inns of the Midwest at your fingertips to make finding your match easier than ever. From lakefront escapes and historic villages to vibrant arts communities and countryside retreats, these weekend getaways from Chicago for couples are designed to offer something a little more meaningful. 

Each of these cities is three to four hours from Chicago and offers a unique opportunity to enjoy unique and memorable romantic weekend getaways near Chicago.

Galena, Illinois

Galena, Illinois, is the second most popular destination in Illinois, outside of Chicago. It makes sense, then, that Galena is also at the top of the list of fabulous weekend getaways from Chicago. The town is packed with historic attractions, unique shopping, wine tastings and tours, plenty of opportunities to stretch your legs on nature trails, and stunning natural beauty you won’t find in Chicago. It’s a go-to destination for weekend trips from Chicago for a reason!

Madison, Wisconsin

You may want to avoid cities altogether on your weekend trips from Chicago, but if you don’t mind a different urban experience, one of the best cities to explore is Madison, Wisconsin. Madison is an innovative, vibrant city with beautiful lakefront paths for walking and biking, a restaurant scene that rivals Chicago, fantastic local breweries, and a surprisingly romantic vibe. It’s great for couples who want energy and style mixed into their couples getaways. 

Cedarburg, Wisconsin

If historic charm is at the top of your list of what you want from your Chicago getaways, head to the quaint town of Cedarburg, Wisconsin. This picture-perfect town just north of Milwaukee is one of the best weekend getaways from Chicago for couples who love history, boutique shopping, and wine tastings. The town has a thriving local arts scene and seasonal festivals for a getaway that simply won’t disappoint. 

Spring Green, Wisconsin

For an architecture-laden weekend getaway from Chicago, don’t miss southern Wisconsin’s Spring Green. This town is home to Frank Lloyd Wright’s Taliesin and the quirky House on the Rock, making it a standout among places to visit near Chicago. It’s also situated on the stunning Lower Wisconsin River, a scenic and unforgettable destination for paddling and outdoor adventure. 

Lanesboro, Minnesota

At around four hours away, Lanesboro is one of the most charming weekend getaways from Minnesota. This Norwegian town is in the heart of Minnesota’s Amish Country, and is known as the Bed and Breakfast capital of Minnesota. It’s home to the popular Root River State Trail, and it’s a welcome retreat for couples looking to enjoy downtime together. 

Mineral Point, Wisconsin

One of the most under-the-radar places to visit near Chicago is Mineral Point, Wisconsin. This charming town is a historic artist colony with stone cottages, working studios, and charming cafés. Its creative atmosphere and walkable downtown make it an inspiring weekend getaway from Chicago for couples who enjoy art, architecture, and something that feels entirely different than the city they left behind. 

Decorah, Iowa

Just beyond the four-hour range from some city dwellers, but absolutely worth the drive, is the charming town of Decorah, Iowa. Decorah is a scenic river town with deep Norwegian roots. With biking trails, waterfalls, and one of the most charming downtowns in Iowa, it’s a hidden gem for weekend getaways from Chicago.

Baraboo, Wisconsin

Finally, don’t miss the quirky but charming (not to mention breathtakingly beautiful) town of Baraboo, Wisconsin. From diving into a bit of unusual Midwest History in this historic circus town – once the home of the famed Ringling Brothers – to exploring the stunning Devil’s Lake State Park, there are plenty of great reasons to make Baraboo your getaway destination. 

These are The Best Weekend Getaways From Chicago 1
Find By
State
These are The Best Weekend Getaways From Chicago 2
Find By
City
These are The Best Weekend Getaways From Chicago 3
Find By
Amenities
These are The Best Weekend Getaways From Chicago 4
View
Alphabeticaly
These are The Best Weekend Getaways From Chicago 5
Search By
Availability
Couple packed up and leaving town for the best weekend getaways from Chicago

Where to Stay for Your Weekend Trips From Chicago

These destinations are all within easy driving distance of Chicago and offer a refreshing change of pace. Whether you’re in the mood for quaint charm, cultural discovery, or laid-back luxury, these weekend getaways from Chicago deliver. Once you know where you want to go, it’s time to find a place to stay. 

The Midwest Association of Independent Inns (MWInns) offers a curated selection of Bed and Breakfasts, Inns, and Boutique Hotels that stand out for their authenticity and personalized service. Unlike generic hotel chains, these establishments provide a unique charm, reflecting their locations’ local culture and history. Whether you’re interested in exploring historic places to visit near Chicago or looking for cabin trips near the city, these inns provide various options to suit your preferences.

The attention to detail, from gourmet breakfasts to personalized recommendations for local attractions, sets these inns apart as ideal choices for weekend trips from Chicago.​ Not only do we guarantee a high-quality place to stay, but choosing one of our Independent Inns also supports local businesses dedicated to preserving the unique character of the Midwest. Our commitment to excellence is evident in the rigorous standards each member inn must meet, including cleanliness, safety, and exceptional service.

We’re the only trustworthy resource focusing on unique stays in the Midwest. Find what you’re looking for in your next getaway, and book your stay today!

Lodging Properties near topics in our blog

Loading...

Brisbane House

  • 7050 Reimann Road
    Arena, Wisconsin 53503
  • 608-576-6696
  • Email Us
Celebrate friends, family, and your story. Beautifully restored for you to fully experience. A rare treat, the charming Brisbane House is on the State and National Registers of Historic Places.
More Details

Cloran Mansion Bed & Breakfast

  • 1237 Franklin Street
    Galena, Illinois 61036
  • 815-777-0583
  • Email Us
Guests to the Cloran will find modern comfort surrounded by historic charm. Treat yourself to 21st-century amenities certain to pamper while taking in the beauty of 1800s Italianate architecture!
More Details

Cameo Rose Victorian Country Inn

  • 1090 Severson Road
    Belleville, Wisconsin 53508
  • 608-424-6340
  • Email Us
Enjoy 120 peaceful acres of forests, mowed trails and gardens. Midway between Madison and New Glarus. Near bike trails, breweries, wineries, great shopping and dining. Memorable 4-Course Breakfast.
More Details

The Buckingham Inn

  • 1615 Summit Avenue
    Madison, Wisconsin 53726
  • 608-819-8029
  • Email Us
Dedicated to service and style near the UW-Madison campus, The Buckingham Inn features luxury guest suites and seasonal fresh breakfasts. Experience award-winning lodging in an award-winning city.
More Details

Lamberson Guest House

  • 113 South Prospect Street
    Galena, Illinois 61036
  • 779-214-0889
  • Email Us
Located in Galena’s scenic Historic District and overlooking the heart of Downtown Galena, our beautiful, traditional-style bed and breakfast is the perfect place for a relaxing getaway.
More Details

Valley Springs Farm Bed & Breakfast

  • E4681 County Road S
    Reedsburg, Wisconsin 53959
  • 608-495-1096
  • Email Us
Valley Springs Farm Bed and Breakfast is located in rural Reedsburg, just minutes from the 400 Bike Trail, Award Winning Cheese Factories, Amish Artisans and the Wisconsin Dells.
More Details

Century Elms Bed and Breakfast

  • 2200 West Memorial Drive
    Janesville, Wisconsin 53548
  • 608-449-5640
  • Email Us
Century Elms, a Bed and Breakfast Inn in Janesville Wisconsin, lovingly restored by Rich and Chris Gallegos, and is a grand old home on the National Historic Registry.
More Details

Inn at Wawanissee Point

  • E13609 Tower Road
    Baraboo, Wisconsin 53913
  • 608-355-9899
  • Email Us
Modern, adult-only Boutique Inn perched atop a pristine 42-acre wooded estate in the Baraboo Hills with a mesmerizing southern vista. Luxurious accommodations offering a peaceful romantic getaway.
More Details

Silver Star Bed and Breakfast Inn

  • 3852 Limmex Hill Road
    Spring Green, Wisconsin 53588
  • 608-935-7297
  • Email Us
Near Spring Green, we are a secluded 10 room log inn on 70 rural acres in the Driftless area of Wisconsin. We provide personal B&B service, with hotel quality beds, hearty breakfasts & fresh cookies.
More Details

The Speckled Hen Inn

  • 5525 Portage Road
    Madison, Wisconsin 53704
  • 608-244-9368
  • Email Us
The Speckled Hen Inn is a farm-stay B&B and features uniquely different Guest Rooms, offering private baths with whirlpool jetted tubs and fireplaces. Close to everything yet feels miles away!
More Details

Lake Ripley Lodge

  • N4376 Friedel Avenue
    Cambridge, Wisconsin 53523
  • 608-217-5075
  • Email Us
Escape to tranquility on the porch swing at our Historic Inn by the glistening lake. Enjoy sunset romance, kayaks, canoes, paddleboards, biking, hiking, & exploring Cambridge’s winery and distillery.
More Details

Hotel Galena

  • 324 Spring Street
    Galena, Illinois 61036
  • 815-777-0123
  • Email Us
Located in historic downtown Galena, Hotel Galena offers a fabulous experience at an exceptional price. Boasting a 5* Google rating, it’s perfect for couples, families, groups, or solo travelers.
More Details

Fargo Mansion Inn

  • 406 Mulberry Street
    Lake Mills, Wisconsin 53551
  • 920-648-3654
  • Email Us
We are 20 minutes from Madison, one hour from Milwaukee and 2 hours from Chicago. Come relax and Make Yourselves at Home!!
More Details

Sunniva Inn Bed and Breakfast

  • 120 North Grove Street
    Mount Horeb, Wisconsin 53572
  • 608-438-4892
  • Email Us
Charming Mount Horeb, B&B. Victorian elegance, cozy rooms, homemade breakfast. Near the Military Ridge Trail. Perfect for a serene southern WI retreat.
More Details

B&B on Broadway

  • 305 West Broadway Street
    Decorah, Iowa 52101
  • 563-382-1420
  • Email Us
Built by Norwegian immigrants in 1910, this home’s architecture provides ample space for gathering with family and friends and finding some quiet time.
More Details

Hotel Ruby Marie

  • 524 East Wilson Street
    Madison, Wisconsin 53703
  • 608-327-7829
  • Email Us
A renovated Victorian railroad inn in the heart of Madison, the Hotel Ruby Marie offers time-tested hospitality as well as convenient access to the modern life of Wisconsin’s capital city.
More Details

Hawk Valley Retreat & Cottages

  • 2752 West Cording Road
    Galena, Illinois 61036
  • 815-777-4100
  • Email Us
You are invited to relax, restore, and explore at our Galena Illinois Bed and Breakfast, a nature lover’s destination. We are located just 8 miles east of downtown Galena, IL.
More Details

Ringling House Bed & Breakfast

  • 201 8th Street
    Baraboo, Wisconsin 53913
  • 608-356-4229
  • Email Us
Historic Georgian Revival B&B with Edwardian decor and modern amenities, formerly owned by Charles & Henry Ringling of Circus fame.
More Details

The Three Elizabeths Guest House

  • 101 West Main Street
    Elizabeth, Illinois 61028
  • 815-990-8618
  • Email Us
Located 15 minutes East of Galena, accommodations include three Guest Rooms, classically styled, each with their own private bath. Reasonable rates and a welcoming front porch entice visitors.
More Details

Hidden Serenity B&B Getaway & Spa

  • 1876 Shalom Drive
    West Bend, Wisconsin 53090
  • 262-623-0148
  • Email Us
Indulge in our all-inclusive spa, complete with jetted tub, steam room and sauna set in a romantic ambiance enveloped by 40 acres of lush forest. Get a massage, play pickle ball or hike our trails.
More Details
Find By
State
Find By
City
Find By
Amenities
View
Alphabeticaly
Search By
Availability
Recent Posts
  • Visit Governor Dodge State Park This Summer June 10, 2025
  • The Best Things to do in Door County This Summer June 10, 2025
  • 10 Minnesota State Parks to Visit This Fall June 10, 2025
  • Find the Best Weekend Trips From Minneapolis May 27, 2025
  • These are The Best Weekend Getaways From Chicago May 20, 2025
PrevPreviousThe Best Things to do in Bayfield This Summer
NextFind the Best Weekend Trips From MinneapolisNext
  • Home
  • Places To Stay
  • About
  • Gift Certificates
  • B&B's For Sale
  • Innkeepers Corner
Facebook Instagram

The Best of the Midwest!

The Midwest Association of Independent Inns was formed to help the discerning traveler find the best Bed and Breakfasts, Inns and Boutique Hotels. Our member properties are located throughout the Midwest with plans to welcome properties from all 13 Midwest states.

Our group of independent lodging properties looks forward to welcoming you to the Midwest.

Get Our Newsletter

  • 715-942-8180
  • info@mwinns.com

Website Accessibility

Privacy Policy

Copyright 2025 Midwest Association of Independent Inns

Website & Digital Marketing by Logan Marketing