Five Luxury Weekend Getaways from Chicago

Chicago is known as everything from the Windy City to The Heart of America or even Chi-Town. So many people feel such great affection for this lovely city that sits on the shore of Lake Michigan. However, living in or visiting our country’s best cities can leave us with the desire to get away for the weekend. What are the best weekend trips from Chicago? Here are our five favorite luxury weekend getaways from Chicago.

Seven Oaks


Seven Oaks Luxury Weekend Getaways from Chicago
Photo courtesy of Seven Oaks


After the short 90-minute drive from Chicago, you’ll feel like you’re much further away as you arrive at Seven Oaks. This area is an outstanding option for weekend getaways from Chicago. This boutique hotel features nine cottages for guests and looks like a snapshot of small-town America with its tree-lined drive, front porches, and perfectly adorable appeal. With suites named for the owners’ favorite places in England, the charm runs deeper than the appearance of the grounds. The hotel is adult-only which helps maintain its serenity. It’s also just a short walk from downtown Lake Geneva and a couple of miles from Big Foot Beach State Park. You’re also in close proximity to great hiking and biking as well as great golf and best of all, excellent spas!

The American Club


The American Club Luxury Weekend trips from Chicago
Photo courtesy of The American Club


A mere two-and-a-half hours out of Chicago is one of the most famous resorts in the region, The American Club. Once a dormitory for immigrant workers at the Kohler Corporation, the Tudor-style building was erected in 1918. The word best used to describe The American Club is elegant with suites named after historical figures. The hotel is also close to excellent golf and even better shopping and is next door to a great spa and fitness center. It’s also home to two restaurants serving upscale cuisine as well as a wine bar and a casual tavern. This makes for one of the best weekend trips from Chicago.

Vrooman Mansion


Vrooman Mansion Luxury Weekend Getaways from Chicago
Photo courtesy of Vrooman Mansion


Just two hours out of Chicago sits a remarkable and historic mansion that is a decadent bed and breakfast. The Vrooman Mansion believes “that you deserve to slow down and seek joy in your life. Everything we do, we do for you, for the community, and for the preservation of this home. Experience our tradition of high standards and warm, inviting, genuine hospitality. Take delight in having our knowledgeable staff here to pamper you. Enjoy our passion for cooking each morning as we tempt you with a beautifully prepared, mouthwatering breakfast. Seek joy in things big and small – in the subtle as well as the obvious.” Weekend trips from Chicago do not get much more decadent!

The Inn at Irish Hollow


The Inn at Irish Hollow Luxury Weekend Trips from Chicago
Photo courtesy of The Inn at Irish Hollow


After a drive that is less than three hours from Chicago, you’ll be amazed to find yourself in a location that feels completely secluded as this bed and breakfast sits on 500 acres of lush farmland. While the main building of The Inn at Irish Hollow has great rooms, we’d recommend booking one of the themed cottages. Our pick is the Station House. As they note, this cottage “features all of the best amenities and comforts of the finest hotels, and hospitality of the best bed and breakfasts.” Beyond enjoying the immense grounds, you can take advantage of hiking and biking and even hunting if you’re so inclined. If you visit in the winter, you may also find yourself skiing. Regardless of what time of year you visit, you should definitely explore Galena and the region and try to take in one of their local events. One of the best weekend getaways from Chicago? We think so!

The Steamboat House


The Steamboat House Luxury Weekend Getaways from Chicago
Photo courtesy of The Steamboat House


While we try not to send you to the same area twice in one list, we’re so enamored with the Galena area and its lodging options that we had to recommend The Steamboat House, too. This area is such a great option for weekend trips from Chicago! This property is less secluded than the last but is equally enjoyable. It’s enjoyable because of its proximity to Main Street allowing easy access to shops, restaurants, wineries, and more. It’s, of course, less than a three-hour drive from Chicago and is all about relaxing and enjoying yourself.


Enjoy modern luxury surrounded by history in a spotlessly clean, fresh atmosphere. This grand 7,000 square foot inn offers privacy in the form of five spacious and beautifully appointed guestrooms, cozy parlors, and a wraparound front porch and screened garden gazebo where you can tuck away to read or work. Social opportunities are also offered in the billiard room, library, formal parlor, and huge formal dining room.


Chicago is a city that is not only a great place to live or visit but also a great city from which to getaway. Which of our weekend getaways from Chicago will be first on your destination list? You might also enjoy these Four Luxury Weekend Getaway Ideas from New York. You really can’t go wrong when you plan one of these luxury weekend trips from Chicago!

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Five Luxury Weekend Getaways from Chicago