Chicago Romantic Weekend Getaway Ideas

Image of a Romantic Trip Abroad

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Chicago is one of the all-time-great cities to live in but once in a while, even the city's biggest boosters require a romantic getaway.

Fortunately, Chicago is well-positioned for quick weekend escapes to a variety of places that offer both a change of pace and scenery.

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North of Chicago: Kohler, Wisconsin

lobby midwest historic
Susan Breslow Sardone.

The American Club ​​at Destination Kohler is two hours north of the city (140 miles) and the Midwest's top resort for couples. If warm and comfortable accommodations, a variety of fine dining options, four golf courses (two of which hold championship matches), and a standalone spa with an inviting couples room appeal, you can spend a happy weekend here or longer.

Although shopping in Chicago is exceptional, this place still has something the Windy City does not: The Kohler Design Center. Here you can furnish your dream house with the latest and greatest bathroom fixtures including sinks that are works of art and tubs big enough to fit a party.

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Northeast of Chicago: Michigan

Grand Hotel in Mackinac Island in Michigan
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Wind your way around Lake Michigan to the neighboring state that gave the waterway its name. Michigan makes good use of its shoreline. Here you can find several classic resort towns where couples go to relax, take in the scenery, and indulge in a variety of activities.

On Michigan's Lower Peninsula, Petoskey is located about 350 miles from Chicago. Scenic US 31 follows Michigan’s Gold Coast, delivering you to six-square-mile Petoskey. A four-season destination, Petoskey has lakefront beaches, a picturesque golf course, nearby ski slopes, a vibrant downtown, and sunsets made for lovers.

Another Great Lakes gem, car-free ​Mackinac ​Island (you'll leave yours at the ferry terminal in Mackinac City on the Lower Peninsula) has charmed couples for more than a century. While there are several places to stay on this island, the Grand Hotel has always been the place to see and be seen.

Further north than Petoskey, Mackinac Island has a shorter season and the hotel is only open May through October.

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North of Chicago: Milwaukee, Wisconsin

Milwaukee Skyline, photographed from the lakefront in Milwaukee, Wisconsin.
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Get your motor running, and head north of Chicago to Milwaukee, Wisconsin for a weekend of all-American fun.

Milwaukee, only a 92-mile drive from Chicago, has a major zoo, several museums and galleries, multiple mansions, gardens and parks, the ​Potawatomi Hotel and Casino, and world-renowned breweries.

Home to Harley-Davidson, Milwaukee is also a mecca for motorcyclists. The Harley-Davidson Museum hosts events ranging from gallery talks to country music concerts.

To experience a somewhat more sophisticated side of Milwaukee, consider a stay at the boutique Iron Horse Hotel. Even if you arrive for your weekend getaway by car, the hotel can arrange for you to rent a Harley-Davidson and take a motorcycle tour of Milwaukee.

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South of Chicago: Sybaris Suites


Sometimes all you need is a weekend alone with no disturbances. You're not looking to go sight-seeing or shopping, rock climbing or night clubbing. You're looking for a place where you can simply be together and make love.

The sexiest getaway in the Midwest, Sybaris Suites are couples-only hotels located south of Chicago in Northbrook, Frankfort, and Downers Grove in Illinois; ​Mequon, Wisconsin; and Indianapolis, Indiana. They boast that they are "devoted to luxury and sensuous pleasure." Some Sybaris suites feature a private heated indoor pool, while others contain a Jacuzzi tub big enough for two.

Be aware there are no restaurants, spas, or Wi-Fi at these hotels and kids are definitely not welcome. The "grounds" are as close as this to nearby highways. And Philippe Starck would fall into a dead faint if he saw the décor. Yet couples rave about Sybaris Hotel Pool Suites and they way they can rejuvenate a relationship.

Don't have enough time for a weekend getaway? Sybaris Suites offers an Afternoon Getaway rate, so you can have the room for a few hours.

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