6 Romantic Getaways for Chicago Couples

Nothing says “I love you” as much as spending time together. Plus, taking a break from chores and carpooling is a total bonus too. Plan a Midwest weekend getaway with your love. Enjoy some one-on-one time (like before the children came along). Even if you want to postpone traveling at the moment, remember these relaxing destinations that will slow you down enough to feel your hearts flutter.

Note: We’re updating our website as quickly as we can, but changes may occur due to COVID-19. Please double check before heading out for the most updated information on safety precautions, travel advisories and any last-minute closings. Stay safe!

Elkhart Lake, Wisconsin

Drive from Chicago: 2 hours and 25 minutes

The Osthoff Resort is a AAA Four Diamond resort located only a few hours away from Chicago. The lovely, all-suite hotel provides plenty of space to lounge around together so you can reconnect your orbit. Relax at the award-winning Aspira Spa featuring healing treatments and SpaSuite Experiences, which offer couples their own private environment to zen out together. Masks are required in public areas for both guests and associates.

Galena, Illinois

Drive from Chicago: 2 hours and 40 minutes

Galena is not that far from Chicago, yet it feels like going back in time. This quaint little town with a historic downtown is perfect for a cozy winter stroll peaking inside shop windows. Warm up with some bourbon, gin, vodka or rye at Blaum Bros. Distilling Co., a hip distillery with fun cocktails and tours.

Then, snuggle in for the night at the Goldmoor Inn. This bed and breakfast makes you feel like you’re in a romantic castle in the countryside with sweeping views of the Mississippi River. Enjoy a whirlpool suite with private fireplace and gourmet in-room breakfast.

St. Joseph, Michigan

Drive from Chicago: 1 hours and 35 minutes

Experience “Romance on the Boulevard” at The Boulevard Inn & Bistro in St. Joseph, Michigan. Located atop a bluff in downtown St. Joseph, the package includes overnight accommodations in a suite with a chilled bottle of champagne, fruit and cheese basket, Kilwins chocolates and a dozen long-stem red roses waiting for you. Masks are required in public areas.

The southwest Michigan retreat also offers easy driving access to many delightful wineries in the surrounding areas. Visit the adorable Lazy Ballerina Winery tasting room right on State Street in St. Joe. May the small batches of family-recipe wine tickle you as much as the skirted tutu chairs.

Kohler, Wisconsin

Drive from Chicago: 2 hours and 14 minutes

Stay at the historic American Club and enjoy the five-star, five-diamond service. Be greeted by smiling doormen tipping their top hats and savor a delicious dinner in an elegant setting at The Wisconsin Room. Chocolate lovers will be enamored with the artistic decadence of Kohler Chocolates.

Yoga on the Lake is a great way to stretch and get the stress out. Spin classes, tennis and snowshoeing are available too. You also simply can’t miss the Kohler Waters Spa. One of only 64 five-star spas in the world, this tranquil retreat is something both men and women truly enjoy. Their body treatments, facials and massages are the heavenly self-care you definitely deserve.

Southern Illinois

Drive from Chicago: 4 hours and 29 minutes

The Grafton Sky Tour aerial lift offers a wonderful way to take in the beauty of Southern Illinois. Stay warm in an enclosed gondola soaring 300 feet high up the bluff to Aerie’s Resort and feel your hearts connect just as the Mississippi and Illinois Rivers join below.

Stay in the charming small town of Alton, where you can indulge in a 24-hour all you can eat chocolate buffet at the Beall Mansion, an elegant B&B. If the weather is suitable for hiking, hold hands walking the trails of Pere Marquette State Park, the largest state park in Illinois.


You can also have a romantic staycation right at home! Hotel EMC2 is a boutique hotel close to the heart of Michigan Avenue that offers you and your boo a calming escape in the middle of downtown Chicago. The art and decor exemplify science and inspire creativity. The glass shower is simply stunning. You can’t help but be enamored with the two robotic butlers, Leo and Cleo, who delightfully deliver towels, water and other requests.

Soak the day away with your love in Aire Ancient Baths. This relaxing respite is a sanctuary for countless Chicago couples. Enjoy a romantic meal at Osteria Via Stato, where the warm ambiance is as lovely as the exemplary service. End your evening at the LondonHouse Chicago rooftop with the best years all-year-round.

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This article originally published on Jan. 29, 2020. It has been updated with the most recent information. 

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