11 Best Romantic Getaways In Chicago, Illinois - Updated 2024

1. Indiana Dunes (from USD 84)

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Embark on a journey to the extraordinary Indiana Dunes, a land of captivating history and awe-inspiring beauty. Explore the renowned Indiana Dunes National Park, where towering glacial dunes and pristine shores invite you to hike, bird watch, and camp in a picturesque setting. Engage in thrilling outdoor adventures, from basking on Lake Michigan’s sandy beaches to traversing scenic trails and conquering majestic dunes.

After a day out exploring the dunes, relax at the Best Western Indian Oak where you can indulge in the relaxation of amenities like a sauna, steam room, and indoor pool. The friendly staff and the hotel’s proximity to Indiana Dunes National Park make it an excellent choice.

2. Lake Geneva (from USD 234)

If you want to embark on a getaway for couples in Chicago, consider Lake Geneva. A resort city by the Geneva Lake, just southeast of Chicago, about 77 miles (124 km) and a 90-minute drive away. The lakeside Shore Path is dotted with many beautiful lakehouses, which act as the perfect backdrop for a romantic walk by the lake at sunset. There are many activities to do, such as swimming, hiking and kayaking in the summer, and skiing and snowboarding the winter. A great place to stay with a lake view is the Grand Geneva Resort and Spa. This beautiful four-star resort has two championship golf courses, a luxury spa and wellness centre, and a waterpark. The beautiful and elegant rooms all have a private balcony with panoramic views.

3. Union Pier (from USD 195)

Union Pier is situated along the shore of Lake Michigan, 73 miles (117 km), and is perfect for a weekend trip from Chicago. There are many things to do here, such as wine tasting at the St. Julian Winery, or visit the Antique Mall of Union Pier. You can also rent bikes to cycle along the lakeside, and also paddle board to paddle in the lake during summer. One lovely and quaint place to stay at Union Pier is The Inn at Union Pier. It is the perfect place, just three minutes away from the sandy lakeside shores. This bed-and-breakfast has beautiful and quaintly furbished rooms, each with a fireplace and a porch or balcony. There is also a hot tub and a sauna for you to enjoy and relax.

4. Milwaukee (from USD 179)

Looking for inexpensive romantic getaways near Chicago? Milwaukee is another city located along Lake Michigan, which is renowned for its many unique neighbourhoods which contribute to the one-of-a-kind culture of the city. It is also known for the number of breweries located in the city. Some of the other tourist attractions you can visit include the Harley-Davidson Museum, the Historic Third Ward and Lake Park. A great place to stay at is the uniquely named Knickerbocker on the Lake, which is located just four minutes from the lakeside, great for romantic walks on the beach. They also have an onsite spa and a restaurant with outdoor seating on the patio which overlooks the lake. Located just 600 m (1969 feet) from the Milwaukee Art Museum, this wonderful city provides one of the best weekend getaways.

5. Galena (from USD 84)

Galena is a small town on the other side of the state, right by the Mississippi River, and is perfect for a romantic weekend getaway from Chicago. It is 170 miles (274 km) and about a 3-hour drive from Chicago. It is most well-known for its well-preserved 19th-century buildings like the 1826 Dowling House. There are a few museums, one of which is the Galena History Museum, perfect for history buffs. You and your significant other can also head down to the Casper Bluff Land & Water Reserve for a hike to take in the breathtaking scenery. WorldMark Galena is a great resort to stay at, with great amenities and facilities for use, such as a heated indoor pool and hot tub, a game room, sauna, and outdoor barbecue pits.

6. Kohler (from USD 210)

Kohler is a village in Wisconsin, along the Sheboygan River, 150 miles (241 km) from Chicago and a 2.5-hour drive. It is a beautiful quaint town, where you can take a trip down to the Whistling Straits Golf Course for a game, visit the Bookworm Gardens, or have some wine at the Blind Horse Winery. One great place, just two minutes away for the town centre, is The Rochester Inn in Johnsonville. It is a beautiful place to stay at during your romantic getaway, with clean facilities and amenities. This charming inn also serves an exceptional breakfast, a must0have before heading out on the rest of your day.

7. Acme (from USD 189)

Acme is the furthest from Chicago, a 5-hour drive and 320 miles (515 km). This town is located right by the East Arm Grand Traverse Bay and offers many lakeside activities, such as swimming, fishing, as well as golfing at the nearby Grand Traverse Resort Golf Courses. The Grand Traverse Resort and Spa is a beautiful and luxurious resort to stay at, you’re bound to have a fun and romantic time with your partner. The resort boasts many facilities, such as three golf courses, on-site dining, a luxurious spa, tennis courts, a swimming pool, and a fitness centre. You can enjoy your time with your partner relaxing, without even leaving the resort.

8. Elkhart Lake (from USD 245)

Elkhart Lake is a small village in Wisconsin, just 150 miles (241 km) and a 2.5-hour drive from Chicago. There are so many fun activities to do at this beautiful lakeside and resort village destination, no matter if it’s in summer or winter. There are spas, historic attractions, and shops and galleries to visit. You can also go swimming, boating, fishing, and kayaking in the beautiful glistening blue-green waters of Lake Elkhart. A good place to stay is the Osthoff Resort. It has a great beachfront location, with an onsite spa and private beach area. Each room also has a balcony facing either the beautiful sights of the lake or the lush gardens.

9. Bloomingdale

Bloomingdale is a small village just 27 miles (43.4 km) from Chicago, a 30-minute drive. Despite being a small quaint place, there are still many activities here to do, such as golfing at the Bloomingdale Golf Club, having fun at the Oasis Water Park, visiting the Bloomingdale Park District Museum, shopping at the Stratford Square Mall, and so much more! It’s a great place for a quiet and peaceful getaway that isn’t too far from the city.

10. Mount Morris (from USD 214)

Mount Morris is a small city in Michigan, 280 miles (451 km) and about 4.5 hours away by car. It is just 10 minutes away from the CS Mott Lake and the Crossroads Village & Huckleberry Railroad. There are many activities to do around there such as fishing in the lake, or visiting the lakeside village, which has historic buildings and a working train. White Pines Resort is an excellent choice to stay at while in Mount Morris. It is located in the White Pines Forest, and the cabins are beautifully furnished as well as clean and well-kept. The resort also offers a restaurant.

11. Dearborn (from USD 170)

Dearborn is a city in Michigan, 277 miles (446 km) from Chicago. It is a four-and-a-half hour drive, or you can also take an hour-long connecting flight to the city of Detroit. Dearborn is a beautiful historical city, which is also home to the largest Muslim population in the US. There are many museums to visit, as well as some parks with great picnic sites, swimming pools and tennis courts. A great place to stay in Dearborn would be The Dearborn Inn, A Marriott Hotel, located just behind the Henry Ford Museum. The beautiful Colonial-style hotel has many amenities, such as traditionally furnished rooms, a heated outdoor pool, a fitness centre and two great restaurants.

Romantic getaway

No matter which resorts or small town you decide to travel to with your significant other, all of them are sure to provide some much-needed relaxation and rejuvenation. So take your time visiting the best romantic places and attractions in Chicago. Just make sure to check out these romantic spots outside the city.

If you would like to explore more romantic getaways, you can also check out these lakefront hotels in Chicago.