10 Romantic Getaways From Chicago, Illinois - Updated 2023

romantic getaways in chicago illinois

Living in such a major city like Chicago, which is one of the largest cities in the United States, there is definitely a want to escape the hustle and bustle of stressful city life. This is especially true for couples, in need of a romantic getaway for honeymoons, anniversaries, or a short holiday. While there are plenty of romantic hotels and romantic staycations, there is still so much more to discover outside of Chicago. For those who don’t want to stray too far away from the city, or only have a short weekend to relax and rejuvenate, finding a romantic and relaxing getaway that is still near the city is key. What are you waiting for? Read on to find ten romantic getaways from Chicago and pick the perfect one of you and your significant other!

1. Lake Geneva (from USD 213)

Source: Photo by Wikimedia Commons user Yinan Chen used under PUBLIC DOMAIN

Lake Geneva is 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.

Grand Geneva Resort & Spa

Wifi Available

Address: 7036 Grand Geneva Wy
Accommodates: 8

Restaurant Room service Meeting/banquet facilities Bar 24-hour front desk Tennis court Sauna Fitness centre

2. Dearborn (from USD 170)

Saint Joseph's Retreat historical marker Dearborn Michigan
Source: Photo by Wikimedia Commons user Dwight Burdette used under CC BY 3.0

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.

The Dearborn Inn, A Marriott Hotel

Wifi Available

Address: 20301 Oakwood Boulevard
Accommodates: 5

Parking Restaurant Room service Meeting/banquet facilities Bar 24-hour front desk Fitness centre Terrace

3. Union Pier (from USD 195)

Grass Dune
Source: Photo by user jeffhutchison used under CC BY 2.0

Union Pier is situated along the shore of Lake Michigan, 73 miles (117 km) and a 1.5-hour drive 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.

The Inn at Union Pier

Wifi Available

Address: 9708 Berrien Street
Accommodates: 3

Meeting/banquet facilities Golf course (within 3 km) Garden Terrace Non-smoking rooms Fishing Skiing Games room

4. Milwaukee (from USD 154)

Milwaukee, WI
Source: Needpix

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.

Knickerbocker on the Lake

Wifi Available

Address: 1028 East Juneau Avenue, Yankee Hill, Milwaukee (WI), United States, 53202
Accommodates: 2

5. Galena (from USD 84)

Galena IL Galena Historic District Downtown
Source: Photo by Wikimedia Commons user IvoShandor used under CC BY-SA 3.0

Galena is a small town on the other side of the state, right by the Mississipi river. 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.

WorldMark Galena

Wifi Available

Address: 5129 West Longhollow Road
Accommodates: 4

Parking Fitness centre Terrace Business centre Laundry Family rooms Games room Free parking

6. Kohler (from USD 235)

Whistling Straits Golf Course, Kohler, Wisconsin
Source: Photo by user Dan Perry used under CC BY 2.0

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.

The Rochester Inn

Wifi Available

Address: 504 Water Street
Accommodates: 2

Parking Golf course (within 3 km) Garden Non-smoking rooms Breakfast in the room Free parking Internet services Hot tub/jacuzzi

7. Acme (from USD 115)

Grand Traverse Resort & Spa
Source: Pixabay

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.

Grand Traverse Resort and Spa

Wifi Available

Address: 100 Grand Traverse Village Boulevard
Accommodates: 4

Parking Restaurant Room service Meeting/banquet facilities Bar 24-hour front desk Tennis court Sauna

8. Elkhart Lake (from USD 240)

Elkhart Lake
Source: Photo by Flickr user Jim Bauer used under CC BY-ND 2.0

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.

Osthoff Resort

Wifi Available

Address: 101 Osthoff Avenue
Accommodates: 2

Parking Restaurant Room service Meeting/banquet facilities Bar 24-hour front desk Tennis court Sauna

9. Bloomingdale

Bloomingdale, IL, USA
Source: Photo by Wikimedia Commons user bogdanstepniak used under CC BY 3.0

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)

Huckleberry Railroad, Flint, Michigan
Source: Photo by Wikimedia Commons user Drew Jacksich used under CC BY-SA 2.0

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.

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.

Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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I'm Nicole, a current university student and lover of big cities as well as quaint hidden gems. For me, half the fun of travelling is getting to write about and share this new perspective with...Read more

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