Get away from Chicago, IL, for a weekend of swimming in indoor & outdoor pools, relaxing at a spa, skiing, a game of golf, boutique shopping and museums. Many nearby hotels, resorts and romantic inns offer affordable room rates and seasonal packages. Whether you are looking to relax on the beach, hike, bike, or go on a fun shopping trip, there is plenty to choose from. We've included diverse day trips and weekend getaways from Chicago, Illinois for couples and families. Scroll to see the full list with photos or jump to the table of contents.


Grand Geneva Resort - 1 hour 30 minutes from Chicago

Grand Geneva Resort - 1 hour 30 minutes from Chicago

Grand Geneva Resort and Spa is one of the best weekend getaways from Chicago for couples, conveniently located between Chicago and Milwaukee, offering a getaway filled with romance and adventure.

The property has golf courses, fitness center and a spa. If you are planning a family trip, Moose Mountain Falls Waterpark offers 50,000 square feet of heated watersides, tubing on the lazy river, hot tubs and lounge chairs.

Other activities include lake cruises, tours of the historic downtown and shopping. In the winter, The Mountain Top offers downhill skiing, snowboarding and cross-country skiing.

7036 Grand Geneva Way, Lake Geneva, WI 53147, Phone: 262-248-8811

Midwest Vacation Ideas: From Minneapolis, Ohio, MN, Iowa, From Detroit, Michigan


Grand Traverse Resort - 5 hours from Chicago

Grand Traverse Resort - 5 hours from Chicago

Located on 1,400 acres on the shores of Lake Michigan, Grand Traverse Resort and Spa is a popular spot for families. There are four 18 hole golf courses, including The Bear designed by Jack Nicklaus, The Wolverine by Gary Player, and Spruce Run by William Newcomb. For those who wish to improve their game, the Grand Traverse Golf Academy can help golfers of any level get even better.

There is a 100,000 square foot spa complex which features treatment space, workout facilities and a tennis center. Arrive early for your treatment to enjoy the sauna, two indoor swimming pools, four whirlpools and the relaxation room. Play tennis, work out and take a yoga class to improve your fitness.

The resort offers several accommodation choices: condominiums, rooms in the hotel or the seventeen-story Tower with views of Lake Michigan. The condos, located either on the fairways or the beachfront, all have a furnished dining area, kitchenette, a living room with a queen-size sofa sleeper, and a bedroom with a queen-size bed. The condos are great for families. Rooms in both the Tower and in the hotel have elevated views of the lake and are centrally located near the restaurant, the spa, and the shops. Guests can select from several restaurants. If you are looking for last minute weekend getaways from Chicago, be sure to ask about seasonal deals, specials and packages.

100 Grand Traverse Resort Village Blvd, Acme, MI 49610

More Vacation Inspiration: Nebraska, Midwest, From Columbus, Small Towns, Missouri


The Abbey Resort - 1 hour 40 minutes

The Abbey Resort - 1 hour 40 minutes

The Abbey Resort is a full service getaway on 90 scenic acres near the Fontana harbor, offering 334 deluxe guestrooms, 13 spacious suites and 13 villas. The 35,000-square-foot Avani Spa offers massages, facials, wraps, aromatherapy and saunas on your weekend trip.

Resort facilities include a fitness center, aerobic studio, indoor and outdoor swimming pools, a disk golf course, and a games arcade for kids. Dining options range from casual cafes to gourmet restaurants, including 240 West, Café Latte, the Waterfront Restaurant Bar & Grill, Bar West and Porto. Weekend activities include watersports, bike rides, golf, walking and jogging around the lake. If you are looking for affordable resorts near Chicago, The Abbey Resort is a great option.

269 Fontana Blvd, Fontana-On-Geneva Lake, WI 53125

More ideas for couples: Anniversary Vacations, From Kansas City, North Dakota, Colorado


Egg Harbor - The Newport Resort - 4 hours 30 minutes

Egg Harbor - The Newport Resort - 4 hours 30 minutes

The Newport Resort is a family friendly getaway in Egg Harbor, Wisconsin's Door County, just minutes from the beach. The resort has 59 rooms and suites with whirlpool tubs, cozy sitting areas and kitchenettes. There is an indoor swimming pool, fitness center, and game room. Guests can read in the library, unwind in the lobby lounge, and stroll through the garden. Located within walking distance of numerous eating establishments in

Egg Harbor, the Newport Resort is a great choice for family vacations and romantic retreats. Sandy beaches, world-class golf courses, and state parks offer plenty of outdoor entertainment during the summer, and cross-counting skiing, snowshoeing, and sledding in the winter.

7888 Church St, Egg Harbor, WI 54209

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The Knickerbocker on the Lake - 1 hour 30 minute

The Knickerbocker on the Lake - 1 hour 30 minute

The Knickerbocker on the Lake is a restored boutique hotel located in the heart of downtown Milwaukee. The property is within walking distance of a number of restaurants, museums, theaters, and transportation options. The 160 guest rooms and suites are decorated with period-influenced furniture and modern conveniences such as fully equipped kitchenettes and Wi-Fi. Some suites have views of the picturesque Lake Michigan shoreline.

The full service Knick Salon and Spa offes invigorating treatments, while the Juneau Room is a spacious area ideal for hosting special events. Guests can work out at the 24-hour fitness center, request custom tailoring and valet dry cleaning.

The Knick Restaurant offers upscale dining, with a menu that provides something to suit every gourmand. Weekend guests should not miss the bountiful Sunday brunche. If you are looking for cheap weekend getaways, this is a good choice. More info

1028 E Juneau Ave, Milwaukee, WI 53202

Browse Best Beaches Near Milwaukee


The Green Tree Inn - 4 hours 25 min

The Green Tree Inn - 4 hours 25 min

With its location in historic Elsah, the Green Tree Inn is surrounded by a choice of things to do. The surrounding valley is quiet and gorgeous, perfect for relaxation. There are five rooms in the inn, each with a unique relaxing atmosphere. They all have air conditioning and private baths, and most have a queen bed although one has two double beds instead. Most rooms have TVs as well.

There is a communal satellite TV, Wi-Fi throughout the property, an antique room, a fireplace, board games, a deck with beautiful views, and bikes to borrow. You can also have an in-room massage.

Guests have access to a fridge with water and soda as well as homemade afternoon snacks and coffee, cider, hot tea, and cocoa. A homemade breakfast is included, and you can also enjoy a homemade evening meal if you would like.

15 Mill St., Elsah IL, 618-374-2821


The American Club, Kohler - 2 hours 30 minutes

The American Club, Kohler  - 2 hours 30 minutes

The American Club, Kohler is one of the most famous resorts near Chicago, offering two accommodation options: The American Club and the more affordable Inn on Woodlake. About two and a half hours from Chicago, this beautiful resort offers great outdoor activities in the summer, and pools and spa relaxation in the winter.

Look for couples, family and golf packages, including golf academy especially for women, golf specials, and more. The Kohler Waters Spa is a destination for the senses, featuring a glass enclosed rooftop deck with a whirlpool, fireplace and lounge. Try the newly renovated couples suite for a relaxing side-by-side massage and other treatments. Yoga on the Lake is a premier yoga studio offering 20 classes a week. More ideas: Things to Do in Illinois

419 Highland Dr, Kohler, WI 53044, Phone: 800-344-2838

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Washington House Inn - 2 hours

Washington House Inn - 2 hours

The Washington House Inn in Cedarburg, Wisconsin, 110 miles north of Chicago, offers stylish accommodations, complimentary, afternoon complimentary wine and cheese social hour and free high speed internet access. Explore Cedarburg's Main Street with more than 70 boutiques, shops selling sweets, and restaurants.

The town has several museums: the General Store Museum, Kuhefuss House Museum and the new Wisconsin Museum of Quilts and Fiber Arts. More info

W62 N573 Washington Ave, Cedarburg, WI 53012, 262-375-3550

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Sweethaven Resort - 1 hour 20 minutes from Chicago

Sweethaven Resort - 1 hour 20 minutes from Chicago

Sweethaven Resort sits on 9 picturesque wooded acres near Lake Michigan beaches, in beautiful Union Pier Michigan.

The resort offers 5 spacious family-friendly cottages, each with screened porches, hot tubs, full bathrooms, and kitchens. Tastefully decorated, the cottages are pet friendly.

The property is perfect for taking long walks through the woods, or relaxing in the sun at a nearby beach.

Guests can take advantage of the fully equipped kitchens in the cottage, or head into town for a diverse selection of dining establishments.

Shopping opportunities abound, with outlet stores and charming boutiques offering something unique and interesting for all.

Explore art galleries, visit a museum, try water sports on Lake Michigan, play golf and get a massage at a nearby day spa. Keep reading for more weekend getaways near me.

9517 Union Pier Rd, Union Pier, MI 49129


Hawk Valley Retreat & Cottages - 2 hours and 45 minutes

Hawk Valley Retreat & Cottages - 2 hours and 45 minutes

Hawk Valley Retreat & Cottages is only eight miles from downtown Galena and has ten acres of secluded gardens and meadows to explore.

There are four private cottages and three rooms within the main house. The main house rooms have private entrances, private baths, satellite TVs with DVD players, and wireless internet.

All cottages have whirlpool tubs, Wi-Fi, air conditioning, TVs with DVD players, full baths, electric fireplaces, king-size beds, sitting areas, eating areas, kitchenettes, and private porches. One of them also has a separate bedroom.

The ten acres of land include a gazebo, a pond, walking trails, and porch swings. The main house has central air conditioning, a living room, a dining room, large picture windows, and a wrap-around deck.

Main house stays come with a complimentary breakfast, and guests have access to home baked cookies, tea, coffee, and water. Things to Do in Galena

2752 W. Cording Rd., Galena IL, 888-777-6016


Mansion Hill Inn for Couples - 2 hours 30 minutes

Mansion Hill Inn for Couples - 2 hours 30 minutes

Located in downtown Madison, Wisconsin, the Mansion Hill Inn is a historic getaway with luxurious guest rooms featuring Frette linens, high-definition flat screen televisions, rain fall showers, and Aveda bath products. If you are planning a romantic getaway, ask for one of the suites with whirlpool baths, in-room gas fireplaces, and access to balconies or verandas with a view. Take advantage of the Pre-Arrival Concierge to customize your stay at the Mansion Hill Inn.

424 N Pinckney St, Madison, WI 53703, 608-255-0172


Vrooman Mansion - 2 hours

Vrooman Mansion - 2 hours

The Vrooman Mansion is a historic bed and breakfast right in Bloomington/Normal. The historic estate offers luxury and privacy with easy access to attractions, restaurants, and shops. The majority of the decorations in the spacious guest rooms are antique period furniture, with each room featuring its own theme. The suites have down pillows, soft fluffy towels, high-quality linens, microfiber robes, and free Wi-Fi. There are five suites and rooms in the Mansion and two in the carriage house.

The numerous common areas include the Safe Room, the Library, the Foyer, the Music Room, the Dining Room, and the Parlor. Throughout the day, you can enjoy bottled water, soft drinks, and snacks and a full gourmet breakfast is included in every stay. Breakfast features tea, coffee, or cocoa, juice, fruit, and a hot entrée. More ideas: Beaches in Illinois

701 East Taylor St., Bloomington IL, 309-828-8816


Galena Log Cabin Getaway - 2 hours and 45 minutes

Galena Log Cabin Getaway - 2 hours and 45 minutes

© Galena Log Cabin Getaway

Galena Log Cabin Getaway covers 45 acres of secluded land as well as the Adventure Creek Alpaca and Labradoodle Farm. This working farm has 12 log cabins, each with one room and over 660 square feet plus an open loft. There is a modern bathroom featuring a six-foot double-whirlpool tub and large skylight. Cabins have a queen bed downstairs with a double bed in the loft, satellite TV, a fridge, a microwave, and a gas log fireplace. Other amenities include DVD players, central air and heat, and platform rockers. Four of the cabins are dog-friendly.

While at this inn, you can visit or enjoy the alpaca farm, and even take an alpaca for a walk. They also breed Goldendoodles, which guests can spend time with. Guests can hike 1.5 miles along the Adventure Creek or head to Casper Bluff or along the Mississippi River. There is very little light pollution in the area, which means gorgeous views of the stars on clear nights. More ideas: Places to Visit in Illinois

9401 W. Hart John Rd., Galena IL, 815-777-4200


Oakwood Resort, Syracuse, IN

Oakwood Resort, Syracuse, IN

© Dariusz Jarzabek/stock.adobe.com

The Oakwood Resort is scenically located on the shores of Lake Wawasee, where it beckons visitors to come and enjoy a well-deserved weekend getaway. The resort covers 27 acres and is semi-surrounded by water, offering water sport enthusiasts a brilliant selection of water sports to enjoy on-site; these include kayaking, paddle-boarding and boating. The resort offers 79 guestrooms and suites, many of which offer excellent views out over the lake. If you are travelling with the family or a group of friends you can consider renting one of the spacious 3, 4 and 5 bedroom vacation homes. On-site amenities include a swimming pier, restaurant/bar, bicycle rentals, and a fitness center.

Oakwood Resort, 702 E. Lake View Road, Syracuse, IN 46567, 574-457-7100


Farmers Guest House - 2 hours 45 minutes

Farmers Guest House - 2 hours 45 minutes

Farmers Guest House is located in historic downtown Galena, giving guests easy access to nearby attractions.

Each of the nine rooms and suites is tastefully decorated, providing an intimate setting perfect for couples. All rooms have flat-screen TVs with Blu-Ray/DVD players to watch movies from the inn’s collection and there is Wi-Fi throughout the property.

Other room amenities include private baths, luxurious bath amenities, individual outlets, irons, hairdryers, and plenty of outlets.

The common areas include the Spa Studio, private gardens, and numerous patios. In the morning, guests enjoy a full breakfast with a signature entrée, homemade pastries or bread, fruit, juice, and homemade granola.

There is also Wine time every evening with cheese and wine, as well as fresh cookies at night. Guests have access to soda, tea, coffee, and bottled water.

344 Spring St., Galena IL, 815-777-3456


Saugatuck

Saugatuck

© sstevens3/stock.adobe.com

Nestled on the shores of Lake Michigan, Saugatuck is renowned as a hub for artists, and also has a long list of activities to appeal to all ages, from relaxing in the sun on Oval Beach to getting active on the water.


Elkhart Lake

Elkhart Lake in Wisconsin is an ideal getaway destination for all nature lovers and water sport enthusiasts, boasting crystal clear lake water and an abundance of activities suitable for all ages. You can choose from a variety of accommodation options which vary from up-market resorts and vacation rentals to getting back to nature at the Broughton March Park campground, where you can pitch a tent or park your RV.

Door County

Door County in Wisconsin is situated on a peninsula which juts out into Lake Michigan and boasts over 300 miles of shoreline with beaches, bays and inlets waiting to be explored. Sun worshippers have an astounding 53 public beaches to choose from and if you would like to go boating there are 12 marinas where you can launch your own craft or charter one.

Weekend Getaways from Chicago: Lake Geneva

Lake Geneva is a resort town situated on the shores of Lake Geneva in southern Wisconsin, offering a great base for exploring the many lake-side activities.

Amish Country

If you would like to try something really different on your next weekend getaway try a visit to Indiana's Amish Country, where you can step back in time and find out all about the Amish way of life.

Milwaukee

The river-side city of Milwaukee is jam-packed with interesting, educational and fun activities to fill every moment of your weekend getaway.

Indianapolis

Indianapolis is famous as the home of the Indianapolis Motor Speedway, but aside from motor sports the city has many other historic and cultural activities to suit all tastes.

Galena

Time seems to have stood still in Galena, whose huge 581 acre historic district seems little changed in 200 years.

Springfield

Springfield is the capital of the state of Illinois and welcomes visitors to a wealth of historic, cultural and outdoor activities. The city is most famous as the home of President Abraham Lincoln and you will find historic sites linked to the Lincoln family around every corner.

Ann Arbor

Ann Arbor is an excellent weekend getaway destination, boasting great museums, vibrant culture and a great selection of outdoor activities.

Driving Distances from Chicago

From Chicago To     Driving Time
Lake Geneva, WI1 hour and 30 minutes
Galena, IL2 hours 45 minutes
Kohler, WI2 hours and 20 minutes
Chesterton, Indiana1 hour
Madison, WI2 hours and 30 minutes
Cedarburg, WI2 hours
Acme, MI5 hours
Bloomingdale, IL40 minutes
Preemption,2 hours and 45 minutes
Rockton1 hour 35 minutes
Oak Park, IL15 min
Springfield, IL3 hours
Henry2 hours
Mt. Vernon, IL4 hours
Taylorville3 hours
Paxton, IL1 hour 45 minutes
West Dundee, IL50 minutes

20 Best Weekend Getaways from Chicago :