Get away from Chicago 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 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 within a few hours from Chicago, Illinois. We've included diverse options for couples and families.
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»Grand Geneva Resort - 1 hour 30 minutes from Chicago
Grand Geneva Resort is conveniently located between Chicago and Milwaukee, offering a getaway filled with romance and adventure. The property has newly renovated guest rooms and suites, a golf course, 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. Call ahead of time to purchase day passes which are based on availability and may be sold out on peak holiday weekends.
The Fitness Center offers classes such as cycling and yoga. Try your skills on the 35-foot climbing wall at the gym - if you've always wanted to try climbing, here is your chance. There is also a basketball court, indoor and outdoor tennis courts, an indoor lap pool and locker rooms with sauna and steam rooms. After the workout, visit the wellness center for a relaxing massage.
There are 36 holes of championship golf, featuring The Brute and The Highlands courses. The Brute offers one of the most challenging layouts in the Midwest. The Highlands is a Scottish style course. Other activities include lake cruises, tours of the historic downtown and shopping. Choose from three main restaurants serving a variety of dishes, including the Champagne Sunday Brunch. In the winter The Mountain Top offers downhill skiing, snowboarding and cross-country skiing. Weekend specials start at $80 per person.
7036 Grand Geneva Way, Lake Geneva, WI 53147, 262-248-8811 (website)
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»Hilton Chicago Indian Lakes - 30 Minutes from Chicago
Located 30 minutes from downtown Chicago, Hilton Chicago/Indian Lakes offers 225 acres of fun, including scenic golf, indoor and outdoor pools, and luxurious spa treatments. Many dining choices are available, whether you want a romantic dinner for two or a family restaurant. Nightly rates start at $129, including free internet access. The resort often offers special packages for families.
250 W Schick Rd, Bloomingdale, IL 60108 (website)
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»Grand Traverse Resort - 5 hours
Located on 1,400 acres on the shores of Lake Michigan, the 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 Jim McLean Golf School 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 three accommodation choices: condominiums, rooms in the hotel or the seventeen-story Tower with views of Lake Michigan. The 236 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 Tower Gallery of Shops. Guests can select from three restaurants, the Trillium Restaurant and Lounge located on the 16th and 17th floors of the Tower, the more casual Sweetwater Café, and the Grille at the resort's clubhouse. Summer is the best time to go because the warm weather enables guests to try out all of the resorts activities.
100 Grand Traverse Resort Village Blvd, Acme, MI 49610 (website)
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»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. Rooms start at $89 per night.
269 Fontana Blvd, Fontana-On-Geneva Lake, WI 53125 (website)
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»The Newport Resort - 4 hours 30 minutes
The Newport Resort is a family-friendly getaway in 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. Rooms start at $79 per night.
7888 Church St, Egg Harbor, WI 54209 (website)
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»The Knickerbocker on the Lake - 1 hour 30 minutes
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. Rooms start at $119 per night.
1028 E Juneau Ave, Milwaukee, WI 53202 (website)
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»Seven Oaks - 1 hour 30 minutes
Seven Oaks offers 9 adult-only luxuriously appointed cottage suites, perfect for a romantic getaway from Chicago. The one-floor buildings have charming front porches, stone fireplaces, comfortable living rooms, and king-sized beds with luxury linens. The garden has a soothing water feature, fire pit and comfortable lounging chairs. Just a short walk from downtown Lake Geneva, guests have easy access to a number of restaurants. Play a round of golf, visit a day spa, go biking, hiking or skiing in the winter. Rates start at $179 per night.
682 S. Wells Street, Lake Geneva, WI 53147, 262-248-4006 (website)
»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. Rates start at $135 per night.
15 Mill St., Elsah IL, 618-374-2821 (website)
»The American Club, Kohler - 2 hours 30 minutes
The American Club, Kohler is a luxury resort with 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.
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»Washington House Inn - 2 hours
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.
Try the Deluxe Package with rates from $250. The package includes: Overnight lodging in any room, Evening social hour in our Gathering room, featuring local wines and cheeses, $100 Spa service certificate at one of the local spas; and Deluxe continental breakfast in the Gathering Room or room service to your room (website).
W62 N573 Washington Ave, Cedarburg, WI 53012, 262-375-3550 (website)
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»The Mansion Bed And Breakfast - 50 minutes
This bed and breakfast is located 35 miles to the west of Chicago and gives you the chance to relax on a private estate built in 1907 on your weekend trip. You will find breathtaking stained glass windows, original lighting, and exquisite woodwork throughout the rooms and common areas. Every room has wireless internet, a cable TV with a VCR, premium pillow top mattresses, Egyptian cotton sheets, an iron with ironing board, a hair dryer, and a desk. There are extended stay options available. Some rooms also have two-person Jacuzzis, private baths, private terraces, and electric fireplaces for added romance.
Guests have access to the extensive video library, board games, and magazines. There are snacks and tea available during the day. A spa, numerous restaurants, and bike trails are just a few minutes away, many of which are within walking distance. Rates start at $139 per night.
305 Oregon Ave., West Dundee, IL, 847-426-7777 (website)
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»Sweet Haven Resort - 1 hour 20 minutes from Chicago
Sweet Haven 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.
9517 Union Pier Rd, Union Pier, MI 49129 (website)
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»Hawk Valley Retreat & Cottages - 2 hours and 45 minutes
This bed and breakfast 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. Rooms start at $90 per night, cottages from $195.
2752 W. Cording Rd., Galena IL, 888-777-6016 (website)
»Bishops Hall - 15 minutes
Bishops Hall was built in 1916 and features Georgian revival style architecture and sits in historic Oak Park. All rooms are decorated in the Georgian style. There are three guest rooms to choose from, each of which is unique and features a private bath and queen-sized four-poster bed. Amenities vary by room but some have balconies, separate dressing rooms, marble baths, fireplaces, multiple seating areas, claw foot tubs, steam rooms, and European hand showers. Every room has toiletries, hair dryers, and robes along with chocolates and fresh flowers.
Guests can enjoy the garden and terrace. The morning begins with a full breakfast available in one of several rooms, giving guests the option of being social or enjoying a private meal. You can eat breakfast on the balcony or terrace in nice weather. Rooms start at $175 per night.
605 Iowa St., Oak Park IL, 708-383-7774 (website)
»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. Rates start at $110 per night.
701 East Taylor St., Bloomington IL, 309-828-8816 (website)
»Galena Log Cabin Getaway - 2 hours and 45 minutes
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. Rates start at $189 per night.
9401 W. Hart John Rd., Galena IL, 815-777-4200 (website)
»Mission Oak Inn - 2 hours
The Mission Oak Inn is home to a seven-acre lake that is perfect for watching migrating birds or going fishing. The suites have warm fires in the fire places when you arrive and there is a whirlpool that fits two people. Suite amenities vary by room, but can include two-sided fireplaces, custom-built tables and beds, satellite TVs, DVD players, CD players, wireless internet, reclining loveseats, porches, fridges, and microwaves.
There are hiking trails throughout the 120 acres of property. While walking along, you will notice wild turkeys, coyotes, foxes, and deer. You can even borrow the inn’s canoe to explore the lake. The day starts off with a gourmet breakfast right in the dining room and you can enjoy dinner in the on-site restaurant. There are add-on packages available, such as in-room massages. Rates start at $175.
1108 County Rd., 930E, Henry IL, 309-370-4083 (website)
»The Steamboat House - 2 hours and 45 minutes
This historic bed and breakfast is a short block away from Main Street for easy access to shops, restaurants, wineries, and more.
There are five guestrooms with private baths, fireplaces, fine linens, LCD televisions, and DVD players. Room decorations vary with some featuring four-poster beds, original hardwood floors, sleigh beds, and private porches. Guests can enjoy the billiard room, library with games, books, and movies, wraparound front porch, screened garden gazebo, or cozy parlor.
There is wine every evening with hot beverages at night. In the morning, cocoa, tea, and coffee are delivered outside your door and a three-course breakfast is included. Guests can also add various packages that include in-room massages, birthday cake, wine, flowers, chocolate, and/or visits to local wineries. Rooms start at $110 per night.
605 S. Prospect St., Galena IL, 800-717-2317 (website)
»Market Street Inn - 3 hours
The Market Street Inn is inside a historic Queen Anne Victorian building built in 1892. The ten guestrooms are inviting and filled with modern amenities. Rooms and common areas have antiques, Oriental rugs, pocket doors, and beveled glass windows.
To get to the eight guestrooms, climb the grand oak staircase. The rooms have private baths, double-whirlpool tubs, complimentary Wi-Fi, cable TV, and air conditioning. The two guest rooms in the Carriage House include a deluxe suite and an ADA-approved one with a kitchenette. Each room in the Main Inn has a fireplace.
Guests have access to the Victorian wraparound porch, perfect for looking at the gardens. There are six original fireplaces throughout the inn. There is a social hour in the evening with fruit, cheese, and beverages and in the morning, guests can enjoy a candlelight breakfast. There is also complimentary soda and bottled water. Rates start at $150 per night.
220 E. Market St., Taylorville IL, 217-824-7220 (website)
»TimberCreek Bed & Breakfast - 1 hour 45 minutes
This is an upscale bed and breakfast in a building that was built specifically to appear like a barn. It is on a 25-acre property with a gate at the end of a picturesque winding lane surrounded by a stream and trees. The English Cottage décor spans the common areas and guest rooms with tile, brick, and hardwood floors, fireplaces, skylights, upscale furnishings, over-sized beds, artwork, and a Jacuzzi. Each guest room has its own bath and there is Wi-Fi throughout. A suite is handicapped accessible.
Guests can request access to hair dryers, irons, and laundry facilities. The Gathering Room is relaxing with floral couches, leather recliners, a stone fireplace, games, and magazines. The Breakfast Room hosts the morning breakfast and the Kitchen has tea and coffee. Rates start at $99 per night.
1559 E. State Route 9, Paxton IL, 217-379-2589 (website)
»The Inn at Irish Hollow and Country English Cottages - 2 hours 45 minutes
The Inn at Irish Hollow is a beautiful bed and breakfast perfect for a romantic getaway that sits on a 500-acre farm. Guests can choose to stay in one of the five private cottages or one of the guest rooms in the Main Inn. These cozy, intimate rooms have iron or claw foot bathtubs, enhanced showers, a sitting area, gas fireplaces, and modern amenities. The cottages vary, but may have king four-poster beds, oriental rugs, private porches, double whirlpool baths, iPod docks, Wi-Fi, and more.
You can also have body work done at the inn. Breakfast is included with your stay and it is hand-made using natural ingredients. You can choose a continental breakfast delivered to your room, the Full Country Gourmet Breakfast in the Old General Store, or a healthy version of this full breakfast. Guests can also order additional meals, including picnics, wine and cheese. Dinner packages start at $345 per night.
2800 S. Irish Hollow Rd., Galena IL, 815-777-6000 (website)
»Farmers Guest House - 2 hours 45 minutes
The 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. Rooms start at $179 per night.
344 Spring St., Galena IL, 815-777-3456 (website)
»Sidwell Friends Bed and Breakfast - 3 hours 45 minutes
This three-room bed and breakfast provides an intimate setting for couples or very small groups to escape. Guests say they enjoy a similar experience to that of a boutique hotel, but nestled among towering trees and stately homes. Every room has a private bath, luxury bed linens, memory foam mattresses, HDTVs with DVD players, complimentary Wi-Fi, a CD player and radio with alarm clock, hair dryers, irons with ironing boards, premium toiletries, towel racks and heated floors in the bathroom, turndown service, and guest robes.
Guests have access to an extensive DVD collection, the library/sunroom, the deck, and the garden patio. The bed and breakfast is just a few blocks from Cedarhurst Center for the Arts with its exhibits and sculptures or you can go to Rend Lake for golfing, hiking, boating, and water skiing. There is a full cooked breakfast every morning. Rates start at $129 per night.
1812 Richview Rd., Mt. Vernon IL, 618-691-8742 (website)
»Mansion Hill Inn - 2 hours 30 minutes
Located in downtown Madison, Wisconsin, 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, mansionhillinn.com
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»Dunes Walk Inn - 1 hour from Chicago
Dunes Walk Inn is a charming restored 1881 mansion on the Lake Michigan coastline, featuring hardwood floors and vertical mullion windows. Explore Indiana Dunes (about 50 miles from Chicago) and stay at this family friendly inn which sleeps 19 guests. Rates start at $125 per night.
DunesWalk Inn at the Furness Mansion, 1491 N Furnleigh Ln, Chesterton, IN 46304, 219-728-6393, duneswalkinn.com
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More Quick Weekend Trips from Chicago
A popular tourist destination year-round, Lake Geneva offers fun weekend activities which range from swimming to stargazing. The beautiful glacier lake features amazing sunsets, perfect for couples planning a romantic celebration.
Lake Geneva Cruise Line offers a unique perspective from the water and includes a historic tour of the area. You can also go on a romantic sunset cruise or a jazz dinner cruise. If you prefer to explore on your own, rent a kayak from Fontana Paddle Company.
Saugatuck is famous for its galleries, restaurants and a slower pace of life. Saugatuck Center for the Arts supports established and emerging artists with unique art exhibits and music events.
Accommodation options in Saugatuck include hotels, resorts, vacation rentals and charming inns. Check into the BaySide Inn which offers romantic rooms with views of the Saugatuck Harbor.
Milwaukee is an easy day trip from Chicago - take the Amtrak train which is more relaxing than driving and you won't have to worry about parking when you get there. The train ride takes an hour and a half. If you decide to spend the night, there are several reasonably priced accommodations in town.
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About three hours from Chicago, Galena features historic mansions, wineries and several great spas. Activities in the area include an alpine slide, Mississippi cruises, Segway tours, mini golf and biking. In the winter, there is skiing, snowboarding and kids’ programs.
Indianapolis is famous for its sports events, White River State Park, museums and an open-air music venue. Downtown has more than 25 hotels, offering accommodations options that range from affordable to upscale. Regardless of your taste in food, you will be able to find something that fits your palate at over 300 restaurants.
|From Chicago, IL To||Driving Time|
|Lake Geneva, WI||1 hour and 30 minutes|
|Galena, IL||2 hours 45 minutes|
|Kohler, WI||2 hours and 20 minutes|
|Chesterton, Indiana||1 hour|
|Madison, WI||2 hours and 30 minutes|
|Cedarburg, WI||2 hours|
|Acme, MI||5 hours|
|Bloomingdale, IL||40 minutes|
|Preemption, IL||2 hours and 45 minutes|
|Rockton, IL||1 hour 35 minutes|
|Oak Park, IL||15 min|
|Springfield, IL||3 hours|
|Henry, IL||2 hours|
|Mt. Vernon, IL||4 hours|
|Henry, IL||2 hours|
|Taylorville, IL||3 hours|
|Paxton, IL||1 hour 45 minutes|
|West Dundee, IL||50 minutes|