Escape from Chicago for an outdoor swimming holiday with indoor pools & outdoor pools, relaxation in the spas, skiing, golfing, boutiques and museums. Many hotel rooms in nearby towns offer affordable hotel prices and seasonal packages.
There are lots of options for relaxing at the beach. Our itinerary includes varying day trip trips and getaway getaways from Chicago, Illinois for couples and family travelers. Please phone the attraction/restaurant before your visit to get current opening times.
01. Grand Geneva Resort - 1 hour 30 minutes from Chicago
Grand Geneva Resort Grand Geneva Resort & Spa is among the best weekends in Chicago for couples located between Minneapolis and Illinois. It is also equipped with a golf course and spa.
Moose Mountain Falls Waterpark offers an outdoor heated pool and hot tub on the lazy river. There are also cruise-boat trips, tours of the historic city center, and retail activities. Winter skiing is available at Mountain Peak downhill, snowboarding or crosscountry skiing. 7036 Grand Geneva Way, Lake Geneva, Wisconsin 53149.
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02. Visit the Art Institute of Chicago
The Art Institutes of Chicago are world class museums containing thousands of paintings a year and many more. The collection covers thousands and features works in various media from painting to prints, photography, sculpture to architectural drawings and other.
The Institute has an extensive collection of impressionistic and postimpressionist paintings including the Georges Seurat 1884 Sunday evening on Grande Jatte, Renoir 1879 acrobats from Cirque Fernando, and several paintings by artists. The major building built by Shepley, Rutan and Coolidge was designed in beaux-arts style to celebrate the 1893 Columbian exhibition.
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03. Grand Traverse Resort - 5 hours
Grand Traverse Resort - Located on a total of 1400 acres on the shores of lake Michigan the Grand Traverse Resort is a favorite place for children. Four 18-hole golf courses can be found at the site such as The Bear designed by Jack Nicklaus, The Wolverines created by Gary Player and Spruce Run by William Newcomb.
Grand Traverse Golf Academy helps people improve their game. The resort has 100k sqm of spas and is equipped with a spa treatment centre, fitness facilities and tennis centre. Arrive early to receive your treatment for your sauna.
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04. Stroll around Navy Pier
In 1916 the Navy Pier was initially built to serve as an amusement park and is currently considered to be a favorite tourist attraction at Chicago. Today, the Navy Pier has around 60 acres of gardens.
There are 150 foot Ferris wheels and a historic carousel on the Pier Park waterfront. Visitors can also enjoy movies at the 3D Imax Theatre by watching actors perform classics for the Chicago Shakespeare Theater. There's also a Chicago children's museum. The waterfront hosts annual festivals such as Chicagos Festival on August 25th.
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05. Walk through Millennium Park
Millennium Park belongs to the bigger Grant Park, located downtown Chicago and is connected to Detroit Avenue in the west, Columbus Drive in the east Randolph Street to the north and Monroe Street in the south.
A 110 meter high statue named the Cloud Gate has polished, mirror-like stainless steel surfaces inspired by liquid mercury. This mirrors the surroundings including buildings and the skies, as well as tourist attractions.
One other major attraction within Millennium Park is the Crown Fountain, a fascinating modern interpretation of ruins and gargoyles giving the appearance of water escaping from projections of Chicagoans.
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06. The American Club, Kohler - 2 hours 30 minutes
The American Club, Kohler The American Club, Kohler, is a well-known resort located near Illinois offering two lodging types: American and the cheapest Inn on Woodlake. The beautiful resort offers great outdoor activities in summer and pools & spas in winter.
Find a couple, family or golf package that includes golf courses for women and golf courses specials. Kohlers Water Spa provides relaxation with glass enclosed rooftops with a pool, fireplace and lounge. Explore our new couples suite for relaxing side to side massages and other treatments.
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07. Weekend Getaways from Chicago: The Abbey Resort - 1 hour 40 minutes
A deluxe hotel on a pristine property close to Fontana Harbor offering 335 luxury rooms, 13 spacious suites and 13 villas. Avani Spa is a 3-day weekend spa offering massage, facial, wrap, Aromatherapy and sauna treatment.
Resort facilities include an exercise studio, a swimming pool, a disc golf course, and an arcade. The menu includes casual and gourmet restaurants like 240 West Café Latte Waterfront and Bar West Porto. Weekend activities include boating, cycling, golfing, walking and jogging on the lakes.
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08. Starved Rock State Park, Illinois: 100 miles southwest of Chicago
Starved Rock State Park is an extraordinary section of the Illinois River with 18 limestone cliffs and 14 waterfalls and abundant wildlife and birds.Belle of the Rock paddleboat excursions, guided hiking excursions, special events and interpretive programs.
Spend the night in rooms or cabins with a hearty meal at a starved rock lodge. If you like to explore further, the neighbor Matthiessen National Park, where five miles of walking trails weave through the mile-long canyon and through rocks.
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09. Indiana Dunes: 54 miles southeast of Chicago
These miles of shoreline offer large sandy shoreline stretches, towering dunes, excellent birding and biking trails and fascinating histories. Head to Chesterton to get creative burgers on the Octave Grill and enjoy a nice meal at Dunes Walk Inn, a restored 1881 house. Find out more about Indiana dunes. 1 of 26.
10. Lake Geneva, Wisconsin: 80 miles northwest of Chicago
It is 7,600 hectares and offers many attractions during the summer and winter. The Hotel, Resort and Restaurant are situated close to the Lake. Most visitors lol on the beaches or cruises on Lake during winter but you may also enjoy the winter warmth during January and February during the annual Winter Fest. See our trip planner in Geneva for more information.
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11. Fox River Valley, Illinois: 60 miles west of Chicago
An hour west of Chicago Loops, the Fox provides soothing backdrops for towns with indulgent food and shops surrounded by historic houses and elegant hotels. The Winery is only minutes from the beautiful Main Street in Oswego and features brick-paved sidewalks.
Three towns en route provide relaxing excursions with an emphasis on history: Catch a household name performing in St Charles' historic Arcada Theater or 3km south explore Geneva's shopping area with boutiques filling preserved storehouses.
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12. Michigan Avenue and the Magnificent Mile
Michigan Avenue is considered a popular shopping street. The famed Magnificent Mile is a portion of Michigan Avenue north of the river Chicago that houses many galleries and boutiques as well.
Some interesting sights on offer are John Hancock Center and Wrigley Towers. Michigan Avenue divides North-South designations on Madison Street. This town has a large number of theaters where the performers play a variety of shows including musicals and comedy. Website: Website.
13. Cedarburg, Wisconsin: 113 miles north of Chicago
Cedarburg is an excellent weekend destination that offers shoppers and historians dozens of brick and mortar homes and more than 70 shops, chocolate stores and delis. Explore town history through the General Store Museum and the Kuhefuss House Museum and enjoy handcrafted art at the Wisconsin Museum of Quilt and Fiber Arts.
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14. Field Museum of Natural History
Field Museum of Natural History was named as a cultural museum based on anthropology and natural history and has hosted a variety of exhibitions, the first being the Columbian Museum of Chicago. It became a nickname after Marshall Field, the museum owner and art patron who was an important benefactor and patron.
The permanent collection comprises approximately 20m artwork and specimens that cover various fields from botany and archaeology. Of particular importance were the permanent display about Ancient Egypt and the cultures of North Central and Southern America and "Sue," the earliest Tyrannosaur rex sleeve of the world.
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15. Museum of Science and Industry
On the northern edge of Jacksonpark stands a 1933 museum of science and industry that could have been Chicago's most impressive museum. The institute focuses on a wide spectrum of natural science and technology applications for industrial purposes. The museum has the potential to be the first in America to integrate "hand-on" exhibition concepts into its program.
In addition the visitor will have the option of a trip to the museum's library. MSI includes permanent and changing displays as well as OrionIMAX cinemas. Locations: 550 East Lake Shore Road, South Lakeshore, Chicago. Official website: www.southlake.org.
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16. Weekend Getaways from Chicago: Market Street Inn - 3 hours
Market Street Inn The Market Street Inn was originally built in a historic Victorian house built by Queen Anne in 1892. Our ten guest rooms offer modern comforts. Some rooms also include an antique collection of oriental rugs, pockets and beveled window frames. To get into the 8 rooms go up the oak stairs.
The room has an enclosed bath with a bathtub and shower, free WiFi, cable TV and air conditioning. Two guestrooms are located at the Carriage House. The two suites are deluxe suites and one has ADA-approved bathrooms. Every room is equipped with a fireplace. Guests can view the Victorian wraparound porch and garden from their comfortable seatings.
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17. Watch the Water Show at Buckingham Fountain
The fountain has been constructed by the Clarence Buckingham family since 1927, and is among the most significant fountains in the world. The fountain was designed to resemble Art Deco style of this time and is surrounded with four sea horses representing the 4 neighboring state of Lake Michigan. Between 8am and 11:59 o’clock each evening, the fountain explodes with 50,000 gallons per minute. In the afternoon water displays will be illuminated.
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18. Lincoln Park Zoo
Another enjoyable family activity in Chicago is a visit to Lincoln Park Zoo. Zoos contain nearly 200 animals of all ages. The exhibit is divided into 16 and showcases the incredible wildlife that lives here. Some interesting animals include penguins and oysters.
Visit Regenstein Center to study African Apeology. Unlike most animal parks in Illinois, zoos are a great place to see wonderful floral displays. The team managed more than 1,000 plants across 1200 plants. courtesy: 2002 Clark Street, IL. Illinois official website: website.
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19. Weekend Getaways near Chicago: The Newport Resort - 4 hours 30 minutes
Newport Resort The Newport Resort provides an easy to find holiday destination for the family within Door County, minutes from the beach. 59 rooms and suites have a whirlpool tub and a cozy seating area and kitchenette.
The resort also features a pool and a gym and there are also games available. Guests may read books in the library, relax in the lobby bar, or take a stroll in the gardens. Easily accessible from numerous restaurants and bars in Egg Harbor, The Newport Resort offers an ideal family holiday and romantic retreat.
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20. Getaways from Chicago, Illinois: Vrooman Mansion - 2 hours
Villa Vrooman is a historic bed and breakfast located just outside Bloomington. This historic estate offers luxury and privacy and is easily accessible from attractions, restaurants and stores.
The majority of the décor in the spacious guestroom is period antique furniture and each bedroom carries its own themes. There is a down pillow and pillowcase in each room. The Mansion offers 5 suites and 2 bedrooms with 2 carriageways. There are many shared spaces like the Safe Room Library, the foyer, the Music Room and the Dining Room.
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21. Shedd Aquarium
The Sheddy Aquarium is a great place to visit for those curious about the aquatic life that is located nearby from Chicago. The exhibit covers water regions across the planet, from the Antarctic to the Caribbean. When you are visiting children, it is essential to see a Polar Play Zone.
Children can get dressed up in animal-themed costumes and go on a makeover trip in a submarine and touch sea stars. Stingray Touch Tumbler has many children's toys and games. This huge tank contains numerous stingrays that are fascinated by being petted by them. Located: 1200 S DuSable Lakeshore Drive, Chicago, Illinois Official Website.
22. Michigan's southwest shore: 70 to 150 miles east of Chicago
The town of New Buffalo provides pristine beaches, great shopping, lakesside restaurants and a front-facing view of Sunset on Lake Michigan. A most accessible stretch on these waters stretches north from Indianapolis 165 miles east to Ludington.
The direction you go will depend on your situation. Visit St Joe's carousel tour working windmills and relax in the sun. Related: A Trip Guide to the Southwest Michigan Shore.
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23. Chicago Riverwalk and Lakefront Trail
The Chicago River runs from the center of the town, parallel to the shore of Lake Michigan and is famous as an impressive bridge. In less than 2 miles the bridge is surrounded by 18 bridges, each capable of bringing big yachts through.
The McCormick Bridgehouse and the Chicago River Museum offers visitors an intimate look into the mechanisms of a famous bridge. The Riverwalk offers various restaurants and organizes various events throughout the year, there are also various river excursions departing from the riverwalk.
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24. Weekend Getaways Near Me: TimberCreek Bed & Breakfast - 1 hour 45 minutes
TimberCreek Bed & Breakfast offers high quality beds in comfortable and clean rooms in an upscale barn-shaped building. It has 25 acres on a gated street at the beginning of an attractive curved lane.
The English Cottage's design extends to common areas and rooms with tile and wood floors, fireplaces, skylights and high-quality furniture. The bedrooms have their bathroom with free WiFi. Suites are wheelchair accessible. In addition, the guest will have access to a hair dryer, iron, and washing machine.
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25. Oakwood Resort, Syracuse, IN
The Oak Forest Resort offers enchanting scenery on Lake Wausee, where visitors are invited to visit for a relaxing holiday. The resort spans 27 acres and is partially covered in pristine water and offers the water sports enthusiast an excellent selection of water sports to enjoy on-site. The resort offers 79 hotel rooms, with many offering superb views across the Lake. If traveling with family or friends you may want to rent a large 3, 4 or 5 bedroom holiday home.
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26. Getaways from Chicago, Illinois: The Steamboat House - 2 hours and 45 minutes
Steamboathouse Steamboat House is a short block away from Galenas main street and has easy access to shops, restaurants and more. The hostel offers five guest rooms en suite including a bathroom. Room decor is varied with several featuring a 4-piece bed with original hardwood flooring.
A pool, billiard rooms, and a library are provided for guests, a porch with a covered patio area or a gazebo. The wine is always available on a nightly basis and hot drinks are served during the night. Coffee and cocoa are provided from the kitchen and breakfast is included.
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27. The Inn at Irish Hollow and Country English Cottages - 2 hours 45 minutes
Ireland Hollow is an elegant bed and breakfast ideal for a romantic stay on a 500-acre farm. In addition, guests can stay in a private cottage in the main hotel or in a hotel suite. The comfortable rooms are adorned with iron / claw foot baths and modern amenities.
Cottages may have two king-size beds and rugs, private porch areas with a shower and a double bathtub. There's bodywork available at this hostel too. All meals are included in your stay with natural materials.
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28. Weekend Getaways near Chicago: Dunes Walk Inn - 1 hour from Chicago
Dunes Walk Inn The dunes walking inn is a lovely restored mansion of the 1881 lakefront. Explore Indiana beaches about 60 miles from Chicago, and spend an evening in an upscale family home. Rates range from $155 per night. DunesWalk Inn at Furness Mansion, 1493 N Furnleigh Lane, Chesterton, IN 46304, 241-682-6393.
29. Lake Geneva, WI
Lake Geneva is a resort city situated along Lake Geneva in southern Wisconsin providing an excellent base to explore many lake-side activities. The lake served as a summer vacation destination since shortly after the Civil War and the site features dozens of historic state buildings starting from the Black Point Mansion in 1888.
You can see a lot of home in a lake cruise with Lake Geneva cruise lines, as well as discover the early days of the Geneva Lake Region Historical Society. Energetic guests are encouraged to take a hike along Lake Geneva Shore Path or take a ziplining tour at Lake Geneva Canopy Rides.
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30. Lake Michigan coastline
Lake Michigan coastline offers wide sandy beaches, towering dunes, great birding, easy bike trails and interesting history. Head to neighboring Chesterton for creative burgers at the Octave Grill and a pleasant night at Dunes Walk Inn, a restored 1881 mansion. Lake Michigan coastline, featuring hardwood floors and vertical mullion windows.
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