Weekend Getaways From Chicago

Road Trips

Weekend Getaways From Chicago | Road Trips from Chicago

Encircled by the beautiful cities, river valleys, and state parks, there are several Weekend Getaways from Chicago for the visitors. These getaways are the perfect place for visitors to indulge in va (Read More)rious adventure sports, enjoy sightseeing and other recreational activities. Some of the weekend getaways from Chicago include Fox River Valley, Apple River Canyon State Park, Woodstock, Lake Geneva, etc.

Here is the list of 27 Weekend Getaways From Chicago

1. Indianapolis, Indiana

Indianapolis, Indiana

Located in Marion County in Michigan, Indianapolis is the most popular state in the U.S. The city is popularly known for its historic sites, sporting events, and several museums. With the largest collection of monuments dedicated to the soldiers/veterans of war casualties, parks, hiking and biking trails, Art and culture centres, etc. the city has a lot to offer. An abode to three Fortune 500 companies the city also hosts the world’s largest single-day sporting event called the Indianapolis 500. Other recreational activities include kayaking, bicycling, cross-country skiing, sightseeing, etc.
Distance From Chicago: 185.4 miles from Chicago
Best Time to Visit: May-September
Popular Attractions: Indianapolis Zoo, The Children’s Museum of Indianapolis, Indiana State Museum, White River State Park, and More.

2. Woodstock, Illinois

Woodstock, Illinois

Located 51 miles northwest of Chicago Woodstock Illinois is a suburb that was named the nation’s Distinctive Destinations in 2007. The city includes a historic town square, which is anchored by Woodstock opera house and Old McHenry County Country House. Woodstock was formerly known as Canterville because of its location at the geographic centre of McHenry County. The historic town square in Woodstock offers many shops and retail establishments that are designed in the late 19th-century Victorian style. From handcrafted jewellery stores to antiques and restaurants the town square includes all. Every year Woodstock hosts several Arts and Entertainment events, festivals, and fairs, which attract a lot of visitors. Some of the events hosted here are the Fair Didley Art Fair, Summer Band Concerts, Farmers Market, Victorian Christmas celebrations, and many more.
Distance From Chicago: 61.5 Miles from Chicago
Best Time to Visit: May to September
Popular Attractions: Woodstock water Works, Emricson Park, Boone Creek Conservation Area, Illinois Railway Museum

3. Midewin National Tallgrass Prairie

Midewin National Tallgrass Prairie

Situated in Northern Illinois, the Midewin National Tallgrass Prairie is the largest conservational site Chicago Wilderness region. Located at the former site of Joilet Army Ammunition Plant, it was the first national tallgrass prairie ever designated in the U.S.
Visitors can enjoy Hiking trails, Bird-watching, native seed-gardens, and biking along with the Midewin’s trail system. The prairie spreads across 9100 acres of land with 16 miles of hike trails, biking trails, which also facilitates horseback riding. More than a hundred bird species are present in the prairie, with a large number of Upland Sandpipers and Loggerhead Shrikes.
Open throughout the year the prairie also hosts guided tours for its visitors.
Distance From Chicago: 50.6 Miles from Chicago
Best Time to Visit: March-June
Popular Attractions: McKinley woods, Lake ChaminWood Preserve, Des Plaines State Fish and Wildlife Area, Foxford Park.

4. Beloit Wisconsin

Beloit Wisconsin

Beloit is a small city located in south Wisconsin, which was originally named New Albany by its founder Caleb Blodgett. The city is a host to festivals including, the Beloit International Film Festival, Winterfest, Beliots Farmers’ Market, etc., which attracts a lot of visitors every year. Hikers and art lovers can also visit the art centres, savannah trails in the Beckman Hill park.
Distance From Chicago: 96.8 Miles from Chicago
Best Time to Visit: Mid June to Early September
Popular Attractions: Wright Museum of Art, Logan Museum of Anthropology, Tefler Park, Beloit Art centre.

5. Apple River Canyon State Park

Apple River Canyon State Park

Located in Jo Daviess County, the Apple River Canyon State Park is situated near the Wisconsin Border. Stretched across a land of 1900-acres the park was built in the year 1932. The scenic canyon is a result of the Apple River switching its course. The river that once flowed eastward into the Pecatonica river started flowing southwest through an erosion gorge to the Mississippi.
State Park offers hiking, fishing, hunting, campgrounds, etc. The six camping sites are available at the Canyon Ridge Campground and Walnut Youth Campground. Pine Ridge, Tower Rock, River Route, Sunset, and Primrose trails are the trails that are available within the Park. The fishing, however, is allowed only during the spring season.
Distance From Chicago: 144.6 Miles from Chicago
Best Time to Visit: Mid April- October End
Popular Attractions: Stagecoach Trails Livery, Thriving Thistle Market, The Cove Bar/ Grill

6. Glencoe, Illinois

Glencoe, Illinois

Located on Chicago's North shore is the village of Glencoe that is surrounded by Lake Michigan, the Cook Country Forest Preserve, and Glencoe Golf Course. The village is nestled with residential homes that are designed using the architectural styles and designs from the 1800s. Many of the homes are designed by known architects which include Llyod wright, Robert Seyfarth, Keck, and Keck, etc. The various parks, beach facilities, golf courses, etc makes it one of the attractive places along the North Shore. Surrounded to the west of the village are the Skokie Lagoons in a forest preserve and the Greenbay Trail that offer bike trails to the visitors. Visitors can enjoy golfing at the public Glencoe Golf Club, Skokie Country Club, and the Lakeshore Country Club or spend their day at the Glencoe Beach.
Distance From Chicago: 24.2 Miles from Chicago
Best Time to Visit: Mid June- Mid September
Popular Attractions: Chicago Botanic Gardens, Skokie Lagoons, Glencoe Beach

7. Lake Mills, Wisconsin

Lake Mills, Wisconsin

The city of Lake Mills is located in Jefferson County, Wisconsin, and occupies the east shore of Rock Lake. In 1866, the city was named Tyranena, but a year later, it was renamed, Lake Mills. Lake Mills is picturesquely surrounded, by several wineries, restaurants, and shops. Home to the Azatalan State park, which nestles the Rock Lake, also offers hiking and biking trails along the Park.
Distance From Chicago: 141. Miles from Chicago
Best Time to Visit: Mid June To early September
Popular Attractions: Rock lake, Aztalan State Park, Sandy Beach, Bartel’s Beach, and More

8. Fox River Valley, Illinois

Fox River Valley, Illinois

Centred on the Fox River in Northern Illinois, the Fox River Valley is also commonly known as the Fox Valley. The city is a mixture of rural, suburban, and 19th-century downtowns developments. With its Fox River Trail System, Trolley Museum, Buffalo Rock State Park, Outdoor theatre, the city offers a lot to its visitors. The 32-miles fox river trail system is perfect for hiking, biking, and cross-country skiing trails. Original electric cars and trains that travel a three-mile route along the fox river, the Trolley Museum commemorates more than a century of electric trolleys. With the cheap ticket prices and the snacks, the outdoor drive-in theatre is another great place to hang out in the city.
Distance From Chicago: 38.5 Miles from Chicago
Best Time to Visit: Mid June To early September
Popular Attractions: the Morton Arboretum, Cantigny Park, Cosley Zoo, Philips Park Zoo, and More

9. Rockford, Illinois

Rockford, Illinois

Located in Northern Illinois and on the banks of Rock river, Rockford is a city in Winnebago County. It is the third-largest city in Illinois.
It is a cultural hub and a focal point of many monuments of historical significance. The notable outdoor recreations of the city include camping, hiking, fishing, boating, and hunting. Several golf courses can elevate the golfing experience for golfers.
Distance From Chicago: 88.8 miles from Chicago
Best Time to Visit: Mid June –Early September
Popular Attractions: Anderson Japanese Gardens, Rock Cut State Park, Discovery Center Museum, Klehm Arboretum, and Botanic Garden, and More.

10. Cedarburg Wisconsin

Cedarburg Wisconsin

Incorporated in the year 1885 and located 20 miles from Milwaukee, Cedarburg is a city in Ozaukee County, Wisconsin. The city has many German cultural associations that culminate the Lutheran churches, European-style spa, and breweries.
A host to several art galleries, tourism is at its peak in the city due to Winter Festival, Strawberry Festival, German-themed October fest, Wine and Harvest Festival, as well Christmas celebrations are commemorated every year.
Distance From Chicago: 112.5 Miles from Chicago
Best Time to Visit: May- September
Popular Attractions: Cedar Creek Winery, Ozaukee Interurban Trail, Cedarburg Art Museum, Chiselled Grape Winery, and More.

11. Mount Morris, Illinois

Mount Morris, Illinois

Mount Morris is a small village in Ogle County, Illinois. The village is built on the former site of Mount Morris College, Illinois first institute dedicated to higher learning. Dillehay Park, Maunder Park, and Zickuhr Park are some of the parks in the village that has a basketball court, playground equipment, and a skating rink.
Distance From Chicago: 106 miles from Chicago
Best Time to Visit: Mid-June To early September
Popular Attractions: Dillehay Park, Maunder Park, Zickuhr Park, Bald Hill Prairie Preserve

12. Holland, Michigan

Holland, Michigan

Located on the shores of Lake Macatawa, Holland is a city in Michigan. Found by the Dutch Americans, the city is thus known for its rich Dutch heritage. Every year the city hosts the must-visit Tulip Time festival, which is the planting of tulips. The festival started in the year 1930, and currently, there are over five million tulips all over the city. Scattered along the shorelines of lake Macatawa are several public beaches and hiking trails of the tunnel park, Holland State Park for the visitors. With over 100 swarming galleries and shops, the city upscales the shopping experience for its visitors.
Distance From Chicago: 150.9 miles from Chicago
Best Time to Visit: Late April or Early May
Popular Attractions: Windmill Island, Nelis’ Dutch Village, Holland State Park, Lake Macatawa, and More

13. Madison, Wisconsin

Madison, Wisconsin

Madison is the second-largest city in Wisconsin and the capital city of Wisconsin. Also known as the City of Four Lakes, Madison encircles four lakes Lake Waubesa, Lake Mendota, Lake Monona, and Lake Kegonsa. The city is a focal point of an extensive network of parks and hiking trails, museums, Several lakes, and zoos. Henry Vilas Zoo in Madison is a 28-acre zoo that has over 70000 visitors every year. Nestled in the zoo are different species of birds, fishes, mammals, reptiles from several continents. Madison Arboretum is four miles from the University of Wisconsin is a research facility that manages many conifer/deciduous forests and prairies. Hikers can also enjoy the 20 miles of hiking trails and over 3 miles of bike trails in the arboretum.
Distance From Chicago: 147.3 Miles from Chicago
Best Time to Visit: July, August
Popular Attractions: Wisconsin State Capitol, Henry Vilas Zoo, Lake Mendota, Madison Children's Museum and More

14. Saugatuck, Michigan

Saugatuck, Michigan

Saugatuck is a city in the Allegan County of Michigan that was incorporated in the year 1868. It has a population of 960 according to the 2019 census. With the many art galleries, restaurants, paddle-wheel boats, historic churches, and other attractions, the city is sprawling with tourists during the summertime. A boon for the art and music lovers as it also hosts art and music festivals throughout the year. The Paddle-wheel boat ride is one of the best in the city, as the boat ride gives daily tours of the river Kalamazoo river and Lake Michigan. Saugatuck church is one of the oldest buildings in the city, which also contributes to a vibrant community.
Distance From Chicago: 140.7 miles from Chicago
Best Time to Visit: May- September
Popular Attractions: Oval Beach, Saugatuck State Park, Saugatuck centre for arts, Mount Baldhead, and more.

15. Lake Geneva, Wisconsin

Lake Geneva, Wisconsin

Lake Geneva is a city located in Walworth County, Wisconsin. Located on the shores of Geneva Lake, the city attracts many visitors from Chicago, Milwaukee, Rockford, etc., throughout the year. Camping sites, beaches, waterparks, hiking, biking, golf courses, museums, sightseeing, etc., the city has a lot to offer for its visitors. Enjoy a relaxed day at the beach, camp out in the various camping sites, or indulge in the various adventure sports, a city is a perfect place for all age groups. Their adventure activities include Zip lining, hot-air balloon rides, safari rides, skydiving, etc. Geneva lake has many beaches the Rivera Beach, Williams Bay Beach, Fontana Beach for the visitors to enjoy the Lake's pristine waters.

Distance From Chicago: 83.0 Miles from Chicago
Best Time to Visit: July, August
Popular Attractions: Grand Geneva Way, Geneva Lake Museum, Big Foot Beach State Park, Lake Geneva Ziplines, and adventures.

16. Grand Rapids, Michigan

Grand Rapids, Michigan

Located on the Grand River and east of Lake Michigan, Grand Rapids is the second-largest city in Michigan. Encompassed in the city are the Van Andel Museum Centre, the Heritage Hill, Frederik Meijer Gardens, and Sculpture Park, etc., which makes it a popular tourist attraction. Found in 1854, the Van Andel Museum Centre is one of the oldest museums in the city. The Heritage Hill, the largest urban historic district, is a home of more than 1300 homes that are designed in more than 60 architectural styles. Spread across 125 acres of land is also the Frederik Meijer Gardens and Sculpture Park, which nestles a world-class botanical garden artwork from American/French artists. Dedicated to the art lovers are also various music concert venues that organize concerts every year.
Outdoor recreation activities include Skiing, snowboarding, Ice fishing, etc.
Distance From Chicago: 177.6 miles from Chicago
Best Time to Visit: April-October
Popular Attractions: John Ball Zoo, Grand Rapids Museum, Millennium Park, Rosa Parks Circle, and More.

17. South Bend Indiana

South Bend Indiana

Situated on the long tributary of Lake Michigan, St Josephs River, the South Bend City is located in Indiana. The city is a cultural hub and the fourth largest city in Indiana. Not only is the city a centre of arts and culture but, also hosts several music festivals every year. The great outdoors, sports venues, museums are some of the attractions that the city offers to its visitors.
Distance From Chicago: 95.7 miles from Chicago
Best Time to Visit: April-September
Popular Attractions: Studebaker National Museum, Potawatomi Zoo, Nore Dam Golden Dome, The History Museum, and More.

18. Shawnee National forest, Illinois

Shawnee National forest, Illinois

Located in Southern Illinois, the Shawnee National Forest is situated between the Ohio and Mississippi river. With a plethora of flora and fauna, the forest is the perfect place for outdoor recreation and sightseeing. Some of the available recreational activities are camping, fishing, Hiking, Hunting, Bicycling, water activities, and much more. The camping experiences range from primitive backpacking to partial hookups camping sites. Swimming, water skiing, boating, etc., are some of the water activities offered to visitors.
Distance From Chicago: 338.6 miles from Chicago
Best Time to Visit: March-June
Popular Attractions: Giant City State Park, Garden of the Gods, Kinkaid Lake, Tunnel Hill State Trail, and More.

19. Traverse City, Michigan

Traverse City, Michigan

Traverse City is the largest city in the Northern Michigan region. With a large production of Tart Cherries in the city, it also hosts the National Cherry Festival every year. Some of its other attractions include freshwater beaches, forests, skiing areas, camping sites, arts and culture centres, etc. Campers can enjoy camping at the 250 camping sites, art lovers can visit the Dennos Museum, which hosts a collection of art by the Arctic people. Kayaking, Swimming, fishing, surrounding wineries are some other recreational activities that are presented at Lake Michigan.

Distance From Chicago: 319.6 miles from Chicago
Best Time to Visit: June- August
Popular Attractions: City Opera House, Clinch Park, East Front Street, Mari Vineyards, and More. "

20. Galena Illinois

Galena Illinois

Located in Jo Daviess County, Galena is a small town in Illinois known for its 19th-century architectural style buildings.
From the many historic sites, local cuisine to a plethora of boutiques and shops, the city has a lot to offer. With a ride in the hot air balloons, hiking, golfing, biking, etc., the city hosts several outdoor adventures along the Mississippi River.
Distance From Chicago: 163.7 miles from Chicago
Best Time to Visit: May- October
Popular Attractions: Galena Grant Park, Belvedere Mansion, Old Blacksmith Shop, and More

21. Elkhart Lake Wisconsin

Elkhart Lake Wisconsin

Elkhart Lake is a village in Sheboygan County in Wisconsin. Located within the Town Rhine the village was popularly known to host road races in the 1900s’. Located a few miles away from the village is a race track called Road America. The village has several historical figures like the Victorian Village theatre, which is a 100-year theatre where still cultural programs are performed. There are two parks called the Broughton Sheboygan Marsh Park and Fireman's Park, which offer campsites, picnicking, fishing, and trails for its visitors. The recreational activities in the village are hosted every Summer, Winter, and Spring Season.
Distance From Chicago: 149.4 Miles from Chicago
Best Time to Visit: June- August
Popular Attractions: Road America, Two Fish Gallery, Crystal Lake, Wade House Historic Sites, and More.

22. Starved Rock State Park, Illinois

Starved Rock State Park, Illinois

The Starved Rock State Park on the Illinois River is a wilderness area in the state of Illinois that offers several recreational activities for the visitors. The park is spread across 2630 acres of land and has waterfalls, 18 sandstone canyons, 13 miles of wooded trails, and diverse wildlife. Established in the year 1911, it attracts a lot of visitors every year. Among other recreational activities, the park offers camping, fishing, boating, horseback riding trails, ice skating, scenic views from the Eagle Cliff Overlook and Beehive Overlook.
Distance From Chicago: 98.9 miles from Chicago
Best Time to Visit: September- December
Popular Attractions: Ottawa Canyon, LaSalle Canyon, Grand Bear Falls Indoor Waterpark, French Canyon, and More

23. Milwaukee, Wisconsin

Milwaukee, Wisconsin

Located on the western shore of Lake Michigan, Milwaukee is the largest city in Wisconsin. The city is known for its breweries, summer fest, and cultural attraction. With Over 140 well-developed parks that facilitate picnic spots, golfing, ice skating, the parks are spread across 15000 acres. The 2 km Monarch Trail highlights the migration of the milkweed butterflies. Nearby local markets and farmers markets sell the produce of local business, which includes seafood, gourmet, plants, and vegetables.
Distance From Chicago: 92.4 miles from Chicago
Best Time to Visit: June - September
Popular Attractions: Milwaukee Art Museum, Harley Davidson Museum, Discovery World, Milwaukee County Zoo, and More.

24. Mineral Point, Wisconsin

Mineral Point, Wisconsin

Mineral Point is a city in Iowa County and the third oldest city in Wisconsin. The city’s historical significance and lead/ Zinc mining centres makes it a popular tourist attraction. Mineral Point is the endpoint of the 76-km Cheese country Trail in Southern Wisconsin. A historic district with many cottages and businesses that were crafted by the Cornish settlers. The restaurants in Mineral Point serve Cornish Foods following the Cornish heritage of the city.
Distance From Chicago: 167 Miles from Chicago
Best Time to Visit: June, July, August
Popular Attractions: The Walker House, Orchard Lawn, Merry Christmas Hill, Pendarvis

25. Lake Forest, Illinois

Lake Forest, Illinois

Founded in the 1900s, lake Forest is a city along the shores of Lake Michigan located in Lake County, Illinois. With the Citadel theatre, the Wildlife Discover Centre, and the Lake Forest Symphony, the city is a cultural hub for visitors.
Distance From Chicago: 32.7 miles from Chicago
Best Time to Visit: Mid-June to Mid-September
Popular Attractions: Wildlife Discovery Centre, Fort Sheridan Forest Preserve, Chicago Botanic Garden, Sunrise Park, and More

26. Ann Arbor, Michigan

Ann Arbor, Michigan

Founded in 1824, Ann Arbour is a city in Michigan that is the focal point of art, natural history, and sciences. Home of the University of Michigan and a sprawling tech-hub, the city draws several companies due to the research programs by the university.
The local cuisine, outdoor activities, unique shopping, renowned arts, and culture, etc., are some of the recreations that the city offers. Seasonal sports like kayaking, canoeing, paddleboarding on the River Huron, ice skating, skiing, and snowshoeing are offered during different months of the year. Hikers can enjoy the best biking trails in the nearby state parks. Art lovers can visit the University of Michigan Museum, which displays century-old arts from all over the world.

Distance From Chicago:
241.4 miles from Chicago
Best Time to Visit: March-September
Popular Attractions: Ann-Arbor Hands-on Museum, Matthaei Botanical Gardens & Nichols, University of Michigan Nichols Arboretum, Gallup Park, and More

27. Indiana Dunes State Park, Indiana

Indiana Dunes State Park, Indiana

Established in the year 1925 and located in Porter County, Indiana, the Indiana Dunes State Park is a few miles away from Chicago. The park is spread across 1530 acres of land and is an abode to several hiking trails and dune landscape. With the several hiking trails, picnic shelters, hiking tours, etc., there are several activities in this state park that the visitors can indulge themselves in. Their hiking trails extend over 16 miles, a bird observation tower for bird watching, swimming in the small portion of Lake Michigan shoreline, around 140 campsites with 50 amp electric hook-ups, and picnicking are some of the recreational adventures that attract a lot of visitors.

Distance From Chicago: 50.1 miles from Chicago
Best Time to Visit: Any time of the year
Popular Attractions: Taltree Arboretum and Gardens, Chapel of the Resurrection, Portage Lakefront and Riverwalk and More

We hope you enjoyed our list of Weekend Getaways from Chicago. Drop your feedback in the comments section below.

This post was published by Akshita Dhiman

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