Chicago Weekend Trips and Escapes

Chicago Weekend Trips
Image by Bert K on Flickr under Creative Commons License.
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Chicago is a magnificently beautiful cosmopolitan city, featuring a wide array of potential day trips, including outdoor and indoor activities for the whole family within its borders and its surrounding areas. An escape from the urban hustle and bustle of Chicago is as simple as a short drive to its outlying regions. Popular destinations include Naperville, Milwaukee, Geneva and several other locations, where you will find lovely natural attractions, a wide selection of recreational opportunities and protected habitats.

Attractions Map

Guide Name: Chicago Weekend Trips and Escapes
Guide Location: USA » Chicago
Guide Type: Self-guided Walking Tour (Day trip)
# of Destinations: 38
Author: AlexanderA
Elkhart, IN

1) Elkhart, IN (includes 3 sights)

A vibrant city in North-Central Indiana, Elkhart is located approximately 109 miles from Chicago, offering a long list of splendid attractions for the family, including a gorgeous modern ice rink during the winter months, which becomes a fun and exciting water park in the summertime. A popular tourist destination featuring a vast array of family-oriented activities and beautiful surroundings you will certainly not want to miss, be sure to check out the following sites that can be found while...
Image by {Guerrilla Futures | Jason Tester} on Flickr under Creative Commons License.
Goshen, IN

2) Goshen, IN (includes 2 sights)

Goshen, a city in Elkhart County in the heart of Amish country, serves as a perfect hub for visiting all major points in the northwest region of Indiana. Many of the streets found in its residential neighborhoods are lined with magnificent maple trees, inspiring Goshen’s popular nickname of Maple City. These splendid trees afford a lush shade during the summer and put on a beautiful display of colors in autumn. When searching for great day trip ideas, be sure to check out Goshen, as well as...
Image by taygete05 on Flickr under Creative Commons License.
Kenosha, WI

3) Kenosha, WI (includes 2 sights)

Located in Kenosha County, Wisconsin, Kenosha is the fourth-largest city in the state, featuring a wide array of recreational green space and gorgeous public parks containing breathtaking scenery. Situated along eight miles of the Lake Michigan shore, its lovely beaches, harbor and parks attract many visitors from near and far to enjoy its natural splendor. Among Kenosha's list of unique attractions you will find Washington Park, which includes the nation’s oldest operating velodrome,...
Image by puroticorico on Flickr under Creative Commons License.
Lake Geneva, WI

4) Lake Geneva, WI (includes 3 sights)

Located in the southeastern region of Wisconsin, Geneva is the well-known site of some of the Midwest’s most breathtaking natural scenery. Not far from Milwaukee, it has long served as a popular vacation spot and weekend getaway, especially for Chicagoans, since the 1871 Great Chicago Fire. A marvelous way to spend a fun and exciting day trip with the entire family, recreational activities available around Lake Geneva include fishing, boating, hiking, water skiing, horseback riding, bicycling...
Image by Royalbroil on Wikimedia under Creative Commons License.
Michigan City, IN

5) Michigan City, IN (includes 2 sights)

Michigan City, located in LaPorte County, Indiana, is not far from the Indiana Dunes National Lakeshore and borders Lake Michigan. This city attracts many tourists during the summer months, especially ones from Chicago and other nearby cities in northern Indiana. A notable landmark and symbol of the city, you will find its beautiful lighthouse, and on clear days you can see the Chicago skyline across the lake. A wonderful reprieve from the urban regions surrounding it, Michigan City offers...
Image by anneh632 on Flickr under Creative Commons License.
Milwaukee, WI

6) Milwaukee, WI (includes 2 sights)

An ideal blend of business and leisure, Milwaukee, Wisconsin attracts millions of visitors each year for its multitude of fun and exciting attractions great for the entire family. Located only ninety miles north of Chicago, this bustling metropolis is the largest city in the state, featuring both urban and small town qualities. Popular for its lakefront and multicultural festivals, and its large breweries, Milwaukee has been undergoing the process of restoring its elegant historic architecture,...
Image by purpleslog on Flickr under Creative Commons License.
Rum Village Park, South Bend, IN

7) Rum Village Park, South Bend, IN

South Bend, a city in St. Joseph County, Indiana close to the southernmost curve of the St. Joseph River, is home to lovely hiking and biking trails, and is a great place to enjoy an assortment of other recreational activities. Inside Rum Village Park, on the south end of the city, you will find the Rum Village Nature Center, featuring fascinating exhibits, a spot for birdwatching and more. Offering 160 acres of magnificent woodland, this park contains deer and fox, as well as an assortment of...
Image by tkwist on Flickr under Creative Commons License.
South Haven, MI

8) South Haven, MI (includes 2 sights)

An experience you will not soon forget, South Haven, Michigan keeps visitors coming back for more. This unique beach town, located along Lake Michigan, features fun in the sun, including swimming, building sand castles, volleyball and a wide assortment of other recreational activities, and is a fantastic destination for a day trip adventure with the entire family. Be sure to visit this gorgeous city to fully appreciate its beautiful scenery, magnificent sunset and picturesque skyline for...
Image by Daniel Morrison on Flickr under Creative Commons License.
New Buffalo, MI, New Buffalo Lakefront Park and Beach

9) New Buffalo, MI, New Buffalo Lakefront Park and Beach

Located at the source of the Galien River close to the border of Indiana and Michigan, New Buffalo hosts a multitude of public events all year long. Within walking distance of the city’s downtown you will find a lovely beach, which includes a scenic harbor. Facilities available to guests include restrooms, food and beverage concessions, a playground for children, and gorgeous dune formations with a boardwalk stretching across the tops of several of them. Though there is a small parking fee,...
Image by Technologik on Flickr under Creative Commons License.
Naperville, IL

10) Naperville, IL (includes 2 sights)

Naperville, situated on the border of DuPage and Will Counties, Illinois, is the fifth largest city in the state. One of the most frequented suburbs lying just outside the Chicago metropolitan district, Naperville is home to several beautiful parks and other natural settings that are perfect for relaxing or a host of leisurely recreations. Centennial Beach, a wonderful place for fun and sun close to downtown Naperville, has grown to become a popular local hangout for teenagers, as well as a...
Image by mjunx on Flickr under Creative Commons License.
Geneva, IL, Fabyan Forest Preserve

11) Geneva, IL, Fabyan Forest Preserve

Located in Kane County, Illinois, about forty miles west of Chicago, Geneva is situated in the Fox River valley, and is famous for its historic charm, including its stunning architecture. The Fabyan Forest Preserve along the Fox River is the city’s most popular natural attraction, welcoming thousands of guests each year for fishing, hiking, biking and jogging along its scenic river bridge path and exploring the preserve’s remaining historic elements, including the Fabyan Villa Museum, the...
Image by jmenard48 on Flickr under Creative Commons License.
Rockford, IL

12) Rockford, IL (includes 2 sights)

A medium-sized city named after the ford running through the Rock River, Rockford was initially settled in 1834 and chartered in 1852, and is popularly known as Forest City. Currently the state’s largest city outside the Chicago Metropolitan Area, Rockford attracts a wide assortment of visitors from all over to enjoy outdoor leisure activities with the entire family, offering breathtaking natural wonders and beautiful parks, as well as a host of exciting city attractions that both parents and...
Image by on Flickr under Creative Commons License.
Loves Park, IL, Volcano Falls

13) Loves Park, IL, Volcano Falls

Located in Winnebago County, Loves Park, Illinois can be found just 80 miles northwest of Chicago, situated along the lovely Rock River. Volcano Falls is an exciting theme park featuring miniature golf beneath a three-story erupting volcano, as well as the nine-hole Palm Course. Sharpen your skills in its batting and soccer cages, and battle your friends in the awesome Laser Zone. This fun attraction also includes go-kart racing, a video game arcade, and an assortment of food and beverage...
Image by kulicki on Flickr under Creative Commons License.
Utica, IL

14) Utica, IL (includes 3 sights)

A small city located in LaSalle County, Illinois, Utica includes such wonderful natural attractions as Starved Rock State Park, which has been a popular tourist destination for nearly one hundred years. Home to less than 1,000 residents according to the 2000 U.S. Census, Utica caters to a significant tourism industry, which has become well-known over the years for its high quality entertainment, breathtaking natural grounds and picturesque scenery. Be sure to check out this quaint little...
Image by vxla on Flickr under Creative Commons License.
Cherry Valley, IL

15) Cherry Valley, IL (includes 2 sights)

Cherry Valley, a modest-sized community of the Kishwaukee River Valley in Winnebago County, Illinois offers a magnificent selection of family-friendly entertainment. Whether you’re looking for action or relaxation, Cherry Valley as something to offer, including fabulous scenery, fascinating native plants and wildlife, a variety of recreational facilities, and some of the nation’s most breathtaking geological formations and natural beauty. Five beautiful nature preserves comprising 2,167...
Image by jasonippolito on Flickr under Creative Commons License.
Glencoe, IL, Glencoe Beach

16) Glencoe, IL, Glencoe Beach

Located just twenty miles north of Chicago, Glencoe, Illinois a fantastic escape from the urban hustle and bustle. Bordered by Lake Michigan, you will find the Cook County Forest Preserve and the Glencoe Golf Course, as well as a host of other parks and facilities near the beach. Opening each season on Memorial Day weekend, Glencoe Beach is a popular destination for boating, swimming, picnics, a variety of outdoor recreation, or simply relaxing in the sun. Offering shelter for rainy days, beach...
Image by spakattacks on Flickr under Creative Commons License.
State Park: Illinois Beach

17) State Park: Illinois Beach

Located in Lake County, Zion is home to the Illinois Beach State Park. Comprising six and one half miles of breathtaking shoreline along Lake Michigan, it is a beautiful site for relaxation and leisure activities, including swimming and sunbathing. Its park contains impressive dune formations and marshes with swales, as well as a forested area with oaks and a wide selection of native plants and wildlife. Covering nearly 4,200 acres of land, visitors will have a blast exploring the scenic trails...
Image by chascarper on Flickr under Creative Commons License.
McHenry, IL

18) McHenry, IL (includes 2 sights)

Located northwest of Chicago, McHenry, Illinois is bisected by the Fox River, which is a prominent feature of this quaint little town. Surrounded by breathtaking natural scenery, including lakes and streams formed by glaciers from the previous Ice Age, Weber’s Park is among its lovely protected habitats, as well as the Moraine Hills State Park and Volo Bog State Natural Area, where visitors are invited to explore the fascinating ecosystem of marshes and peat bogs and discover its unique...
Image by James Jordan on Flickr under Creative Commons License.
Marengo, IL, Coral Woods Conservation Area

19) Marengo, IL, Coral Woods Conservation Area

Located in McHenry County just 56 miles northwest of Chicago, Marengo, Illinois offers a variety of recreation, including boating, fishing and hiking. Hugging the west side of the Marengo Moraine, a 15,000 year old glacial formation, you will find the lovely Coral Woods Conservation Area here. Featuring five miles of heavily wooded trails, you can see beautiful red and white oaks, and an assortment of ash, hickory, maple and other trees. Pets are permitted provided they are leashed, and covered...
Image by romana klee on Flickr under Creative Commons License.
Woodstock, IL, Woodstock Water Works

20) Woodstock, IL, Woodstock Water Works

A suburb in McHenry County northwest of Chicago, Woodstock is a popular destination due to its abundance of fairs, festivals and other public events. The Woodstock Water Works is an exciting theme park fun for the entire family, which includes a double flume slide, an enormous pool with low and high diving boards, a baby pool and playground, sheltered pavilions, food and beverage concessions, ample parking and lots of wide open space for leisure activities and relaxation. A splendid day trip...
Image by Jeff Klinefelter on Flickr under Creative Commons License.
Volo, IL

21) Volo, IL (includes 3 sights)

Located in Lake County, Volo is an historic village in Illinois which is thought to have been inhabited for a minimum of 160 years. Initially named Forksville, it received its present name in 1872, though Volo was not officially recognized until 1993 because the citizens had wanted to prevent its incorporation into the surrounding communities. The Volo Bog State Natural Area, a beautiful protected region, and Fish Lake Beach, a private resort, are among the city’s most popular attractions, as...
Image by puroticorico on Flickr under Creative Commons License.
South Elgin, IL

22) South Elgin, IL (includes 3 sights)

Rich in history and natural beauty, the Fox River runs through this picturesque landscape in northeastern Illinois. South Elgin is home to a wealth of natural resources that offer fun and adventure to the entire family. In the shallow waters south of the Panton Mill Park Dam, angling is a popular way to pass the time, and Pickerel Point along the river is a peaceful site for fishing as well. Other popular South Elgin destinations include the Jon Duerr Forest Preserve, and an assortment of other...
Image by sscornelius on Flickr under Creative Commons License.
Des Plaines, IL

23) Des Plaines, IL (includes 2 sights)

A city in Cook County, Des Plaines, Illinois also goes by its official moniker, the City of Destiny. Located about seventeen miles from downtown Chicago, the Des Plaines Park District sponsors two golf courses, a driving range and an exciting waterpark, as well as a wide assortment of splendid public events throughout the year. Surrounding the Des Plaines River, spanning much of the city’s eastern border, you will find a lovely forest preserve, and the beautiful Lake Park, which also provides...
Image by Zol87 on Flickr under Creative Commons License.
Batavia, IL

24) Batavia, IL (includes 3 sights)

Founded in 1833, Batavia, Illinois was Kane County’s first city, though some of it extends into DuPage County. A multitude of recreational activities can be enjoyed in its numerous natural green spaces, which consists of thirty parks covering over 300 acres of land. Included in Batavia’s long list of amenities, you will find several playgrounds, tennis and basketball courts, numerous picnic areas, an assortment of sports fields and scenic trails, as well as plenty of natural bodies of water...
Image by Jason Sturner 72 on Flickr under Creative Commons License.
Skokie, IL

25) Skokie, IL (includes 2 sights)

From a Native American word meaning “fire,” Skokie, located in Cook County, Illinois, is considered a suburb of Chicago, and for several years has been referred to as the World's Largest Village. Home to a multitude of great public sites and historic landmarks comprising over 240 acres of land, Skokie was a recent recipient of the Gold Medal for Excellence for the wonderful management of its local parks. Since 1991 the Skokie Festival of Cultures, celebrating the diversity of its...
Image by Zol87 on Flickr under Creative Commons License.
Elmhurst, IL

26) Elmhurst, IL (includes 2 sights)

Located in both DuPage and Cook Counties, Elmhurst, Illinois is thought to have been originally settled by the Potawatomi tribe, who had inhabited the southern region along Salt Creek. Around 1836, settlers from Europe began populating this area, and in 1882 Elmhurst was officially incorporated as a village. Since 1918, the city’s Memorial Day Parade has been a popular event, as well as its famous St. Patrick's Day Parade, which considered the largest public gathering of its kind in the...
Image by fitzgene on Flickr under Creative Commons License.
Evanston, IL

27) Evanston, IL (includes 2 sights)

Located only ten miles north of downtown Chicago, Evanston, Illinois is a suburb of this bustling metropolis, a community on the North Shore along Lake Michigan. Being so close to Chicago, public transportation in and around the city could not be more convenient. Featuring beautiful beaches on the lakeshore, historic homes, streets and bicycle paths lined with stately trees, lovely public parks and a thriving business district, Evanston is home to a wide assortment of attractions guests of all...
Image by JeremyA on Wikimedia under Creative Commons License.
Lisle, IL

28) Lisle, IL (includes 2 sights)

A small village in DuPage County, Lisle, Illinois is considered part of the Chicago Metropolitan Area, as well as a component of the Illinois Technology and Research Corridor. Its citizens are affectionately referred to as Lilacs or Lileseans. A couple of its most fascinating attractions include the Morton Arboretum and Sea Lion Aquatic Park. The Eyes to the Skies Festival, devoted to hot air ballooning, is an enormously popular public event held in Lisle that attracts over 200,000 guests each...
Image by Jason Sturner 72 on Flickr under Creative Commons License.
Chesterton, IN, Coffee Creek Watershed Preserve

29) Chesterton, IN, Coffee Creek Watershed Preserve

Chesterton, located in Porter County, Indiana less than an hour’s drive from Chicago, offers both the tranquility and friendliness of a small town, with the cultural opportunities of a big city. Attracting millions of tourists annually, among the city’s most popular destinations is the Coffee Creek Watershed Preserve. Here, guests are invited to hike and bike its scenic trails and discover its natural beauty, offering a variety of breathtaking views with each change of the season. Around...
Image by Sarah Douthitt on Flickr under Creative Commons License.
Gurnee, IL

30) Gurnee, IL (includes 2 sights)

Located in Lake County, Gurnee, Illinois is a village bordering Waukegan, and is a component of the Chicago Metropolitan Area. Gurnee is perhaps most famous as the site of Six Flags Great America and the Gurnee Mills Outlet Mall. Also popular with tourists, the KeyLime Cove Indoor Waterpark Resort is a great family attraction. Situated halfway between Milwaukee and Chicago, this quaint little town has been a popular site of tourism for years, attracting visitors from both of these major...
Image by puroticorico on Flickr under Creative Commons License.
Northbrook, IL, Somme Prairie Grove

31) Northbrook, IL, Somme Prairie Grove

Located on the northern border of Cook County, Northbrook, Illinois maintains numerous beautiful public parks and natural spaces, such as the Somme Prairie Grove, a lovely 90-acre preserve. Here visitors can see a unique blend of terrains, much of it comprised of tall grass savannas and impressive woodland. Two small prairies can be found adjacent to the railroad tracks, as well as numerous ephemeral ponds that vary in depth by the season, and dry up during the summer. This breathtaking natural...
Image by Urban Woodswalker on Flickr under Creative Commons License.
Winnetka, IL, Elder Lane Park and Beach

32) Winnetka, IL, Elder Lane Park and Beach

An affluent village approximately 14 miles north of Chicago, Winnetka, Illinois, located in Cook County, is considered one of the wealthiest communities in the United States. Elder Lane Park contains a tranquil beach that is great for relaxing in the sun, as well as the lovely Centennial Park and Pioneer Doyle Cabin just to the north. This beach includes restrooms, a playground, ample parking space, and a beach house that can be rented for private events from May to October 15th. A wonderful...
Image by tipiro on Flickr under Creative Commons License.
Wilmette, IL, Gillson Park

33) Wilmette, IL, Gillson Park

A lovely suburb on Chicago’s famous North Shore, Wilmette is known for its beautiful lakefront, tree-lined streets, and roads paved with brick. Spanning 60 acres, Gillson Park is the perfect spot to enjoy picnicking, bicycling, volleyball, and a host of other outdoor activities, including tennis and baseball. Swimming is permitted in designated zones. Additionally amenities include Gillson Beach, the Lakeview Center, fitness equipment, picnicking facilities, a dog park, sailboat rentals and...
Image by Flickr in time on Flickr under Creative Commons License.
Nature Preserve: Salt Creek Woods

34) Nature Preserve: Salt Creek Woods

A village in Cook County, Illinois, La Grange Park can be found along the popular Salt Creek Trail. The Salt Creek Woods Nature Preserve consists of a woodland, a floodplain around Salt Creek, and several stretches of open prairie. The Salt Creek Woods are distributed from the dryer upper slopes, and the delicate Tinley Moraine, to the damper grounds surrounding the creek itself. Bur, white oak and hickory comprise much of the dryer grounds, with elm, cottonwood and silver maple located in the...
Image by Oak Park Cycle Club on Flickr under Creative Commons License.
Elk Grove Village, IL

35) Elk Grove Village, IL (includes 2 sights)

Found in northeastern Illinois near the O'Hare International Airport in Chicago, Elk Grove Village maintains a small herd of elk in a grove inside the Busse Woods. Home to several wonderful attractions good for the entire family, among its most popular destinations you will find the Ned Brown Preserve, spanning some 3,700 acres, which includes a beautiful lake and over 11 miles of trails for hiking, jogging or cycling. It has been said that this lovely protected habitat attracts more annual...
Image by Martin Pinnau on Flickr under Creative Commons License.
Barrington, IL

36) Barrington, IL (includes 2 sights)

Located in both Cook and Lake Counties, Barrington, Illinois can be found just over thirty miles northwest of Chicago. Featuring wetlands, forests, several public parks and horse trails, this lovely rural and suburban destination includes Citizens Park, Langendorf Park, Miller Park and Ron Beese Park. Within Barrington’s beautiful natural sites, guests can enjoy an assortment of recreational activities, including sports such as baseball and volleyball, as well as exploring the region’s...
Image by keith011764 on Flickr under Creative Commons License.
Janesville, WI

37) Janesville, WI (includes 3 sights)

Located at the junction of the Illinois, Iowa and Michigan borders, Janesville, Wisconsin is home to a vast assortment of public parks, featuring impressive natural scenery, including lakes and wide open spaces great for picnics with family and friends and a host of outdoor recreational activities. Nicknamed the City of Parks, Janesville is home to over fifty of them, rightfully earning its popularity as a great destination for families and nature-lovers, attracting visitors from the surrounding...
Image by compujeramey on Flickr under Creative Commons License.
Koshkonong, WI, Lake Koshkonong

38) Koshkonong, WI, Lake Koshkonong

Located in Jefferson County, Koshkonong, Wisconsin is known as the nation’s largest Norwegian community. A favorite recreational attraction, Lake Koshkonong is home to an assortment of boating activities, including canoeing, sailing and more. Tubing, and water and jet skiing are other popular activities enjoyed here, as well as fishing, the lake being annually populated with game fish and meticulously maintained by the city. Winter activities, such as ice fishing and ice skating have gained...
Image by lisahumes on Flickr under Creative Commons License.


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