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Point  ($$) 9.5
stay time indicator 1.0-2.0 hr stay Closed now Check Hours of Operation
Architecture, Skyscraper, Landmark

Local Favorite, Wheelchair Accessible, Trendy, Breathtaking Views, Famous, Family Fun, Exhibitions, Souvenirs, Photography

233 S Wacker Dr, chicago

Willis tower, formerly the Sears Tower, is a 110-story skyscraper, and this skyscraper is Chicago's most dominant structure and 2nd tallest building in the Western Hemisphere. On a clear day, one can see approximately 40-50 miles (65 - 80 kilometers), allowing one to easily see four states – Illinois, Indiana, Wisconsin, and Michigan. Skydeck has a ledge glass box extending 4.3 feet from the Skydeck, providing a clear view of 1,353 straight down.

Point
2. Navy Pier
 (Free Entry) 8.5
stay time indicator 1.0-3.0 hr stay Closed now Check Hours of Operation
Piers And Boardwalk, Landmark, Novelty Attraction

Local Favorite, Wheelchair Accessible, Trendy, Dine In, Shopping, Family Fun, Free Entry, Exhibitions, Walking Around, People Watching, Sightseeing, Photography, Music, Movie Night

600 E Grand Ave, chicago

Chicago's lakefront treasure, Navy Pier, is 50 acres of unparalleled attraction space. Nearly nine million people visit Navy Pier annually, making it the most visited attraction in Illinois and the Midwest. There are many indoor and outdoor attractions at Navy Pier, such as Chicago Shakespeare Theater, Chicago Children's Museum, impressively large Centennial Wheel, Carousel, Drop Tower, Navy Pier Beer Garden, and many more. You will also find shops, eateries, and theatres.

Point  (Free Entry) 8.7
stay time indicator 0.5-1.0 hr stay Closed now Check Hours of Operation
Landmark, Scenic

Local Favorite, Breathtaking Views, Family Fun, Free Entry, Lush, Exhibitions, Walking Around, People Watching, Photography, Romantic, Kids Friendly

301 S. Columbus Dr., chicago

Buckingham fountain, one of the largest in the world, runs daily from early May through mid-October. Visitors can enjoy a major water display for 20 minutes every hour when the water goes 150 feet in the air. It is considered one of the finest ornamental fountains in America.

Point  (Free Entry) 8.4
stay time indicator 1.0-3.0 hr stay Open now Check Hours of Operation
Public Park, Exhibition, Sightseeing

Local Favorite, Wheelchair Accessible, Shopping, Breathtaking Views, Family Fun, Free Entry, Lush, Exhibitions, Walking Around, People Watching, Concerts, Sightseeing, Photography, Private Events, Various Food Options, Romantic, Kids Friendly

331 E Randolph St, chicago

312.98 acres Grant Park, proudly referred to as Chicago's front yard offers many different attractions in its ample open space, including Millennium Park, Maggie Daley Park, Buckingham Fountain, the Art Institute of Chicago, and the Museum Campus. It is home to baseball diamonds, tennis courts, and breathtaking gardens. The park hosts music and food events, including the famous Taste of Chicago event, Grant Park Music Festival, and Lollapalooza, a well-known outdoor music festival.

Point  (Free Entry) 8.7
stay time indicator 1.0-2.0 hr stay Closed now Check Hours of Operation
Architecture, Historic Place, Landmark

Wheelchair Accessible, Trendy, Shopping, Free Entry, Free Entry, Exhibitions, Photography, Music, Art Gallery, Educational Workshops, Live Shows

78 E Washington St, chicago

The Chicago Cultural Center, which opened in 1897, is a Landmark housing designed to impress and prove that Chicago had grown into a cosmopolitan metropolis. The building currently boasts two magnificent glass strained-glass domes, including the world's largest stained glass Tiffany dome ― 38 feet in diameter with some 30,000 pieces of glass. It also features mosaic walls, free music, dance and theater events, films, lecturers, art exhibitions, and family events.

Point  (Free Entry) 8.2
stay time indicator 0.75-1.5 hr stay Closed now Check Hours of Operation
Conservatory, Scenic, Botanical Garden

Local Favorite, Wheelchair Accessible, Relaxing, Famous, Family Fun, Free Entry, Exhibitions, Walking Around, People Watching, Concerts, Sightseeing, Photography, Music, Private Events, Romantic

300 N Central Park Ave, chicago

One of the largest and most stunning conservatories was designed by renowned landscape architect Jens Jensen and was opened to the public in April 1908. This two-acre "Landscape art under glass" occupies contains many permanent plant exhibits incorporating specimens from around the world. The beautiful glass building is separated by theme and temperature/ humidity. There is a room for desert plants, one for food-producing plants, and a treehouse room for kids. Beautiful specimen plants, exquisitely well maintained. There are also ten-acre outdoor gardens.

Point
7. The 606
 (Free Entry) 8.5
stay time indicator 0.5-1.0 hr stay Open now Check Hours of Operation
Trail, Scenic, Hike

Local Favorite, Trendy, Dog Friendly, Hiking, Biking, Breathtaking Views, Street Performance, Family Fun, Free Entry, Lush, Exhibitions, Walking Around, People Watching, Photography, Romantic

1805 N Ridgeway Ave, chicago

The 606 is a former elevated rail line, the Bloomingdale Line, converted into a combination walking, jogging, and biking path from Ashland Avenue to North Ridgeway Avenue. The trail connects to ground-level neighborhood parks, an observatory, art installations, and other amenities. There is a lot to see architecturally, lovely plantings along the way, with many entrances and exits along the route.

Point  (Free Entry) 9.1
stay time indicator 0.75-2.0 hr stay Open now Check Hours of Operation
Scenic, Hike, Outdoor Activities

Local Favorite, Hiking, Biking, Breathtaking Views, Family Fun, Free Entry, Walking Around, Photography, Beach, Picnic, Romantic, Lake

Lakefront Trl, chicago

Chicago's 18-mile-long scenic Lakefront Trail is an 18-mile-long stretch that extends from Ardmore Street on the North Side to 71st Street on the South, connecting to great neighborhoods, parks, and beaches. The trail passes through Edgewater, Uptown, Lakeview, Lincoln Park, South Loop, and Hyde Park neighborhoods. Each neighborhood offers its own unique experiences and a lot of things to do. Visitors and locals enjoy walking, running, biking, and rollerblading on the trail. Popular places on the route include south park shore, Jackson park, promontory point, 31st street harbor, northerly island, grant park, Maggie Daley park, Ohio Street beach, North Ave beach, Lincoln Park zoo, Belmont harbor, Montrose beach, and Foster Beach.

Point  (Free Entry) 8.5
stay time indicator 0.5-1.0 hr stay Open now Check Hours of Operation
Beach, Hike, Scenic

Local Favorite, Breathtaking Views, Street Performance, Family Fun, Walking Around, People Watching, Sightseeing, Photography, Picnic, Sunbathing, Swimming, Lake

1600 N Lake Shore Dr., chicago

One of Chicago’s most famous beaches, it features a unique and popular beach house with 22,000 square feet of space that features something for everyone and is permanently docked along this beach. This sleek, ocean liner-inspired building, decked out in a crisp blue and white, boasts one of the best views in the city. The beach house has upper decks and portholes for looking at the magnificent horizon or the multitudes of bikers, runners, walkers, and rollerbladers streaming down the lakefront trail.

Point
10. Chinatown
 (Free Entry) 8.7
stay time indicator 0.75-2.0 hr stay Closed now Check Hours of Operation
Sightseeing, Neighbourhood, Historic Place

Famous, Free Entry, Walking Around, Sightseeing, Photography

2206 S Wentworth Ave, chicago

Chicago's century-old Chinatown is one of the oldest Chinese-American communities in the nation. As soon as you set foot in this historic neighborhood, you're in for the rich culture, regional Chinese cuisines, karaoke bars, and unique architecture. Stroll through elaborately adorned streets filled with traditional specialty shops, ornate architecture, storefronts packed with colorful wares and souvenirs, and family-owned restaurants with dishes you'll be craving long after home.