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Point  ($$) 9.5
stay time indicator 1.0-2.0 hr stay Open 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.

stay time indicator 0.5-1.0 hr stay Open now Check Hours of Operation
Scenic, Skyscraper, Landmark

Local Favorite, Wheelchair Accessible, Shopping, Breathtaking Views, Family Fun, Exhibitions, Walking Around, People Watching, Concerts, Sightseeing, Private Events

875 N Michigan Ave, chicago

360 Chicago is an observatory located on the 94th floor of the historic John Hancock Center in the heart of downtown Chicago. It offers breathtaking views of the city and Lake Michigan from over 1,000 feet above the Magnificent Mile. Visitors can also experience "The Tilt" for an additional fee; a series of floor-to-ceiling windows slowly tilt outside the building to 30°. There is also a Bar (CloudBar) to enjoy a drink (or two) while overlooking the view.

Point  ($$$) 8.8
stay time indicator 1.0-2.0 hr stay Open now Check Hours of Operation
Aquarium, Landmark

Local Favorite, Walking Around, Wildlife, Sea World, Aquarium, Educational Workshops, Kids Friendly

1200 S DuSable Lake Shore Dr., chicago

Shedd Aquarium, a national historic landmark, has been home to more than 32,000 unique animals since 1930. It welcomes more than 2 million visitors to meet beluga whales and bluegills, rockhopper penguins and rockfish, alligators and an alligator snapping turtle, and so much more from the world's oceans, lakes, rivers, and reefs. Several permanent exhibits at Shedd include Waters of the World, Caribbean Reef, Amazon Rising, Wild Reef, Stingray Touch, Oceanarium, Fantasea, One World, and 4D Theater.

Point
4. Navy Pier
 (Free Entry) 8.5
stay time indicator 1.0-3.0 hr stay Open 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 Open 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) 8.7
stay time indicator 1.0-2.0 hr stay Open 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  (Price varies) 8.8
stay time indicator 0.5-1.5 hr stay Open now Check Hours of Operation
Theatre

Local Favorite, Wheelchair Accessible, Trendy, Movie Night

230 W North Ave, chicago

The improv comedy club has launched some of the biggest names in the business, including John Belushi, Dan Aykroyd, Mike Myers, Steve Carell, Stephen Colbert, Tina Fey, and about 500 others. They also offer improv lessons. The comedy shows are filled with never-ending laughter. There are many levels of shows, from amateur to professional, with their own charms. It is the oldest running improv club.

Point  (Free Entry) 8.7
stay time indicator 1.0-2.0 hr stay Open now Check Hours of Operation
Sightseeing, Neighbourhood, Shopping Place

Local Favorite, Trendy, Biking, Shopping, Family Fun, Free Entry, Walking Around, People Watching, Sightseeing, Date Night, Kids Friendly

N Lincoln Ave & W Fullerton Pkwy, chicago

Lincoln Park is one of the most affluent and picturesque neighborhoods in Chicago. It's a few stops from the city with many exciting places, including the namesake park (Lincoln Park), beach, restaurants, museums, theatres, shops, and bars. The neighborhood is home to the country's oldest free zoo. Visitors will enjoy the manicured gardens, many lakefront green spaces, and breathtaking city views.

Point  (Free Entry) 8.2
stay time indicator 0.75-1.5 hr stay Open 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  ($$) 8.5
stay time indicator 1.0-1.5 hr stay Open now Check Hours of Operation
Museum

Wheelchair Accessible, Family Fun, Exhibitions, Art Gallery, Private Events, Birthday Parties, Free Wifi, Takes Reservations

220 E Chicago Ave, chicago

A contemporary art museum near Water Tower Place is one of the world's largest contemporary art venues. Visitors can experience the work and ideas of living artists and understand the historical, social, and cultural context. The museum includes sculpture, photography, dance, performance, and music. Museum's collection consists of more than 2,000 works, 2,500 artworks spanning media and movements from the 1920s to the present.

Point  (Price varies) 8.8
stay time indicator 1.0-2.0 hr stay Open now Check Hours of Operation
Architecture, Historic Place, Live Shows

Local Favorite, Wheelchair Accessible, Trendy, Famous, Nightlife, Music, Dance, Movie Night, Romantic, Cocktails, Date Night

175 N State St, chicago

Legendary theatre in downtown Chicago hosts concerts, comedians, theatrical productions, and special events every year. The 3,600-seat auditorium is seven stories high, and the vertical "C-H-I-C-A-G-O" sign is one of the few such signs in existence today. The building is built in the French Baroque style featuring a miniature replica of Paris' Arc de Triomphe, and the grand lobby is modeled after the Royal Chapel at Versailles. The theater is exquisite and quite beautiful.

Point
12. 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) 8.9
stay time indicator 1.0-3.0 hr stay Open now Check Hours of Operation
Sightseeing, Neighbourhood, Shopping Place

Local Favorite, Wheelchair Accessible, Trendy, Dine In, Shopping, Relaxing, Street Performance, Famous, Family Fun, Free Entry, Exhibitions, Sightseeing Tours, Walking Around, People Watching, Sightseeing, Live Shows, Romantic, Date Night

Magnificent Mile, chicago

Visitors can see the Blue Man Group or House of Blues show. There is also "The Comedy Bar" for a fun time. The Chicago Cubs' official store is there if you are into sports. Many eateries are either along the Mile or on cross streets. There are some great street performances on the walkways. There are always some special events; check them out at https://www.themagnificentmile.com/things-to-do/events/ before you go. Endlessly high-end brand-name stores like LV, Burberry, Gucci, and more. Public Restrooms are available at 900 North Michigan Shops, Water Tower Place (835 N. Michigan Avenue), and The Shops at North Bridge (520 N. Michigan Avenue).

Point  (Free Entry) 8.6
stay time indicator 0.5-1.5 hr stay Open now Check Hours of Operation
Scenic, Architecture, Hike

Local Favorite, Wheelchair Accessible, Dog Friendly, Breathtaking Views, Famous, Family Fun, Free Entry, Lush, Sightseeing Tours, Walking Around, People Watching, Romantic

Riverwalk, chicago

The 1.25-mile path from the lakefront to Lake Street, Chicago Riverwalk, is an open, pedestrian waterfront located on the Chicago River in downtown Chicago. It connects four distinct districts; The Confluence, The Arcade, The Civic, and the Esplanade, with many places to stop and relax, various tours, and food vendors. The riverwalk offers glamorous architectural views of the city and refuge from the city's hustle and bustle.

stay time indicator 1.5-2.0 hr stay Open now Check Hours of Operation
Scenic, Architecture, Tour

Breathtaking Views, Famous, Family Fun, Lush, Sightseeing Tours, Walking Around, People Watching, Full Bar, Romantic

112 E. Wacker Drive, chicago

Chicago's riverboat architecture tours are well known among visitors and locals alike. The 90-minute tour discusses more than 50 famous historic and modern landmarks, including Willis Tower, Navy Pier, the Wrigley Building, Tribune Tower, Merchandise Mart, Lyric Opera, 333 West Wacker, Marina City, and many more. The tour guide also tells the fascinating stories of how a small settlement grew into a world-famous Chicago city.

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  ($) 8.4
stay time indicator 0.5-2.0 hr stay Open now Check Hours of Operation
Architecture, Historic Place, Theatre

Local Favorite, Wheelchair Accessible, Trendy, Relaxing, Music, Dance, Movie Night

3733 N Southport Ave, chicago

Opened in 1929 with a capacity of 700 seats, Music Box has been a premier venue for independent and foreign films in Chicago for the last two decades and is the largest theatre space operated full-time in Chicago. The theatre has the same architecture and design as it was when it opened with a dark blue ceiling with twinkling stars and moving cloud formations as we see in the night sky. The walls, towers, and blue ceiling take the viewers to an Italian courtyard in an open-air Tuscan palazzo.

Point  (Free Entry) 8.7
stay time indicator 1.0-2.0 hr stay Open now Check Hours of Operation
Sightseeing, Neighbourhood, Shopping Place

Local Favorite, Trendy, Biking, Shopping, Family Fun, Free Entry, Walking Around, People Watching, Sightseeing, Date Night

N Damen Ave & N Milwaukee Ave, chicago

Wicker park is famous for being an artsy neighborhood that always has something cool going on. There is something for everyone, including unique shopping places, trendy restaurants, coffee houses, and bars. The neighborhood is home to the historic victorian style homes built between 1873 and 1903.

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.