<
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.

stay time indicator 0.5-1.0 hr stay Closed 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
3. 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) 8.3
stay time indicator 0.5-2.0 hr stay Open now Check Hours of Operation
Public Park, Scenic, Outdoor Activities

Local Favorite, Trendy, Hiking, Family Fun, Free Entry, Lush, Exhibitions, Walking Around, People Watching, Sightseeing, Private Events, Picnic, Various Food Options, Romantic, Kids Friendly

337 E Randolph St, chicago

Maggie Daley Park is a 20-acre magnificent recreation park offering a children's playground, a climbing wall, mini golf, picnic groves, a skating ribbon, tennis courts, roller blades, Micro Scooters & Bungee, and a formal garden. It also hosts a popular summer day camp. The park is named in honor of Maggie C. Daley (1943 – 2011), Chicago's longtime first lady, who was deeply committed to improving the lives of children and making the city culturally rich for all its citizens.

Point
5. 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) 8.6
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 Closed 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) 8.3
stay time indicator 1.0-2.0 hr stay Closed now Check Hours of Operation
Historic Place, Pub, Live Shows

Local Favorite, Live Shows, Cocktails, Happy Hours, Romantic, Date Night

4802 N Broadway St, chicago

Known for its jazz and poetry performances, this oldest continuously running jazz club in the U.S. opened in 1907. The bar still has the same sitting as it was 100 years ago. There's plenty of room for dancing to the fantastic live music. the Green Mill has appeared in many films. They have some excellent cocktails, and the live music is always good. The place is filled with lots of mob history in Chicago; Al Capone had a dedicated booth.

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) 8.7
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.