Fun and Entertaining Places in Chicago

The city of Chicago will not disappoint you when it comes to entertainment. Be it the vibrant shopping streets, bustling nightlife, or creative theaters, you will find different fun and entertainment options in Chicago. Here is the extensive list of all the entertainment places in Chicago that are bound to make your vacation a memorable one. With so many options to choose from, you will never have to worry about what to do in Chicago anymore.

Let's explore the best places for fun and entertainment in Chicago:

  1. Millennium Park

    Park, Landmark, Bridge, Walking Area

    Any Chicagoan will tell you; this is the city’s favorite haunt. It’s become famous for it’s beautiful, landscaped natural art, art exhibits and just general awesomeness. There’s an uber modern concert pavilion (The Pritzker), the kid-favorite Crown Fountain; the mercury-inspired Cloud Gate is always visually fascinating. Those looking to crossover from the Millenium Park...Read more
  2. Michigan Avenue

    Museum, Cafe, Pubs, Restaurant

    A major street going north-south, the Michigan Avenue in Chicago can be called as the economic, cultural and social hub of the city. The famous (with shopaholics) Magnificent Mile along with the bustling North Michigan Avenue are part of the Michigan Avenue. Along the avenue, you will find many commercial offices, restaurants, museums, cafes, pubs, boutiques, shops, department stores and archi...Read more
  3. John Hancock Center

    4.6 (5611 Votes)
    John Hancock Center

    Landmark, View Point, Observatory, Leisure

    Like skyscrapers everywhere, you’ll come to this place for it’s awesome observatory on the 94th floor. For the best views, visit at night. The restaurant here is pretty reasonably priced for the location, so it’s actually quite a good spot to take your beloved out to. Though you’d be charged for the observatory, their skyline bar itself is free, and the view from there i...Read more
  4. Wrigley Field

    4.8 (5083 Votes)
    Wrigley Field

    Bar, Park, Stadium, Food And Drinks

    Wrigley Field Chicago is a baseball park located on the North Side of Chicago. Take Wrigley Field Tours to explore all that happens in confidentiality, home to the Chicago Cubs. The park is among the top five ballparks in the country. The 104th season of Major League Baseball in 2018 will be held at the spectacular Wrigley Field which was built in the year 1914. It’s got many firsts to it...Read more
  5. Lincoln Park

    4.7 (1021 Votes)
    Lincoln Park

    Museum, Park, Walking Area, Restaurant

    A designated community area in Chicago, Lincoln Park is a serene locality boasting of parks, museums, quaint houses and bustling restaurants. The actual park, after which the neighbourhood was named, is spread across a huge area and encompasses the Lincoln Park Zoo and the Lincoln Park Conservatory. It also houses an outdoor theatre, the Chicago History Museum, a rowing canal and the Peggy Note...Read more
  6. Chicago Cultural Center

    4.7 (2514 Votes)
    Chicago Cultural Center

    Landmark, Entertainment, Performance, Concert

    A beautiful landmark building in Chicago, the Chicago Cultural Centre is one of the most visited attractions in the city. Hosting interesting free public events, the centre draws hundreds of thousands of visitors every year. Housing two splendid stained-glass domes, events hosted within the centre include music events, dance and theatre events, lectures, film screenings and even art exhib...Read more
  7. Magnificent Mile

    Hotel, Bar, Museum, Landmark

    The name isn’t an idle boast. The mile packs bars, shops, boutiques, restaurants, hotels and museums into a pretty tight space. Places to note include the Michigan Avenue Bridge, the John Hancock Cente, the Tribune Tower, and the Old Water Tower. Clean airy and inviting, people watching here, like in Times Square, is the treat of the day. Also, visit the popular attractions in the c...Read more
  8. Lakefront Trail

    Beach, Trail, Waterfront, Garden

    An impressive 18-mile long stretch, Chicago’s Lakefront Trail is the place to be for outdoorsy people. The trail is a paved path that runs from the Ardmore Street to the 71st Street. Along the trail, you will find lush green gardens, playgrounds for children, parks, soccer fields, volleyball nets, tennis courts, beaches and amenities such as washrooms and drinking water fountains. Popula...Read more
  9. Crown Fountain

    4.7 (1460 Votes)
    Crown Fountain

    Landmark, Entertainment, Tower, Architecture

    Located within the Millennium Park, the Crown Fountain is a major attraction in Chicago. Designed by Spanish artist Jaume Plensa, the fountain is made up of two 50 feet tall glass block towers made up of many LED screens. These screens project images of many Chicago citizens with their mouths open from where the water of the fountain falls. An interesting piece of architecture, the founta...Read more
  10. United Center

    4.6 (942 Votes)
    United Center

    Arena, Stadium, Entertainment, Concert

    The United Centre - an indoor sports arena. It is home to the teams of Chicago Bulls (basketball) and the Chicago Blackhawks (hockey). If you are in the city while the arena is hosting a thrilling game, it would be a crime not to go watch it! When not hosting sporting events, the arena is also known to host concerts and other entertainment events. Scoreboard messages price ...Read more
  11. Brookfield Zoo

    4.6 (399 Votes)
    Brookfield Zoo


    Located around half an hour’s drive from Chicago, Chicago Zoological Society’s Brookfield Zoo is home to over 450 species of animals and birds. Spread across an area of 216 acres, animals within the zoo include polar bears, penguins, dolphins, bison, wolfs, giraffes, kangaroos, seals, zebras, African lions, snow leopards, bald eagles, spider monkeys, small-clawed otters and a lot m...Read more
  12. Chicago Loop

    Food And Drinks, Neighborhoods , Nightlife

    The central business district of Chicago, The Loop is the commercial core of the city. With a skyline made up of skyscrapers and high-rises, the Loop houses many companies, offices and businesses. But, the Loop is not just all work and no play! Boasting some of the city’s favourite attractions, the area is full of place to dine, drink, shop and stay. A perfect place to visit for sig...Read more
  13. House Of Blues

    4.5 (423 Votes)
    House Of Blues

    Food And Drinks, Restaurant, Entertainment, Performance

    The House of Blues Chicago is a New Orleans’ style food and events centre. A must visit place for the lovers of music, the House of Blues Chicago has some or the other music event happening almost every day. While there, do grab a bite at the Crossroads restaurant. It serves heavenly food! If you like traditional and contemporary Gospel songs, the House of Blues also has a Gospel Brunch ...Read more
  14. Kingston Mines

    4.7 (71 Votes)
    Kingston Mines

    Bar, Entertainment, Performance, Nightlife

    A famous blues nightclub situated in Lincoln Park, Chicago, the Kingston Mines has live performance every single night of the year. Having 2 stages, the place hosts 2 bands every night. A must visit for music lovers, in the year 2014, Kingston Mines was awarded the "Keeping the Blues Alive Award" by the Blues Foundation. Trivia: The Kingston Mines is the oldest, continuously operating blues cl...Read more
  15. Symphony Center

    4.8 (601 Votes)
    Symphony Center

    Entertainment, Performance, Concert

    A feast for the eyes and ears, the Chicago Symphony is always family friendly. It’s small, and intimate, and the acoustics are wonderful. Patron after patron has talked about how it feels that the performance solely is for his or her benefit. This isn’t just Chicago’s treasure, but one that belongs to the world. If you want, you can just walk around the parks nearby, and stil...Read more