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1.5-3.0 hr stay

Adler Planetarium ($$)

1300 S. DuSable Lake Shore Dr, chicago

The Adler Planetarium museum is dedicated to studying astronomy and astrophysics, founded by Max Adler. The planetarium is a twelve-sided building that includes two sky theaters. The theaters depict the night sky and allow visitors an up-close look at distant planets, moons, and galaxies. There are full-size theaters, extensive space science exhibitions, and a significant collection of antique scientific instruments and print materials. Its exhibits Astronomy in Culture, Chicago’s Night Sky, Mission Moon, Our Solar System, Planet Explorers, Space Visualization Lab, Telescopes: Through the Looking Glass, The Universe: A Walk Through Space and Time, and many more.

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1.0-3.0 hr stay

Grant Park (Free Entry)

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.

1.0-2.0 hr stay

The Chicago Theatre (Price varies)

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.

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0.5-1.5 hr stay

The Second City (Price varies)

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.

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1.0-2.0 hr stay

Chicago History Museum ($$)

1601 N Clark St, chicago

It is a museum and research center for Chicago and U.S. history. Museum offers a variety of programs, dynamic exhibitions, tours, publications, special events, and programming that connects people to Chicago's history and each other. It is excellent for kids and adults to get a basic understanding of the city by going through different periods in history. The Museum Store has many fun Chicago goodies, from posters to Frank Lloyd Wright-style items, books, DVDs, toys, mugs, magnets, ornaments, coasters, jewelry, and more.

1.0-1.5 hr stay

Museum of Contemporary Art ($$)

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.

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Eat BREAKFAST

0.5-1.0 hr stay

The 606 (Free Entry)

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.

0.5-2.0 hr stay

Music Box Theatre ($)

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.

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1.0-2.0 hr stay

Green Mill Jazz Club (Free Entry)

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.

1.0-3.0 hr stay

The Magnificent Mile (Free Entry)

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).

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0.5-1.5 hr stay

Thalia Hall (Price varies)

1807 S. Allport St., chicago

Thalia is a historic building landmark built in 1892 by John Dusek as a community hall. Currently, it hosts concerts by well-known artists and special events. In addition to the thalia hall, there is a central meeting place with a tavern, Dusek's board & beer, and two bars, Punch House and Tack Room. There is a standing room on the floor and seats on the balconies. The artists come from many different genres, but they're always great picks.

Eat LUNCH

0.75-2.0 hr stay

Chinatown (Free Entry)

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.

1.0-2.0 hr stay

Shakespeare Theatre (Price varies)

800 E Grand Ave, chicago

A Tony award recipient, Shakespeare Theatre runs 650 performances annually with twenty productions featuring plays, musicals, world premiers, family productions, and theatrical presentations from around the globe. It also offers educational programming for students, teachers, and lifelong learners and has been honored with many national and international awards. Recently, the theatre was recognized as a national leader in a white house ceremony.

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