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0.5-1.0 hr stay

John Hancock Building & 360 Chicago ($$)

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.

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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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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2.0-3.0 hr stay

The Field Museum ($$$)

1400 S DuSable Lake Shore Dr., chicago

Named after Marshall Field, who donated $1 million to build the museum, The natural history museum has nearly 40 million artifacts and specimens, showcasing 4.5+ billion years of history. One cannot see so many artifacts in a day, let alone a few hours, so visitors should devise a plan beforehand on what to cover. There are additional exhibits that cost extra.

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1.0-2.0 hr stay

Shedd Aquarium ($$$)

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.

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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0.5-1.5 hr stay

Wrigley Field (Price varies)

1060 W Addison St, chicago

The home of the Chicago Cubs, originally known as Weeghman Park, was built in 1914. A unique piece of sports history still stands while most other venues get knocked down and rebuilt, it is the second oldest ballpark. An iconic landmark, it is known for its ivy-covered brick outfield wall and hand-turned scoreboard. Visitors can see this place from the outside for free or buy tour tickets to go inside, and they can also purchase tickets on the game day to get the real experience. The games are fun and exciting, regardless of the outcome.

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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.

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.

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1.0-3.0 hr stay

Lincoln Park Zoo (Free Entry)

2001 North Clark Street, chicago

This 35-acre, beautifully landscaped zoo is the only privately managed free zoo in the USA. Established in 1868 has one of the best collections of gorillas and chimpanzees in the world. They are home to snow leopards, sea lions, penguins, Stilts, polar bears, snakes, and many more. There are plenty of hands-on exhibits, with displays set up to be informative and engaging.

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1.0-2.0 hr stay

The Peggy Notebaert Nature Museum ($)

2430 N Cannon Dr, chicago

This family-friendly nature museum offers exhibits from live native animals to nature-inspired art, from toddler-friendly place spaces to dozens of exotic butterfly species; they are sure to entertain, educate, and excite guests of all ages. They have demonstrations with live animals and displays to engage the senses, which is excellent for children. There are also outside nature trails for families to indulge in nature.

1.0-2.0 hr stay

Lincoln Park (Free Entry)

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.

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1.0-3.0 hr stay

Navy Pier (Free Entry)

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.

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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.

0.75-2.0 hr stay

Chicago Lakefront Trail (Free Entry)

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.

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2.0-4.0 hr stay

Museum of Science and Industry ($$)

5700 S DuSable Lake Shore Dr., chicago

One of the largest science museums in the Western Hemisphere! This fourteen acres museum offers more than 35,000 artifacts, including the World War II submarine, five-story movie screen, 40-foot tornado, and the actual United Airlines Boeing 727, hands-on activities, and interactive experiences with impressive displays. MSI is not a place where you walk around quietly and observe but to explore and expedite.

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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.

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.

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0.5-1.0 hr stay

Buckingham Fountain (Free Entry)

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.

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.

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0.5-2.0 hr stay

Maggie Daley Park (Free Entry)

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.

1.0-2.0 hr stay

Chicago Cultural Center (Free Entry)

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.

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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.

0.5-1.0 hr stay

North Ave Beach (Free Entry)

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.

0.5-1.0 hr stay

Starbucks Reserve Chicago Roastery (Free Entry)

646 N Michigan Ave, chicago

The world's largest Starbucks Reserve Roastery in Chicago offers a selection of the rarest, most extraordinary coffees Starbucks has to offer. It's where Starbucks pushes its craft boundaries, developing a unique roast for each individual lot before experimenting with coffee as an art form—brewing, aging, infusing, and blending it into imaginative and often surprising creations. Starbucks shares these discoveries and the enjoyment of exceptional coffee with the world in the roastery.

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0.75-1.5 hr stay

Garfield Park Conservatory (Free Entry)

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.

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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.

1.0-2.0 hr stay

Wicker Park (Free Entry)

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.

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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