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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.

Eat LUNCH

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.

1.0-2.0 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

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.

Eat LUNCH

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.

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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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.

Eat LUNCH

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.

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.

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Eat BREAKFAST

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.

0.5-1.5 hr stay

Chicago Riverwalk (Free Entry)

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.

Eat LUNCH

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.

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.

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Eat BREAKFAST

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.

Eat LUNCH

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.

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