Chicago Layover Guide (MDW)

Willis Tower Skydeck and The Ledge Experience

This might be the most famous building in Chicago and it offers an unrivaled view of the city from the Skydeck on the 103rd floor. The Ledge is not for the faint hearted, it is made of a series of 4 glass-paneled boxes that extend out from the building’s facade and gives a dizzying vertigo-inducing view straight down. » book this tour

90-Minute Mob and Crime Bus Tour

Discover Chicago’s underworld of criminals and gangsters on a luxury 90-minute bus tour. This tour offers insights in the world’s most famous criminals, mobsters, and gangsters conned their way through the city. Learn about crime scenes from as far back as the 19th century through modern times. Find out the history of Al Capone, the Untouchables, the Chicago Mob, John Dillinger, Terrible Tommy O’Connor, H. H. Holmes, the Chicago Black Sox, Leopold and Loeb, bank heists, Cap George Streeter, and more. » book this tour

Chicago River Architecture Cruise

This 75-minute cruise takes you to all three branches of the Chicago River, and marvel at the architecture that has made Chicago legendary. The tour gives insights into the buildings and engineering of a city that gave birth to the skyscraper. View over 40 landmark buildings from the cruise and find out why Chicago is the spiritual home of modern American architecture. » book this tour

Music Box Theatre

This 1929 Chicago theatre used to show gorgeous two-screen movies. It is still perfect for movie lovers who enjoy the latest art-house films and documentaries. The main theater is gorgeous, and regularly hosts the director’s question sections. They also offer midnight screenings of cult classics. Grab some popcorn from the concession stand and make sure to catch a movie.

Time required: Set aside 1 to 2 hours to visit the Music Box Theatre.

Airport to here: Typically takes a Taxi 30 minutes and public transport takes an hour.

Wrigleyville

Wrigley Field is the home of the Chicago Cubs and might be one of the most famous places to see a baseball game. The stadium is very well designed and has a feel of nostalgia as you see the outfield walls and the manual scoreboard. Even the stands take you back and let you enjoy games whether the Cubs are performing.

Time required: Set aside 1 or 2 hours to explore the stadium.

Airport to here: Typically takes a Taxi 40 minutes and public transport takes an hour.

The Empty Bottle

The Empty Bottle might be the best rock club in the States. It is a proving ground for local and touring musicians to make their names in the music industry. It has the capacity to hold over 300 people as they rock out to electronic acts and experimental musicians on the rise. A visit to the Empty Bottle almost always guarantees a memorable show.

Time required: Set aside 2 to 3 hours to enjoy The Empty Bottle.

Airport to here: Typically takes a taxi 40 minutes and public transport takes an hour.

Steppenwolf Theatre Company

The Steppenwolf Theatre Company was founded in the basement of a Highland Park church, but has grown to embody the hardworking ethos of the Chicago theater community. It was home to some of the world’s most famous acting groups including Gary Sinise, John Mahoney, and William Petersen. It is still running and you can see great shows nearly every night of the week.

Time required: Set aside an hour or 2 to enjoy the theatre.

Airport to here: Taxi takes an average of 35 minutes while public transport typically takes an hour.

Museum Campus

Museum Campus is a massive natural history museum that was founded back in 1893. It has a permanent exhibition that spans 350,000 square feet. The most recommended part of the institution is the popular “Inside Ancient Egypt” exhibit, that recreates the tomb of the pharaoh’s son Unis-Ankh. It is full of Egyptian artifacts some aged over 5000 years old and it has the largest collection of mummies in the United States.

Time required: 2-3 hours.

Airport to here: Typically takes a Taxi 40 minutes while public transport can take more than an hour.

Millennium Park

The Millennium Park is a 25-acre park that is one of the most popular gathering spots in the city. This because it is the home of iconic public art installations like the Cloud Gate. During summer, there are free concerts and movie screenings.While in the winters, there are ice rinks.

Time required: You will need at least 2 hours to enjoy Millennium Park.

Airport to here: Taxi takes an average of 40 minutes while public transport typically takes a little over an hour.

East Garfield Park

Garfield Park Conservatory has a gorgeous glass structure housing more than 100,000 plants. Even better admission is always free though donations are welcomed. The Palm House is the conservatory’s largest room and is a great place to take a walk, it is almost like a paradise. Another room attempts to recreate the vegetation in Illinois millions of years ago, so make sure to check out the Fern Room.

Time required: 2 hours to 3 hours.

Airport to here: Taxi takes an average of 30 minutes while public transport takes an hour.