Tourist Attractions in Chicago

Chicago is a city located in Illinois in the northern United States. This is where Al Capone and his mobsters held court, where John Dillinger took his last steps and where the St. Valentine's massacre took place, but it is also a place known for its skyscrapers and the beauty of Lake Michigan. has listed some of the activities available when exploring the city. Below is an excerpt of those activities all of which are within a reasonable distance from Chicago Midway Airport.

Chicago: 360 Observation Deck and TILT with Mob Bus Tour

This 3-hour tour begins with a skip-the-line entry ticket to 360 Chicago, one of the city’s most impressive landmarks, where you can ride up to the 94th floor to soak up the panoramic views of the city from the observation deck. From here you can see the city’s skyline as well as the lakefront and 4 neighbouring states.

This is also where you find TILT, probably the most thrilling Chicago attraction there is, where you get to see the city from a downward facing angle from over 1,000 ft/304 m height over ground. TILT is the first of its kind in the world allowing you to experience Chicago tilting over the city.

The exciting view of the city from above is contrasted with the 1.5-hour bus tour that follows it where you get to discover the underground world of infamous criminals, gangsters and mobsters. You will hear tales about Al Capone, the Untouchables, the Chicago Mob, John Dillinger and more, see sites such as the St. Valentine’s Day massacre and walk the last steps of John Dillinger, perhaps the most famous Chicago bank robber, maybe even in the United States.

Chicago Lakefront Segway Tour

Explore Chicago’s Lakefront as you glide effortlessly on your personal set of wheels – a Segway – while learning about the city’s history from the friendly and professional tour guide.

The eight-mile/13 km tour will let you view and learn about many of Chicago’s attractions in this unique way that also allows for some stunning phone opportunities. Some of the sites you will see and learn about are The Bean, The BP Bridge, The Buckingham Fountain, Field Museum, Grant Park, Michigan Avenue, Shedd Aquarium and Soldier Field as well as the gorgeous views of Lake Michigan and the majestic Chicago skyline.

The tour guide is a certified Segway tour guide and the tour includes a training session of how to ride the Segway safely, a helmet and a bag on the Segway to store your personal belongings during the tour.

Chicago: Art Institute Tour before Opening Hours with Guide

This tour is excellent if you want to experience a guided tour of some of the world’s greatest and most iconic art pieces at the Art Institute of Chicago without the crowds as it takes place before opening hours.

Your expert tour guide will meet you early to avoid the crowds and the lines and you will be able to stroll peacefully among the pieces, get up closer and more personal, than if there are crowds there, with works of art by famous artists like Pablo Picasso, Salvador Dali, Andy Warhol and Edward Hopper while your guide provides expert information and knowledge about the collection as well as the museum’s history and hidden gems.

The tour is approximately 2.5 hours long and has a get your money back guarantee if you are not satisfied.

Chicago River: 1.5-Hour Guided Architecture Cruise

This comprehensive sightseeing tour will not only take you on the main Chicago River, but also on the North Branch, as far as the Old Montgomery Ward Building, and on the South Branch, almost as far as Chinatown while you are entertained by the friendly expert tour guides as they talk about the 130 year-long history behind the skyline while staff and bartenders keep you comfortable.

Choose to enjoy the tour either on the open-air deck or in the comfort of the climate-controlled indoor area.

The tour begins at the Michigan Avenue (DuSable) bridge from where it goes up the main branch of the river and past Wolf Point followed by cruising along the north and the south branches before it is time to head back past the Chicago Riverwalk towards Lake Michigan.

You will see, and learn about, ornate, historic early skyscrapers like the Wrigley Building and the Tribune Tower, art deco buildings like Merchandise Mart, mid-century skyscrapers like Mies Van der Rohe AMA Building, the circular Marina City Towers, the majestic Willis Tower (formerly Sears Towers) – the tallest building in Chicago, as well as more modern structures like the Trump Tower and the new Vista Tower.

The full service cash bar provides authentic Chicago products, including local beer and spirits, and Garett’s Popcorn, not included in the price.

Chicago: Gangsters and Ghosts 2-Hour Walking Tour

This 2-hour guided walking tour is 1.5 miles/2.4 km long and it includes a 20-minute break at a famous gangster hangout. Children aged 6 and below may join this tour for free in the company of a guardian.

The tour will guide you through the Chicago Loop, known as the vice district of Chicago during the 1920s and 1930s. You will visit haunted locations and old crime scenes while hearing spooky tales of the ghosts and gangsters of Chicago from your historian tour guide.

You will stop at the Congress Hotel, Death Alley and the Palmer House and see places where mobsters and gangsters like Al Capone used to party, carry out threats and make deals.

Chicago: Hop-on Hop-off Open Top Bus Tour

The open top double-decker sightseeing bus gives you a vantage point from where you can enjoy a panoramic view of Chicago’s finest skyscrapers, including the Willis Tower (formerly the Sears Tower, and the tallest building in Chicago) and the Wrigley Building.

The tour has 13 stops, including the first stop where the ticket has to be redeemed, where you can hop-off to explore and visit attractions of your interest, and hop-on again when you are ready to go to the next site of your interest.

During the tour a tour guide will provide entertaining commentary and insights into Chicago’s history making the tour enjoyable even if you stay on the bus without hopping on or off.

Tickets come in different variations and include free WiFi on the bus as well as Big Bus App and Bus Tracker to keep track of when the next bus arrives at the stop you have hopped off at so you know when you need to be ready to hop back on.

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