Things to do in
Gold Coast Historic District

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Gold Coast Historic District: Our most recommended tours and activities

Chicago: 90-Minute Mob and Crime Bus Tour

1. Chicago: 90-Minute Mob and Crime Bus Tour

Experience Chicago’s underworld of criminals and gangsters on a luxury 90-minute bus tour. Find out how some of the world’s most famous criminals, mobsters, and gangsters conned their way through the city. Ride comfortably in luxury, on a climate-controlled bus, as you see famous Chicago crime scenes that range from the 19th century through modern times. Unlike Chicago walking tours, this Mob and Crime Tour isn’t affected by the Windy City weather. Learn from a local expert tour guide giving interactive live commentary about 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. Grab your camera for a drive-by shooting of the historic criminal courthouse, a Chicago architectural landmark where some of Chicago's most notorious cases were tried. You'll also view historic video footage, receive an informative pamphlet with photos, and can even take part in a crime quiz. Stake out crime scenes like the Biograph Theatre, Holy Name Cathedral, Clark Street Bridge, and other Chicago landmarks. See the site of the St. Valentine's Day Massacre, one of Chicago's most notorious murder scenes. Get off the bus and walk the path that notorious Chicago gangsters John Dillinger and Hymie Weiss followed just before their deaths. Travel into the criminal past of Chicago's River North, Gold Coast, Lincoln Park, Old Town, Loop, and Magnificent Mile neighborhoods.

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

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

From your vantage point on the double-decker sightseeing bus you'll enjoy panoramic views of Chicago’s finest skyscrapers, including the 875 N Michigan, the Willis Tower and the Wrigley Building. Take in the city's impressive landmarks as your tour guide provides entertaining commentary and insight into Chicago's history. Enjoy exploring this dynamic city with the freedom to hop-on and hop-off as many times as you wish to visit attractions such as the Shedd Aquarium and the Field Museum. You’ll travel down the famous Magnificent Mile, considered one of the great avenues of the world, and continue across the Michigan Avenue Bridge over the Chicago River. The bridge connects the north and south sides of the city. This hop-on, hop-off bus tour of Chicago makes it easy for you to explore the city's sights at your own pace. There are 13 stops, where you can hop-off to visit attractions and explore places of interest. The stops are conveniently located to make navigating your way around the city easy, and with a choice of Classic, Premium or Deluxe tickets, you can take your time discovering Chicago. Be sure to take advantage of admission to the Chicago Architecture Center, included with the Premium and Deluxe tickets, to dive deeper into the city that invented the skyscraper. So don't wait, just hop-on an exciting journey through Chicago.

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Chicago: 3-Hour Private Speakeasy Cocktail VIP Tour

3. Chicago: 3-Hour Private Speakeasy Cocktail VIP Tour

Spend an evening visiting the Chicago speakeasies that have been open since the Prohibition Era in the 1920s, many preserved in their original conditions. With your own private group, enter by way of secret entrances and enjoy the same cocktails ordered by infamous Chicago gangsters and bank robbers at these venues nearly a century ago. Relive the glamor of the 1920s while listening to stories of the rampant racketeering and bootlegging of the era.   Alcohol is available for purchase at the three to four different speakeasy stops. Your private tour guide will make Prohibition Era drink recommendations and tell you the stories behind them. Travel around with your young, professional guide and be chauffeured in luxury transportation, ranging from a luxury SUV to a full-sized luxury motor coach.

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Chicago Crimes Night Tour

4. Chicago Crimes Night Tour

Uncover how some of the world’s most famous criminals, mobsters, and gangsters conned their way through the Windy City. Ride in luxury on a climate-controlled bus, as you explore famous Chicago crime scenes ranging from the 19th century through to modern times. Learn about Al Capone, the Untouchables, the Chicago Mob, John Dillinger, The Lady in Red, Captain George Streeter, Frank "The Enforcer" Nitti, Bugs Moran, Johnny Torrio and more. Grab your camera for a drive-by shooting of historic and architectural landmarks, and stake out crime scenes like the Biograph Theatre, Holy Name Cathedral and St. Valentine's Day Massacre, one of Chicago's most notorious murder sites. Walk the path that notorious Chicago gangsters John Dillinger and Hymie Weiss followed just before their deaths. Travel into the criminal past of Chicago's River North, Gold Coast, Lincoln Park, Old Town, Loop, and Magnificent Mile neighborhoods.

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Bobby's Bike Hike Chicago: Lakefront Neighborhoods Tour

5. Bobby's Bike Hike Chicago: Lakefront Neighborhoods Tour

Hop on a bike and explore Chicago's lakefront neighborhoods! Bobby's Lakefront Neighborhoods Bicycle Tour is Chicago's longest-running and most popular bike tour. Veer off the beaten path and into the opulent neighborhoods, pristine parks, and packed beaches of the near north-side of Chicago. Explore the Gold Coast mansions, Old Town historic district, Lincoln Park, and the zoo, all on the bike. Pass by North Avenue beach and Chicago's lakefront while an experienced, knowledgeable guide explains the rich history and culture of the area. This tour is designed for all ages and fitness levels. Safety is our top priority, and guests follow bike paths for a majority of the tour. Bikes and helmets are provided.

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Chicago: Private Architecture Tour - 3 or 6 Hours

6. Chicago: Private Architecture Tour - 3 or 6 Hours

Start with pickup from your hotel and meet your local tour guide, an expert on the architecture of Chicago. Travel through the city in luxury private transportation to discover its rich architectural history. See famous buildings such as the Sears Tower, The John Hancock Building, and the Wrigley Building Discover Gothic gems along the Magnificent Mile, historic brownstones, and the Frank Lloyd Wright homes of Oak Park. Enjoy a unique added value opportunity to view not only the outside but the amazing hidden interior of many of the buildings on the tour. At your discretion, make numerous stops along the tour to go to the top of the sky decks of famous skyscrapers. Walk along the Chicago River and enter the inside of buildings designed by many famous architects. This tour has several different options. Enjoy the sites of the downtown Chicago area with its many skyscrapers, amazing interiors and great photo opportunities. You may also choose the Oak Park Frank Lloyd Wright Homes and Studio option in lieu of the downtown tour where you will have the opportunity to view the interior of his very first home and studio along with over two dozen of his original structures lining Forest Street in Oak Park anchored by Unity Temple, considered to be the world's first building of the modern architectural style. Each of the above separate options are 3 hours long. If you are to choose both options for a full 6-hour touring experience, enjoy a lunch stop at one of Chicago's many famous hot dog stands or deep-dish pizza joints.

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Other Sightseeing Options in Gold Coast Historic District

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What people are saying about Gold Coast Historic District

Overall rating

4.3 / 5

based on 692 reviews

Kai was an excellent guide for our activity last night. She had so much knowledge of Chicago history and when we requested more of history/ gangster knowledge vs just the speak easy stops, she made a significant pivot to make our activity specific to our requests. Would highly recommend this tour and Kai!

I was having a little bit of hard time finding the meeting spot but the customer service were very helpful and quick helped me to find it. Got to see the whole downtown. Over all it is a good experience and it’s worth the the try must try it!

A great way to figure out where you want to spend additional time. Canopy on the roof keeps you warm, even when chilly.

Such a fun way to see Chicago and get an over all feel of the city along with meaningful history!

A perfect way to see things you may not even think of! It’s was a great ride.