Chicago also known as the Windy City is next to Lake Michigan and the third most inhabited metropolis in America. It boasts several iconic buildings, landmarks, and museums such as the Chicago Theatre, Field Museum, John Hancock Center, Pritzker Pavilion, Shedd Aquarium, and Willis Tower. The city also gained infamous for the actions of the Italian mob, especially during the prohibition in the 20s and 30s when the US Government instituted a nationwide band on alcohol. This resulted in plenty of deaths and haunted spots around Chicago that are worth discovering. Check out our comprehensive list of Halloween tours in Chicago, USA and book your favorite one today!
If you can hold your liquor and willing to explore the darker side of Chicago, then this haunted evening pub tour may be for you. This gripping tour begins at the Red Lion Bar, where you’ll meet your colorful guide that adorns period dress. After ordering you drink and getting acquainted with everyone in your tour group, you’ll head off into the night.
Your guide will take you through creepy alleyways and cemeteries and tell you stories about murdered mobsters, disappearing hitchhikers, and scary ghosts. The entire tour covers a distance of 1.6 kilometers (1 mile) from Lincoln Station. You’ll visit three pubs along the way, and you can order drinks at your own expense. Please be aware that this tour is only for people 21 years of age and older.
Haunted Chicago Ghost and Pub Walking Tour
Duration: 2 hours 30 minutes
The Halloween excursions we’ve already covered are either walking or bus tours. But how about taking a moonlit tour with a Segway? Sounds like a ton of fun, right? Well, you’ll have much to look forward to after meeting your costumed guide at Millennium Park. Everyone partaking in this tour will undergo a short orientation to understand how the Segway operates and for safety reasons.
After that’s done, you’ll all head off into the alley where many died in the Iroquois Theater fire of 1903. Then, you’ll visit a hotel ballroom at Michigan Avenue where you’ll hear a piano being played without a human in sight! Furthermore, you’ll visit the Chicago River where hundreds of people drowned in 1915, and learn about mob-related crimes and landmark buildings in the area.
2-Hour Haunted Segway Tour of Chicago
Duration: 2 hours
This tour’s expert guide has comprehensive knowledge about Al Capone and other nefarious gangsters. Thus, this tour is ideal for those that wish to learn more about these characters and the Chicago Loop, a vice district for bootleggers, mobsters, speakeasies, and secret tunnels. Participants will also visit various gangster hideouts and haunted sites such as Congress Hotel, Death Alley, and Palmer House.
This tour isn’t just about gangsters, as the tour guide will also reveal much about ghost sightings in the area, accompanied with scary ghost stories. This tour takes place during the evenings and participants meet their guide next to the Wyndham Grand Riverfront Hotel.
Gangsters and Ghosts Tour in Chicago
Duration: 2 hours
It seems that every nook and cranny in Chicago features some spine-chilling secret. And this particular tour does a great job of emphasizing the more macabre side of the city, even if it’s actually a pleasant place to visit. If you can stomach stories about murdered gangsters and serial killers, then you’re going to have blast. Furthermore, you’ll visit places where horrific events occurred such as Death Alley, Murder Castle, and Old Congress Hotel.
Keep in mind that this is a private tour, and caters to those with disabilities. Tourists staying at select hotels qualify for a pickup so ask the tour about these hotels beforehand.
Private Haunted History of Chicago Ghost Tour
Duration: 3 hours
Chicago is famous for its notorious Italian mobsters and delicious deep-dish pizza. There’s no better way to gain insight in these two fascinating topics, then partaking in this crime and pizza walk. You’ll visit various historic buildings and sites where Chicago’s gangsters congregated and committed crimes, many of which are in the River North and Gold Coast neighborhoods.
Hollywood movies have glamorized the Italian mafia; however, this tour reveals their horrific actions and will leave you with much to ponder. Learning about these seedy characters may leave you feeling a little a grim, but you’ll do so with two slices of deep-dish pizza from the legendary Pizzeria Uno. Make the most of this walk by bringing along a bottle of water and wear comfortable shoes.
Crime and Pizza Walking Tour in Chicago
Do ghosts fascinate you? Do you get excited when things go bump in the night? Then, you’re bound to have a good time on this ghost bus tour that delves deeper into Chicago’s spookier side. You’ll be transported to interesting locales such as the City Cemetery, Death Valley, Levee Vice District, and Prairie Avenue and learn about the horrifying St. Valentine’s Day massacre.
The guide has ample knowledge about the grotesque murders that occurred at these places and haunted areas where spirits still linger. This tour is limited to 15 people and is ideal for families and groups of friends, and starts and ends at the Chicago History Museum.
Chicago Hauntings Original Ghost Bus Tour
Duration: 2 hours 30 minutes
Get your fill of ghosts and gangsters
Chicago is a fascinating city, but one with a dark past that’s terrifying and thought-provoking. If you’re not squeamish, then book one or more of these tours that will keep you on edge but also entertained.
Get Trip101 in your inbox
You can buy and claim online, even after you've left home. Travel insurance from WorldNomads.com is available to people from 140 countries. It’s designed for adventurous travellers with cover for overseas medical, evacuation, baggage and a range of adventure sports and activities.
*5% off when you book with our promo code: TRIP101
*For our Canadian and US travellers, unfortunately due to financial services laws, we cannot provide a discount. This promotional code cannot be used with any other discount offer, including World Nomads Members’ discount for travel insurance policy holders.