Halloween and Autumn Tours in Chicago


Summertime Chi has officially taken a bow and in comes it’s pumpkin-spiced counterpart: autumn. Autumn in Chicago isn’t brimming with street festivals every weekend, but there is still a lot to do in the city; just don’t forget to bring your jacket! The city has the usual pumpkin patches, farmers markets, and haunted houses to check out, but if you want to do something a little more exciting and even educational, there are some pretty fun tours that you can take around the city.   

We’ve put together a list of some of the more interesting tours offered this season and that we recommend you check out! Most of them are halloween-themed, but if you love nature and cooking or want to learn about what lays below our downtown sidewalks, we’ve got something for you too! Be a tourist for a day and learn some cool Chicago facts while enjoying the view of autumn’s leaves adorning our beautiful city.  


Weird Chicago – Haunted History Tour  

This spooky bus tour is three hours long, open to all ages, and is based on 25 years of research and experience. Be sure to check the website out for available dates and times. We recommend booking ASAP to ensure you get a time and date that works for you! 

Adult Price: $40* 
Kids: $30* 

Schedule: Various dates available through December, check the website for more information. 


From the Weird Chicago website:  

Not another boring tour with made-up legends and shoddy research, but a mixture of ghosts, gangsters, true stories, and everything else that makes our tour so great and has earned us so many fantastic reviews! Join us and experience Chicago’s many ghosts, haunted history, and all around strangeness! We don’t just drive past Chicago’s spooky places, we let you experience them first-hand! Often imitated, but never equaled, it’s a tour of the Windy City that you won’t soon forget! 


Seadog Cruises – Chicago Haunted River Tours  

This nautical cruise along the Chicago River is sure to deliver frights and sights. Hop aboard the iconic Seadog docked at Navy Pier and enjoy a spooky boat ride before the river freezes over. The tour will cover fun and scary stories of Chicago’s past, while you enjoy some of the best views of the city.   

Adult Price: $41.95*  
Kids: $24.95* 

Schedule: Fridays – Sundays, October 1st – November 3rd, check website for times. 


From the Seadog Cruises website:  

Experience the sights, lights, and frights of Chicago this Halloween! Through the month of October, discover Chicago’s spookier side aboard Seadog’s Haunted River Tours. Let our talented tour guides divulge the many secrets, spirits, scandals, and sins of the Windy City through spine tingling tales of mysterious supernatural occurrences and infamous figures along the beautiful Chicago River. 


Atlas Obscura – Haunted History Cruise on the River  

This spooky yacht tour along the Chicago River is hosted by Adam, who also hosts the “Hidden Stories at Graceland Cemetery” tour, and has a few published books to his name, including Ghosts of Chicago. The tour only has a few dates left and is safe for kids aged 5+. 

Tour Price: $33* 

Schedule: Only a few dates left, check the website for updated information.  


From the Atlas Obscura website:  

Enjoy a dark twist on the world’s greatest architecture tour route. Over the course of this 90-minute cruise along the Chicago River, you’ll learn about infamous murders, strange submarines, gruesome disasters, unsolved mysteries, ghost stories, urban legends and other strange tales from the windy city’s history, all while viewing some its most iconic sights. 


Atlas Obscura – Hidden Stories at Graceland Cemetery 

This unconventional cemetery tour at Graceland Cemetery is hosted by Adam, who also hosts the “Haunted History Cruise on the River” tour among others. Adam has a few published books to his name, including Ghosts of Chicago. The tour only has a few dates left and is safe for kids aged 5+. 

Tour Price: $20* 

Schedule: Only one date left (Sat, Oct 12), check the website for updated information.  


From the Atlas Obscura website:  

Meet at Graceland’s historic entrance for an in-depth tour of the most fascinating stories and monuments at the cemetery, presenting a unique view of Chicago (and American) history. Stories in the cemetery go far beyond the industrialists and “movers and shakers” who ended up with streets named after them. Though the tour will of course include the famous “Inez” and “Eternal Silence” statues, I’ll focus on lesser-known but equally interesting tales, some of which have never been published. Though the route can vary from tour to tour, some of the stories here include Underground Railroad workers, a woman who funded the research behind the first birth control pill, a detective murdered by Jesse James, America’s first known female spy, a man whose cause of death was listed as “brutality of policeman,” a reporter who saw Einstein naked, and more. The stories will be endlessly fascinating and often hilarious. 


Atlas Obscura – Old Joliet Prison: History and Hollywood 

Take a tour of one of the better-known Chicagoland prisons and get to know some of the star-studded and spooky history of the Old Joliet Prison. The tour includes a 90-minute guided walking tour through the prison and ends with a look at the different TV shows and movies that have featured the famous location.


Tour Price: $35* 

Schedule: Only two remaining dates available (Oct. 13, Nov. 9), check the website for updated information.  


From the website:   

Trace the footsteps of inmates, guards, and movie stars on this exclusive tour of a 160-year-old suburban Chicago prison. First, you’ll meet me outside the barbed-wire fence of Old Joliet Prison. Then, a docent from the Joliet Area Historical Museum will take you inside the former correctional center for a 90-minute walking tour that highlights the prison’s sally ports, cellblocks, chapel, yard, and solitary confinement cells. Finally, you’ll make your way to the gymnasium, where we will explore how Hollywood has incorporated Old Joliet Prison in films like The Blues Brothers and Derailed and the TV series Prison Break and Empire.


Atlas Obscura – The Chicago Underground Scavenger Hunt 

This isn’t a conventional tour, but a scavenger hunt makes for a fun way to get to know Chicago’s underground pedway! The hunt is anywhere from 1-2 hours, but it all depends on how quickly you are able to get through the scavenger hunt. If you get stuck, you can always call the host for help.  


Tour Price: $45* 

Schedule: Only a few dates available (Oct. 5, Nov. 2, Dec. 7), check the website for updated information.  


From the Atlas Obscura website:   

Join me for a unique scavenger hunt game that will help you learn the history of the Chicago Pedway and how to navigate the city completely underground—something many Chicagoans don’t know how to do. When we meet, I’ll give you a set of 10 questions to answer, all corresponding to locations in the Pedway. It’s a race to find the location, write down the answer, and follow the directions to the next question. You can use your smart phones to help you, but you’ll still have to visit each location to win. I’ll be hiding in a secret, last location. To win, be the first to find me with the correct answers. If you’re the first one to arrive, you’ll get a prize! No matter what, everyone is a winner, and each guest will receive one drink of their choice. 


Odd Produce – Foraging Tour 

Last, but not least, is a one of a kind nature-centered foraging tour that ends with a foraged meal whipped up for guests at Carnivore.  


Price: $40* (tour, $70* for a pair of tickets) + $25* (per meal, includes one beverage. BYOB); 

Schedule: Sep. 29 and Oct. 20 – 10:00 AM  1:00 PM, check the website for more details. 


From the Odd Produce website:  

Forage with Chicago’s renowned professional forager Dave Odd. Learn over 50 species of edible plants and possibly some mushrooms too! Followed by a wonderful 3 course meal made from the foraged things seen, marvelously prepared by chef Brad Knaub and Erik Williams.  Mushrooms should be a poppin’.  Meet right in front of Carnivore 1042 Pleasant St, Oak Park. 

Call or text Dave at 847-409-8623 to RSVP 

Whether you’re into spooky history tours, underground architectural scavenger hunts, or learning about foraging local vegetation, one of these tours will give you a reason to get outside and enjoy the crisp Chicago autumn breeze before the frigid winter temps hit us again and the city starts hibernating.  

* Please note: the above listed prices may not include taxes or processing fees. Be aware that each tour company has a different age range for kids’ pricing. Be sure to check website for any updates or changes to pricing as they are subject to change.  


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