City Cast Chicago logo

The Best Midwest Haunted Road Trips

Posted on September 26, 2023   |   Updated on September 30, 2025
Sidney Madden

Sidney Madden

A two-story red-brick mansion surrounded by trees and grass in Alton, Illinois.

McPike Mansion in Alton, Illinois. (Black.Doll / Flickr)

Itching for a weekend getaway and want to get into the Halloween spirit? Hop in the car and drive to nearby scary destinations.

⏰ 1 hour and 35 minutes

🚗 90 miles north of the Loop

Once a graveyard, the Capone brothers owned the building as a speakeasy and brothel. Later, serial killer Jeffrey Dahmer frequented the spot. Today, patrons can tour the haunted bar and stay overnight above the bar. City Cast Chicago lead producer Simone Alicea is making a pit stop …

⏰ 2 hours and 30 minutes

🚗 167 miles southwest of the Loop

Believed to be built on cursed ground, the Central Illinois library’s first three directors died unusually. Ghosts are thought to haunt the library to this day.

A statue of an angel with wings and arms spread out in the Oakland Cemetery in Iowa City, Iowa.

The Black Angel statue in the Oakland Cemetery in Iowa City, Iowa. (Krista Kennedy / Flickr)

⏰ 3 hours and 30 minutes

🚗 221 miles west of the Loop

Legend has it that the Black Angel statue has been struck by lightning and that virgins will die if they touch the 9-foot sculpture.

⏰ 4 hours and 30 minutes

🚗 287 miles southwest of the Loop

McPike Mansion is supposedly home to ghosts of former residents and servants. Unitarian Church and Mineral Springs are also popular haunted sites in the town. Hop on a ghost tour if you don’t want to explore alone.

⏰ 5 hours and 15 minutes

🚗 345 miles east of the Loop

Stay on the fourth floor of the historic hotel, where guests have seen toilets mysteriously flush and employees have heard doors shut in empty rooms.

Share article

Hey Chicago

Stay connected to City Cast Chicago and get ready to join the local conversation.

Can't subscribe? Turn off your ad blocker and try again.

The latest in Chicago

Chicago, ExplainedAugust 21

Take This Week's Chicago News Trivia Quiz

How closely were you paying attention to this week's current events in Chicago? Test yourself in our weekly trivia quiz.

A man in a cubs uniform bracing for a man in a white sox stealing a base
Keep It LocalAugust 20

How Transit Tees Turns Chicago’s Quirks Into Board Games

From board games about the city’s history to puzzles of iconic maps to card decks featuring local wildlife, Transit Tees’ teams of creato...

A person writing on a gridded paper that says "Chicago 1893" There's also a board game with an assortment of different houses for the board game on it. There is also A bowl of popcorn and a soda on the table
Keep It LocalAugust 20

Your Guide to Chicago’s Toy Stores

From vintage toys to a workshop series for aspiring toy inventors, Here's a list of places that’ll help you spoil the kids in your life a...

A table with an assortment of different stuffed animals
Keep It LocalAugust 13

Your Guide to Chicago’s Stationery Stores

Whether you’re actually going back to school soon or you just love analog hobbies, these local shops will help you find all kinds of stat...

A large group of people inside a store. They are looking at an assortment of items
Food & DrinkAugust 13

5 New Spots to Dine and Drink

Chicago is hot AF right now — and so is the dining scene. These recent openings have caught our eye.

A room with velvet drapes on every wall. On the ceiling there are chandeliers and people are sitting at a booth
Keep It LocalAugust 13

Family-Run Atlas Stationers Has Supplied Chicago’s Pens For Decades

For decades, the family-run shop delivered office supplies in bulk to offices in the Loop.

The outside of a brick building, the sign says "Atlas Stationers Inc"
Keep It LocalAugust 6

Your Guide to Dog-Friendly Patios

Want to enjoy patio weather, but hate leaving your pup at home? Check out our guide on the best dog-friendly patios in Chicago.

A curly-haired golden doodle wearing a harness steps into a small blue kiddie pool filled with colorful beach balls at a dog-friendly outdoor patio, with diners seated under blue and white striped umbrellas in the background.
Keep It LocalJuly 30

Why Creatives Love Epiphany Center for the Arts

Five years ago, a group of artists transformed a shuttered, historic church at 201 S. Ashland Ave. into Epiphany Center for the Arts. Sin...

An indoor space with hanging lights and a wood floor. The walls are short but the roof is very tall. There are small remnants of a church left like the windows