A Halloween Weekend in Chicago

Few cities boast a history as rich as Chicago’s. As a gritty town that transformed with astonishing speed into a global metropolis, it inevitably endured a number of growing pains along the way — and some of those pains were dark, even sinister.

Evidence of those ominous times is on display at the International Museum of Surgical Science, the first stop in your spooky Chicago adventure. Use the museum’s mobile app during your visit to go on a self-guided tour exposing you to grim secrets from the past and some of the darkest tools in the history of medicine.

Venture out into the sunlight and down to the Chicago Historic Water Tower. On the surface, it seems like a harmless destination — until you learn that a fireman who perished fighting the Great Chicago Fire of 1871 continues to haunt the iconic building to this day.  

Don’t worry, your next stop will be free from ghosts and evil influences. Meander south and pop into Eataly or Rosebud on Rush for a Chicago-style lunch. Next up is a stroll along the Magnificent Mile, one of the nation’s most renowned shopping corridors, where you’ll be amazed at the number of retailers, boutiques and department stores that anchor this area of the city. 

Rest your weary feet at Palm Court in the Drake Hotel, a stylish cafe renowned for its afternoon tea, where you’ll have 17 unique tea blends and a variety of gourmet pastries to choose from. It’s a highly popular experience, so we recommend making reservations ahead of time.

Next, we go up...and up...and up. The Signature Room at the 95th sits atop a skyscraper, supplying unbelievable views from all angles and an outstanding dinner menu, including a raw bar. Order dinner, or simply enjoy a cocktail and opt for dinner elsewhere. Adobo Grill is one of the best Mexican restaurants in the city, and it’s surrounded by the many attractions that call the Old Town neighborhood home. 

Now that night has fallen, it’s time to delve into the more mysterious, chilling aspects of Chicago’s checkered history. If exploring the city on foot piques your interest, sign up for a Haunted History Downtown Walking Tour with Weird Chicago. They change up the tour regularly, so you never know what’ll be lurking around the next gloomy street corner. 

What’s that you say? You have the moxie to spend the night on the water, paddling the murky Chicago River? Book a City Lights Night Paddle with Kayak Chicago, and see a side of the city that few others ever do. 

Those who want to experience some of the city’s most haunted pubs and alleys should partake in a Nightly Spirits Ghost Tour & Pub Crawl. You’ll cover one notoriously creepy mile over a two-hour period. Spots fill quickly, so make sure to register ahead of time.

If the night has left you yearning for a soft bed into which you can burrow for comfort and safety, we don’t blame you. Chicago is home to dozens of exceptional hotels, so feel free to search for your perfect option. 

It’s worth highlighting a few well-known hotels deserving of your consideration. The Drake Hotel (where you enjoyed tea earlier in the afternoon) is an illustrious establishment with a storied history that spans more than 100 years. Dating back to 1893, the Chicago Athletic Association is a historic landmark in its own right, with a host of amenities that will make for a memorable stay.

Steps from the beautiful Lincoln Park, Hotel Lincoln has an authentic, vintage feel. On its roof, you’ll find the J. Parker, widely considered one of Chicago’s best rooftop bars. A bit further north, you can check into the Hotel Versey Days Inn by Wyndham, a boutique hotel with European-style charm.

Embark on your day with a walk to Lincoln Park, but don’t hurry — look around, and observe the city coming to life.  The morning sun reflecting off the lively red, yellow and brown leaves will make the park a sight to behold as you approach.  

Stroll through the pristine gardens, and don’t overlook Lincoln Park Zoo, one of the best free wildlife experiences around. While inside, you may even hear the unnerving sound of a wolf’s howl, or the menacing flap of a bat’s wings as it zips through a dimly lit corridor. 

Oh, that reminds us: both the park and the zoo sit on land that once served as the original city cemetery. But one night, when officials attempted to move the bodies further from Lake Michigan, the Great Chicago Fire hit...so their ultimate fate remains a mystery to this day.

Speaking of graveyards, the Chicago History Museum is situated on a former burial site. Many believe that, because of the disruption to their resting place, the spirits who previously resided on this property now haunt the museum itself. Ask around — if you’re lucky, you’ll hear secretive chatter of ghostly anecdotes and inexplicable sightings. 

When hunger calls, wander a few blocks away on Clark Street and stop at R.J. Grunts. Anything on the weekend brunch menu will quickly and deliciously restore your energy, and the funky ‘70s vibe is sure to leave you in good spirits. 

It’s a beautiful autumn afternoon and Navy Pier beckons. Spend some time meandering the pier, checking out its myriad attractions. Before the last rays of daylight disappear from view, step into the Navy Pier Beer Garden, a scenic waterfront spot for free, live music performances and local craft beer from Tangled Roots Brewery.

Luckily, you won’t need to travel a great distance for dinner — Giordano’s Pizza at Navy Pier is just the ticket. Nothing warms you up on a cool fall evening quite like a gooey, stuffed deep-dish pizza from this legendary Chicago restaurant. 

Once you’re done eating, any Instagrammers in the group should make sure to have their phones at the ready, because you’ll want to post some photos of the Pier Pumpkin Lights installation, where you can expect to find jack-o'-lanterns galore all October long.

Hopefully, you’re ready to plunge back into the shadows of the city’s squalid underbelly. Your first option is the Chicago Hauntings Ghost Tour back up in Lincoln Park. With this eerie expedition, unlike some of the others, you won’t be relegated to passive bystander — you’ll get to actively hunt ghouls amid the lost graves of the cemetery and at the site of the St. Valentine’s Day Massacre. 

Or, instead, you can opt for the Windy City Ghosts haunted tour of the North Side. In addition to the spooky nooks and crannies of Lincoln Park, you’ll explore haunted taverns, ghostly theaters, and other Chicago sites where mystifying, supernatural occurrences are too commonplace for comfort. 

You’ve done a lot of walking; perhaps you’d prefer to give your feet a rest? Then go with an Absolutely Chicago Segway haunted tour downtown instead. Led by a guide, you’ll flit through notorious city streets, learning about famous disasters, murders, bad actors and frightening stories scattered throughout Chicago’s history. 

You could retire to your hotel at this point, but a Halloween-themed jaunt through the city isn’t truly complete until you visit the Red Lion Pub. Many people are convinced that the tavern is haunted by several ghosts, one of which is a young woman who smells strongly of lavender. It’s safe to pay the bar a visit, but once you catch a scent of lavender, you may want to officially call it a night.

Today’s agenda brings us to the South Side. At Plein Air Cafe in Hyde Park, you’ll be revived by superb artisanal coffee and comfort dishes in an elegant, French-inspired setting.

Those craving the flavors of a Mexican-style meal should instead head to Frida Room or 5 Rabanitos in Pilsen. At the former, you’ll find staples like chilaquiles, pancakes, and paninis. At the latter, a creative weekend brunch menu with dishes like huevos rancheros and breakfast enchiladas awaits to tickle your taste buds.

Once you finish up, it’s time to choose the cultural adventure of the day at one of Chicago’s staple institutions. The National Museum of Mexican Art’s annual Day of the Dead exhibition, which runs through mid-December, gives visitors an opportunity to join in on the tradition of honoring and celebrating the lives of lost loved ones.

If you’d rather err on the spooky side, one of the most popular exhibits at the Museum of Science and Industry happens to have a haunted element as well. You can experience the legend of the Museum’s German U-505 submarine via an immersive onboard tour, complete with dramatic lighting, sound effects, and an illuminating Q&A session.