Leisurely walking tours are nice and all, but some people want pure adventure. Thank goodness Chicago offers exhilarating experiences for those out there on the wilder side. Have a look at the activities that you’ll want to check off your bucket list the next time that you’re around. 

Imagine staring straight down from more than 1,000 feet above. Yikes! When the fear of heights is not an issue, give TILT 360 Chicago a try. Located on the 94th floor of 875 North Michigan Avenue, the former John Hancock building, this innovative thrill ride offers a new window to the city with a glass-enclosed steel platform that tilts groups of up to eight ever so slightly a little over the edge. It’s worth it with the amazing views of the Magnificent Mile and the skyline that you won’t quite experience anywhere else. 

Meanwhile, on the water, the Seadog Speed Boat takes passengers on a riveting ride complete with twists and turns at a super-fast pace. Also, when the cruise is not zipping away, the experience includes interesting narration about the great city that is Chicago. You should note that getting wet will probably not be super difficult during this 30-minute boat ride that certainly flies!

Now it’s possible to feel the rush of floating in the air without having to jump out of a plane at iFLY Chicago, an indoor skydiving experience at Lincoln Park. This adrenaline-rushing activity involves putting a flight suit and experiencing unforgettable body flight in a gravity-defying, vertical wind tunnel two times per visit. The activity is safe and ideal for people of all ages and fitness levels. Plus, it’s great for families and groups. 

It’s okay to humblebrag after touring downtown Chicago from a helicopter. Prime views are what to expect when you sign up for a private helicopter ride from Chicago Aerial Tours. After departing from the Vertiport Chicago Heliport terminal, you’ll get to view the famous skyline and lake from a bird’s eye perspective. Ready? 

A little on the tamer side is taking in the fireworks at Navy Pier from the comfort of your seat on the Centennial Wheel. These are not just regular fireworks, by the way. They are a colorful pyrotechnic show synchronized to music overlooking gorgeous Lake Michigan that takes place Wednesday through Sunday from Memorial to Labor Day. 

Listen up ghouls and gals, Halloween will soon be here, and there are quite a few ways to celebrate the occasion. Whether you want to dress up and show off your costume, check out something scary or go trick-or-treating, there is so much to do in Chicago all month long. So what will it be?

So Wild

Families looking for a safe alternative to trick-or-treating should head out to Lincoln Park Zoo for Spooky Zoo, taking place on Saturday, October 26, 2019. Part of the annual Fall Fest, the beloved tradition also offers other fun activities from animal enrichment experiences to a fun corn maze, and more. Older kids and grown-ups who want to learn about the zoo’s haunted history can take a thrilling tour if they dare on October 29 and 30. Led by author, podcaster, and host of Mysterious Chicago Tours, this fascinating, 75-minute walkabout reveals scary things that you probably didn’t know including its cemetery past.

Phantoms of the Opera

Don your finest costume and wear a mask for the lively Lyric Halloween Masquerade. Hosted by the Lyric Opera of Chicago, this annual affair returns for an epic night of music by DJ Metro, dancing, signature cocktails, and bites from local restaurants. Besides, it’s all for a good cause with proceeds benefiting the emerging operatic talent of The Patrick G. and Shirley W. Ryan Opera Center. It goes down on Saturday, October 26 from 8 p.m. until midnight, so be there!

Halloween Fun at Navy Pier

Of course, Chicago’s iconic destination, Navy Pier, has a few things going on in honor of Halloween. Trick-or-treaters should bring a big bag and stock up on candy courtesy of participating establishments from 2 to 6 p.m. on October 26, 27 and 31st. Meanwhile, the Haunted Maze, is bound to instill frights thanks to spine-tingling twists and turns featuring ghosts from the Capone era and other dark moments from the city’s history. New this year is Cosplay on the Pier: Halloween Fest 2019, featuring a designated cosplay photo area, costume contests, and more on Saturday, October 26, from 2 to 10 p.m. What are you going to wear?

Not for the Faint of Heart

Stories of paranormal sightings and other grisly tales are in store during the Chicago Hauntings: Original Ghost Bus Tour offered throughout the year, including on Halloween. Veteran paranormal researcher Ursula Bielski brings brave groups to notorious sites from unfortunate tragedies, including the Eastland disaster, the Iroquois Theater Fire, and the St. Valentine’s Day massacre to the Hull House, which inspired the chilling movie Rosemary’s Baby. Known as the “World-Famous Supernatural Excursion,” this 2.5 to 3-hour excursion may have you sleeping with the lights on after it’s all over.

Ah, October—it’s a fine time for folks to revel in sweater weather, head outdoors for pumpkin-related festivities, pop into a museum, and enjoy exciting events with friends and family around town. Good thing there is a lot is going on, so be sure to make some room on the calendar for these worthwhile pursuits happening this month. 

Hey, Pumpkin

This is the season for all things pumpkin—pies, lattes, Jack O’Lanterns, parties. So, if you’re in the mood for some pumpkin, get to Jack’s Pumpkin Pop-up pronto. The cool interactive experience on Goose Island in downtown Chicago has plenty of displays of the bright orange fruit plus a challenging corn maze, carnival games, music, food trucks, bars, and a lively celebration open to all ages through November 3.

The inaugural Pier Pumpkin Lights event at Navy Pier is sure to become another fall favorite with its colorful pumpkin installations perfect for viewing after dusk with themed creations such as the Juggernaut of Jack-o-Lanterns and Pumpkin Picasso. Running through November 2, the seasonal celebration is a free public program that also features glowing light displays and deals on food and drinks at participating establishments.

Exciting Exhibitions

For those who prefer to be indoors, nothing beats spending a few hours immersed in culture. At the Art Institute of Chicago through January 5, 2020, “Rubens, Rembrandt, and Drawing the Golden Age” showcases the pinnacle of artistic creation in the Netherlands during the 17th-century.

On the other end of the spectrum, “Andy Warhol – From A to B and Back Again,” opening on October 20, is the first major U.S. retrospective of the Pop Art genius’ work since 1989 and will feature more than 350 works spanning the course of his career, including brilliant paintings of the famous soup cans and celebrity portraits as well as drawings, sculpture, video, and archival elements.

Festival Circuit

Cinema buffs won’t want to miss the Chicago International Film Festival taking place October 16-27, 2019. Presented by Cinema Chicago, the festival features an exciting line-up of movies from around the world, along with special presentations of the most highly anticipated releases, and themed programs including Architecture x Design, Women in Cinema and Documentaries including a Closing Night screening of The Torch that shines the spotlight on local blues musician Buddy Guy, who be in attendance.

The free public festival OpenHouse Chicago returns October 19-20, 2019 and offers an excellent opportunity to get an intimate look at more than 350 buildings throughout the diverse neighborhoods around the city. Hosted by the Chicago Architecture Center, the event offers access to skyscrapers, mansions, theaters and exclusive clubs with fascinating tours and talks that you don’t want to miss.

As far a comedy is concerned, Chicago is known for bringing lots of laughs. From improv to sketch and stand up, the city has established itself as a top destination for humor, hands down. On any given night, you can take your pick of places to see up and coming performers or famous faces commanding the mic. So the next time you’re in the mood to LOL, make your way to one of these popular spots.

Fans of improv pretty much have a definite destination in mind when they’re in Chicago: 1515 North Well Street in Old Town. The venerable address is home to The Second City, the legendary club, theater and school of improvisation that has been entertaining crowds since 1959. Outrageous and spontaneous skits keep the crowds coming, and don’t be surprised if the talented people you see on stage become famous on Saturday Night Live and beyond. Bill Murray, Dan Akroyd, Chris Farley, Tina Fey, Steve Carell, and Stephen Colbert are all alumni.

If you can’t get enough improv, the iO Theater in Lincoln Park is also a good bet. Founded by legend Del Close and Charna Halpern, the shows are sure to make you chuckle, especially any that involve long-form, anything can happen zany scenes of brilliance known as the Harold. The theater has also had a fair share of well-known comedians hone their chops here, notably Mike Meyers, Vince Vaughn, Amy Poehler, Seth Meyers, Jason Sudeikis, and Cecily Strong, to name a few.

Those who prefer stand-up should look no further than the Laugh Factory, the Chicago outpost of the famous California comedy club. Its weekly Chicago’s Best Standup Show is a showcase of rising local talent, but the venue is also known for drawing in headliners such as Dave Chapelle, Tim Allen, Whitney Cummings, Chris D’Elia and Kevin Nealon on occasion.

For something for the entire family, The ComedySportz Theater offers all-ages entertainment in its comedy, sports, and game mashup that involves a bumbling referee overseeing a hilarious battle of the wits unfolding along with anything-goes audience suggestions.

Along with these clubs on the circuit, big-name comedians also take their acts to Chicago. In August, watch out for Ali Wong at The Chicago Theatre, Judah Friedlander at The Hideout and Jeremy Piven at the Vic Theatre; and Norm Macdonald and Marc Maron at the Vic in September.

Ready for a romance in Chicago? Whether you’re in a blossoming relationship, have been together for years or are just looking for something fun to do on a first date, the city is full of terrific activities just for two. Who knows—maybe experiencing these attractions together will spark even more attraction!

When you want an easy, breezy, casual activity, a twirl around the Navy Pier Centennial Wheel may be in order. Besides, no matter how many times you have been on this classic Ferris wheel, the surrounding scenery and skyline never get old. You’ll always have something interesting to talk about with that special someone when you’re taking in the views high above at 200 feet.

Another low-key but lovely activity is going on a bicycle tour. Bike and Roll is the spot for rentals since it’s located adjacent to the 18-mile bike trail along the western shore of Lake Michigan. You’ll be in sync as you ride in tandem and take in the surrounding sites including Buckingham Fountain and The Shedd Aquarium, Field Museum, Millennium Park, Lincoln Park, and its zoo, to name a few. Oh, and helmets and locks are included with all rentals.  

What better way to see if there are fireworks than aboard an Odyssey Chicago River Fireworks Cruise? The two-and-a-half hour experience is available Wednesdays and Saturday evenings through August 31, 2019. Along with dancing, a DJ and a delicious dinner, couples enjoy dazzling views of the fireworks show from Navy Pier. For those who prefer a daytime date, one of the lunch cruises is always an option.

Cocktails, conversation and paint night are in order at Bottle & Bottega Chicago Downtown. The BYOB studio regularly hosts themed events that will inspire you and your special someone to hone your inner artistes including the Tuesday Happy Hour, the Couples and BFFs Painting Party, and the Chicago Skyline Painting Party.

If you’re searching for something that stands out for a date, Adler After Dark at the Adler Planetarium will make quite the good impression. The experience is never the same as themes change monthly. The 21+ over event happens the third Thursday of every month from 6:30 p.m. to 10:30 p.m. May through August, and 6 p.m. to 10 p.m. the rest of the time. From walking hand-in-hand through the exhibition galleries to gazing at the sky shows, dancing, and having drinks, the evening offers so much possibility.