Adventure Activities in Chicago -- Try if You Dare

Adventure Activities Chicago

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Do any of us in Chicago even know what "Toddlin' Town" means? It was Frank Sinatra who coined the phrase in his famous song "Chicago, Chicago," but in all honesty, most of us who live here don't really have a clue. But we do know he was spot on when he described this place as "the city that never sleeps". If you're looking for an adventure activity in Chicago, you can find one at any hour of any day, any week of the year. You'd be hard pressed to find a city more up and awake; up all day, up all night, up to sharing its culture, food, architecture, diversity, fun and excitement at a moment's notice.

Here are my top five adventure activities in Chicago. They may not be out-of-body or mind experiences, but they are pretty intense, dare-devil ideas to try in Chicago, and you are unlikely to forget them easily.

1. See the (weird) sites: The Weird Chicago Tour

Step right up to the Weird Chicago bus and begin your first adventure activity in Chicago by taking a tour of the "most haunted city in America," according to tour creator Troy Taylor. The Weird Chicago Tour is based on the book 'Weird Illinois,' written by Taylor. He and his staff take you to see the bizarre, crazy, haunted, and of course weird places in Chicago. These adventures often deal with ghosts (Taylor has himself written nearly 40 books on ghosts). You'll finish the tour convinced ghosts are crawling the city of Chicago, and will be able to point out haunted buildings, blocks, neighborhoods, restaurants and pubs.

At some locations, you stay on the bus, while at others you disembark for further exploration and ghost hunting. Some sights are truly dark and creepy and the staff is rather odd but funny, as you might expect. They don't promise a ghost sighting -- but local legend has it that weird things have happened on this tour. Tours take place on Friday and Saturday nights and cost $30 per adult or $20 for kids aged 10-12. Children under 10 aren't allowed to come (due to the likelihood of nightmares).

Weird Chicago Tours, Chicago, IL 60622, 888-446-7859

2. Walk out on a (high) ledge: The Sky Deck

It used to be called Sears Tower and was the tallest building in the United States. Now it is called Willis Tower (although to locals the name will never catch on). Before you think "big deal: a 110-story building, 1,450 feet high, is not necessarily a big dare," think about walking out on a see-through ledge at that height and looking down.

A glass-enclosed box that extends four feet out from the 103rd floor (the sky deck), at 1353 feet above the ground, this adventure activity in Chicago is better known as "the ledge." You're likely to enjoy fantastic views that stretch for 50 miles and cover four states, if the weather is good and if you dare to open your eyes. Between the three layers of half-inch thick glass and the 1,500-pound glass panels used in the construction, you should certainly feel safe -- maybe. If you're not up for this well-known Chicago adventure, you can just watch other people freak out as they step into the box. The tower is located on the Miracle Mile in Chicago (to find it, just look up) and is open daily 9AM-10PM April to September and 10AM-8PM October to March. It's best to obtain tickets in advance through the website: the basic trip costs $15.95 for an adult and $11.00 for a child aged 3-11, although there are more expensive options including a queue-jumping ticket. This adventure will make your vacation unforgettable.

The Sky Deck, 233 S Wacker Drive, Chicago, IL 60606, 312-875-9696
Hours: April-September 9AM-10PM, October-March 10AM-8PM

3. Check out (punky) Delilah's

No Chicago adventure vacation would be worth its weight in Lake Michigan water without a trip to Lincoln Park to visit Delilah's. Yes, it is a punk dive bar with black painted walls, weird monthly rotating artwork and rockabilly-punk music. But it is so much more than just a punk dive bar: intimidating-looking bartenders who are actually nice; creepy movies like "Killer Klowns From Outer Space" on the tube; mismatched junk furniture patched up with duct tape, and over 400 types of whiskey.

The social aspect is boundless at Delilah's, with a diverse crowd of bikers, punks with tattoos galore, people with piercings in places you never thought possible, hipsters, and gawkers taking it all in. Most patrons seem to march to their own drum, but hey, it's Chicago. Be adventurous and visit Delilah's to enjoy two floors of fun, free pool tables, pinball machines and a ton of craft and microbrews. They also have 12 kinds of absinthe for those who like to dream up daring drinking activities and games.

Note that this Chicago adventure in entertainment and drinking is only open to patrons aged 21 and over. Take ID.

Delilah's, 2771 N Lincoln Avenue, Chicago, IL 60614, 773-472-2771
Hours: Sun-Fri 4PM-2AM, Sat 4PM-3AM

4. Eat some (elk) sausage at Hot Doug's

If you have to wait in line for food, it may as well be at Hot Doug's. Don't be a wimp and order a hot dog when you can have rattlesnake sausage with all the trimmings. My personal favorite is the bacon and cheddar elk sausage sandwich with bacon-garlic mayo and Black Mountain garlic-white wine cheese, served with duck fries. It's not so easy to pronounce all this, so I just point and smile.

Hot Doug's bills itself as "The Sausage Superstore and Encased Meat Emporium." In fact they also sell T-shirts with the slogan: There are no two finer words in the English language than "encased meat." Besides the usual duck, bison and alligator dogs, they have celebrity dogs like the Salma Hayek ("mighty, mighty, mighty hot" andouille sausage) and the Elvis ("smoked and savory" Polish sausage). Bring your dare-devil spirit, as well as cash; they don't take credit cards.

Hot Doug's, 3324 N California, Chicago, IL 60618, 773-279-9550
Hours: Mon-Sat 10:30AM-4PM

5. Ride the (L) train

There is nothing like the elevated L train system in Chicago. It runs all over the city like the spokes of a bicycle wheel. There is a pink line, a blue line, a red line and so on, so read the signage to get a handle on where each line takes you. The sights, sounds, and smells on the L can be rather unusual and daunting, but it is part and parcel of that "city" experience. The L is also fast, (sometimes) dirty, and gritty with as diverse a crowd as you are ever going to see.

It's definitely a unique family adventure activity in Chicago. When someone breaks out into song and dance on the L or starts preaching religion, it's all in a days work. Toss them a few coins if you like or simply ignore them -- it's up to you. Chicago sure is a melting pot, with some melting at a faster rate than others. Hop on an L train to experience "that Toddlin Town." Whatever that means. For more information on the L train, check the website of the Chicago Transit Authority.

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