There’s a lot to see in the Windy City. It’s not just about pizza and 1920s gangsters — Chicago features some of the best waterfront museums and parks I’ve ever encountered, plus fascinating architecture and great food. It’s also an incredibly easy city to get around in. Here are a few ways to see the city. Try them all and see the many attractions Chicago has to offer.
What you’ll see: Chicago Riverwalk, public art
Chicago is mostly flat, and it’s pedestrian-friendly, with lots of crossings and wide sidewalks throughout the city. And then there’s the Chicago Riverwalk, 6 blocks of pedestrian walkway in the heart of downtown, underneath Chicago’s cool bridges. Even cooler is that each block is meant to have its own personality.
Plus, if you explore on foot, you might run across some of the cool public art that seems to crop up every so often. The famous Cloud Gate (aka the Chicago Bean) is only one such piece.
What you’ll see: Chicago’s architecture
One of the things you absolutely cannot miss in Chicago is an architecture cruise down the Chicago River. It’s a bit touristy, yes, but it’s also a great way to learn a lot about the city’s history. Shoreline Sightseeing has fun tour guides, and you can buy discounted tickets using a Go Chicago card. And obviously to see some really cool buildings. The delicious Bloody Marys on board are just a bonus.
On a train
What you’ll see: different neighborhoods, Garfield Park Conservatory
Far from being just a transportation option, Chicago’s L train system can be a great way to see the city too. The downtown portion of it, called the Loop, passes right in between some of the city buildings. Trains and stations are older and functional, but sometimes they can be quirky too. And they’ll take you to attractions like the Garfield Park Conservatory, a donation-based educational building that houses various flora and a Chihuly installation. Great rainy-day activity!
From a skyscraper
What you’ll see: Chicago, view from the top
Chicago has a lot of tall buildings. From two of them, you can get a birds-eye view of the city and all it has to offer. Each of them came up with a different gimmick, so you can check out both towers and still have a different experience.
The Willis Tower (formerly known as the Sears Tower) allows you to be 103 floors above the ground on what is known as the Skydeck. The big draw here is the Ledge — you can step out into the air, sort of, with nothing but some glass between you and a painful fall to earth. Don’t worry though, that glass is 3 layers of half inch thick panels, with steel and iron supports.
The wait here is looooong. You must go through security just to get into the building, and there’s no fast pass or any such way to skip this line. Go early and bring your patience. Also, when you actually make it to the top, remember that the Ledge is the attraction, and there are lines here too. Take as many pictures as you like, but remember that there are a bunch of people waiting behind you. Luckily, there are a few ledges and there are several lines for each, so it’s really not too bad of a wait.
The other tower is the Hancock Tower. From here you have an amazing view of the Magnificent Mile. The observation deck is called 360 Chicago and it’s 94 floors up. They have a cool package called Sun and Stars, where for $21 you can visit twice in 48 hours so you can check out the view during the day and at night.
360 Chicago’s gimmick is called Tilt. Basically, one of the windows in Hancock Tower is something like a ride. You face out, brace your feet, hold on to some metal bars… and the platform underneath you tilts down 30 degrees. If you can keep your balance, it sounds like an interesting experience. However, Tilt requires a separate ticket and it’s extremely popular, so plan ahead!
What you’ll see: parks and plenty of attractions
Chicago is a bike-friendly city. The Lakefront Trail from Foster Beach south to the Museum of Science and Industry is 18 miles of paved path with Lake Michigan on one side and the city skyline on the other. Along the way you’ll pass such attractions as Lincoln Park, Millennium Park, Navy Pier, Shedd Aquarium, the Field Museum, and Burnham Park.
There are tons of rentals all around, the largest of which is Bike and Roll. Then there’s the bike sharing outfit Divvy. For another fun experience, you can try Wheel Fun Rentals. You’ll find them at Foster Beach or the Riverwalk. You can rent bikes, but you can also rent fun cycles for two or more people, like the Deuce Coupe or the Surrey. As someone who has trouble riding a bike, it was fun for me to still get around Chicago while sharing the cycling tasks with a friend.