Chicago is the Midwest's biggest city, and with its famously tall skyscrapers, notorious mob history, and famously decadent takes on everything from pizza to hot dogs to popcorn, it's definitely the most personality-packed as well. Whether you're sticking to the Magnificent Mile for some high-end, totally luxe shopping, going to Wrigleyville to immerse yourself in the thrill of a Cubs game, or heading out to Logan Square and Wicker Park to hang out with the hipsters, you'll see that there are many sides to Chicago that are all worth exploring.
1046 West Diversey Avenue, Chicago, Illinois, United States
Yes, Navy Pier is touristy...but it's still pretty fun. The massive Ferris Wheel is worth a ride at least once, and it can be nice to stroll past all the vendors hawking tchotchkes and enjoy the breeze and lakeside views. Fun fact: the world's first-ever Ferris Wheel debuted at the 1893 Chicago World's Fair!
When you're ready to work off that sandwich, head to Millennium Park. It's pretty huge, and home to all kinds of Chicago icons. You can't stop by the Windy City without taking a selfie by The Bean (aka Cloud Gate), or visiting the classic fountain. This park pretty much always has something going on, so plan to spend some time exploring.
By now hopefully you've worked up a big appetite, because Gino's East makes the best Chicago-style deep dish pizza in the city, and it is, in a word, intense. Nosh on slices of pizza with a rich, buttery cornmeal crust that's filled to the brim with gooey cheese, tomato sauce, and loads of toppings.
565 West Jackson Boulevard, Chicago, Illinois, United States
Southeast Corner of Michigan and Wacker, Chicago, IL, US
Chicago Architecture Foundation River Cruise aboard Chicago's First Lady Cruises
If you're afraid of heights, then you'll maybe want to pass on a trip to the Skydeck. It's located on the 103rd floor of the Willis Tower (better known as the Sears Tower, the tallest building in Chicago, and the Western hemisphere), which offers views stretching 50 miles into 4 states. And if you aren't afraid of heights, then you'll want to step onto The Ledge, a glass-floored box that lets you look straight down!
For a late-late night drink (we're talking 4 a.m. here), the Wieners Circle is perfect for night owls who are a little bit hungry...that is, if you can handle a side of verbal abuse with your hot dog and fries. The service is quick, the dogs are tasty, and the people-watching is incredible, the servers are famously sassy, and the crowd is often drunk.
1046 West Diversey Avenue, Chicago, Illinois, United States
Saint Joseph, Michigan, United States
Holland State Park, Holland, Michigan, United States
Holland, Michigan, United States
The best time of year to have a 48 hour adventure in Chicago: Winters (heck, even early spring and late fall) here can be brutally cold and windy...and it snows quite often, so aim to visit during warmer weather, unless a little chill doesn't bother you. Keep in mind, you'll be using public transportation and walking a bit, so dress appropriately.