Some time ago, my work took me from one side of the world to another: I moved all the way from Hong Kong to Chicago! After exploring all the nooks and crannies during my expat stint in the city, I’ve made a guide to help travelers visiting Chi Town for the first time. Keep reading to find my tips on where to stay, how to enjoy Chicago’s culture, and what to do on a night out!
Where to Stay
Before you start making your Chicago itinerary, you’ll need to decide where to stay. Below, I’ve put together some popular neighborhoods and included my honest opinion on each.
- The Loop is Chicago’s business district, and nothing really goes on here once the working day has finished. Being central, therefore, doesn’t mean being close to the action!
- West Loop is popular with a younger crowd, close to the center, and full of great restaurants and cafés. My only issues with the area is that I didn’t feel safe at night, and the public transport links were pretty poor.
- Wicker Park is really the place to be, but everyone knows that, so it’s very busy! There are interesting restaurants, quirky vintage shops, and always a special event going on.
- Old Town has tons of character, and lots to do in the evenings.
- Lincoln Park is full of older, beautiful brick houses, and lots of good foodie spots, but it’s fairly residential.
- De Paul is Chicago’s student area, but it’s far quieter than your typical college neighborhood.
Do a Boat Tour
You’ve decided on a hotel, hostel, or apartment, now it’s time to take in the city! A boat tour is a summer-only activity. Several tour companies also offer bars on their lower decks, so you can learn about Chicago with a drink in your hand!
Catch a concert at Millennium Park
It’s an incredible and purpose-designed concert space. Despite being outside, the acoustics are great. It might rain, but that certainly won’t dampen the atmosphere!
Try Your Hand at Whirlyball
What do you get if you mix basketball, lacrosse, hockey, and bumper cars? Whirlyball! No really, someone made this happen, and they are my hero. With three locations across Chicago it’s worth reserving a court in advance. It’ll set you back 25 US Dollars per person for each half an hour, and possibly some medical bills too. It’s a good idea to watch a video of a game in action before you try it yourself!
Visit the Chicago Cultural Center
Even if you only get as far as the lobby, the vaulted ceiling and stained-glass domes are incredible. In fact, it’s home to the largest Tiffany stained glass dome in the world! Check the website before your trip, as there are several events, exhibitions, and tours you won’t want to miss out on.
Go to the Beach
No really, there’s a beach in Chicago – over 40 kilometers of beach, in fact. Okay, it may only be warm enough to use it for a couple of months a year, but Chicagoans really know how to make the most of it. You’ll find volleyball tournaments, as well as people just hanging out and soaking up some rays. My favorites were North Avenue or Montrose, but there are plenty to choose from.
Check out the Roller Derby
It’s utterly addictive to watch! In fact, there are multiple leagues and teams in Chicago: Bruise Brothers, The Outfit, and Windy City Rollers are the ones that I saw. Try and go with someone who knows the rules, because the referees almost speak another language! You’ll find popcorn, hot dogs, and beer — all the American sporting classics to enjoy while you cheer on.
Take Part in a Brewery Tour
I’d recommend checking out Revolution Brewery, where you’ll find guided tours multiple times a week. You can’t pre-book, and tours fill up pretty quickly, so try to arrive as a group and be prepared to enjoy one of their brews for an hour or two as you wait for your tour slot.
Embrace your Inner Child
All those arcade games you used to play as a kid just got so much better; you can now enjoy them alongside a cocktail, beer, or glass of wine! Many bars have shuffleboard tables, but few have gone as far as Emporium in Wicker Park, which is packed full of games from air hockey to driving simulators and pinball machines.