Have at least three cheap umbrellas and one good umbrella at all times
No matter how many people tell you that the nickname ‘the Windy City’ comes not from weather but from 1800s politicians, the fact is, Chicago is really, really windy. Naturally, when going out in a storm, it’s important to have a strong umbrella to hold up against the wind. However, sometimes a good Chicago wind can mangle even the toughest umbrellas, and you don’t want to waste a big chunk of money on a new one every week. Keep a stash of cheap, easily replaceable umbrellas on hand for these situations.
The CTA monthly pass is your friend
If you ride public transportation to work, the $100 CTA 30-day pass will pay for itself just from your commute plus a few weekend trips. There’s something incredibly relaxing about knowing that you can take unlimited CTA rides without putting up any extra money. It’s pouring rain, and one of your three cheap umbrellas has just broken? No problem. Head to the nearest bus stop and rest assured that no matter how short your trip is, it won’t cost you any extra. On that note, learn the bus routes. There are buses running along the majority of streets.
Find excellent entertainment for free
Looking to see a show, watch a movie, hear some music, or just simply be entertained? You may not need to spend any money. For movie fans, Millennium Park’s Summer Film Series offers free outdoor screenings in the park during summertime. Millennium Park also offers a variety of shows, concerts, and activities through the rest of the year. Fans of stand-up comedy should check out the many open mic nights throughout Chicago, such as the Saturday night show at the Annoyance Theatre. No matter your interest, Chicago probably offers it somewhere for free.
Carry a backpack if you’re going to be out all day
Chicago weather will shift 50 degrees at the drop of a hat. When you’re planning an entire day out, it’s a good idea to keep a bag full of clothes for all types of weather. Maybe you’re shivering when you leave your apartment in the morning, but that doesn’t mean it won’t be a sweaty 80 degrees by mid-afternoon. And that doesn’t mean you won’t be freezing again by the time you get back home that night. Having shorts, long pants, and a sweatshirt on hand will ensure at least some level of comfort while riding the Chicago weather roller coaster.
Whenever possible, avoid riding the train at 5PM
Five o’clock is the obvious time to ride the train, since it’s when almost every person with an office job in the entire city of Chicago starts the commute home. If you are among those people, you probably often find yourself feeling like a sardine. Luckily, you can avoid at least a few of these sweaty, too-close-for-comfort trips with a little schedule restructuring. Is there a grocery store near your office? A gym? A bank? You’ll have to do all these errands eventually, so you might as well plan to do them before hopping on the train home from work.