1. The weather in the Midwest gets crazy sometimes. Locals joke about snow one day and 60 degree weather the next, but those jokes have root in the truth. I’ve seen it. The best (read, most consistent) time of year to visit is the fall, between September and early November. That’s when the bounty of trees in the city start changing colors, which gives the city skyline an even more colorful view. Just make sure to check the weather before you arrive.
2. That being said, summer in Chicago is one of the best times of the year, if you can stand the heat. It’s often cooler in the city thanks to lake effect winds from Lake Michigan, but the combination of high temperatures and high humidity make it hard for some people to bear. However, Chicago’s peppered with food festivals and fun runs throughout the entire summer like Taste of Chicago, which debuts every July and showcases the wide variety of Chicago’s dining scene. More on that in Eat.
3. As with most large cities, public transit is going to be your best option for getting around. The Chicago Transit Authority (CTA) was actually the first time I’d taken a bus or a train, and if I could figure it out, anyone can. Purchase a Ventra card if you’re going to be taking the El, Chicago’s train system. It’s a reloadable card that you put money on and swipe through in order to gain access to the trains. If the weather’s nice, they also have bike rental stations that are pretty cheap. It’s a great option for exploring the city.
4. The closer you get to the lake, and to Lake Shore Drive, the more expensive things will be. That goes for just about everything, including food, accommodations, and shopping. It’s the most popular/touristy area of the city, so definitely pay it a visit, but don’t spend your whole time there.
5. That being said, Lake Michigan (commonly called “The Lake”) will be the closest thing you can get to a beach in the Midwest. It has sand and water, so we’ll call it a beach. Unless you’re visiting in the summer, the lake will be cold so don’t plan to do lots of swimming while you’re there.
6. Download this playlist to listen to while you travel there. It’s 45 minutes of songs about loving Chicago, so it’s the perfect set of tracks to get you in the mood for going to the city.
7. You can nab coupons for just about everything at Union Station. It’s a historical landmark as well, so take some time to look around at the wonderful architecture.
8. The Sears Tower is now officially called The Willis Tower. No one actually calls it by its new name.
9. You can purchase a city pass that grants you access to the most visited museums and attractions in the city: Shedd Aquarium, Skydeck Chicago, The Field Museum, Museum of Science and Industry (Or Chicago 360), and The Adler Planetarium (or The Art Institute Chicago). With the pass you can skip the lines and enjoy special privileges.