As Amazon Associates, we may receive a commission for purchases made through our affiliate links.
Chicago is seriously one of the best cities in America.
I love it because it’s a perfect mix of those stunning skyscrapers, world-famous deep-dish pizza, and a super rich culture.
It’s got a little bit of everything.
It is a huge place, though, so knowing a few key things before you arrive can save you time and make your trip way more fun.
Trust me, having the inside scoop makes a huge difference!
If you want to feel like a total local and see the best of the Windy City, you need to read these tips.
Here are 15 things every traveler should know before visiting Chicago.
1. Weather is Wild
Okay, first things first: the weather in Chicago is completely intense, so you have to pack for everything!
When I was there, I seriously learned why they call it the “Windy City.”
The winters are no joke!
They are super cold, and that wind whipping off the lake cuts right through you.
But then the summers are totally different, really hot and humid.
My advice is always to pack layers, even in the spring and fall, because the weather can change superfast from one hour to the next.
Do not underestimate that lake breeze!
2. Pick the Right Season
If you can choose your dates, you should absolutely aim for late spring or early fall.
Trust me, those are the sweet spots!
When I went in May, the weather was perfect.
It was sunny but not super hot, and the crowds hadn’t totally arrived yet.
Same for September and October.
By this time the city is beautiful, the heat and humidity are gone, and you can actually get into those popular restaurants without an hour wait.
Skip mid-summer if you hate huge crowds, and definitely avoid deep winter unless you love the cold!
3. Get on the “L”
You definitely do not need to worry about renting a car because the public transit here is seriously easy and awesome.
They call the train system the “L” (short for elevated), and it connects almost everything you need to see.
I used a reloadable Ventra card the whole time, and it was so simple to hop on the train or a bus.
The system is great because it is way cheaper than Uber and superfast for getting you from downtown out to those cool local neighborhoods without any fuss.
4. Walking is Key Downtown
One thing I quickly figured out is that you will be doing a lot of walking, especially right in the middle of the city.
The Loop, the Riverwalk, and spots like Millennium Park are totally designed for people to wander around.
I loved just putting on comfy shoes and exploring because everything is right there!
You can easily walk from The Bean to the Art Institute without needing a train.
It’s the best way to soak up all that famous architecture and feel the awesome energy of the city.
5. Passes Save Money
Okay, this is a super important money-saving hack.
If you plan to visit a few of the big places like the Field Museum, the Shedd Aquarium, or the Skydeck, you absolutely have to get the CityPASS.
I did this, and it saved me so much cash compared to buying tickets individually.
Plus, the pass sometimes lets you use a separate, faster entrance lane, which means less time waiting in line.
It’s totally worth it if you are doing the big-name attractions!
6. Layer Up Always
Seriously, one thing I learned is that you can never trust the temperature reading on your phone!
I was there in July and figured a tank top was fine, but that huge Lake Michigan breeze is a total trick.
The air whipping off the water can make things feel super cool, even when the sun is out.
I always carried a light jacket or a sweater in my backpack, even during the summer afternoons, because you will absolutely need it when you walk along the Riverwalk or near the lakefront.
Better safe than cold!
7. Eat Everything Famous
You literally cannot leave Chicago without trying the famous foods, it is mandatory!
I went on a serious food mission when I was there.
You have to experience a slice of deep-dish pizza.
It’s basically a pie, and it is totally different from regular pizza.
Also, you must try a Chicago-style hot dog, but remember the golden rule: no ketchup allowed!
Seriously, they will judge you.
And finally, get an Italian beef sandwich dipped in gravy, it is messy, but trust me, it is completely delicious and worth the risk to your shirt.
8. Museum Game is Strong
Chicago’s museums are seriously next-level, so you need to set aside a whole day for them.
I was totally blown away!
The Art Institute is famous for those amazing Impressionist paintings, and you could spend hours just wandering the halls.
Then you have the Museum Campus right on the lake, where you can see the dinosaurs at the Field Museum.
Check out the fish at the Shedd Aquarium, or explore science at the Museum of Science and Industry (MSI).
They are all massive, world-class spots that are definitely worth the ticket price, so choose your favorites!
9. Explore the Neighborhoods
The downtown area is cool, but you totally miss out if you don’t explore the local spots!
The neighborhoods outside the Loop all have their own unique personality, and I loved getting a real feel for the city by exploring them.
For example, I loved walking around Wicker Park for the cool shops and trendy coffee spots.
Then there’s Pilsen, which is absolutely covered in incredible, vibrant street art and amazing Mexican food.
Make sure you hop on the “L” train and spend an afternoon getting lost in one of these cool local areas!
10. Amazing Free Spots
If you’re traveling on a budget (which, hello, who isn’t?), Chicago has some seriously awesome free places to visit!
My favorite was the Lincoln Park Zoo because it’s completely free and you can still see amazing animals like polar bears and gorillas.
The Chicago Cultural Center is another hidden gem.
You have to go inside and look up at the giant, beautiful Tiffany stained-glass dome.
And of course, just walking along the Riverwalk is totally free and gives you incredible city views.
You can have a super fun day without spending any money!
11. Sports Are a Big Deal
You have to know that sports are a huge part of Chicago life, people here are seriously dedicated to their teams!
Even if you are not a major sports fan, trying to catch a game is a really cool experience.
I took a tour of Wrigley Field (where the Cubs play), and walking through that historic ballpark with the ivy-covered walls was amazing.
Whether it’s basketball with the Bulls, hockey with the Blackhawks, or football with the Bears, the energy in the city on game day is completely infectious and super fun to be around!
12. The Lakefront is Everything
The absolute best part of Chicago is having that massive, beautiful Lake Michigan right there.
I spent a whole afternoon biking along the 18-mile Lakefront Trail, and it was totally worth it.
The views of the water on one side and the stunning city skyline on the other are just unbeatable.
Plus, you can find little beaches and parks all along the trail.
It makes the city feel huge but also really open and connected to nature.
It is the perfect place to run, bike, or just take a long, relaxing walk.
13. Traffic Can Be Tough
Seriously, listen to me on this one: do not drive downtown! I mean it.
The traffic in Chicago can be a total nightmare, and finding parking is not only impossible but also ridiculously expensive.
I almost lost my mind trying to find a spot.
You are way better off just embracing the CTA (the “L” train) or using rideshares to get to those spots the train doesn’t reach easily.
Save yourself the stress and the money!
You’ll be much happier exploring on foot and using public transport!
14. Stay Aware and Safe
Just like in any big city, you need to be smart and aware of your surroundings to stay safe, which is super easy to do in Chicago!
When I was out exploring, I always made sure to stick to the busy, well-lit areas, especially when it got dark.
Downtown and the main tourist spots are usually buzzing with people, so you feel totally fine there.
If you’re going out at night, just be mindful, maybe stick with a friend or use a rideshare instead of walking long distances through empty streets.
Common sense goes a long way here!
15. Festivals Are Huge
Oh my gosh, one of the biggest reasons to visit Chicago is the totally massive festival scene they have all year!
I went during the summer, and it felt like there was something amazing happening every single weekend.
You have the famous Lollapalooza for music lovers.
Then there are also amazing food events like Taste of Chicago where you can try all the best local restaurants.
Then you have things like the Chicago Jazz Festival which is seriously so cool and laid-back.
It’s the best because it means the city is always buzzing with energy and fun things to do!
Conclusion
Okay, we just covered fifteen totally essential tips for visiting Chicago!
Seriously, knowing these things before you go will make your trip so much smoother and more fun.
Chicago is an amazing city that is just waiting to be explored.
It’s got that big-city excitement, incredible food, and some truly beautiful spots along Lake Michigan.