Chicago, Illinois and Lake Michigan

Planning A Trip To Chicago? Here Are 10 VERY Useful Things To Consider First!

Planning a trip to Chicago anytime soon?

Chicago is a great city with so much to offer in all seasons.

It’s a city with so much liveliness no matter when you come to visit, with countless things to do and see within and beyond the city.

Along with this, the fact that it is such a diverse city (which I love) further offers everything from food options, cultural neighborhood clusters, a variety of languages spoken throughout the city, and so much more!

This makes the city such an amazing place to visit in the Midwest and the States as a whole!

So, as a somewhat local (I don’t live in the city, but I travel often to the city, and the school where I studied was located in the heart of the city) I have learned my fair share of do’s and don’ts and what to expect when you visit Chicago.

So below, I’ve gathered up some of my top 10 VERY useful things to consider if you’re planning a trip to Chicago!


10 very useful things to consider if you're visiting Chicago

1. Don’t plan on there being much activity in The Loop after 6pm…

Perhaps it is because of the sight of all the skyscrapers and such that we think it is where all the action is, but many times that’s not the case.

When planning a trip to Chicago, make sure to make plans to explore a little more beyond The Loop, especially if you’re visiting during the weekday.

Chicago’s Loop is essentially the business district of the city, and when 5 o’clock hits, you might as well go into a Starbucks or a museum and get out of the way of crowds of business commuters on their way to their trains and cars back home.

I’m not trying to discourage anyone from visiting this area, but just be mindful that like business districts in every city, after a certain time during the day, it gets quiet and it’s not really popping with locals.

Especially if it’s winter, you’ll most likely find the locals dining at one of the many restaurants throughout Chicago, mostly their favorite local neighborhood joints, or ordering in from Grub Hub if it’s too cold out to leave the warmth of their homes.

2. Take the weather warnings seriously

Just this year on January 30th, our humble city of Chicago hit a new record low of dropping down to -23 Fahrenheit (-30 Celcius).

Since living in Illinois (around 16 years now) I’ve had just about the same amount of snow days related to temperature drops than to actual snow accumulations because oftentimes, those are the most dangerous conditions to walk out into if you’re underdressed.

When you visit Chicago (especially if you come in the Winter) make sure to check out the weather forecast often, and pack accordingly.

If you don’t have a good jacket and you plan to walk outside visiting the Bean and Michigan Avenue, I’d suggest you purchase one while you’re here.

The good thing is that being in a city with frigid temperatures, you’ll have many options to choose from, amongst many different and stylish designs that serve both style and functionality to protect you from Chicago’s frigid temperatures.

Read More: The Ultimate Winter Packing List: Chicago Edition

3. Don’t skip out on visiting Chicago in the winter!

That being said, however, if you happen to be visiting the Windy City during colder climates, don’t think there won’t be anything to do! Chicagoans know how to still have fun even when it’s an ungodly temperature outside by having lots of indoor events and activities to keep everyone entertained.

Get your culture on and visit the different history, science, and culture museums throughout the city, test your problem-solving skills and experience an escape room, have a laugh, and go see a future comedy star in action at one of the many stand up comedy shows throughout the city, and so much more!

There are many fun things to experience uniquely during the winter in Chicago that will make you tolerate the cold just a tad more.

Just think of it all as the Chicago experience. It’s about perspective, right? 🙂

Read More: What To Do in Chicago During The Holidays

4. The “Willis” Tower

Just thought I would slip this one into the list, just think of it as some local culture. I am sure that other Chicagoans reading this one have their own opinion on what this building should be referred to…

10 very useful things to consider if you're visiting Chicago

For as long as I can remember (and many others), this building was called the Sears Tower. In 2009, the insurance broker Willis Group purchased the city’s tallest building and changed the name.

Since then, people have been slightly divided on what to call the building, although officially, it is the Willis Tower.

For many Chicagoans, including yours truly, it will probably keep being called the Sears Tower. So, just so you know, there’s a little Chicago culture for ya.

5. Don’t just think it’s Chicago Dogs and deep-dish pizza here…

Visit one of Chicago’s 7,000+ restaurants serving everything from world-class cuisine to yes, deep-dish pizza!

As I mentioned in my How To Become an Everyday Explorer/Traveler Video – there is such diversity in the city of Chicago in its people, neighborhoods, and cultural influences, and as a result, it is reflected in the food options.

Everything from Mexican food, to Italian classics, and Vietnamese and Thai.

In addition, Chicago is home to some of the most amazing, talented chefs creating their mark on the culinary scene.

Chefs like Rick Bayless who has some of the best Mexican food you’ll have outside of La Villita and Pilsen (Mexican cultural neighborhoods), or Chef Grant Achatz’s (whom you might have seen on Netflix’s The Final Table) and is known worldwide for his progressive work in the culinary world through molecular gastronomy.

Whether you’re looking for a high-end culinary experience, or you’re looking for that authentic Chicago flavor, there’s something for everyone, no matter what you’re looking for.

10 very useful things to consider if you're visiting Chicago
With Chef Rick Bayless at one of my favorite restaurants in the city, Xoco

Additionally, Chicago has many vegan options to choose from, you can check out this list and see for yourself just a sliver of the possibilities.

I can personally attest that the food at The Chicago Diner (the first option on the list) was AMAZING, and it’s definitely a place I would recommend to anyone looking for a delicious vegan option while in the city.

6. Not a lot of public toilets

Just thought you’d know this important thing. Unless it’s summer and there’s some kind of festival going on, chances are that you’ll have to stop by a Walgreens, buy something, and hope they let you use their bathroom.

7. Go beyond the city’s attractions

This is very important, and something I don’t think gets talked about a lot. If you’re in the city for a couple of days, my recommendation is that you fit in at least one day trip from the city! One of my favorite things to do when I travel to a different city is trying to go a little beyond the city and see other things along the way. Why? Because it allows you to really get a feel for what the local people and scene are really like, it’s more of an authentic feel of where you’re at. Your curiosity will flare up when you’re outside of the touristy areas.

10 very useful things to consider if you're visiting Chicago

Read More: How To Be A Curious Traveler

If you’re interested in finding out just which day trips are worth the trek outside of the city, then I encourage you to download my Chicago Day Trip List. As someone who has made it their mission to visit different parts of Illinois to learn more about my area, I have found so many hidden gems and picturesque localities that are SO worth the commute out of the city. Download by leaving me your name and email address down below!


The list is a great start to get an idea of just what places you’re able to go to either using Metra (a commuter railroad system within the Chicagoland area) the L (the elevated train), or an uber ride!

8. Metra’s ticket system – avoid getting overcharged!

Metra is a train commuter system (4th busiest and most commonly used in the U.S) that has approximately 11 different rail lines, each taking you in a different direction from the city.

The Metra is easy to use for your day trips around the Chicagoland area, using the Ventra app to buy train tickets, and track different train routes all within the palm of your hand. Specifically, if you are taking the Metra, you have to make sure that you either:

  1. Buy your ticket at the train station before boarding
  2. You download the app before you board the train, you open an account on the app, and you load your form of payment, and you purchase your ticket that way.

If you don’t do one of these 2 things, the train conductor will charge you a surcharge of ~$3.00 to purchase a paper ticket on board. Don’t get caught off guard, just buy your paper ticket before boarding or have the app ready to go with your purchased ticket on the screen to show your conductor.

9. Don’t pay full price at museums

If you’re a Bank of America or Merril Lynch cardholder, this one is specifically for you! If you fall into this category, then you are able to use this to your advantage, as the banks’ Museum’s On Us program will allow free entry to some of the most popular and world-renowned museums across the U.S, including in Chicago. Click here to get a full list of allllll the museums you can go into FO’ FREE just by flashing your card at the time of ticket purchase at the museum.

10 very useful things to consider if you're visiting Chicago

Just keep in mind that this offer is only available during the first weekend of each month. Some other limitations vary depending on the museum you choose, but still, it’s a pretty good offer. So if that happens to fall in line with your plans, then you’re set for free entry to all the best museums in Chicago, including The Art Institute of Chicago and the Chicago History Museum.

Even if you’re not a Bank of America or Merril Lynch cardholder, don’t fret! This should still serve as awareness for you to look into the hidden benefits that your card has that you can take advantage of here or in your home state! Chances are your credit card has some sort of airline benefits, hotel discounts, or in-ground transportation perks. I encourage you to most definitely look these up before your trip.

10. Bring yo’ money – Chicago is not a cheap destination

I would say Chicago is a little more on the expensive side, but it’s also not too expensive. It’s definitely not New York City expensive, but it can vary depending on your budget and the time of year that you’re traveling to the Windy City. For example, at the time that I am writing this post (November) a hotel room in the city, like in the heart of the city, for two can set you back around ~$109 (not bad!). However, I know for a fact that during peak travel season (June-July) prices can start around ~$300 per night minimum.

Like I said, It depends on if you want to stay in the downtown area or if you don’t mind staying a little outside, or even by the airport (~40-minute drive to the city). A sit-down restaurant meal in the city can cost around an average of ~$20 per person minimum, per meal, and shopping and activities can vary, but a museum entrance to the Art Institute, for instance, would be around ~$16.00 (not including special exhibits). Chicago does have attraction passes where you pay a total amount, and get access to all tourist attractions. So if this is something that would be within your budget and interest, then definitely consider it.

**Also side note, if you’re shopping in the city, you’ll be charged for the actual shopping bags, and there is an additional tax on soda products. So just be prepared for that little nugget of knowledge!

Concluding thoughts on Planning A Trip To Chicago? Here Are 10 VERY Useful Things To Consider First!

So there it is! My top tips to consider when traveling to Chicago. It truly is a city to come and see and experience for yourself. I will say that I think that Chicago receives a bad rep for the negative news coverage over crime and violence, and therefore tainting it as an extremely dangerous place. I won’t deny that the city does unfortunately have this issue of violence and crime throughout its neighborhoods, but it’s not as bad as the media likes to say it is. The city is safe to walk through and enjoy for yourself, and just like with any other city, you just have to be aware of your surroundings and you’ll be fine 🙂

Don’t forget to download your list for some of the best day trips from the city! Click below for your copy, just leave me your name and address and your list will be on its way.


If you liked this post, make sure to let me know in the comments below: Have you been to Chicago? If so, what did you like about it? What didn’t you?

Until next time,

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