travel guide to chicago, illinois

This pandemic has put a dent or straight-up halt to a lot of traveling this last year, so I decided to incorporate a lot of domestic travel on my agenda for 2021, starting with Chicago, a city I’ve always wanted to visit!

Chicago Vlog:

Now let’s jump into this guide to help you plan your trip to Chi-town:


My flight’s total cost was $108.20 with a United Airlines roundtrip with a carryon and personal item for free. Checked bags were $35 each way, saving me $70 the entire trip. I flew out of the Orlando International Airport (MCO), which had people in it but was pretty empty for the most part.

This airline was also following the boarding from back to front rule and on arrival, releasing passengers in batches (which everyone actually listened to surprisingly, lol). Snacks and a water bottle were given in a goodie bag, and some middle seats were empty.

Florida to Chicago is about 2 hours + 30 minutes, so it was a smooth flight, and I opted in for in-flight Wi-fi for $14, which was great for me, as I just started my online business as a virtual assistant (@yourpersonalva).


Chicago has (2) main airports: Chicago O’ Hare International Airport and Chicago Midway International Airport. I flew into O’Hare just based on how far it was from my hotel. A Google search will help you figure this out, so you know the best choice for you.

Leaving the airport, we took the metro to get to our hotel, which included a bit of walking with our carryons, but it was fine, just cold! You can read more about navigating through the metro below:


We stayed at the Hampton Inn Chicago Downtown/N Loop/Michigan Ave located at 68 E Wacker Pl, Chicago, IL 60601:

At a rate of $82.47 for 3 nights came out to $290.45 with tax. However, I was traveling with one other person, so it was $145.26 for us both (win!). We got the very comfortable double beds, and the room was pretty big for what I expected.

Breakfast here was pretty basic due to COVID: the option of bottled water or cup of coffee with a goody bag of a Nutri-Grain bar, yogurt, and a pastry. They also have a small gym available for use!

My favorite part was the digital key for check-in! I didn’t have to get a physical key; I got to choose my room + what floor I was on through the app, and they have a chat feature for the front desk, which was convenient. I would stay again!

I always try to be as cheap as possible for my domestic travels if you didn’t know! I’m not too picky as long as I have space and the area is clean, and the Hampton Inn was just that.



Chicago’s metro system operates using the Chicago Transit Authority (CTA). Leaving the airport and leading to the trains, there is a CTA ticket booth where you can purchase a pass based on how long you’re staying: a day, 3 days, etc. I chose the 3-day pass for $20, which was perfect for my length of stay. 

The metro can be figured out via Google Maps, as it tells you where to stop, which is great. I just struggled with knowing what “line” to hop on and where the stations were located throughout the city, as Google Maps wasn’t the best with walking directions. Thankfully, my friend was good with this, lol. We got lost a few times, but I love getting lost when I travel. You always find new things. 

We aren’t city girls, so taking a train was actually a first for me! I can imagine how annoying it gets as a resident, but from a tourist POV, the views were worth it. 


Uber/Lyft can get very pricey very quickly, but it is an option of getting around the city! 

Your Legs

Walking is my #1 suggestion besides the metro if you have a pass! If the weather is right, definitely just walk because it will never be that far if you stay in the right place. 


Chicago has been doing a great job with implementing COVID precautions to help limit the spread of the virus. Keeping this in mind, many restaurants are just now opening up for dine-in vs. just doing carry-out. Also, a lot of hotels and main attractions are closed either due to COVID or just renovation purposes.

There will most likely be a sign on the door once you get there, even though Google will say it is open, so check on the actual website of your desired attraction and call before you leave!


I am not a big fan of trying new food and consider myself to be whatever the opposite of a foodie is, lol, but I did find a couple of great places to eat if you’re in the area:

Wildberry Pancakes & Cafe *Brunch*

This place gets a solid 20/10 from me because wow. Probably the best brunch I have ever had in my life, no exaggerations! The service here is so good, the staff is super nice, and the portions are huge. My meal was $15 for what is shown in the image. I want them to open a location in Florida, haha!

Rock Bottom Restaurant & Brewery *Lunch/Dinner*

Another 20/10! We visited this restaurant at a great time because they had just opened after months of being closed due to COVID. THANK THE LORD because I would’ve hated to miss out on this place that I ended up finding by accident! I ordered a kids meal for around $5-10, and the portion is so big you wouldn’t believe it was meant for a kid. Try their Mac and cheese, then literally D.M. me on Instagram to tell me how you liked it! 

Nutella Cafe *Brunch*

As if it wasn’t obvious from the name if you absolutely hate Nutella, do not come here! Sometimes restaurants have foods that aren’t dedicated to what they are solely known for, but not here. I don’t really have Nutella on the regular, but I don’t mind it either, so when I saw this cute place, I knew I had to try it! I ordered the French toast, which was delicious. I will say that I do not think their prices are worth what you will get, but it was a great experience. Just don’t come here when you are super hungry!

Nando’s Peri-Peri *Lunch/Dinner*

Nando’s is the first restaurant we visited on our first night in Chicago, and eh. The service was okay, as the staff was very nice, but our meal took over 30 minutes to come out when we were the only ones there, and mind you it was only one meal we were splitting (big mistake). Florida girls who saw a $15 meal and decided that must be enough to split the meal and *spoiler alert* it wasn’t! The food was good, but I was starving after and had to go order pizza later that night.

Chicago is known for their deep-dish pizza, but I’ll have to try a slice on my next visit!


Haitian-American Museum

Adding this to the closed attraction list of Chicago during this time, but this one hurt personally. As a Haitian-American, I would have LOVED to go through historical pieces, timelines, and facts of my own history in a city that was founded by a Haitian (merci anpil, Jean-Baptist-Point Du Sable). However, if you go and it isn’t closed, this is a cool place to visit!

I would also love to add that Chicago, in general, is a place that cherishes culture. There are museums for everything: Puerto-Rican American, Chinese-American, and I love that.

Take a picture at The Bean

I am naming this Chicago’s #2 attraction. Before I even went to the Bean, I was researching the significance because I didn’t understand what the hype was about, but it really is a piece of art when you get up close. It’s just a “how did they do that” moment.” This was designed by Anish Kapoor, and it worth taking a quick flick with. 


This is Chicago’s #1 attraction; ya know the picture people take standing on a glass however many feet up high!? Well, as much as I would have loved to take that same shot, they were closed at the time for renovations! However, I still think that it is definitely still worth visiting. 

Visit Obama’s Family House

This is just literally seeing the house, as you can’t actually go inside, and there is a sign that says the Secret Service is watching so approach at your own risk lol! However, I always find it exciting to see things like this because it’s like, “omg, Obama used to live here.” Cool tangs. 


Museums of Illusions

This is a museum that is supposed to test and trip out your mind into seeing things that aren’t exactly there. I paid $18 to get in as a student, and it is $21 for adults, but honestly don’t think this is worth the money at all. I found the entire thing to be underwhelming, and I feel that the price should go down to like $5-7 dollars, truthfully, but that’s what this guide is for to save you the hassles!


This is one that you may or may not have heard of. Boxville is a black-owned marketplace hub. It’s this really cool place where the box containers are little shops next to each other and have different services/products. One sold Carmel apples. The other had tea and herbs. The next had energy readings, etc. It was just an entirely different world that we stumbled upon on accident, and this was my favorite part of my trip. It was very freeing to see another Black space.

Boxville is located at 330 E 51st St, Chicago, IL 60615!


A neighborhood in Chicago where most of Chicago’s Chinese population lives! It is literally China in Chicago, lol, and as “duh” as that sounds, I’ve been to plenty of Chinatowns that weren’t really a great reflection of why it is named so. Here literally the banks, restaurants, laundromats, hair salons, schools, and churches are all Chinese-based, and I loved the strong sense of community I felt here. I am all for a community-based living for that exact reason.

Chinese people could go their entire lives without ever leaving this area because everything they need is in one place made by their own for their own.

The Largest Starbucks in the World

Yes! I was excited about this one because out of all places I would have never expected the largest Starbucks to be in the U.S. honestly! This Starbucks is 4 stories high and was pretty cool to see. The menu is different than regular Starbucks as well! It was one big Starbucks coffee factory and was a great experience. 


  1. Be patient with taking the metro. You are bound to get lost if it’s not something you are used to, but I wouldn’t have discovered Boxville without it, so I am grateful!
  2. Call ahead for every restaurant and activity you want to do before you get there, or even check their Instagram page to see if they’re open.
  3. Bring a student I.D. card if you have one, never know when a student I.D. can come in handy! (I forgot mine, but I’m usually able to get by). 
  4. Buy your metro card pass at the airport and just take it straight to your hotel vs. Uber/taxi. It will save you a lot of money. 

It was my first time seeing snow!


I hope this guide was informative for you and that you have an amazing time in Chicago! I loved this city and will be back. It inspired me to get out there domestically and see more of what the U.S. has to offer. If you are more of a visual person, my vlog just went up:


Love Always,

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