72 Hours in Chicago: Solo Traveler’s Guide to Food, Sights & Getting Around

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If you only have 72 hours in Chicago alone – what should you do? what should you eat? I recently took a solo trip to Chicago, and of course I collected all the experiences I did to help you navigate a solo trip to Chicago. In a previous blog, I talked about food spots in Chicago and my first accidental solo trip there. But this time I went for my birthday so let me give y’all the play by play

TRANSPORTATION

Understand that there is a difference between CTA vs Metra. CTA covers the train and bus. I downloaded the Ventra app and purcahsed a CTA for 3 days for $15. I chose that option so that I don’t have to pay separately every time when I used public transportation.  BUT there is something called the Metra train that lets you get to certain parts of Chicago quicker. The only caveat is that there is a seperate fee you have to pay on the Ventra app AND it only comes at certain times that are pretty far apart. 

Why did you take the Metra train then ayo? Because I stayed in Hyde Park which is in Southside so oftentimes google maps continually shows Metra train as the number one/main recommendation so I used it a few times. The Metra train can be quicker BUT they only come at certain times. I am explaining this because I wish someone talked to me about this before I was alone in Chicago and embarassed myself on the train by not having the correct transportation ticket. 

SIGHTSEEING

Obama Presidential Center

I didn’t expect to cry during this but this center got me more emotional than expected. Warning: the museum is booked until November BUT there is more to do than just the museum. There is an outdoor park, a public library, an indoor basketball gym, an auditorium and a restaurant (that I will share more about later in this blog). If you only have 72 hours in Chicago – THIS is a must see

Architecture Tour

I have been to Downtown Chicago plenty of times so I am used to seeing the boats in the water. There are many architecture tour options but after some deep dive research it looks like the First Lady Architecture Tour is the one to go to. It was so beautiful and I feel like a popular tourist attraction that is worth it

The Art Institute of Chicago

This is one of the best art museums in the world so I had to try it out for myself. Between you and me sometimes art museums can be.. odd (iykyk). Mind you, I LOVE me a good art museum but sometimes it’s a little too abstract so not gonna lie I definitely skipped some parts.

72 hours in chicago

American Writers Museum

Did you know that there is a museum to celebrate writers only? Yeah, I know right – wild! I found out about it by accident. I wish I spent more time in it but had to rush it because it was about to close. If you are a lover of writers – this is a great spot to get inspiration

72 hours in chicago

Beaches

There are quite a few beaches in Chicago. Since I stayed in Hyde Park, I ran along 57th beach. But for my birthday I went out to North Avenue Beach for photos and videos. Warning – that beach can be CROWDED especially when the weather is nice but I found a more quieter spot and had a good time solo.

FOOD

Gino's Eats

I have been to Chicago a few times but have NEVER tried deep dish pizza. Gino’s Eats is a popular one and wwowwww. This was amazing. Mind you, I don’t like crust like that but I ate all of that crust with deep satisfaction

Tafari's Kitchen

Rumor has it that the food here is really good so I had to try it for myself. I got the tuna melt and ohhh myyy that left me so deeply satisfied. Make sure when you add Obama Presidential Center to your “things I have to do for 72 hours in Chicago” list you stop by this restaurant in the center.

Kitchen & Kocktails

Of course I had to try a Black owned restaurant and this one was so cute. The vibes were giving me life and the food tasted good. Warning: this is on the pricier end so beware that you might be spending a lot during your 72 hours in Chicago if you do decide to slide through here.

72 hours in chicago

I hope this gives you some things to do if you only got 72 hours in Chicago by yourself. Chicago is such an amazing place so I hope you enjoy yourself! If you want to see more videos of things that I did, check out my latest vlog below!

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