My guide to Chicago: The Do’s & Don’ts

Ok! I’m so excited to share our trip to CHICAGO with you all!

a.k.a CHI-TOWN! (Ryan is cooler than me, so he calls it “Chi-town”)

Let me start off by saying, I always thought I was more of a beach vaca type of gal

I love the beach, a nice tropical drink and doing absolutely nothing

Why? Because my job requires a lot out of me

So at least 1 week out of the year, I would like to not plan anything, not worry about anything and just relax

Ideally, by the beach, with a pina collada in hand, getting a nice tan, reading a great book.

So before Ryan, my vacations were Cancun, Vegas, Miami, Brasil

Technically, mostly places where I got to chill by the beach or pool all day

Here’s where life gets interesting

You end up meeting someone the complete opposite of you as far as planning goes

And you meet somewhere in the middle after some vaca struggles of learning each others ways.

Compromising is so key if you want to make a relationship work, as no two people are the same.

Ryan loves to plan out details

He will read books about the places we’re traveling to, map the places out, search the hot spots, you name it

It’s exhausting just thinking about all the hours he puts into planning everything. But he loves it!

It’s his thing. And I am totally okay with letting him have it!

So rewind to last year, he surprised me for my birthday with tickets to Chicago for this May

It was pretty damn awesome and I didn’t even know how to react. I thought it was a joke for like 5 minutes..

Probably the sweetest thing anyone has ever done for me (thank you again baby!)

Cheesy shit aside and getting to what you guys want to know…

Last Friday was the big weekend

We got there around 12:30-1ish?

The flight was only 2 hours long from Boston, which is unbeatable and not tiring (check check)

We had all day to explore, so we first explored “The Loop,” which is the area we stayed in

We ended up at a restaurant called, “The Gage“

What can I say about my first eating experience in Chicago..

I was blown away.

If you are in Chicago, go to The Gage and order their poutine dish.

TRUSSSST ME on this

Their drinks were definitely descent and the service was incredible

We ordered pountine as an appetizer (although, it could’ve definitely been an entry, as you can see above)

And then I ordered tacos because cinco de mayo and Ryan ordered their burger.

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Our next mind blowing experience was just sight-seeing downtown Chicago

I mean, it’s so damn gorgeous!

I was so blown-away by how much green you see everywhere compared to Boston

And Ryan was blown-away by how modern every building looked and how everything just went together like a puzzle

The water was a gorgeous green by the museums and The Navy Pier but I wouldn’t recommend going that way

We did because I was super curious to see why the hype was non-existing there LOL!

And basically, it’s because there’s not much there, aside from the ferries wheel and some okay restaurants

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But let’s go back to some must-do’s

Chicago is known to have some of the best rooftop bars

LH Rooftop is definitely one of them

I highly recommend dressing up for this hot spot, if you’re going there at night

We went there during the day and as you can see below, some people definitely dressed casual

Here, you will mostly find old money or new money

Gucci/Versace boys and girls all day and night

The views are to die for and they also have an indoor bar that is super sick

Crowd is pretty good-looking, too.

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RAISED BAR 

Another hot spot with amazing views

RAISED saved our night with their heated lamps

Which keep in mind, Chicago was still pretty freezing cold in May

So I’d try going in the summer, if you don’t mind the crowds

The weekend we went was so cold and windy, every day

Thankfully, we were loving Chicago so much that we almost didn’t mind

But it’s obvious that the experience would’ve been enhanced if the weather was warmer

The good thing about it not being a busy tourist season, was we didn’t deal with the lines everywhere

We also lucked out with no rain 🙂

But back to Raised, winter or summer, they got you covered.

Great vibes, you don’t need to get too decked out there

Everyone is just chilling and enjoying the views

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River Walk

Umm..I’d say we may or may not have done this river walk the right way

We walked it a bit. It wasn’t anything out of this world but then again, it was freezing

I think in the summer, it must definitely be popping

The restaurants around there are all amazing, too

I’m not completely turned off by it yet and would definitely give it another look.

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Three Dashes and a Dot

I’ve never been to a place like it.

It’s a secret entrance to a basement that turns into a Hawaiian themed restaurant/bar

It’s so hard to even explain it but it’s a must if you’re in Chicago

We went there for the cool cocktails but the food looked very inviting, too.

I think the food is mostly Asian

As I’m typing this, I wish I could go back in time and order some food there

haha!

So yeah, definitely go to Three Dashes and a Dot. You will NOT regret it!

Make sure you reserve a table ahead of time to enjoy their dining experience, as well.

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Giordano’s

Holy deep dish pizza

I could have a slice or five right about now.

Their deep dish looks like a thick pie

It was by far, the best pizza I’ve ever had and I’ve been to Italy before.

Need more convincing?

Didn’t think so.

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The Chicago Bean

I mean, I’m not going to lie. I don’t get what the hype is about

I guess it’s cool to look at for a minute and take a picture but that’s about it

I’d say go for a walk downtown and walk by it, so you don’t get “fomo” (fear of missing out)

Otherwise, you’re looking at it.

Truthfully, I was shocked by the amount of people just standing there looking at it

Maybe I just don’t have the same creative mind to appreciate it

I don’t know

Either way, not the greatest thing we saw in Chicago, in my opinion.

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Willis Tower

You know, the place you go and take this infamous picture to show you are brave 😉

This was a place I really wanted to check out

I think what’s good to know ahead of time is that you will be in line for at least an hour

You will be in line to get inside to buy tickets and once you get inside there’s another line to get to the elevator

And once you get to the elevator, there is YET another line of people lining up to take pictures

SOOOOO, if you don’t have a lot of patience- skip this spot.

I don’t regret it but I wouldn’t go again

And Ryan was running on fumes because it was very frustrating to just stand there for a picture

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The Field Museum

You can literally spend an entire day here and still not have seen everything.

From dinosaurs and mummies, you will really never run out of things to explore at this museum

Ryan and I spent a good amount of time there

I don’t even remember how long we stayed, I just remembered we both couldn’t feel our legs at some point

And that was our cue to leave.

LOVED IT!

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Wrigley Field

The last thing we did in Chicago was go see a baseball game at “The home of the cubs”

This was my gift to Ryan

He loves baseball, so what’s cooler than actually watching a Cubs vs Yankees game in Chicago?

We loved Wrigley Field you guys!

It was so huge compared to Fenway Park and the fans were super awesome

Everything about it, aside from the freezing cold weather was perfect

I highly suggest planning vacations around some awesome event that will be happening that week

I think it’s definitely something we will do going forward.

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Chicago is enormous

I can write about it for days.

But I hope this was helpful and gave you guys a little taste of what it would be like to travel there

And some ideas of places to check out and not to check out 😉

Thank you for stopping by!

Until next time

-T