Best Things to do in Chicago if You're Anything Like Me

It’s no secret that I love traveling and running around the city. Often times I end up exploring a place that I’ve been to many times before simply for the purpose of trying to figure out what I haven’t seen yet. Last weekend Dylon and I took a mini-trip to Chicago for a few days just because we wanted to get away.  I live in Indianapolis so it only takes a few hours for me to reach the Windy City. Because I love Chicago so much, I figured it would only be fitting to share with you some of my favorite things to do while visiting.

Pizza is always a good idea- the gluten-free kind of course. I LOVE Chicago pizza… unfortunately, Chicago pizza does not always love me. Because of my gluten allergy, I have to seek out pizzerias that cater to those of us who just can’t indulge in a hearty deep-dish. The good news is that I found a couple and now have an absolute favorite. So it turns out that Gino’s does usually carry a gluten free option, however they were not very well stocked during my stay and ran out before I could try it. I’ve always liked Gino’s pizza though so I’m sure that the gluten-free kind is just as good.

(Candid picture of me hunting for pizza)

My new favorite spot though? It’s called Pizzaria Due and apparently it’s more well know by locals than most other restaurants. So obviously we had to try it and let me tell ya, I could rave all day! I have never had a better gluten-free pizza in my life. At first, I even questioned whether or not it was actually gluten-free because it was so dense- very similar to a real Chicago deep-dish. I feel like I’ve really been missing out this past year! My fiancé even loved it and requested that we go back twice.

 Eat on the water. I wanted to do something that I had never done before in Chicago (not many options there). Really, one of the only things I haven’t done is take a cruise off Navy Pier and so Dylon and I decided to just go all out with it. So we booked a cruise on the Odyssey Cruise Ship through Entertainment Cruises for a two-hour dinner cruise with full-service bar and amazing staff. We were greeted with a complementary glass of strawberry champaign and warm smiles.


Seriously though, the staff far exceeds expectations. Our personal host, Jamar, was incredible and so accommodating. He enthusiastically took a whole portfolio of pictures to fulfill my moment-capturing madness and made our trip extra enjoyable. So if you decide the Odyssey Cruise is right for you (which it is), be sure to request Jamar!


Shopping. The only activity I love just as much as I love eating is shopping. If you have never shopped your heart out in Chicago, then you are sorely missing out. Some of my favorite places to go? My first stop was at the insanely large Express store on Magnificent Mile. I picked of a few new pairs of jeans and  a couple quarter-sleeve sweaters and then rolled on. Express is kind of my go-to for all of my clothes so I was in heaven at the huge one in Chicago.


My next stop? Zara of course! If you’ve ever shopped there, you know that they’re only located in major cities (so not Indianapolis unfortunately). I absolutely love going to Zara simply because of the wide variety of clothes stocked at some pretty amazing prices that won’t break the bank. Although you probably won’t catch me buying a 3-piece suit at Zara, I did however make some basic professional purchases for my corporate job. Another great thing about Zara is that they turnover their clothing every two weeks so there’s a slim chance that you’ll be out matching with a fellow Zara shopper. 

If neither of those stores stand out to you, I promise there’s something for everyone. Just take a stroll along the Magnificent Mile and I garuntee you’ll manage to get sucked into the black hole of shopping.

 Find a boutique hotel. How many chain hotels are you going to stay in before you crazy? If you’re anything like myself, you’re a frequent traveler, sometimes by choice and sometimes because someone told you that you had to. And usually you end up in the same old chain hotel you always stay in. Chicago is known for fabulous boutique hotels. Even though you’re probably not spending a ton of time in your temporary home, when you decide to tuck in for the night, you certainly don’t want to lose the Chicago experience.

Suggestions? Personally, I love the Cambria (Disclaimer: Yes, the Cambria is a chain hotel. However, this Cambria recently bought out the boutique style hotel that we stay in and renamed it Cambria. I digress.) I’ve stayed there almost every time I go to Chicago. The rooms have been recently elegantly renovated and new and the recently update lobby is a perfect lounge spot.  Great price. Large, multi-leveled rooms. And the staff go above and beyond to make sure that you have a great experience.

Rooftop lounges. The Cambria also has a rooftop bar called 52Eighty that overlooks the city. Speaking of, make sure you hit as many rooftop bars as you can. The loung-y vibes of an open rooftop bar are the perfect place to look over the city and maybe even make a few new friends. Another one of my favorites was the GreenRiver rooftop bar. They have fabulous wine selection and a detailed break down of all of their cocktails which are also top-notch.


Those are just a few of my favorite things to do and see and Chicago. Of course, the best suggestion I could ever give anyone who wants to spend a few days in the city is to go explore and figure out what you love best! Until next time, happy exploring!

- Ariel♡

1 comment

  • Love Chicago style pizza! Haven’t visited yet, one day I’ll check these places out.The boutique hotels and spots are my kind of style. Xo


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