Monday, June 6, 2016


Three years ago we had our plane tickets and hotel reserved for our first trip to Chicago. I was excited as I have wanted to go to Chicago for such a long time. Unfortunately, we had to cancel our trip (no refunds, lesson learned, always get insurance!) as Sean’s training in Texas for his new job began the same day we were suppose to leave for Chicago. I was bummed but obviously the big picture. I kept saying to myself, "the big picture".

Life certainly got in the way but three years later we were finally able to make it happen! And it was everything plus more than I had imagined. I just love, love Chicago. I’m the biggest fan of skyscrapers. I know it has to do with growing up in the city but I just have this thing for freakishly tall buildings. I admire the architecture and think about all the work and imagination it took to get that building to where it is. Chicago gave me my fix and if I tell you how many pictures of just buildings I took you might think me insane. But that’s OK. For this, I don’t mind.

This is one trip that I'm super excited to recap so you'll have to bear with me because I went picture crazy (as per usual). It was seriously the most fun I've had in such a long time and I treasured every single moment of it. It just felt so good to be well enough to travel and although I never took our trips for granted it felt like so much more to me this trip. I think if you read this blog you like pictures so I won't apologize too much. But be prepared.

We traveled with Spirit and that was our only mistake the whole trip. You get what you paid for and we’ll never fly Spirit again. Due to them changing their flights schedule any which way they choose we lost out on a full day in Chicago. And in order for us to be able to enjoy our last night without having to be in bed by 7pm we decided to get last minute plane tickets with American Airlines. We did this that way we could fly out later that way we could have a fun night and enjoy a few more hours in Chicago the following day. That worked out perfectly but I hate that we had to do it. But yeah, unless you don’t mind inconvenience when you’re traveling, don’t fly Spirit.

When we finally arrived in Chicago we took the subway to our hotel. I think this is another city thing in me but whenever I have the opportunity to take the subway I do it. I know it’s strange since the subway is often a dirty, smelly place but it makes me feel like I’m at home so I do it. Luckily for me, Sean does it without gritting his teeth too hard.

Once we arrived to our hotel (we stayed at the Hard Rock Hotel - great experience!) we quickly checked in, dropped off our belongings and were walking around within minutes. We found a little tiki bar at the Riverwalk and stopped for a few drinks and admired downtown Chicago. It wasn’t long before we had to get back to our hotel to get ready for the night. We had dinner reservations at Catch 35.

The restaurant was gorgeous inside and the food was so, so good. I forgot to take pictures of our meal to share on here. Sorry! But take my word for it. So, so good. I ordered the shrimp and crab bisque, Lake Superior Whitefish Milanese and for dessert crème brulee. Sean ordered a Caesar Salad, Filet Mignon Medallions and also a crème brulee. I should have taken pictures!

After dinner we went to Vertigo Sky Lounge and they have a gorgeous rooftop bar! The drinks were good, music was perfect and it just had a great vibe overall. After that we went to Mr. Brown's Lounge and enjoyed some reggae before calling it a night. It wouldn't be our last visit to Mr. Brown's Lounge as we soon found that they also served Jamaican food. Sean and I had not had really good Jamaican food since we went to Jamaica on our honeymoon so we were excited when we saw those around us eating and enjoying their food.

I only took pictures on my phone which I shared on my Instagram and Snapchat. But here's a few below:

That night when we went to bed we talked about all the fun we already had and could not wait for the next day as we were going to a Cubs' baseball game at the Wrigley Field!


  1. I love Chicago with every ounce of my being, but we had this whole conversation on Snap Chat when you were there. Your experience with Sean sounds amazing. I am now on a personal mission to try Jamaican food.

  2. OMG when did you go? I was there over Memorial Weekend and took in the Cubs game on Saturday afternoon! If you were there over the same weekend - I'll be so bummed that we didn't connect for a drink somewhere! So far, it looks like you hand a wonderful night!

  3. I loved Chicago! It's such a fun trip. Girl spirit fortunately hasn't screwed me over too bad *knock on wood because I have three flights with them this summer* but I've heard horror stories!

  4. So excited to read all your recap about Chicago. I so love that we were there at the same time :).

    OMG I hate Spirit too, used them last Summer and never again. I am a Southwest fan through and through, worth every penny.

    Our major regret was not staying in the city, we did save on the cost of the hotel but wasted so much time getting in and out of the city.

    I was in skyscraper heaven too and I just loved the skyline. Neil is from London and couldn't understand the fascination.

    Now to go sort all of my pictures so I can do a recap too :)

  5. I LOVED following along on your trip! I love Chicago and have high hopes to get back again soon!
    Also. The subway. Talk about major intimidation for this small town girl!

  6. Glad you finally made it there and your snaps made me really want to go there and visit. Spirit SUCKS. I hate it that they always show up cheapest in search engines and then you find out about their stupid add on for everything policy. I also hate how difficult airlines make it to switch flights. It's not necessary to charge people hundreds to switch flights. They will still get their money!! Ugh. Anyway. Glad you had a blast despite the airline difficulties.

  7. I'm so jealous of your trip - you did everything I still have on my bucket list for Chicago, and I've been there three times now! Ha! (But in my defense never in the warm Spring). Loved following along on guys are my kind of, fun, and drinks! Good to know about Spirit...I've always wondered how it would be to fly with them.

  8. I am gonna have to bookmark ALL of this and get my butt to Chicago! Your trip looked amazing.


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