7 Favorite Chicago Moments

I checked off an item from my Bucket List last year when I visited Chicago for the first time with some of my best girlfriends, Samantha and Lauren. It was an amazing trip and anything positive anyone has to say about Chicago, is true. It is such a great city! Although I loved every moment of this perfect trip, here are some of my favorite moments and to-dos I would definitely recommend anyone plan on their first trip to Chi-town!

1) Admiring the Chicago River for the First Time

Nothing makes a big city more beautiful than a river flowing right through the middle of it. Crossing the famous Chicago River for the first time, as we walked from the Blue Line to our hotel, took my breath away. I was instantly in love. And of course we had to stop for a photo op.
Crossing the Chicago River

2) The Purple Pig

One of the many reasons why I love traveling with these girls is that they are foodies just like me. We wanted to share everything we ate and try the most adventurous, server recommended dishes we could. Like Pig’s Ear, from The Purple Pig, a favorite spot among locals and celebs alike and tucked away on a side street off Michigan Avenue.

The Purple Pig - Chicago

We found the restaurant while exploring the city on our way to the Navy Pier. When I whipped out my “TV Food Maps” app, this restaurant popped up and seemed right up our allies.

The Purple Pig

This is where we had our first celebratory cocktails in Chicago, and they were pretty amazing — the sangria was delicious.

Our First Drinks in Chicago - The Purple Pig

We shared several dishes and all were amazing, but the most unexpected dish that became our ultimate favorite of the trip was << You heard it here, folks >> Pig’s Ear!

Pig's Ear - The Purple Pig

The server said that this dish is “The Purple Pig restaurant in a bowl.” So naturally, we had to have it. We’d recommend it to anyone. Go ahead, try it — be adventurous!

3) Flamingo Wall Art 

Before I left for Chicago, someone told me about this amazing flamingo painted wall and I made it a mission to find it. It turns out that the wall was down the street from the Best Western we were staying in. I could see it from the lobby window!

Flamingo Wall - Chicago

The wall is at The Flamingo Rum Club (601 N. Wells Street). On our last day, we had a photo shoot and got some great pictures!

4) Chicago Dogs

Obviously a must when you visit Chicago — and we had them twice during our adventure so I’m pretty much an expert at Chicago Dog tasting. If you want to try a Chicago Dog for the first time, do it at Wrigley Field. These $12 hot dogs are AMAZING. And I’m not even upset about the cost. They are that good.

Chicago Dogs - Wrigley - Chicago

We also went to the famous Portillo’s, walking distance from our hotel, before we ventured back to the airport for one last taste. These cheaper dogs ($3) were definitely tasty, although less superior to the jumbo Wrigley Field version. But our wallets were happy and our tummies were satisfied.

5) Rooftop Bars

We enjoyed several rooftop bars on our trip, including theWit and Joy District.

the Wit - Chicago

We had a few drinks as the sun set on the first night at theWit and then the next night started off at Joy District. Both are fun and super hip places to enjoy an amazing view and a tasty beverage.

Joy District - Chicago

6. The view from the John Hancock Building

We didn’t make it to the Skydeck this trip, but instead made it up to the 95th floor of the John Hancock Building. Which I have to say was amazing. It’s not as touristy as I can image the Skydeck is, and it’s free to get up there!

John Hancock Building - Chicago And the best part? The view from the ladies bathroom.

Chicago - View from John Hancock

No line to stand on a piece of glass here. And check out that view! The dining room view was gorgeous as well, but ladies, if you make it up to the 95th floor, going to the bathroom is a must.

And as much as I can keep going on my favorite moments from Chicago, this is a list of 7. So I must conclude it with this.

7. Traveling with Friends. 

Traveling with friends is one of the best things you can do together.

Chicago - The Bean

Old friends, or new, on this trip we all made lifelong memories that we’ll share forever and remember the special bond that ties us all together.

Best Friends - The Pretty filter

It was crazy to me that this was the first time I traveled out of the state with two of my best friends. These girls are amazing friends and travel buddies and this trip would not have been the same without them.

2 Comments on 7 Favorite Chicago Moments

  1. Brian
    May 21, 2017 at 1:29 pm (6 months ago)

    Wow, this was definitely a great trip! I feel envious haha, just kidding. I wish to go to Chicago as well and I’ll do it, this summer maybe? It’s such a beatiful city.
    Brian recently posted…5 Proven Benefits Of Bench Press (#3 Is WOW)My Profile

    • Jane
      June 24, 2017 at 10:35 am (5 months ago)

      It was such a great trip! I hope I inspired you to go as well! I can’t wait to go back!


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