7 Favorite Chicago Moments I’ll Never Forget

Visiting Chicago was definitely a checkmark on the bucket list for me. I went a few years ago for the first time with some of my best girlfriends, and I’ve had wanderlust lately thinking about the amazing—pretty perfect— trip we had. Although I loved every moment of this trip, I’ve made a list of my top 7 favorite Chicago moments I would definitely recommend anyone plan on their first trip to Chi-town.

If your feeling wanderlust like me, and dreaming of planning your next vacation, keep reading for a list of my top 7 favorite Chicago moments!

1) Crossing the Chicago River for the First Time

Obviously a must and mostly likely will happen organically on a trip to Chicago. But it was such an incredible and memorable part of my trip. 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. When you go, don’t forget to snap a picture.

2) Eating At The Purple Pig

One of the many reasons why I love traveling with my 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.

The first restaurant we ate at was was called The Purple Pig, tucked away on a side street off Michigan Avenue. We found it while exploring the city on our way to the Navy Pier, using “TV Food Maps” on my phone. It seemed right up our allies and was an amazing first impression of our Chicago eats adventure.

The cocktails were amazing (you gotta try the sangria!) and made for a great celebratory toast to kick off the trip. 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!

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 and try it—be adventurous!

3) Flamingo Wall Art Photo Op

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

The wall is at what is now The Diver restaurant (601 N. Wells Street). If your looking for an amazing photo op on your trip, this is definitely it.

4) Experiencing Chicago Dogs

This is a must when you visit Chicago and we had them twice during our trip, 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.

We also went to the famous Portillo’s, which was walking distance from our hotel for another taste. This outta bounds, Guy Fieri recommended restaurant is a must visit if you’re not heading to the field. These cheaper dogs ($3) were very tasty and our wallets were happy, too.

5) Drinks at Rooftop Bars

Grabbing a few cocktails at rooftop bars in a gorgeous city like Chicago is a must. We visited two amazing rooftop bars, and got a taste of two totally different experiences.

On our first night, we went to the top of theWit hotel for a lovely rooftop happy hour. The next night, we started off the evening at Joy District. Both are fun and super hip places, with great atmospheres to enjoy an amazing view and a tasty beverage.

6. Seeing The View From The John Hancock Building

We didn’t make it to the Skydeck, but we did make it up to the 95th floor of the John Hancock Building to The Signature Room, where we enjoyed their amazing wine list and stunning views of the city. It felt like the high-end, classier version of the touristy Skydeck experience, and the best part was, it was free to get up there.

No line to stand on a piece of glass here. And check out that view—seen from the ladies bathroom! 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 about my favorite moments from Chicago, this is a list of 7. So I must conclude it with this.

7. Traveling With Friends

What made this trip even more special, was that I got to do it with two of my best friends, plus I got to meet a group of amazing people that I am still friends with today. And I totally realized first hand that traveling with friends is one of the best things you can do together.

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