Chicago has always been high on my list of cities that I love. I cannot get enough of the excitement of this city. Simply put, Chicago is a blast!! My husband and I traveled there to take much-needed parents getaway break from our two kids. I did extensive research before I went and ended up having an incredible time. I want to share my Always5Star tips of experiences you will not want to miss in the fabulous windy city of Chicago!
5StarTips🌟:
Here are my top 5 must-see Chicago sights!
🌟 Rooftop Bars & A Sidewalk Bar
Oh, how I love a rooftop bar!! Nothing quite like enjoying a summer afternoon above the city chaos with a refreshing drink in hand. Not convinced yet? Let me show you some photos from a few of my favorite rooftop bars we visited while in Chicago!
“Howl at the Jun” cocktail – Cindy’s
Cindy’s Rooftop
I loved the beach-like atmosphere at Cindy’s rooftop bar. Whether you sit inside or outside, the vibe is fantastic!! However, you can’t beat the views from the terrace! You have sweeping views of Lake Michigan, Millennium Park and more. I ordered the “Howl at the Jun cocktail”, and oh my was it good!!!
The J. Parker Rooftop
Located at the Hotel Lincoln, the J. Parker is another rooftop bar with breathtaking views! From the 13th floor, you can look out over Lincoln Park while enjoying your cocktail or bubbly.
I felt this was a bit louder than Cindy’s but we lucked out, and after hovering over a group of people getting ready to leave lol, we snagged an outdoor table against the edge!
This was a moment that I wanted a special glass of bubbly to celebrate these amazing views! Cheers!
Café Brauer Sidewalk Bar
Café Brauer isn’t a rooftop bar; however, the views from the patio are so peaceful I had to include it! For parents reading this, let me paint you a picture. You are been running around the Lincoln Park Zoo trying to make sure each child has seen their favorite animal. You have said no to souvenirs at least 126 times! Then, out of snacks, your children are on the verge of becoming mini Hulks and you are wondering why you thought this was a good idea… That’s when you head over to Café Brauer to get a snack for the littles and an adult juice for you! 😉
5StarTip🌟:
It is always fun to try the signature drinks at Chicago (or any city) bars. Be adventurous and enjoy something new and exciting! I did!
🌟 Rent A Bike
Riding a bike around Chicago was probably one of my favorite things we did while we were there! I was a bit hesitant at first because I was worried I’d get run off the road by a taxi or car, but we stuck to the path along the waterfront, and it was a blast!
Great way to avoid traffic and see the city!
Throughout the city are Divvy bike stations which make renting and returning the bikes easy since you do not need to return the bike to the same station you borrowed it from. Download the app to help you locate the closest station. For more, information click here: Divvy Bikes to see their affordable rates and how easy it is to download!
🌟 Architecture Boat Tour
This was such a fascinating tour! Very touristy but still a must-see! The 1.5-hour boat ride down the Chicago River gives a wonderful lesson about the history of Chicago and all that goes into making a city as grand and pleasing to the eye as is Chicago. Plus you’re on a boat!! Who doesn’t love that?!?!?!
🌟 Wabash Arts Corridor
We like street art, yes we do, we like street art, how ‘bout you? The Wabash Arts Corridor was started in 2013 by Columbia College Chicago. Online are resources to help you locate where these impressive murals are located. Make sure to wear comfy shoes because once you see one, you’re going to want to find the others. It’s like a scavenger hunt! Here are a few of the pieces we saw when we were there to entice you to go!
🌟 Visit The City Parks
I love a city park – a peaceful oasis inside a busy, hectic city! We visited Millennium Park and Lincoln Park – two very iconic places!
Millennium Park
I loved the mixture of nature and art! Of course, you have the famous Bean statue but I was surprised to find that the park offers free concerts during summer at the Jay Pritzker Pavilion. I also had never heard of the Crown Fountain until we were there! The fountain is two 50 foot glass block towers on each side of a shallow pool. Faces are shown on the towers and water will flow out of the tower into the pool below – it makes it look like the person on the screen is spitting out water! Great place for kids to cool off and it’s free!
Lincoln Park
We didn’t spend as much time in Lincoln Park as we did Millennium Park, but is home to the Lincoln Park Zoo which is free! This is also where Café Brauer is located, which I mentioned above.
Where To Stay:
There are many hotels in Chicago that qualify for Always5Star luxury. However, one that my Mom highly recommends and appreciates is the Park Hyatt Chicago. Not only for its central location to downtown but because of the luxury that she loves.
Note: I stayed at another hotel that was not one that I would recommend. Next time, I will check this out!
Final Thoughts
Chicago has so much to see and do! Chicago is a beautiful mixture of architecture, culture, art, fabulous bars, incredible culinary choices and if you need a beach fix, they have Lake Michigan! With so much you can experience, I hope these tips give you a start! Be sure to check the weather though! I have been there when it truly earns its fame as being the windy city! 😉 Happy travels to Chicago everyone!
An Always5Star Jr. Cheers to Chicago! 🌟🌟🌟🌟🌟
Note: Brittany was not compensated for this post by any of the companies she referred to. The opinions are her own as well as the pictures. This experience was paid for entirely by Brittany.
A bit about the author: Brittany James
Brittany James is married and has two beautiful children. She is also the Social Media Manager for Always5Star. Her passion for travel came from her mother, Always5Star (at least that is what I am going to take credit for 😉). She is beginning her journey to Always5Star travel and enjoys sharing her family, friends and couples travel tips as a mother of small children. She has more dimes than dollars, but enjoys researching ways to enjoy Always5Star travel on a budget.
About Pamela Rossi
I am passionate about travel and taking each moment and making it a five star experience. My goal is to create those experiences for YOU!
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