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I flew to Chicago ✈️

YKWIM !

Been more than a year since the airport happened to me or I sat in the window seat and felt the vibrations of the plane taking off or experienced the turbulence of the aircraft up in the sky. Who knew this will be such a privilege. But here we are ...!

After a while of thinking through I was able to plan a "family free' trip aka a "girl's trip" to Chicago.

Just FYI - To board the plane, a negative Covid test (valid within 72hrs) was required since every state is practicing its own rule for visitors and so is Illinois.


I had an early morning flight and I absolutely enjoyed the quiet morning drive to the airport with full excitement. Going through security and making it to the gate was a great feeling as I was expecting. Fell in love all over again with the feeling of looking through the airplane windows and flying through the clouds, an eye to eye contact with the moon and finally admiring the Chicago's beautiful skyline along Lake Michigan just before landing.

Chicago is a beautiful city with gorgeous river views, amazing architecture, wonderful bridges, and rich history which is extremely interesting. Not to forget the super cool rooftop bar experience. The variety of food in Chicago is also top-notch and all my research came in handy while I explored the city. In case I haven’t 'sold' you the Chicago dream yet ... keep reading!




My first encounter with the 'Windy City' lived up to its words when I went to check out the famous London House rooftop for my brunch. https://londonhousechicago.com/rooftop/

Chicago gets its name from the frigid breezes that blow off Lake Michigan and sweep through the city’s streets making it super windy which obviously made it extremely difficult for me to enjoy the brunch for which I had made reservations. On request, the server was able to move me inside and then I got to enjoy the beautiful bar indoors. Since it was pretty early in the day they were able to do so, but they are strict reservations so it's highly recommended. LH is on the 21st floor of the beautiful hotel which has the best views of the river walk and bridges.



Chicago riverwalk is an iconic 1.25-mile stretch located on the south bank of the Chicago River, right in the heart of downtown Chicago. It is indeed a perfect place to stroll during the day for explorers. One end of the riverwalk offers river cruises to cover the architecture alongside the river for which the tickets are easily available.

More river walk scenes.


Another absolute delight was the Millennium Park and the Bean. The Bean's reflective surface is inspired by liquid mercury. This shiny exterior reflects the people moving around the park, the lights of Michigan Avenue, and the surrounding skyline and green space — perfectly encapsulating the Millennium Park experience. I stayed very close to the park and went to the bean a number of times.



Now by the evening, it was time for another rooftop experience. Chicago is truly a concrete jungle and rooftop bars and restaurants are the only way to capture the beauty of the city. That's why dinner was planned at the John Hancock building 95th floor. https://www.signatureroom.com/

I would say the menu had limited choices but views were worth paying for. (Insider info: instead of dinner try the bar on 96th floor on a first come first serve basis or even better the ladies room has a panoramic view of the lit-up city so its perfect to get cool pics)




Day 2 - the day started with the long wait to try one of the most famous breakfast places wildberry pancakes. (They don’t take reservations but take your name down and call when they are ready) But the good thing is they are right across millennium park so use your time to check that out.


So that's what I did ... :)


Next on my list was to cover Navy Pier and luckily it opened the same weekend as it was an unofficial kickoff to summer and the celebration was amazing with the beautiful fireworks, so it was worth the visit during both daytime and nighttime. https://navypier.org/






Another insta spot is the Chicago theater that has a Times Square vibe.


One of the best ways to cover many different spots around downtown is on the bikes. The new uber-cool electric bikes and scooters renting stations are everywhere and they are really easy to avail. It was a super fun idea to ride the bike all the way to Navy Pier.

It’s a fun and lively place which has tons of seafood places and is home to the famous Chicago Eye.


The night called for another rooftop at theWIT https://roofonthewit.com/

This place was my most favorite with an amazing club like ambience and killer drinks.


The land of skyscrapers has other spots that I walked around to cover like Buckingham falls (good picture spot) and walk around the beautiful lake wolf. At dusk, Buckingham Fountain comes to life. Head to the park after sunset and you’ll be treated to a spectacular light and music show every hour on the hour.


My next day's brunch was scheduled at another solid rooftop view of the bean at Cindy’s. Great looking food and a perfect vibe. Highly recommended. Since it was so close to the bean I didn’t want to miss the opportunity to take pictures around the crown fountain and Michigan Avenue.




During the day I was also able to squeeze the all-around view of the city at Chicago 360 to soak in the city from 360 angles and enjoy a drink to go with it.

As I was getting closer to the last evening of my trip I was able to grab a slice of deep-dish pizza at Lou Malnati’s and a cup of caffeine at the iconic 3 levels Starbucks Roastery which is one of a kind. This Starbucks offers all sorts of cocktails and an amazing dessert bar.


I was ready to end the trip by celebrating at the most beautiful tiki bar called "Three dots and a dash..which was a great recommendation and is located in an alley that is a little hard to find.

These drinks are mastered with a vision and contain fresh juices and spices.


All in all Chicago has lot to offer if you want to enjoy a city-like vibe. But I do recommend keeping a close eye on the weather before you plan to visit the Windy City.

Until next time! Keep the travel itch going

✌️✌️✌️✌️















1 Comment


Bhoomika Datta
Bhoomika Datta
Jun 01, 2021

Looks to be such an amazing place and you look stunner as always..😍

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WhatsApp Image 2021-01-27 at 10.22.41 AM

Hi, thanks for stopping by!

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