( Originally published Sep 2017)

WithloveTiffyjo: Original Blog

Hello all!

Long time no chat! I decide to take a short break from blogging ( Everyone could use a little break from the internet once in while) and I’m baccck!! Yay!

I wanted to bring my little hiatus to a close by blogging all about our trip to… CHICAGO!! This was my first time at in the big city and boy was I excited!

(captured this cool Photo while into the car)
(Me standing in front of the Chicago theatre)

The crazy and awesome thing about this trip is that it was my first experience being in a big metropolitan area and boy did it take some getting use to. There was tons of people everywhere, loads of traffic, and ginormous buildings! It was beautiful and overwhelming to my senses at the same time! There were plenty of moments where I had to grab on tight to my hubbys arm due to all the stimulation but I grew to love it!!

( My Husband being a daredevil and an amazing view of the buildings)


Now you might be thinking, This is your first “Big” city you must not travel often but I am here to tell you that Ive been to a few places in my day lol including San Diego, New Orleans, Orlando (Honeymooned there and it was pure awesomeness), Dallas, Houston, San Antonio, Austin (Pretty much all of Texas lol), Myrtle beach, and Atlanta! I still have many more cities on my bucket list that I plan on traveling to! And Chicago was one of them! Yass one Check mark off the bucket list!

(Usies at Oak Street Beach)

I was in dyer need of a vacation, believe it or not it had been almost 3 years since I taken a vacation due to the many responsibilities of life, so I was long over due! It just so happened to be the perfect time due my husband and I celebrating our 11th year anniversary of togetherness as a couple (only been married 4 years and some change lol)  I guess you can call us college sweethearts since we meet the summer before college! Anywho back to the topic at hand lol We decide this trip was perfect timing so we set out on a road trip to Chicago! (Yes you heard correctly) Roadtrip and it was SO much fun! It took us about 12 hours to get there with a couple of Stops in between!

(Husband in front of the Art Museum)
(A sneak peek at some Art! Some of this might look familiar to you! Hint: Famous Rapper for Chicago Art on the cover of one of his most successful albums)

(Chicago has Amazing Art Work all over Its Downtown Area)


Once we arrived, we stayed at this cute little Hotel in Downtown Chicago and it was the perfect location! It was right in the middle of everything! The Magnificent Mile, A few blocks from Oak Street Beach,  The Bean, Historical buildings, and 2 beautifully parks, and only a short uber drive away from the Navy Pier! And yes we did it all!

(The Best Popcorn And cocktails EVER!)


(The Chicago Famous Bean)

(Hotdogs: Chicago Style)


( Chicago Deep Dish Pizza)

We has about 2 full days and one half day and we took full advantage of it! One of the most mesmerizing things about Chicago is that there was so much to do! We barely spent any money on outings due to all the free events going on around downtown, ranging from a jazz festival, a dance party at the park, tons of roof top venues, afterwork game room lounges, cool tours, and the beach! The only things we paid for  were food, drinks, the art museum, and a night club! So that’s pretty much AMAZING! Chicago can definitely be a budget friendly trip if you plan it correctly!



Overall I would say the experience surpassed my expectations, everyone was really helpful, there was TONS of things to go, and loads of beautiful architecture and scenery! I almost thought about quiting my job, packing all my things, and moving to Chicago until I looked up the expense of living Downtown Chicago lol Then I came to my senses and said coming back for more visits will have to do!



I hope you all enjoyed reading about my trip as much as I enjoyed writing about it!

With Love,

Tiffy Jo