Chicago | Travel & Portrait Photography

If you haven't embarked on a trip with your best friend, it's an experience worth having! In September, I ventured to Chicago with my best friend, Kristin, marking nearly fifteen years of our friendship—an occasion we felt deserved celebration. Given our tradition of traveling with our husbands for anniversaries, why not extend the same for our friendship anniversary?

A massive shout-out goes to Kristin's husband, Dustin, who generously covered our plane tickets and hotel using hard-earned credit card points. Thanks, Dustin!

Choosing the perfect destination for our four-day getaway proved challenging. With busy schedules, we opted for a quick flight to maximize our time together. While Puerto Rico was considered, we ultimately settled on Chicago, a city Kristin and I had always wanted to explore. Decision made.

Here are some snapshots from our incredible trip together. Kristin took charge of all the photos of me; she might need to join the Hailey Tash Photography team! I'm thrilled that we managed to explore so much of the city in such a short time. Navigating the bus and subway routes was a breeze, and we covered over twenty miles on foot! We even ventured to Northwestern University to wander around the campus. An unfortunate discovery was that the Ferris wheel at Navy Pier was being dismantled during our visit, making way for a new one. Looks like I'll need to return to Chicago soon!

I adore these next two shots of Kristin. One of the things I love about her is that she's just as keen on touristy activities as I am. It's always a concern that my travel companions won't share my enthusiasm for such things, but Kristin gets just as excited. A highlight of our trip was visiting the Skydeck—sitting on a glass deck 1,353 feet above Chicago was simply fantastic!

We also opted for a sunset cruise around Lake Michigan and the Chicago River, a decision that turned out to be one of the best parts of our adventure. The Chicago skyline at sunset is truly breathtaking. It got a bit windy…
My favorite moment of the trip was our first sight of "Cloud Gate," aka "The Bean." I had wanted to see it for years! When we arrived in Chicago, we set out to find it without a clear direction. Wandering around, unsure if we were lost, we saw it shining through the trees. We both gasped in excitement simultaneously, reached for each other, and burst into laughter.

Deciding we wanted a quieter visit, we returned to "The Bean" on our last day in Chicago, walking there at sunrise. Surprisingly, I, not being a morning person, showcased a surprising amount of energy in those shots.
We wrapped up our trip with cupcakes and coffee at Magnolia Bakery.

Having visited numerous cities, Chicago easily ranks in my top three favorites. I can't wait for my next visit!

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