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Who’s Got The Best City: Chicago or Philly?

Who’s Got The Best City: Chicago or Philly?

Chicago or Philadelphia? Who’s got the better city, the Windy City or the City of Brotherly Love? While both are great places with large reputations, one city has got to be more superior than the other, so let’s break it down and see for ourselves!


Oh how I love Chicago. I was actually lucky enough to spend a year living and breathing in the beautiful Windy City, and it will be a time I will always look back on fondly. However, as a fellow Philadelphian, I am rightfully torn between the two, so let me fill you in on what made Chicago so unforgettable for me and probably countless others.


1. Navy Pier

Think of Navy Pier as Philadelphia’s Harbor Park but…better. While living in Chicago, I lived a walking distance from the very popular Navy Pier and found myself either walking or biking over there on the weekends during the warm summer months. Navy Pier is a huge attraction for many locals, tourists, and especially families within the area—offering tours, museums, movies, restaurants, cruises and of course, the iconic Centennial Wheel. The highlight of my Navy Pier experience has to hands down be getting a chance to sight-see the city aboard the very top of the Centennial Wheel. When in line for the wheel, you won’t believe it’s massive size—towering over the constant lines of eager passengers like an inanimate Godzilla, you are left in awe. With my palms sweating, my heart excitedly pumping, my pod slowly began making its much anticipated ascent to the top—the real star of the show. Once finally atop, you are granted a view for the ages—200 feet in the air, there is nothing left to do but soak in the 360 degree view of the beautiful city of Chicago.

2. Deep Dish Pizza

You will never have a better pizza in your entire life than a true and authentic slice of deep dish pizza straight from Chicago. Cheesesteaks are great, fantastic if you go to the right spot, but it just simply can’t be compared to the feeling of your teeth sinking further and further into the never-ending, crispy and gooey wonder of these pizzas. During my time in Chicago, I hopped from place to place to place, tasting every deep dish pizza this city’s endless restaurants had to offer—Lou Malnati’s, Pequod’s, Giordano’s, and my favorite, Exchequer. Every time, you are left stuffed, satisfied, maybe a little confused as to what just went down at your table. It is an unforgettable experience that everyone should try at least once in their lifetime.


3. Willis Tower

Touristy? Yes, but who cares? The Willis Tower, formerly known as the Sears Tower, stands as the second tallest building in the United States. If you did not know, the Willis Tower is a huge, if not the biggest, tourist attraction in the city. The tower offers people an opportunity to climb into its elevator—traveling at a speed of 1,800 feet per minute—and view the city from their Skydeck, located on the 103rd floor. The sky deck is famously equipped with a glass bottomed floor—that draws much yelps and screams from the eager tourists who anxiously wait in line. Standing on top of the glass floor, staring 103 floors down, I think it is safe to say Chicago easily wins the competition for “Best Observation Deck” against Philadelphia.


4. CTA

I am sorry Philadelphia, but Chicago’s CTA transit system absolutely blows Septa out of the water—it’s not even a competition. While in Chicago, I held many jobs all throughout the massive city, and there was never a place I could not reach by train alone. No trolleys, no inconveniences, all I needed was my trusty Ventra card, and I was as good as gold. Again, not trying to hate on Philadelphia…but Chicago also does do a much better job with the disposal of garbage on the train cars, and even the streets for that matter. Not every train car HAS to smell like urine at 9AM on a Monday. CTA is a breath of fresh air when you’re so used to having to deal with Septa and all of the frustration that comes with it.

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5. Lake Beaches

Now the competition is beginning to get unfair, but I can’t hold a debate between the two cities without mentioning the fact that Chicago is packed with 24 beautiful and scenic beaches. I lived just a two minute walk away from Oak Street Beach and it was without a doubt the cherry on top of my sweet summer in Chicago. There is nothing quite like sprawling out on a towel, feet dunked in warm grainy sand, and rolling your head to the side so you can stare out at a beautiful view of Chicago’s skyline. Luckily, this beach lay only a short walk from Navy Pier, so there was never a lack of things to do. One of my favorite memories of Chicago’s beautiful lakes is when I got the opportunity to rent a jet ski and speed down it, no shortage of views—my old Philadelphia summers momentarily erased from my mind. With bars, retail stores, restaurants, and shops all decorated just a short stroll from the beach, you will find that this beats any other lake beach experience. 

6. Wrigley Field

Wrigley Field stands as one of the oldest and most historic baseball stadiums in history. While attending a baseball game in Chicago, the experience was a lot different than any I’ve had at a Phillies game back at home. Once off of the train and in Wrigleyville, there are no shortages of bars to pregame at before the big event. Places are packed with excitement—fans huddled around bar tables and televisions, anxiously waiting for the Cubs. The most interesting part about actually being at the Cubs game was looking out from my seat at the tops of roofs, where fans are able to pay to view the game from. Chicago never ceases to amaze me with both its history and innovation.


Chicago and Philadelphia are two great cities with so much to offer. If you find yourself in Chicago, let us know what impressed you the most about it!