18:02 PM

Chicago: The flight, bites and sights in the Windy City

Editor's note: Ashley Iaccarino is TPA's social media guru who also happens to enjoy food more than anyone we know. She recently scored an amazing Frontier deal on Chicago airfare and was kind enough to share her adventures, which naturally include lots and lots of delicious meals. Here's her story.

It was 1:58 a.m. outside Chicago O’Hare International Airport when I took my first breath of cold, crisp air. I froze for a second as my lungs rejoiced at the refreshing feeling, then continued to scan the road for my Uber, a grey Toyota Corolla that would take me to the heart of the Windy City. Once I arrived, I took in the sights of tall buildings, the long, icy river and the signature Potbelly’s Sandwich shop on every corner.

My first trip to Chicago was full of food, architecture and frosty air and ended way too soon.

It finally made sense to me why the destination is one of the most traveled from Tampa International Airport.

The flight:

Tampa International Airport serves up to 16 flights a day across five different airlines to Chicago Airports, O’Hare and Midway, so flight options were endless. Between luck and good timing, I was able to find a roundtrip flight to O’Hare for $44 (including taxes!) on Frontier Airlines – meaning more in the budget for food and sightseeing. The flight was a quick 2 hours and 50 minutes, and comfortable enough for myself and my 6-foot-2 travel partner.


The bites:

So maybe I ate my way through Chicago, but I did so with no regrets. The city is full of brunch spots worth booking a plane ticket for and pizza so good you’ll forget it’s 7 degrees outside. Our favorites: Hutch American Café in River North, Giordano's and Portillo's.


Hutch looked like a hole in the wall until we walked in, thankful we’d made a reservation a week before. The spot was poppin’ with mimosas, cool décor and probably the best brunch food I’ve ever tasted. The go to: Totchos. Just try them. These nacho derivatives landed on the table lookin' like a whole meal, full of tater tots smothered in truffle cheese fondue, fresh and crunchy pico de gallo and two over-easy fried eggs.


Giordano's was on the list for best deep dish pizza in downtown Chicago, and it definitely lived up to its name. The “stuffed pizza” was nearly three inches thick stuffed with spinach, sausage, mushrooms and more cheese than you can buy at the Publix deli – all the while the crust still packed a delicious, crispy crunch. Did we go back for seconds? I will not disclose. 


If you’ve been to Chicago, you’ve probably had Portillo's. The signature hot dog and sandwich shop got its origins in Chi-town as one of the city’s landmarks. The two-story restaurant was bustling during the lunch rush, and was well worth the wait. Order the jumbo dog with everything and you’ll enjoy a ¼ lb beef frank with onions, neon relish, celery, tomatoes, mustard, a dill pickle spear and of course, those famous sport peppers. 3 bites and it was gone? Perhaps. 


The sights: 

Chicago is FULL of history and beautiful neck-breaking architechture that you'll enjoy even if you're not into that kind of stuff. On our first full day in the city, we made our way to Millenium park to take mirror selfies at a large, rounded reflective sculpture - also known as "The Bean," then 2,000 steps lead us to the Willis Tower - formerly known as the Sears Tower - where we enjoyed a unique view of the city from one of the world's tallest buildings - a sight that included all of Chicago from above as well as parts of Indiana, Wisconsin and Michigan.


The next day, we hopped on an Architechture River Tour which took us all along the river, as our tour guide boasted his knowledge of the historic riverside buidings. We were fed knowledge on the great architechts who built the city's major landmarks and enjoyed a beautiful view of the city from atop the water. The tour was $30 on Shoreline Sightseeing and was worth every penny! 


On our last day of travel, we had to hit Navy Pier - one of the most well-known tourist destinations in Chicago and a 3/4 mile of lakeside city views. The pier, although very slow on a Monday morning in November, is typically full with live music, food spots, concerts and events and even has a museum and a ferris wheel on the 1.5 million square-foot land.


So, as Frank Sinatra sang, "bet your bottom dollar you lose the blues in Chicago," it's true! Pick a weekend, book a cheap flight and enjoy the beautiful city! Oh, and, get the totchos.