A Quick Trip To The Windy City
We arrived to Chicago on a Friday afternoon. After sitting in traffic for over an hour to get from the airport to our hotel downtown, we quickly checked in and then set out to explore. We stayed at the Virgin Hotel and it was a really cool vibe and a great location!
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Our first stop was a donut shop called Stan’s Donuts where Shelby declared the red velvet donut she ordered “life changing”. High praise from a donut connoisseur. After our donut appetizer, we took a leisurely stroll down by the river on our way to dinner.
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Our Uber driver told us where to get the best pizza in town, and even took a quick detour on our way to the hotel to drive by it so he could show us where it was. It was a location many of you recommended as well, so we decided to head to Lou Malnati’s for some Chicago deep dish pizza. We got there early, like 6PM, and there was already a 30+ minute wait. The hostess suggested we go inside and look at the menu to pre-order our pizza. This was a new concept for us, but everyone was doing it, so I’m glad we did to. Turns out it takes like 35 minutes for the pizza to cook, so this just helps speed things along while you’re waiting for your table. We snagged a table outside, which was nice because we got to take in the city views. But the line of people trying to get a table outside this place was crazy! At one point I heard the hostess say the wait was 2 hours! And this was not a tiny place. So we knew the pizza must be good! And it was tasty… but we just are not huge fans of this style of pizza. We’re New Yorkers after all, and I personally prefer a really thin crust, but we are so glad we got to try the famous Chicago style deep dish.
After dinner we walked back to our hotel, taking in the beautiful city views, and had an early night in preparation for a busy next day.
On Saturday we headed to Create and Cultivate. This was the main reason for our trip. We’ve attended several Create and Cultivate events in the past, and they never disappoint. The day is filled with panel discussions, small group mentor sessions, and lots of networking. we got to hear from industry leading experts on a variety of topics, and even some celebrities like Shay Mitchell, Whitney Port, and Jennifer Hudson! Btw, Whitney confirmed she is indeed returning to TV on The Hills reboot and they are going to start filming next month! Can’t wait for that! After a long day, we headed to Nando’s for a quick dinner. This is one of our favorite spots in London, and there happen to be a few locations of this chain in Chicago so we couldn’t resist.
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On Sunday we had planned to spend the day walking and exploring the city. But the weather was miserably hot and Shelby woke up with a migraine which is not a fun combination. We made it to brunch at Goddess and the Baker and walked over to Millennium Park to see The Bean before taking refuge from the heat inside a Starbucks.
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We quickly realized it was just to hot outside to enjoy wandering around. I happened to see that one of those hop on hop off bus tours had a stop right outside the Starbucks we were sitting in, so I suggested we do that. We never take these bus tours, because we believe in experiencing the cities we travel to in a different way, but on this hot summer day with one of us having a dizzying migraine, this was the best way we could take advantage of seeing a little bit of Chicago and not melting from the heat. We got off the bus at Navy Pier, and walked around there for a bit making at pit stop at Garrett’s Popcorn, before hopping back on the bus and finishing the tour landing back at our hotel. Given the situation, this was the ideal way to spend our day, but if you have more time I wouldn’t recommend you do this bus tour. We found it a bit overpriced and not that informative or interesting.
After picking up our bags at the hotel, we set off for the airport to head back to NYC! It was a whirlwind trip but really fun! I would definitely love to head back to Chicago to explore more, but just maybe in the fall so it’s not so hot but before it gets too cold!
Have you ever been to Chicago? What are your favorite things to do there?
-Ash
P.S. You can watch our travel vlog from our weekend below!