Chicago, Illinois

Chicago, Illinois

In September 2019 two girl friends and I were supposed to go on a Carribean cruise. We thought we had caught a screaming deal on our tickets, but then we realized they were so cheap because it was smack in the middle of hurricane season. Ultimately the cruise ended up getting cancelled, but thankfully we were safe in Texas when the hurricane hit. And, United let us change our flights without the normal $200 change fee. So to Chicago we went.


We arrived pretty early in the day (even with our flight delay) so we were able to do a decent amount. We stayed at the Hilton Garden Inn Chicago Downtown/Magnificent Mile.

  • Millenium Park

-The Bean: as picture-esque as it looks on Instagram, just hard to get a picture without a bunch of random people in the background or the reflection

-Buckingham Fountain: quite a large fountain

-we had lunch at Panera

-for dinner we got drinks along the river (I can’t remember where but they had the best Frose) and then had deep dish pizza at Pizzeria Uno

Our first day was pretty laid back. Lots of walking, then hanging out in the hotel room and pre-gaming before going out to a few bars later in the evening. I found out that bars do not close at 2am in Chicago.


We rallied after our late night out to get an early start to our first full day of exploring Chicago. Our hotel provided a breakfast buffet and a restaurant-style breakfast. It was a nice 60 degree morning, so we walked to the John Hancock Tower. This tower rivals the Sears (now Willis) Tower with it’s height, but we saw online that it was less crowded and had a gorgeous panoramic view. We had purchased tickets to ride the elevator up to the top of the tower and go on something they called “the tilt”. The tilt were these floor to ceiling window panels that you could stand on, and they slowly tilted them forwards over the side of the building. It provided a neat birds-eye view of the city below, along with a little thrill from being tilted over the side of one of the tallest buildings in Chicago. The regular floor itself allowed visitors the most amazing view of the entire city of Chicago, along with the brilliantly turquoise-blue Lake Michigan.

After going up in the tower, we walked back through the town to get lunch at Portillo’s. Portillo’s had been recommended to me by a friend as a must-have hot dog place. I’m not a huge onion or relish person, but the dogs were pretty good.

We took a little nap at the hotel before heading back out to walk around Navy Pier before dinner. We met my friend’s family at Carmine’s for Italian food, and then we went to Hugo’s Frog Bar for dessert. Both restaurants were absolutely delicious; I had the best red wine I’ve ever drank at Carmine’s and Hugo’s has this giant dessert (I can’t really describe it too well but it was a mixture of many things). We had a great time.


For our final day of Chicago, we hit up the Ohio Street Beach to try and emulate our cruise. While it was probably 40 degrees cooler than it would’ve been in the Carribean, we enjoyed sitting in front of the clear (cold) blue water and resting our feet in the sand. There are lots of sidewalks and bike paths along the lake for miles, so we rented some bikes for an hour and took a little ride along the brilliantly blue water. With the wind blowing through our hair and the sun on our backs, we cruised along and had a great time.

For lunch we just ate PF Chang’s. We walked around downtown for a bit before going on a 90 minute river boat architecture tour. It was very interesting and informative, although a bit chilly once the sun set! We ordered pizza from Gino’s East on the way back to the hotel. I think Pizzareia Uno won the deep-dish pizza contest, although we had no problem at all eating both pizzas.

Thus concluded our last-minute trip to Chicago. I had a great time in this unique city.  

Links: à Hilton Garden Inn à Pizzeria Uno à Carmine’s à Hugo’s Frog Bar à Portillo’s à Gino’s East à John Hancock Tower à Ohio Street Beach

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