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10.31.19 – 11.03.19

Another trip in the books as we head out to Chicago for Halloween! (Not really for Halloween, but we did leave the day of hehe).

Abby and I made it to our AirBnb around 8pm their time (2 hours ahead from California). April got a later flight so she would meet us there the following morning. It was pretty late to actually go out for dinner (we didn’t have a car either) so we DoorDashed some food. Silly me made the mistake of meeting our driver outside only wearing one sweater (it was actually snowing earlier in the day!) and nearly came back with hypothermia!!

The following morning Abby, April and I headed out to the city via Lyft and started with breakfast at Kanela Breakfast Club. While looking up our itinerary, Navy Pier was listed as the “must see” spots as they have a carnival/fair type of event like Santa Monica Pier. It didn’t occur to me that it may not even be up because its winter time and well yeah, it wasn’t there haha.

We decided to be true locals and get bus passes to head to our next destination of Millennium Park aka “The Bean”!

I really loved navigating and walking through the city. They were putting up Christmas decorations and it all looked so magical with small piles of snow slowly melting away. It reminded me of a smaller NYC/Toronto mixture and wasn’t so busy or dirty either. (Probably because the wind blows all the trash away lolll, but it wasn’t so windy at this time).

After being total tourists at The Bean, we navigated our way to Crown Fountain. Btw, at this time of year, the Crown Fountain, Buckingham Fountain and Grant Park are basically dead. The city didn’t turn on the water so the fountains were uneventful and Grant Park lost all their leaves already haha.

After the slight inconvenience, we made our way to Skydeck Chicago at the Willis Tower. I feel like with every trip I go to, I always end up at some kind of skydeck tower.. Toronto, NYC, Seattle, LA, etc. etc. It is a good opportunity for photos and see the locations from a vantage point!

We had a cruise tour scheduled for 5pm so we took the time to take the bus and navigate to another part of the city. Michigan Ave. to be exact and if you know, you know! Of course I spotted the Apple Store and made my way in to check out their glass building. We went to the Chicago Architecture Tour that navigates alongside the Chicago River and learned about the different structures of the city. It was really beautiful and we were lucky to see the city at night with all of the lights lit up. (Btw, if you decide to do this tour, depending on the season, BUNDLE UP! We had hand, toe, and body warmers but it definitely wasn’t enough. I was freezing my booty off!).

Later that night we made our way to an underground Tiki Bar, Three Dots and a Dash for quick drinks and of course got some deep dish pizza at Lou Malnati’s. Personally, deep dish isn’t my cup of (pizza?) but when in Chicago you just have to. You may get full after one slice.. which is absurd in my book because I could eat a whole thin crust pizza myself but to each their own. We tried to get dessert at this one place (their hours were 10pm-3am.. weird right?) but unfortunately they were going under construction.

We basically hit every spot we had on our list in one day (we did that in San Francisco as well). Travel with us if you want to get it all done in one day and have plenty of leisure time 😉

The next day was planned for museums but after ending the night with drinks and food, we woke up pretty late and had a late start to the day. And by late I mean, after brunch at Little Goat Diner, every museum was near closing! I can’t really remember what we did but we did end up at this Milk Bar dessert place for a shake.

After having a quick dessert, we headed down in the subways to see the Chicago Theater as our final tourist destination. Jerry Seinfeld had a sold out show and that was pretty cool lol.

I really really loved Chicago. I felt like I belonged there and had some kind of purpose. Chicago is definitely being added to my list of possible relocations in the future so we’ll see!

And of course I have a series of photos below this post and thanks again for reading all of this hehe. I have also linked a lot of the places I mentioned in this post so click on their names for more info!

I made a quick little vlog style video for my IGTV on Instagram. Here it is if you’d like to see a visual of Chicago! Hopefully the music doesn’t get removed but if it does, play “Sail Away” by Mome in the background or watch with your own music of choice haha!

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