I took a solo trip to Chicago, although I did get to spend a chunk of my time with my friend, who also hosted me! I remember the weather being cold and windy in the morning, and warm during the day (but still a bit windy) so the best way to cope is to come prepared in layers so you can + or - a layer throughout the day. Then very cold in the night again.
I got to spend about 2 full days in Chicago, which isn't much. I ended up not going to places that would cost money and decided to go to free stuff + roam around the city on my own. I purchased a transit day pass to make it easier on myself. I've always found it less stressful for myself to buy a day pass for a new city vs per ride.
I started my trip by taking the Chicago Architecture Tour via boat. It was a great experience, informative, and it's always fun to be on a boat as long as you don't get boatsick. I will say that the ticket price was a heftier than I expected, and it was freeeeeezing.
I mostly spent the rest of the day walking around the city, getting to see the sights, and just being able to experience Chicago.
Of course I visited the Bean in Millennium Park, as well as the Chicago Cultural Center, which was pretty stunning. It's open to the public and it looks like they have rotating social art/education installations, and some events.
Portillo's gave me the chance to try an authentic Chicago hot dog, but I didn't like it. Call me Californian, but it wasn't my cup of tea. To be fair, I'm not a huge fan of hot dogs in general, so, there's that, too.
For dinner, my friend and I made reservations for Girl & The Goat, which ended up better than I expected! Their dishes are meant to be shared so we got their Roasted Cauliflower off of their veggie list, the Wood Oven Roasted Pig Face from their meat list, and the Confit Goat Belly from their goat list. Three dishes was for sure enough for the three of us. All three dishes were incredibly delicious, but to our surprise, the cauliflower was our favourite!
I expected it to be super pricy because it's a pretty high end restaurant with an impossible reservation calendar. We ended up paying about $100 for all three dishes + a glass of wine each, and tax and tip.
My friend and I took the bus to Lincoln Park and visited the Lincoln Park Conservatory. They have really wonderful volunteers to give free tours, which was a special treat. It's a great place to spend a half day since the conservatory is part of a park, and at the other end, they have a farmers market (at least on Saturdays).
The best part of the greenhouse was a room full of hydrangeas, which are my favourite flowers! <3_<3
We for sure spent the most time inside that room taking pictures and taking it all in.
I was really set on trying Au Cheval but was very quickly discouraged by friends about how long their lines were. I compromised and went to Small Cheval instead in Wicker Park. I ordered the burger as is and it was GOOD. Solid burger. Probably not the best burger I've ever had but really solid and thoroughly enjoyed my experience eating it.
Walking through Wicker Park was really pleasant. It's a hip with a bit of grungy in it, but you can tell a lot of newer and hipper stores are coming in to replace the old. It reminds me a lot of Melrose Ave. in LA if you've ever been.
Later in the evening, I went to watch a show at Second City(we watched Best Of, which is a hybrid of written sketches + improv). The experience itself was really nice. It's first come first serve in terms of seating, and you can order food and drinks at your seat with your server. It's definitely worth going to, but to be completely honest, I think I enjoyed Second City shows in LA & NY better, but I believe it's because the shows I watched in other cities were pure improv the entire time.
Dinner was saved for an authentic taste of some Chicago deep dish @Lou Malnati's. We probably waited a solid 45 minutes (spent most of that time at a McDonalds about half a mile away, which was super bougie by the way). A lot of Bay area friends warned me that I'd be disappointed. I don't think I was necessarily disappointed per say, but I will say Bay area has pretty comparable deep dish, which is more of a compliment to these pizzerias, than a diss on Chicago.
Afterwards, we went up to the top floor of the John Hancock building and went to the restroom (apparently that's the best place to take photos and enjoy the view). It was really a beautiful nightview and I'm glad I made myself go even though I was tired and freezing.
Fair warning: there is a sizable line going up and especially going down.
I for sure did not have enough time to do everything I should've done! Here are some things I have on my list for next time:
Here's my Google Map of Chicago if you wanted some suggestions (thanks for my friends who gave me suggestions as I put this together)!