Chicago has been pretty high on my domestic to-visit list for some time now, so when I was able to snag a ~$350 roundtrip flight out of the Bay Area for a holiday weekend, I jumped on that just about as fast as I could.

I landed around 3pm and  took public transit (“The L”) from the airport to the 47th St station.  I walked about half a mile to my Airbnb, which was located in the Grand Boulevard District which has deep roots in the Harlem Renaissance movement.  It was a warm day and many people were sitting out on their porches enjoying the sunshine–everyone was super friendly!  My Airbnb host was super welcoming and gave me a bunch of recommendations for the rest of the evening.  I decided to go to Giordano’s Pizza and ordered a small classic (onions, green bell peppers, and sausage) which also ended up serving as breakfast for the next 3 days. I walked back to the Airbnb through beautiful tree-lined neighborhoods with gorgeous old houses and went to bed pretty early since the day of traveling had been pretty exhausting.

(full) day one: river cruise, the bean, skydeck, old gay town

I woke up the next morning pretty early and booked an architecture river cruise on Tripadvisor through Shoreline Sightseeing.  I took the bus up to Navy Pier and walked around for a bit before boarding.  I sat next to a really nice French guy who just so happened to have the same camera as I did.  He showed me some of his favorite shots from his trip so far and recommended some places around the city for the best views.  The cruise itself was pretty neat, the guide was very knowledgeable and even though I’ve been pretty sensitive to seasickness in the past, I didn’t feel queasy at all.

I thought this building, Aqua, was super neat!  The wavy white balconies were planned to give the tenants the best views–where there isn’t a good view, there isn’t a balcony.

This concrete brutalist building at 55 W Wacker was super neat, especially amongst all the shiny blue windowed buildings in the area.

This building, 150 North Riverside, was super neat because the base of the building had to be super small to accommodate for zoning requirements around the adjacent riverwalk and train tracks.

The gray facade concealing this building’s elevator shafts is a large map of the area along this segment of the river–and the red rectangle represents where this building is!

I just really appreciated the angles on this building and how I was able to get such a well-proportioned photo on a moving boat.  I also felt like the cruise helped to give me a better sense of direction, and also helped me locate an Apple store where I bought a new phone shortly thereafter because I was tired of having to keep my iPhone 7 constantly plugged into my bulky external battery.  Planned obsolescence wins again, but hey, now I have portrait mode.

I met up with a good friend of mine and lifetime Illinoisan, Kathie, shortly afterwards and we headed over to Portillo’s to grab hotdogs and beer for lunch.  I got the classic chicago hotdog with everything on it—poppy seed bun with yellow mustard, chopped white onions, bright green sweet pickle relish, a dill pickle spear, tomato slices or wedges, pickled sport peppers and a dash of celery salt.  I’m not usually one for sweet pickle relish, but it seemed to bring in the sweetness ketchup normally would and I wasn’t mad at it.

We walked over to Cloudgate (“The Bean”) and took some cute boomerangs before enjoying some delicious pride inspired cupcakes from Kathie’s hometown of Highland Park.

We then headed over to Willis Tower (formerly known as the Sears Tower) to take photos at the Willis Skydeck.  We didn’t have to wait at all to get up to the top, and waited about 10 minutes to sit in the extruding plastic boxes.  The top floor reminded me of Seattle’s Space Needle—just enough to make you want to do a few laps around the top, but not enough to make you feel comfortable taking up space for an extended period of time.

We decided to head over to the old gay district and get burgers at Hamburger Mary’s and watch the season finale of Ru Pauls’ Drag Race.  Neither of us had watched any of the current season, but the restaurant’s reaction (and the hosting drag queen) had elaborate enough responses to suggest how we too should also be feeling about the results and spilled tea.  I was really happy with my burger, which was topped with fig jam, goat cheese, and arugula.

We headed across the street and went to a highly recommended martini bar, Marty’s Martini Bar.  We both got French 75’s—chilled gin, triple sec with sour, and a sparkling float and a sugared rim—described by our waiter as “ethereal”.  I agree.  Very tasty, would get again.

day two: interior architecture tour, the art institute

When I booked my airbnb for this trip, I also booked an Airbnb Experience for an interior architecture walking tour.  Kathie and I met up with the rest of our group at the bottom of Willis Tower around 11, and spent the next few hours walking around and learning about the history of some really neat buildings and their interiors.  I don’t think I would’ve known to go into a lot of these buildings (or really, feel comfortable going into them and taking as many pictures as I did).

These first two photos were taken inside of 311 South Wacker.  I thought the two-tiered “winter garden” lobby was neat, as well as the sculpture which reportedly is supposed to evoke the feeling of wind in the windy city.

We then went to the Chicago Board of Trade and spent a while analyzing various agricultural motifs present in the building’s art deco interior.  We also got to take a peak at the basement vault which is no longer in operation.

We made a stop at The Rookery, a mishmash of designs from famous architects like Burnham and Root and Frank Lloyd Wright.  Magical floating staircase aside, I thought it was really interesting to hear how each architect put their own spin on elements in the lobby over time.

We also stopped at The Marquette and admired the Tiffany glass murals and bronze busts of various historical figures around their multi-leveled lobby.

The tour concluded at the Chicago Cultural Center.  We had a lot of fun admiring the impressive tiffany glass dome, which was constructed in such a way that each piece is individually replaceable–if one piece were to break, they wouldn’t need to remove an entire section, they’d just need to replace the one piece.

After the architecture tour, we grabbed lunch at a German restaurant named the Berghoff Restaurant.  I got sausages, sauerkraut, and potato salad and we shared a big pretzel.  Everything was really tasty, I’d visit again.

We then went to the Art Institute of Chicago and spent a lot of time wandering around the religious/renaissance style paintings before realizing the museum would be closing soon and i made a very quick dash to the sections I was actually interested in seeing–modern, post modern, etc.  Got to see the iconic paintings I wanted to see, but definitely didn’t spend as much time admiring them as I’d wanted.

We then went over to Ballast Point brewery and each got a flight, and then a pint of our favorite beers from the flight.  I really enjoyed the aloha sculpin–would definitely get again!

day three: downtown, botanical garden, lakefront

I ate my last leftover slice of Giordano’s for breakfast and decided to head into town and take some pictures of the L.  I found some tips online pointing me towards this parking garage to get some sick pictures of the L going around a sharp turn.  I spent about an hour in the parking garage messing with my camera and an ND filter and waited for trains to come.  I’m pretty happy with my results!

I watched the memorial day parade for about an hour before getting bored of seeing a bunch of high school ROTC students marching out of step.  I decided to take a bus up to the Lincoln Park Conservatory botanical garden and meandered through the greenhouse before taking a quick walk through the zoo—both of which were totally free!

I then met up with Kathie at Ben’s Noodles & Rice and got a huge, affordable lunch with pad thai, chicken satay, and thai iced tea.  We walked around for a bit and decided to explore the Wicker Park district before deciding to go relax along the lakefront.  While we were taking cute pictures of each other, Kathie was approached by a Univision reporter and gave a full on interview in Spanish!

We got a bit thirsty and decided to get some super, super tasty drinks from Three Dots and a Dash—an underground tiki bar with lots of character.  The entrance is tucked away in an alley, and if you didn’t really know what you were looking for you’d probably miss it (at least we did, several times).

We then went down the street to Henry’s, got some reasonably priced well drinks, and split a giant pretzel and some fries.  We parted ways around midnight (her return bus stop was right across from the Apple store we met at—how poetic!) and I headed back to my airbnb to pack for my flight the following morning.

It took awhile for me to actually sit down and write this blog post, but I’m glad I finally did.  This was a really fun long weekend, and I feel super blessed to have been able to spend so much time with such a dear friend.  I got super lucky with the weather—it was supposed to rain (thunderstorm, even) several days, but it all ended up happening at night while I was asleep, leaving me with absolutely perfect weather during the day.  Looking forward to my next visit already!