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That toddlin’ town

Recently, I ventured to Chicago for the first time ever (flying through doesn’t count) to see the sights and meet a BFF from LA “in the middle,” so to speak. We had a ball and all our Midwest assumptions were squashed immediately upon seeing the Blue Line station at O’Hare. “Damn, this is some nice public transpo,” we thought. And it just got better from there. Here are some of the major reasons why we love Chicago and wouldn’t be opposed to be being Midwestern if this is what it entails (except for that winter, oof!).

Frank Sinatra sang about it

At each new discovery, we both broke out singing “Chicago, Chicago.” It seemed a fitting anthem for the weekend. Set this to play as you keep scrolling.

Prices you can live with

Coming from LA and NYC, we are constantly hovering in a state of financial precariousness and every credit card swipe for those delicious $25+ brunches is like a little stab wound. We went to two amazing brunches in Wicker Park (Milk & Honey Cafe) and Andersonville (M.Henry) where we had our food minds blown and paid max $15 total per person/per meal/per place (that includes tip, all our coffees, side dishes, etc). Above are the incredible huevos rancheros ($6.75, holy bananas!!) and lavender cake at Milk and Honey (couldn’t resist it, I love lavender in food).


Everything about Chicago (well, the parts that we saw) was clean. And organized. And pretty (so many picture perfect tulips!). With miles of elevated track all over, you’d think there would be lots of under-the-bridge nastiness going on. No, siree. Not in Chicago. It was clean as a whistle, and in fact, the turn-of-the-century iron elevated tracks add tons of character. Pictured here is the Blue Line cutting through Wicker Park.

Cultural Gems

Every corner you go around at The Art Institute, you think “Wait, THIS IS HERE?!” One of the best surprises was seeing Seurat’s Un dimanche après-midi à l’Île de la Grande Jatte or A Sunday Afternoon on the Island of La Grande Jatte. I had this weird moment where I saw it at the end of a dark tunnel and I was teleported in my mind back to Mrs. Rushford’s 10th grade humanities class. I did a project on pointillism and after all my research, I felt oddly close to the painting. Seeing it in person all these years later felt like a homecoming of sorts.

Enviable real estate

We saw so many gorgeous Victorians in Wicker Park, but the whole city is covered in beautiful pre-war apartment buildings with big apartments, many with those classic Chicago back staircase terraces, some with enviable waterfront views, all at much better prices than New York. What did I tell you?! So much to love, especially for someone who values having a good home space.


Drawing courtesy of University of Michigan

As our guide book told us, Chicago is a city of neighborhoods. We explored mostly the Loop, Wicker Park, Lakeview and Lincoln Park. We strolled past so many lovely boutiques, cafes, book shops, restaurants and tree-lined streets that 2.5 days didn’t seem like enough to take it all in, but it just gives us more reason to go back! Next time I want to see the University of Chicago, Hyde Park (Obamas!) and venture north toward Jefferson Park to get a taste of Little Poland.

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