chicago
01 .............Introduction
02 ..................quick hits
03 .............................EAT
04 .........................DRINK
05 .............................SEE
06 ...........................SHOP
07 ............................STAY
08 .............................MAP
09 .....................FULL LIST
01 introduction
I grew up and went to school just outside Chicago and lived downtown for my first few years out of college before I (unexpectedly!) hauled off to Seattle. I was a consultant during the time I lived downtown, meaning I had to travel Monday through Friday most weeks, sometimes for two at a time. The more places I traveled, the more of the world I saw, the more I was convinced: this is the city that has always been and will always feel like home to me.
I've been lucky to have seen much of the world, but Chicago is consistently my favorite city. The people are friendly, the streets are clean, the shows are fabulous (and affordable!), the neighborhoods are endlessly different, the food...oh my stars, don't even get me started on the food. If you haven't visited, you really should, and if you do, tag me in all the pictures so I can devolve into a hysterical ball of homesickness the way I do every time I see a picture of the most beautiful skyline in all the world.
02 quick hits
wicker park
la la la
la la la
west loop
lincoln park
la la la
pilsen
la la la
la la la
logan squre
03 eat
Ok, to be completely transparent, I went through the holy grail note on my phone of my Chicago restaurant recommendations and pared it down to only my absolute hands-down favorites and…I ended up with 54. I realize that I'm someone who does everything overboard, but even I can realize that is way, way, way too many for a Greatest Hits list.
You cannot begin to imagine the anxiety I was put through trying to pare the list down further. I ended up with 20, and I can’t be bothered to pare it down anymore, because the food scene is easily, easily the thing I miss most about Chicago (besides *heh heh* my people, of course *ahem* sorry guys, you definitely don't *ha ha* take backseat to Ann Sathers or anything like that *cough*).
Also, I’m also giving you the extreme privilege of seeing the full list here. No need to thank me.
04 drink
So full disclosure: I'm not one of those people who, when they go out, sling em back left and right and dance on tables and chat up the bouncer to get into clubs and stuff. That sounds like Dante's third ring of hell to me. No, when I go out, I want to bring some friends, find somewhere marginally cozy, and settle in for a while and drink bourbon or wine or cheep beer and probably eat fries at some point. If it's a dive bar with a jukebox and gummy bears or goldfish in jars, even better. If there's trivia, great. And if there is live music playing I’ll probably weep tears of joy and come back the next night forevermore.
TL;DR: if you're looking for clubs in this list, you won't find them! If you're looking for neighborhood haunts? Check out these babies (and let's be friends).
05 see
I think DC might be the only place in the entire world where I recommend more things to see than I do things to eat. In pretty much every other place in the world that I travel, I orient each trip around what I want to eat and where I’m going to eat it. In DC, though, food comes second to the infinite things to see and do.
Beyond even the museums and monuments, which can easily fill a week-long trip, DC has too rate theater, sports, parks, and neighborhoods. I’ve listed fifteen top hits here with over 30 sites, and this list barely scratches the surface. Don’t beat yourself up if you don’t see everything, and realize that to really see all of DC you’d have to spend a month making the rounds. And if it’s the summer—bring a refillable water bottle. You don’t know what humidity is until you’ve experienced summer in DC.
06 shop
I’m really, really not a huge shopper, and I often find shopping while visiting a new place kind of a waste of time in the face of all the sites (and restaurants…) clamoring for my attention. Plus, I’m a chronic over-packer, and there is never room in my suitcase to bring anything resembling a souvenir back with me. But if in the course of my wandering I happen to pass any place that looks unique (or, let’s be honest, any bookshop), I pop in for a minute. I love shop owners who are doing something truly different and pour their energy into curating something special, and I want to appreciate them, even if I don’t buy anything. Here are a few places I’ve popped into over the course of my time in DC that are doing just that and deserve a look if you happen to be in the neighborhood.
07 stay
Places to stay in DC fall into three main categories: high-end luxury hotels filled to the brim with antiques that probably graced the homes of our Founding Fathers back in the day, modern hotels that don't cost as much and look better in an Instagram, and bed and breakfasts that definitely do the East Coast B&B scene (and Lorelai Gilmore) proud.
When you're looking for a place to stay, make sure to map it in relation to where you want to spend your time--if you're hoping to stay near the Mall and you pick a spot in Adams Morgan, you're probably going to be disappointed. That said, though, I highly recommend looking at places in Adams Morgan, DuPont Circle, and Georgetown. They're cheaper, quieter, cuter, and the DC Metro system is so easy to navigate.
08 map
09 full list
eat
Need more ideas? Drop me a line!