Chicago, Illinois. If you know me, you know I love Chicago. I lived there in my late teens and twenties. I visit two to three times a year and act out of pocket every time. “Chicago Abby” is a different breed, and she emerges the second I get on the Blue Line at O’Hare. Imagine a drunken Midwestern Union worker sprinkled with Pall Mall Red 100’s ash, outfitted in thrift store couture. She is a vision. I’ve ventured all over the city, eating, drinking and partying. I’ve compiled a list of my favorite places. I hope this list helps you plan your next trip to Chicago.

Dives:

Whirl-a-way:

If you are looking to drown your sorrows in heavily poured one in one’s, look no further than Whirlaway Lounge on Fullerton. The year was 2011, I was devastatingly poor, I did not have internet in my studio apartment, what’s a girl to do? This girl put on her “good slippers” (rubber sole), grabbed her massive laptop and headed over to Whirlaway to binge Roseanne on stolen WIFI and $6 whiskey gingers. The drinks are strong, the ambiance is dark and Fabuloso-d, they sell cigarettes. It’s everything you need it to be. Whirlaway is very much “come as you are” leave drunk as fuck.

Rainbo Club:

Want to feel like you are in a David Lynch movie? Rainbo Club is for you. This bar is straight out of a fever dream in the best way. There’s an old stage behind the bar, the wooden panels smell like time and the bar glows. I spent many hazy nights pretending I knew more about art than I did and hoping that I’d become more charming and less obvious with each whiskey I tossed back. Spoiler alert, it did not. One of our teachers moved back from Paris and stayed with us for a few weeks. I remember talking with her at Rainbo Club about all the psychotropic drugs her psychiatrist put her on… while we chugged booze. If I could pick one dive to go to every night for the rest of my life it would be Rainbo Club.

Skylark:

This may come as a shock to you, but I’ve only been denied service at one and half bars my entire life. I was denied entry at Bowen House in 2020 because my sister-in-law and I were holding each other up trying to get in the front door. #iconic The other bar I was almost denied entry was Skylark in Pilsen. I had already moved back to Dallas but was visiting my friends Claudia and Jesse in February. I quite literally fell into the bar. The security guard looked at me and said, “yeah I can’t let you in here”. My response? “Oh no it’s ok, I’m not drunk, I just slipped on the ice. I’m from Texas. We don’t have ice there”.  After a little back and forth I also assured him, I wasn’t violent… “what am I going to do? Stab someone”? I am nothing if not exhausting, so he let me in. I promptly fell asleep in my chair. Skylark is the best. It’s a beer and a shot type of establishment. No nonsense. No frills. Just booze and body heat.

Delilah:

Delilah is one of the first Chicago bars I took Nick to; Nick cannot name a punk band to save his life, but for some reason, he loves punk bars. He seems to find one in every city we visit. Delilah is very much a punk bar with an impressive whiskey and beer selection. The vibe is haunted house and obviously the music is always on point.

Cocktails:

Sportsman:

Dark wood, prison lighting, animal heads. Sportsman is an elevated dive with a real deal cocktail program. Back in 2020 they set up tables out back socially distanced by fire pits. Naturally, I got overly excited/stimulated and blacked out on Negronis. Sportsman is all Midwest and the perfect warming station in the winter months. They also make their own amaro blend that is incredible.

Kumiko:

Kumiko is a big boy cocktail bar. The ambiance is soft luxury, expensive scents and sleek seating. I’ve been to Kumiko to start an evening, to end an evening and for dinner. Each experience was 10/10. Cocktails range from N/A to high proof. There is something for every palette. Everything (especially the glassware) is hyper intentional and aesthetically driven. You get sexier the second you enter the space.

Aviary:

I’m obviously not blowing anyone’s mind by including The Aviary. We’ve been several times, and each visit is better than the last. The decor is nothing to write home about, but it doesn’t matter. Don’t let your taste preferences impact your order, everything is good. This is the place to try something new.

Scofflaw:

Scofflaw is a cozy gin bar with a fireplace. The space feels weathered and matured without pretense or performance. Their cocktails change every three months and is a full staff collaboration. One detail that I really love about Scofflaw is the actual menu; there is a small illustration of each cocktail next to the description. Scofflaw is the kind of bar where you are confident that the bartender could answer any spirit or palette question/ recommend you something you will love. In addition to great cocktails, their food menu is delicious too.

Food:

Longman & Eagle:

Longman & Eagle opened when I was still living in Logan Square. My roommate, Erin and I became fast regulars based on the Bloody Lawrence alone (bLOODY mARY WITH WHISKEY). I try to go to Longman every time I’m in Chicago. The interior is masculine and poetic. Think restaurant scene in There Will Be Blood. Their whiskey collection is extensive, and their food menu is meaty and well executed. Go for any meal (including brunch) and you will fall in love with this place.

Lula Cafe:

Lula Cafe has been around forever. Their hyper local menu is always changing and always impressive. The space is charming and effortlessly cool. It’s a throwback track that never feels trite or forced. I truly feel like Lula is one of the best restaurants in Chicago. The staff is knowledgeable and friendly, and I’ve never ordered something I didn’t love. From house made pastries and pastas to well executed cocktails Lula delivers on all levels.

St. Claire Supper Club:

Located under Roisters, St. Claire Supper Club is chef Grant Achatz ode to the traditional Midwestern Supper Club. I want to live in this restaurant. The decor is old Chicago with a soundtrack to match. They have a prime rib program that is everything you want and more. The sides are massive and comforting, the drinks are classic and strong, and the desserts are straight out of a Midwestern church potluck. If you are a nostalgia junky and romanticize the Midwest, St. Claire Supper Club is a must.

Oasis:

If you know, you know. Hidden in Jewlers row, Oasis is heavily portioned Mediterranean food served in Styrofoam. The best comfort meal. Nothing better than sitting down to watch Netflix with take out from Oasis. The hummus is creamy, the lamb is fragrant and perfectly kabob-d. It really is a hidden gem.

Honky Tonk BBQ:

BBQ in Illinois? 100%. Honky Tonk has become a Pilsen institution. It provides that smack of smoke the second you walk in the door. The interior is rich cowboy homestead (but just enough kitschy “pew pew”). They have live music most nights and their food is great. The St. Louis ribs have my heart forever.

Tank Noodle:

Best Pho in Chicago. The basil and bean sprouts pop with freshness and the gallons of broth cut the chill of the elements. This sprawling dining room is full 90% of the time. Expect to wait in a short line. More than worth it.

Panes Bread Cafe:

Panes is about 200 feet from the Wellington Brown Line stop. I lived off the Wellington stop in 2009 in a carriage house with four other girls. Wild. We got Panes sandwiches all the time. It’s a small, unassuming space with delicious breads and sandwiches. If you are from Dallas, Panes gives serious Lakewood vibes. Homey and unpretentious.

Art:

The Art Institute of Chicago:

One of the best museums in the United States. People really seem to care about their miniature collection… I have no idea why… but if you are into little things, make sure you check it out. If miniatures aren’t your thing, The Art Institutes permanent collection is very impressive. Don’t miss the modern wing.

Museum of Contemporary Art:

I love the MCA. Check it out then head over to Michigan Avenue and pretend you’re rich enough to shop at Chanel.

First Fridays:

First Fridays used to be my nightmare. There isn’t a single thing that caused me more anxiety than First Fridays. First Fridays are the first Friday of the month when all the galleries open and you just hit one after the other. This means you are in very small spaces with a lot of people who know a lot more about art than you do (at least that is what my imposter syndrome demon would scream at me the entire time). So, what did I do to quiet that pesky demon? Get really drunk and run through the streets of Chicago like a wild animal. I’d burst through the doors of a 10X10 space, packed to the gills with teachers and coeds, make a few drunken comments about the work, then disappear into the streets. Low self-confidence is a hell of a drug. I thought everyone else was the next Mapplethorpe, and I viewed myself as a community center artist at best. It wasn’t my best look. Since graduating I’ve been to many first Fridays and I’m happy to report that I don’t need to get super drunk anymore to get through them. Dare I say, I enjoy it now. If you find yourself in Chicago on a first Friday, it’s a great way to see great art. Listed below are some of my favorite galleries.

Kavi Gupta

Rhona Hoffman

Andrew Rafacz

Western Exhibitions

Heaven Gallery

Coffee:

New Wave:

New Wave served as my unemployment office for many months in 2011. I would go there every day and scour Craigslist (yes, Craigslist) for a job. The interior is arcade adjacent and full of crusty locals. They have pastries, strong espresso and a very Gen X playlist. Gainfully employed and just want a place to hang out? They have a ton of board games and ample seating. New Wave is your art teacher at a Christian school; they wear a vest and Sambas and let you play with their pet rat instead of going to PE. That’s New Wave.

Grocery:

Devon Market:

Devon is my Pleasentville. In 2012, I moved north a stop away from Evanston on The Red Line to the Devon neighborhood. Tree lined streets, cinematic brownstones, Montessori pre-schools, Loyola University, golden retrievers… idyllic. Devon Market is my favorite grocery store in Chicago. A neighborhood grocery store with an impressive inventory. Everything about it is quaint and necessary. They also have the best re-usable bags. I still have a few in the bowels of my closet.