For my money, Chicago is a top three food city in the country, and there is no better part of town to experience the Windy City's bounty then on the west side. From hole in the wall Korean and Ukrainian joints to fine dining from Latin America, the West Loop, West Town, and Wicker Park quite literally have it all.
This place needs no introduction. The burger is world famous at this point. But that beauty in the picture to your left is the bologna sandwich. It is a wonder to behold. Paired with an Old Style, you will be left in a food coma for the ages.
If you're staying at an Airbnb in the area, this is a great place to pick up groceries and unique Asian snacks you won't find elsewhere in the city. But it is also a great place for a meal, with an extensive food court and a bar to boot!
This place is a classic. It has been in the neighborhood for almost 60 years, serving hearty Puerto Rican dishes in an atmosphere untouched by time. They don't make them like this anymore, highly recommend.
Unique brewery serving beers you won't find anywhere else. But their burger is what makes this place really stand out. The giardiniera mayo is the the special sauce that makes that bad boy shine.
This place has been serving delicious Filipino comfort food in an unassuming diner for decades. The skirt steak and longanisa sausage are delectable. The service is impeccable, including a free dish of arroz caldo (Filipino rice porridge) to start your meal.
This place is on the pricier end, but the pastries and breads are top notch. They have a nice little patio to enjoy your bounty on a warm summer morning. If you're taking something home with you, the toasted sesame bread is amazing and you'll be hard pressed not to finish it in one sitting.
Traditional Ukrainian food in the heart of Ukrainian Village. We had the varenyky (pierogis) and the holubtsi (stuffed cabbage), which will fill you right up. As a bonus, Shokolad is BYOB and you can grab Ukrainian beers down the street at Tabb's Food and Liquor.
Aya serves some serious pastries. The croissants are all on point and the samoa cakes are deadly. For any fans of the classic Girl Scout cookie, this is nostalgia in cake form.
Bari makes a mean Italian sub. The cold cuts are fresh and the hot peppers are hot. You order your sub in the back of a small, Italian grocery store that's been in the neighborhood forever. The price is fair for a sub the size of your forearm.
A newcomer to the neighborhood, Diego has fit right in. The "vibes" are immaculate, with a great patio and lively music and atmosphere. But the food holds its own too. The ceviches and fish tacos will leave you in a summer state of mind, even if it's 20 degrees out.
In the land of deep dish and tavern pies, Coalfire is serving a classic thin crust pizza with massive flavor. I recommend ordering at least two for the table (even if you're eating alone) so you can try their various offerings. The Honey & Salami and Pepperoni & Whipped Ricotta both slap and the meatballs are a must order to start.
The food at Big Star won't blow your hair back, but you're here for the patio and people watching. Set on a corner in the heart of West Town, this is where you want to be on a warm summer evening, sipping a Pacifico or margarita.
Tempesta has received a lot of pub and accolades over the years, and all well deserved. The sandwiches are pricey, but they know what they're doing. My wife is partial to the B. Franklin, while I am a fan of the Grand Pastrami, but you can't go wrong. The also serve some very underrated gelato.
JJ serves some legit Thai food, with dishes you won't find at many other places in the city. The crispy pork belly is delightful, as is the beef curry noodle soup. Start your meal off with a refreshing papaya salad and you're in for a hell of a time.
Alegrias is well known on the Chicago foodie circuit, so when I went my expectations were high. It surpassed them. This place is a destination and you must go with a group that likes to eat and likes having a good time. Order one of the group platters and you will experience seafood flavors you've never dreamed of. It's BYOB so the party can really get going. Pick up beers at Ashland Market down the street.
This is one of the few restaurants outside of Chinatown serving legit Sichuan cuisine, with dishes that will stun you. Try something you've never had before. The mala fish filet is fun and Zhong's dumplings left us in a daze. It's BYOB and you can pick up beers across the street at Jewel.
Kasama needs no introduction. The lines that form 20 minutes before it opens are a testament to that. I hate to admit it, but it lives up to the hype. The breakfast sandwiches are heavenly, all of the pastries are amazing, but the Kasama combo sandwich for lunch is what did it for me. It's their version of the Italian beef and it's godly. Lines are almost unavoidable, but you might get lucky on a weekday.
Very solid Korean food in a neighborhood with very few other options to meet your fill for bulgogi and bibimbap. My favorite is the dakgalbi, spicy chicken smothered in cheese. Very delicious, very satisfying.
A classic red sauce Italian joint, serving all your favorites. You can't go wrong with anything on the menu, but their braciole is legendary. No better place to warm up a cold, Chicago evening.
For a nice dinner out, that's not too stuffy, Amaru is the place to be. They serve delicious and creative food from all over Latin America. We like the sweet plantains, octopus, and pernil. You are guaranteed to have a great time here.
I've been a regular here since it opened. When you don't want to cook and you want something quick and easy, you can't miss at Phodega. The pho is different than what you'll find at other Vietnamese restaurants in the city, but it hits the spot. I also really like some of the non-pho items on the menu: the Phodega Fries, the Viet Dip, and the Hainan Style Chicken Rice.
The Perch works for a lot of occasions and situations. The food is solid and they brew their own beer. It's a big space that is kid-friendly with a big patio out front. There's something for everyone on the menu and it is in a prime location on Division St., so the people watching is top notch.
Nothing kills a hangover like Dove's burnt ends hash with a healthy dose of the homemade salsa macha. This places stays busy, so arrive early if possible. It is a lively place and you'll be sitting on top of strangers, but it's part of the fun.
Chicago is slowing adding more restaurants where you can grab a quick slice, and Paulie Gee's is one of the best in the business. Open until 2 AM on weekends, it is a great option for a late night snack. But fortunately, even while sober these slices will do you right.
Craft Pizza just serves solid thin crust pie. There's a nice little patio and it's BYOB. There are few better places in the city to enjoy a few slices, a few laughs, and a bottle of wine on a nice summer evening.
From the brains behind Au Cheval, Small Cheval has several locations throughout Chicago. This is the more casual cousin, serving just very delicious, diner-style burgers, killer fries, shakes, and beer. You can do far worse for a quick, cheap, and filling meal.
A cute spot, perfect for a date night or dinner with friends. Quite possibly the only Costa Rican restaurant in Chicago, they serve comforting dishes of fried pork, melty cheese, plantains, and avocado. In a great location to watch the Wicker Park scene pass you by, it is also BYOB, so have yourself a good time.
Super fun ice cream spot with unique flavors you won't find anywhere else. Their soft serve is Instagram-famous and is indeed extremely photogenic. They also service boba and other drinks from all over east Asia. It is in the heart of Wicker Park, so makes a great pit stop if you're bouncing around the neighborhood.
Aba is a place to see and be seen. Fabulous people come here for the very good Mediterranean food, beautiful interior, and luxurious patio. All of the spreads are great, but I'm partial to the short rib hummus. The raw fish dishes are a refreshing way to kick off your feast and the kebabs are always a winner. Reservations are a must.
Very cool spot for inventive and traditional ramen flavors. Definitely try those, but the tuna tartare, wings, dumplings are also great. They play loud 90's hip-hop (a requirement for any "cool" ramen place in the city), serve draft Asahi in frosty mugs, have an unreal whiskey selection, and are open late. You will have a good time here.
Beatrix is a a solid option for brunch, with options to fill any craving. They have lots to eat and drink for the health conscious, which is good, because if you do Chicago right, the rest of your time here will be spent consuming some very unhealthy delicacies.
A fun, casual brewery in the heart of the West Loop. The beers are creative and pair perfectly with the food. I always order one of the tlayudas (a Oaxacan food that resembles a large pizza on a crispy tortilla) to share. If you're not in the mood for beer, a pitcher of margaritas will always play.
Parson's is a great place for a group and a great place to day drink and eat during the summer. They have a fantastic patio and serve delicious slushies that will have you feeling like the coolest kid in town. The fried chicken is obviously the thing here, but the fried fish sandwich and the burger are remarkably good as well.
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Bars
Chicago is America's best drinking town. Period. Bar none (lol). I am partial to dimly lit dive bars, which you will find plenty of in this guide, but you will also find swanky cocktail bars and boisterous breweries. I would advise not to hit all these places in one day, but if you do, I respect the hell out of you.
Not quite a dive bar, but not fancy either, Aberdeen Tap is the perfect place to watch a game or meet up with a friend you haven't seen in a while. The beer selection is great and the wings and other food are good enough to convince you to have a nibble while you drink.
Most certainly a dive bar, in fact this is a Chicago original known as a slashie (liquor store slash bar). The Old Style is cheap, the Malort is flowing, and the bartender has just that level of sass your looking for. I came here once on New Years Day during a snowstorm and the bartender ordered pizza for the whole bar. It's that kind of place.
This is the place to be if you're a soccer (football, futbol) fanatic. I'm not, but my wife is Colombian so we came here to watch some World Cup games. It was a hell of a time. During international tournaments it turns into a veritable UN, with expats from all over the world jamming into this compact watering hole.
This place is cool as hell. The décor transports you to a different time and place, like a desert oasis filled with interesting looking people and killer drinks. The concept is that the menu is split between high ABV drinks and low ABV drinks, so it appeals to everyone. They also have a fireplace, which is crucial during the winter hibernation.
J&M Tap is a dive's dive. It's the dive boss at the end of the game. Very little signage outside, cash only, minimal interior lighting, ragged pool table in the back, and cheap beer. Every time I've come here I've had long conversations with remarkable strangers. My first time here the bartender poured me several shots of mint schnapps on the house. I love this place.
Somewhere to take the whole family. District Brew Yards is a huge establishment with a very cool concept. At any given time 4-5 breweries use their space. All the beer is self-serve and you pay per ounce poured. It is a great way to try several different beers, just be careful with those heavy pours! Lillie Q also operates out of there, serving great BBQ and fried chicken. Their patio is a must visit on a nice day.
Dante's will never disappoint. It is a little nicer than a true dive, but they keep it real dark and nobody will bother you there. The cherry on top is their pizza, which is served in a whole pie or via their massive slices.
Another bar that works for a lot of occasions. You could just as easily catch up with a friend or show up with a crew and post up all day. They have a great beer selection, solid cocktails, and cheap bottles of High Life if that's your bag. They also have a small but tasty food menu focused on hot dogs and sausages - hence the bangers.
A Division Street classic. I couldn't put a date on it, but Phyllis' feels like it's been here since the bad old days. A definite dive, but with the twist that you're liable to catch some live music their most nights.
Very cool spot. Queen Mary has a nautical theme that turns just another bar into a little bit of an adventure. You can't go wrong with the Daily Grog, a rum punch that changes up regularly. I never got to try their food, but they serve oysters, conservas, and other delicacies of the ocean, so you're bound to be whisked away to the high seas.
A lovely little spot with a fantastic patio and elaborate charcuterie plates. Even in the winter the keep the heaters going, so you will be comfortable hanging outside. Cocktails are great too.
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Shops and Sites
You will need to catch your breath between eating and drinking. A stop at a local boutique can't hurt. A nap in a park might help. Here are some of my favorites places.
As the kids say, this place is 1 of 1. You might see somewhere like this in Austin, but you will not find any others like it in Chicago. It is amazing how many cowboys there are around these parts. Even if you are not in the market for $2,000 ostrich boots, this store is worth a visit just to gawk.
A huge green space right at the start of West Town, this park has a playground, basketball courts, and a (possibly no longer active) swimming pool. A great place for a nap or to people watch, with some killer views of the Chicago skyline.
It was a little intimidating coming into this place, not being a biker and all. But the attendant was super friendly and welcoming. Even you don't ride a hog, they have cool t-shirts and hoodies, sunglasses, and leather gear that could give Alcala's a run for its money.
West Town also contains the neighborhood known as Ukrainian Village. In addition to the various Ukrainian restaurants nearby, there is also this beautiful church right in the middle of it all.
A beautiful urban park with a bustling farmer's market held year round. There's a huge grassy field as well as baseball diamonds where you catch a game of mushball, a local softball-type game played with a massive ball. This is the heart of the Wicker Park neighborhood as well, so if you need a pit stop, this is the place to take it.
One of my favorite places in the city. This is Chicago's answer to the Highline in New York, but it needs no comparison. It is a long park stretching over several neighborhoods and a great place to run, bike (you can rent a Divvy bike at various stops along the route), and chill.
Foxtrots are sprouting all over the city like mushrooms. It is a one stop shop for coffee, snacks, breakfast, groceries, beer, and wine. You will never be disappointing grabbing something here and you can hang out, sipping your coffee for a bit if you need to rest.
If you need a haircut while in town, you could do worse than stopping by Ruben's. A haircut is about $35 (unfortunately the going rate these days), but these guys earn every penny. Even for someone who is hanging on to their last hairs for dear life, the barbers here put in a lot of care and I always left feeling great about my look.
You will not find places like this anymore in a major American city. But if you want the freshest chicken and the freshest eggs then look no further. If you don't want those things, but you want to smell the freshest chickens right before they meet their maker, then come take a look.
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Hotels
I never stayed at any of these places, but they will all put you right in the middle of the action.
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