The Cakejam Guide to Hanging in Chi-town
I want to eat something delicious but I’m sort of poor
Big Star Tacos and whiskey
1531 N. Damen Ave.
It’s always crowded and it can be oppressively hipster-y, but ahhh! Guhhhh! The tacos! Website
Sultan’s Middle eastern
2057 W. North Ave.
I always get the spicy falafel pita with jerusalem salad. I have never tried anything else and do not intend to. Website
Sol del Sur Mexican
3268 W. Fullerton Ave
I suggest a veggie burrito as big as your head, or perhaps a taco salad as big as your head, or maybe a couple tacos with a mound of cilantro as big as your head.
Boiler Room Pizza
2210 N. California Ave.
Get the PB&J, which is a tallboy PBR, a slice, and a shot of Jameson for $7.50. Also, if you use their ATM, they will reimburse you for the fee by giving you a shot of whiskey. But you have to save the receipt; they will not take pity on you and give you the shot anyway. Website
Xoco Fancy Mexican
449 N. Clark St.
This place isn’t CHEAP exactly, but it’s a relatively inexpensive way to try some of Rick Bayless’s food. Lunch will run you about $12-15. The tortas, churros and coffee are all amazing. Website
I want to eat something delicious and I have some money to spend
Blackbird New American/fine dining
619 W. Randolph St.
Yes. Yesssss. I did my externship in the pastry kitchen here – I’m not sure whether that should make me more or less likely to recommend it, but the food and the service and the drinks are all fantastic, despite the fact that they let someone like me make the components for the desserts. Reservations recommended, obvs. Website
Longman & Eagle Regional American/gastropub
2657 N. Kedzie Blvd.
I had my last dinner in Chicago here. Of all the restaurants with ampersands in the name that employ lots of people with beards, this one is by far my favorite. Don’t go here if: you mind waiting for a table, you are freaked out by things like marrow and pickled ramps, or you’re a picky vegetarian (they do have a good vegetarian menu, but it’s small). The rest of us will see you later. Website
Lula Cafe (Regional American/farm-to-table)
2537 N. Kedzie Blvd.
I loved this place before I even moved to Chicago. The food is amazing but not too fussy, they do brunch every day, and there’s a great patio in the warmer months. The menu changes often – I never get the same thing twice. Website
Frontera Grill Fancy Mexican
445 N. Clark St.
This one time, I was in Frontera, and I saw Rick Bayless…ahem. Anyway. Be prepared for a crowd because the guy is famous, it’s downtown, and the food is really good. Try an off-peak time so you don’t gnaw your arm off before you get a table. Website
I want to have some cheap beers in a fun neighborhood bar
The Whirlaway
3224 W. Fullerton Ave.
I might have cried a little when I said goodbye to this bar. Good place to watch the Bears, Bulls or Blackhawks, or just play board games. Say hi to Maria and play 6501 on the jukebox. Or 6105. Something like that. Website
Cole’s
2338 N. Milwaukee Ave.
If you’re a bartender, it’s part of your job to flirt with me. They understand that here. Also – good beer selection, cheap drinks, pool table, and regular live music and comedy nights. But most importantly the flirting thing. Website
I want to drink some fancy beers but still in a fun neighborhood bar
Small Bar
2049 W. Division, 1415 W. Fullerton Ave., 2956 N. Albany
My favorite for beer geeks. Huge bottle selection and a selection of drafts that changes often, plus really great food. Also if you’re into soccer this is your place. I am not into soccer until the World Cup, when I jump all over that bandwagon and use it as an excuse to get drunk at weird times of the day. Website
Revolution Brewing
2323 N. Milwaukee Ave.
Logan Square’s very own brewery. Another place with an extensive beer list and really great food. Get the mussels. Website
Map Room
1949 N. Hoyne Ave.
Ridiculously ridiculous beer selection and a good crowd. Website
Bangers & Lace
1670 W. Division St.
Of the four this is probably my least favorite, but it’s a great pick if you’re in this neighborhood. One of the few places I’ve seen the particular kind of sweet Faro that I like. Website
I want to have some fancy cocktails
Gilt Bar
230 W. Kinzie St.
Whenever I work in the loop I like to try to stop here for a cocktail once in a while. The upstairs bar is a good sit-by-yourself and chat with strangers bar – the bartenders are really friendly and there’s a steady stream of people just off work and business travelers waiting for tables. If you’re with a group, hit the downstairs bar in the basement, which is cash-only but way cooler. Website
Longman & Eagle
2657 N. Kedzie Blvd.
It’s hard to get a seat at the bar during peak hours, especially dinnertime, but man they have good drinks here. I highly recommend getting drunk on a Sunday afternoon on the patio in the summer. Website
The Whistler
2421 N. Milwaukee Ave.
I like this place because you’ll get cocktails just as good or better than you would at someplace like Violet Hour, but they’re $8-10 instead of $12-15 and the crowd is better. Sometimes on the weekends you will be subjected to some weird live ambient electronic noise fuzz but them’s the perils of going out in Logan Square. Website
It’s 2am and I’m not ready to go home yet
These are the 4am bars I’ve been to, in ascending order of likelihood that you’ll see someone get cracked over the head with a pool cue before last call:
The Owl
2421 N. Milwaukee Ave.
Nice enough that people actually hang out here before 2am. Website
Bonnie’s
2417 N. Milwaukee Ave.
Usually less waiting in line and more dancing than The Owl.
Alice’s
3556 W. Belmont Ave.
Karaoke. That’s probably all I have to say.
I want some deep dish pizza/Chicago dogs/well-known Chicago food
Burt’s Place (Deep dish)
8541 Ferris Ave., Morton Grove, IL
This is the place that was on the Chicago episode of No Reservations. It’s in the suburbs, but totally worth the drive. When we went, we didn’t make a reservation, showed up less than an hour before closing, and didn’t bring cash. They were super nice about it, but don’t be dicks like us.
Kuma’s Corner (Burgers)
2900 W. Belmont Ave.
This isn’t exactly “Chicago food,” I guess, but Kuma’s is sort of an institution. Fantastic burgers in a metal-themed place. You’ll wait a long time for a table but it’s worth it. Website
Hot Doug’s (Encased meats)
3324 N. California Ave.
I have to be honest – I only went here once and I had such a bad food coma afterward that I felt drugged for twelve hours. But it was delicious, and if you’re in Chicago it’s kind of a must-do. I personally don’t think the duck fat fries are particularly special, but they do them on the weekends if you’re determined to get them. Go when it’s warm because the line will be around the block. Website
I want to see some downtown Chicago shit while I’m eating/drinking
Signature Lounge
875 N. Michigan Ave.
Great place to take visitors. Go up to the bar on the 95th floor for a drink – it will be an expensive drink, but it’s cheaper than doing dinner or the observatory and you’ll get the same amazing view of the city. Website
Purple Pig
500 N. Michigan Ave.
Really great food if you end up stuck on Michigan Avenue and hungry. Small plates, communal tables, cheese, wine, pork-y things. Website
I want brunch
Lula Cafe (Regional American/farm-to-table)
2537 N. Kedzie Blvd.
Always my #1 brunch choice. Significantly less expensive than going to dinner (see “I want to eat something delicious and I have some money to spend”, above.) Website
Longman & Eagle
2657 N. Kedzie Blvd.
This is right up there with Lula for brunch. Right around the corner too. Website
The Bedford
1612 W. Division St.
I had a duck confit gravy over grits here that cured the worst hangover I can remember since my college years. Really awesome space, built in an old bank. They kept the vault and a lot of the other details. Also the ladies’ room is bigger than my apartment. Also ALSO the bloody marys have kimchee in them. Website
The Bristol
2152 N. Damen Ave.
More hangover breakfast. No really, there is something called the Hangover Breakfast on the menu and you should get it, whether or not you’re hungover. Also their pastry chef is quite good so order whatever breakfast pastries they’re selling. Website
I need some coffee/a place to hang out and check my email
Star Coffee Lounge
2521 W. Chicago Ave.
My favorite coffee shop in the city. They roast their own special blend of coffee upstairs, and the place is staffed with a bunch of cute, friendly coffee geeks. Website
New Wave Coffee
2557 N. Milwaukee Ave. / 3103 W Logan Blvd.
Their drip coffee is not my favorite, but the baristas are good. If you like sweet drinks the Hail Mary (chai with two shots of espresso) is the way to go. Lots of space, good for working on your laptop and loitering. Website
PS: You should go to __________ for the ____________.
Dunlay’s – Bloody Mary
3137 W. Logan Blvd.
It comes with a snack and a High Life pony. Website
The Handlebar – Peanut butter and jelly handpies
2311 W North Ave
Fried dough filled with warm pb&j. Website
Ipsento Coffee – Ipsento latte
2035 N. Western Ave.
A spicy latte with coconut milk, cayenne, and honey.
Doughnut Vault – Old fashioned
400 N. Franklin St.
Any of the doughnuts, really. Website
Edzo’s Burgers – Burger, fries and Speculoos shake
1571 Sherman Avenue, Evanston, IL
Mostly the Speculoos shake. Website
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