Where To Go On A Date In Chicago: A Neighborhood Guide

We’ve all been there. We have a list a mile long of places we want to try in this eclectic dining city, and then the time comes to pick a place and we go to deer-in-headlights mode, ending back at our go-to date place, where all the waiters take bets on whether or not this one will last. It’s easy to fall into our comfort zones go back to a bar where everybody knows your name. But whether it’s a first date, a boyfriend, or a gal pal, trying a new place can enhance the night by both of you experiencing something new for the first time. So these Chicago singles have put together a list of our fave spots for dining and drinking to help give you some ideas for your dating adventures.

River North

Cafe Iberico ($$) offers up not only a great variety, but a fun atmosphere. They serve small plates, so it’s great for a date. You order tons of food and share. Great way to keep the conversation flowing. – Nycole

There are so many great options in River North!  Siena Tavern ($$$) is a fave, but forewarning, if I do go there on a date, I WILL flirt with Fabio Viviani.  It is a bit more expensive Italian, but coming from a true Italian, I recommend it. Rockit Bar and Grill ($$$) is my standard go-to place.  And I have two words: Truffle. Tots.  Cantina Laredo ($$) has amazing happy hour specials and sangria…it’s a win/win. Bin 36 ($$) Monday night $10 wine flights, um… yes please! – Laura

I don’t think I’ve ever left Fogo de Chao ($$$) and not wanted to immediately take a nap. Come hungry! Brazilian steak houses are known for their meat selections but people often overlook the amazing salad/side bar that they offer as well. – Gina

Quartino ($$) is an oldie, but a goodie in my book. Great wines, fun food sharing, and always a lively atmosphere! – Chloe

GT Fish & Oyster ($$$) is perfect if you want to wine and dine. Know something about oysters, and you’d do yourself a favor. But stay away from ever inviting someone to the Public House. A reservation at RPM Italian ($$$) reads “I have style and like al dente pasta.”  If you want to show off your wallet, go to Sixteen at the Trump ($$$$) but beware, if your date’s a lush you might end up broke. For a cheaper night… wait, this is River North. – Brandy

Chloe and I tend to agree on a lot of things, Quartino ($$) is one of them. It’s great and has an upbeat atmosphere, perfect for group dates, or for introducing friends or family to your new boyfriend or girlfriend. – Nick

Bucktown / Wicker Park

Caffe Gelato ($) is small, cute, and the right spot for a casual and fun treat. The gelato is authentic, creamy, and full of flavor. Club Lucky ($$) is deceptively large; you walk into a small bar and if you don’t walk towards the back you might miss the larger dining room in the back. Typical Italian sized portions (large) but definitely tasty. Drinks and dishes are moderately priced.  LoKal doesn’t have huge portions, but they’re definitely filling and affordable. Opens up as a bar at night and has a small dance floor and dj. The music can be varied depending on the night. – Gina

Via Carducci La Sorella ($$) is perfect this time of year because it’s super cozy and quaint.Their food is incredible and reasonably priced. And I love Division Street during the holidays! Big Star ($$) can be fun in the colder months, too. Even though it’s almost impossible to sit down, why would you want to? I love standing in the back, grabbing a few tacos and one of their ginger beer concoctions and just people watching. – Chloe

Bluebird ($$) is great for an easy and relaxing date without feeling like you are at a bar (Sadly, as of June 25th the Bluebird has been closed). The same goes for Hot Chocolate ($$) right next door. For a casual first date, I’ll echo Chloe and say hit up Big Star ($$) for tacos and tequila then get your dance on at Danny’s ($). If all else fails, play hide-and-go-seek in the corner Walgreen’s. – Brandy

 Lakeview

This is my hood!  Taverna 750 ($$) has good food (smaller Italian style tapas) and drinks too.  Bonus:  if your date doesn’t compliment you, most likely the waiters will. Twisted Vine ($$) is a cute, newer smaller wine bar.  It’s great for a quick drink or two as a first date, but there’s a minimal food menu, so do not go expecting to eat dinner.  Sheffields ($$) is a good Sunday afternoon date during football season. It is your typical bar, nothing fancy. Matilda ($$) is good for a weeknight meetup drinks and has a somewhat diverse drinking menu from wine to beer to cocktails so it’s easy to accommodate even the pickiest date. – Laura 

I agree with Laura– Taverna 750 ($$) is a great little spot to hit up. It is small enough for anintimate date, but not so much so that you are on top of one another. They are known for their drinks, and super cute, gay waiters (It’s in THAT part of Lakeview, what did you expect?). Seriously though, trying to get one of their phone numbers is all but a national pastime for my friends and I. Don’t take you date here unless you want to feel insecure the whole time, or get a  threeway going. – Nick
Filippo’s ($$) is the best Italian in the city. Their pastas are to die for, but I end up getting their salmon and mashed potatoes every time because they melt in your mouth. This spot is so quaint and cute, and it’s right near the movie theatre, too. Love, love, love. – Chloe

The Kit Kat Lounge & Supper Club ($$) is a great place to stop for a casual drink, and theyalso have great food. In the summer time they have a patio which is fun if you’re there just for a meal, but I’d suggest going inside to see the (drag) show as well! I hear they have a good brunch, but have yet to go. Tango Sur ($$) is definitely a small and intimate place but the food is well worth it. Must. Love. Meat (and bread). It can be a bit loud due to the size but again, definitely worth it. – Gina

 Lincoln Park

 Sono Wood Fired ($$) is a pretty well kept secret. They have pizzas and small plates–all meant for sharing, which I always like on a date. Especially if your grasping for something to talk about. Their dishes are really unique, as are their wines. They have live music every Wednesday, too. Another super cozy spot for the upcoming winter months. – Chloe

Cafe BaBaReeba ($$) Can’t. Go. Wrong.  The food is amazing, the pitchers of sangria.  The staff.  The atmosphere.   All make the beginning of a beautiful date. – Laura

Perrennial Virant ($$$) then head up to the J Parker bar on the roof. – Brandy

Downtown / West Loop / Greektown

Boarding House ($$) for their wine glass chandelier, or anything on Rush if you want to look like you live in the suburbs or only go out for “special occasions.” (Hint: Don’t do it.) – Brandy

La Scarola ($$) is my favorite restaurant in Chicago, hands down. The food is traditional Italian and absolutely delicious. Reservations are a must and be prepared to wait next door at the little hole in the wall bar while your table is being prepared. – Nycole

Though I haven’t been to The Parthenon for an actual date, I do recommend it as an authentic Greek restaurant experience.  Flaming cheese – what is not to love?! – Laura

Artopolis Bakery is better during the warmer months when you can sit by the open windows. You can choose from the restaurant or the bakery, but either way you should end the visit with a frappe! Portions are large(ish) and the desserts are delicious. – Gina

Old 5th for whiskey and pizza. I also hear there’s a kicking Mariano’s wine bar too, but only do that if you are on like, the tenth date or so, anything sooner would just look weird. – Brandy

Five Star ($$) is a fun bar spot to hit up on date because they always have a great beer and burger selection. There’s also a stripper pole in the back. Do what you want with that piece of information. – Chloe

I only ever make it this far into downtown (Im a RoPo-er; It’s a miracle I make it as far as Wrigleyville) when I am visiting my cousin and her boyfriend on west Madison. They live 50 feet away from the Beer Bistro ($$). From the name you can guess, it is known for its wide selection of beers. Its a great “neighborhood bar,” and while popular, isn’t overcrowded. I highly recommend for group dates or a place to introduce your new boo to your friends. – Nick

South Loop / Hyde Park

Flo and Santo’s ($) for the vodka flights and craft cocktails as well as good pizza. Tell them Brandy sent ya. – Brandy

If this isn’t a first date, and you’d like to watch a game together The Scout ($$) is great. There are tons of TVs all over the entire bar. Good bar food menu and endless beer choices. Promontory Point ($) is this great little park off the lake where you can build bonfires and bring grills. This is a fun outdoorsy type of date when it’s nice and warm out. You have to bring all your own materials. There are about 5 new high end foodie type restaurants opening in the next few months that will be great too! – Nycole

Logan Square / Avondale

Call ahead to Kuma’s Corner ($$) to see if there’s a wait! If there is, I suggest asking to sit at the bar because you’ll get seated quickly. The burgers are big and the beer selection is good. Don’t let the names on the menu or the music scare you.  Siboney ($$) is great for groups or just one-on-one. Servings aren’t too big, but they’re filling and definitely tasty. Service is friendly, and if you come on a weeknight you should stay for the music and dancing. – Gina

Katakana Sushi  ($$) is one of my favorite sushi spots in the city. It’s BYOB with no corkage fee. Great service. Fresh food and tons of options. Gorgeous room with a romantic feel. – Nycole

Longman & Eagle ($$) has crazy good food, although it’s also known for its whiskey selection. I’m not much of a whiskey drinker (it makes me mean…ok, meaner), but I love spots that have old school atmospheres and comfort food. – Chloe

Yusho ($$) for some kicking delicious food. Telegraph ($$) for cocktails after. If you’re a beer nut, Revolution Brewery ($$) all the way. For a Monday date and good food, Lula Cafe ($$). – Brandy

Wrigleyville 

This is my hood!  I suppose living a block away from Wrigley Field, I try to have my dates a bit further out.  However, next summer when the Cubs win (yeah, that’s right… the power of positive thinking!) a fun date would be grabbing food and beer at The Cubby Bear ($$) or Sports Corner ($$). But let’s be honest and I’d have a few more drinks so ($$$) before attending a game. – Laura

Cozy Noodles & Rice ($$) is a BYOB and small with entertaining decor, and the food is really good. – Gina

Wrigleyville North ($) is the place to go if you want a date with a bit of an adventure. It’s one of the best dive bars in the city. They have live music on Saturdays, and if you ask really nicely, they’ll let you karaoke with the band. If you need a snack, just ask Kermit behind the bar to sell you a bag of chips. I always go for the Honey Mustard Wheat Thins. Because they are amazing. – Chloe

Other Neighborhood Haunts

Seadog Sushi ($$) is a great secret in Noble Square on Division, but east of Ashland. It’s a BYO spot with super creative and delicious sushi rolls. If you pay in all cash, they take 10% off your bill, too. – Chloe

Sticky Rice ($) in North Center is the best Thai around and BYOB. Turquoise Cafe ($) in Roscoe Village for some of the best Turkish food in the city. – Brandy

The Little Goat Diner on the Near West Side is awesome, and honestly underrated when you compare it to the more popular Girl & The Goat, both owned by chef Stephanie Zard. I also couldn’t go without mentioning at least one best kept secret from my own neighborhood of Rogers Park. Act One Pub ($), located within the Mayne Stage, does the best brunch with bottomless mimosas and Bloody Marys. Go on a Sunday, stay for a beer, then get lunch and just enjoy the whole day parked at the bar watching the Bears. You’ll probably see me there! – Nick

Old Town Pour House ($$) in Old Town.  Having a first date here is good, especially if you are like me and the Stanley Cup happens to be there.  Also, I choose the beers based on what the beer tap looks like, which makes for a different conversation starter – with your date…or bartender.  The food menu is pretty decent, too. – Laura

If you’re in the West Town area, hit up Butterfly Sushi Bar & Thai Cuisine ($$), there are three locations, but I’m most familiar with the Grand Ave location. It’s a small and intimate setting, is BYOB, and has some amazing sushi. Definitely a date night spot. If you’re in Chinatown hit up Lao Sze Chuan ($$). It’s authentic food, especially if you’re feeling a bit adventurous. Break away from the usual menu items. – Gina

In the Pilsen neighborhood, the year-old restaurant Pl-zen ($$) is one of my favorites. They have a very creative, yet affordable menu. The lights are always dim and it makes for a nice relaxed and romantic vibe. – Nycole