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The One-Two Punch: A Date Night Dinner & Drinks Guide

The ultimate guide to dinner and drinks.

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25 Spots
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29 Spots
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It all starts out so well. You’ve picked an awesome place for dinner, the meal is great, the conversation is easy, you’ve found out you have tons of things in common (you both like yoga! and puppies!), and you both want to keep the night going. Score.

But then you realize you have no idea where the f*ck to take this person next. You were so caught up in picking out a dinner place that you forgot about what happens if things go well.

Don’t let this be you. The one-two punch, dinner-then-drinks date is your proven road to date night glory, whether it’s your third date or thirtieth. And we’ve plotted all the best ones out for you. We can’t promise these plans will convince someone to go home with you, but we can promise they’ll be a rock solid foundation on which to seal the deal.

the one-two punches

Maude's Liquor Bar

French  in  West Loop
$$$$ 840 W Randolph St

Nothing says romance like a nice French restaurant, but a nice French restaurant can be too fancy and formal. That's why Maude's is great, because it delivers French food in a hip space with much cooler style. Share the French onion fondue to start because who doesn't like to dip bread in cheese.

Facebook/Lone Wolf

Lone Wolf

$$$$ 806 W Randolph St

After you've romanced one another over modern French food, head next door to Lone Wolf. The lighting in here is perfect, meaning it's kind of dark with minimal visibility to the outside world. That's the perfect scenario to keep this night trending in the right direction.


AmericanKorean  in  Avondale
$$$$ 3500 N Elston Ave

Parachute says you're ready to take this whole dating thing to the next step. Not because Parachute is fancy or a crazy romantic restaurant, but because it's such a good restaurant that the person you take should be important. They serve an interesting twist on Korean-American food in Avondale, but a date at Parachute is worth the trip even if you don't live nearby.

Chief O'Neill's Pub & Restaurant

$$$$ 3471 N Elston Ave

The problem with a date at Parachute is that there isn't much nearby if you don't know where to look. And the place to look is the random-looking Irish bar across the street, Chief O'Neill's. There's even a nice garden area to sit in out back if you find yourself in the position to do so.


$$$$ 1020 W Madison St

We compared Monteverde to Steph Curry when we first discussed it, saying it didn't sound very exciting on paper but was putting on an impressive show. The question then became longevity - could it be consistently great? Answer: there's no end in sight, for both Monteverde and Steph.

Facebook/Booze Box

Booze Box

$$$$ 823 W Randolph St

You could stay at Monteverde all night and drink at the bar there. But if you want to go somewhere else, skip the sports bars on Madison and head back towards Randolph St. instead. Booze Box is a dark dungeon bar full of people and drinks. The good kind of dungeon. Do good dungeons exist? The bottom line is Booze Box will be fun, just don't miss the entrance off the Green St. alleyway between Soho House and Sushi Dokku.

Facebook/Lost Lake

Lost Lake

$$$$ 3154 W. Diversey Ave.

You loved Fat Rice. Your date loved Fat Rice. You think you love your date. Keep the good vibes going at Lost Lake, an awesome tiki bar that salvages the bad reputation of sh*tty tiki bars all over the world.

Facebook/Riccardo Trattoria

Riccardo Trattoria

$$$$ 2119 N Clark St

Riccardo Trattoria is like a page out of Italy. It's slightly upscale without being pretentious and stuffy, and it's the kind of place you want to sit, hang, and drink wine. When we want a slightly nicer date night for Italian food without too much of a scene, this is the move.

The J. Parker

$$$$ 1816 N Clark St Fl 13

You know what Italy doesn't have? Excellent views of Lake Michigan. Take that, Italy. Luckily, the J Parker does, and it's a short walk from Riccardo Trattoria. Cap of your Italian meal with a good drink and even better view.


$$$$ 1012 N Western Ave

Traditional steakhouses are nice and all, but maybe you're looking for something a little different that won't induce the meat sweats. And that's where Boeufhaus has you covered. It’s more like a hip, underground, meat-centric club - a type of tavern or brasserie that just happens to serve a really great piece of meat. Get a 55-day dry aged ribeye to share plus some other appetizers and sides.

Sportsman's Club

$$$$ 948 Western Ave.

You've successfully avoided the meat sweats and now you're really ready to put on the moves. Do it At Sportman's Club. The small bar is ideal for sitting close together, or, if it's nice outside, hit up the quaint patio out back. Either way, no meat sweats, so that's a victory in and of itself.

Le Bouchon

French  in  Bucktown
$$$$ 1958 N Damen Ave

A classic French Bistro is never a bad idea, which is why you would be wise to do date night at Le Bouchon. Get mussels, steak frites, and don't be afraid to overdo it on a little French wine. Le Bouchon will set the perfect mood before you ever open your mouth and inevitably say something dumb, so it's good to know you're already a step ahead.

The Map Room

$$$$ 1949 N. Hoyne Ave.

Unsurprisingly, the Map Room is covered in maps. But we promise it's not as dorky as it sounds. It's got a divey-cool thing going on in a dark space, plus an excellent beer list. You just focus on navigating your way into your date's heart, but don't say sh*t like that out loud because you'll sound like a cheesy idiot.


American  in  Pilsen
$$$$ 1227 W 18th St

Dusek's is like Ariana Grande - it has range. This place can hit the whole octave from Brittany Spears to Whitney Houston, meaning it can cater to a date night or whatever else you need. And Dusek's even has post-dinner drink options built in (more on that below). We know this is the one-two punch guide, but Dusek's makes for a great one-two-three punch.

Punch House

$$$$ 1227 W 18th St

If you're into basement bars and homemade alcoholic punches, then head downstairs to Punch House as soon as you finish dinner. No need to put a pause on your night because we all know that's how things unravel quickly.

Tack Room

$$$$ 1227 W 18th St

More of a classic cocktails and piano bar fan? Head to the adjacent Tack Room, which is also owned by Dusek's and connected next door. There's always somebody on the piano at night, and nothing helps lead to the no pants dance like some live tunes.


$$$$ 660 N Orleans St

Bernie's is ideal when you need or want to do dinner in River North but you don't want it to be too "River Northy." Translation - a River North restaurant not full of *ssholes and try-hards. The food has a slight Mediterranean influence, and there's something for everyone.

Green Door Tavern

$$$$ 678 N. Orleans St.

No need for a fancy cocktail lounge after dinner. Head two doors down to Green Door Tavern, legitimately one of the oldest bars in the city. The building looks like it was built in 1825 by General Custer and used to be an actual prohibition tavern. Hang in the main bar area, or check out The Drifter in the basement, a speakeasy that serves as a throwback to the prohibition days.

California Clipper

$$$$ 1002 N California Ave

Kick the coolness level up a notch at California Clipper, a retro style bar where you can grab your own table or booth and sip on cocktails. There's often live music and a $5 cover at night, so make sure you have some cash before you ruin a good thing.

Lula Cafe

$$$$ 2537 N Kedzie Ave

There are a lot of good date night options in Logan Square, but Lula Cafe is the move. It's the original spot that got Logan Square rolling as a destination dining neighborhood, and it's always a great place to take someone you're trying to get to know.

Mezcaleria Las Flores

$$$$ 3149 W Logan Blvd

A Mezcal bar, inside an old flower shop, inside a diner - welcome to Mezcaleria Las Flores. The mezcal focused cocktail bar is inside of the expanded Johnny's Grill, and coming here for a post-dinner drink is always a good idea. Of course, this move hinges on your date being into mezcal, and you have two options in case they're not: 1. Ditch 'em, because they're lame. 2. Head next door to Billy Sunday where mezcal won't be the total focus of the bar.

GT Fish & Oyster

$$$$ 531 N Wells St

Oysters are an aphrodisiac, so of course you're going to want a dozen to start the meal. The beauty of GT is it's a shared plates situation, so you can order as much or little as you like. Get yourself at least one fried oyster po' boy too. We're not sure if frying oysters affects their aphrodisiac status or not but they taste damn good.


$$$$ 111 W. Hubbard St.

Listen carefully, because wrong one move on Hubbard Street and your night will be a disaster. You can't just go wandering around River North expecting to walk into a cool bar - you might accidentally end up at, well, let's just say you don't want to end up at a lot of places nearby. Head over to Celeste, which is a good cocktail bar opposed to some of the other riff raff around.

La Sirena Clandestina

$$$$ 954 W Fulton Market

La Sirena Clandestina is a Fulton Market restaurant housed in a former warehouse building that has an industrial style. If you feel like you've heard that before about a place in Fulton Market it's because you have. So does La Sirena Clandestina separate itself at all? Yup. And it’s doing so by serving some pretty good Brazilian-inspired food. Anything Brazilian is sexy, so let that be the confidence you need for your date.

Clayton Hauck


$$$$ 660 W Lake

You might not expect to find a cool bar right off the highway exit and underneath the L tracks, but that's exactly what Moneygun is. It's small and dark with a bunch of bar seats and a few booths. The cocktails here are serious, which will help you get serious about whether or not you want to plan a future with your date. If there's no future in sight, Moneygun will also be there to help you move on.

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