The Best Spot for Every Single Type of Chicago Date Night

Lonesome Rose

Dating sucks. Anyone who has been on the apps or in the online dating world can tell you that. BUT, it does give you the opportunity to try some amazing Chicago restaurants and bars while you’re on the hunt for love. And once you find your perfect person, you can keep right on hitting the town while you dig into delicious meals with your favorite person. So there’s definitely some silver lining in the dating game! Want to make the most of it? We’ve done the exhaustive research and found all the perfect date spots from your first Bumble meet-up to your ten-year anniversary, and every date in between…

Blind Date: Lonesome Rose

Blind dates are tricky because you don’t know the person, but you both have a mutual contact and are coming recommended. So there’s a built in assumption that you’ll like each other simply because your friend says you will! Take the pressure off the start of the date with a margarita at the Lonesome Rose bar or their famous queso to start your meal. You’ll automatically like someone more if you have queso to share! This spot is also great because if the date does go well, you can head down to their secret basement bar for a nightcap.

Casual Co-Worker Happy Hour Meet Up: Tanta

Having a work crush can be exhilarating but also petrifying. To feel out if you and your cubicle crush have chemistry outside of the board room, ask them out for fun after-work drinks. If you hit it off, Tanta has an amazing dinner menu and a romantic rooftop so your drinks can turn into a meal. If you decide you’re actually better as friends, their River North bar is casual and fun enough that you can play this “not date” as just after-work drinks and your co-worker will be none the wiser on Monday.

Tinder Date: Estereo

The key with any online date is to have an easy out in case it goes horribly wrong. Ideally that won’t happen, but any experienced dater knows it’s a definite possibility. So, a casual cocktail bar like Estereo is the perfect spot! They’re a drinks-only spot so you won’t get wrapped into an uncomfortable dinner if you’re not hitting it off, but it’s super trendy and close to other awesome restaurants if things DO go well. And either way, you’ll get a great cocktail out of the night!

Group Date: Starbucks Reserve® Roastery

Group dates call for an activity. It keeps things interesting, provokes conversation, and let’s you get to know people in a more organic way. You can book organized tours at the Chicago Starbucks Reserve® Roastery if you’re someone who wants a plan, but it’s also the perfect place to just wander and explore! There are multiple floors for coffee tastings, espresso martini flights and light bites perfect for sharing with your fellow date-ees.

Third “I Think I Like You” Date: Bar Siena

There’s nothing more pressure-filled than a date with someone you think you might be falling for. You want to make a good impression but not look like you’re TRYING to make a good impression. Bar Siena is always packed with activity so you’ll be high energy for this date, and their menu is full of classic and delicious Italian plates. Share a pizza and cheers with a few rounds of cocktails and just try to keep your cool. If the date goes well, you can also head out to one of the West Loop’s bars for an aperitif - we recommend The Darling or Lazy Bird.

Morning After…But Make It Cute: Stax Cafe

You sealed the deal (good for you!) but now you want to keep those good vibes going for the morning after. Stax is perfect for just that! Bright and welcoming, with a wide menu of creative breakfast and brunch items, your date is sure to love it. And if you’re still in love in the light of day, you’ll know it’s meant to be 😉

Trying to Impress: BLVD Steakhouse

So, you’re in love. But how to show some extra attention to your special person now that you know it’s the real deal? A great meal always does the trick! Add in some sexy decor, and you’ve got the perfect night. BLVD Steakhouse has been lauded for both it’s design and it’s menu, so come for an early drink at their bar before enjoying a late dinner. We recommend going with the oysters to start and the decadent Lobster Thermidor for an extra special meal.

Meeting the Parents: Pizzeria Portofino

Don’t mess this one up. Seriously. Making a good impression on the parents is HUGE in most relationships. So, pick Pizzeria Portofino for it’s stunning city and river views, it’s approachable menu of pastas and pizzas, and it’s elevated vibe, complete with top notch service. There’s something for everyone, and the staff will treat you like family. Hey, if the dinner goes well, you might end up being family!

Engagement: Z Bar at The Peninsula Chicago

You can’t just go to any old place for your engagement. You need ROMANCE. You need VIEWS. You need Z Bar. The rooftop of The Peninsula is perfect for a little drama and a lot of Chicago romance. You can host any out-of-town family and friends in for the exciting news at the hotel itself, and after you pop the question, you can all head to Shanghai Terrace for a celebratory dinner!

Rehearsal Dinner: The Dearborn

The day before your wedding should be as low-stress as possible. The team at The Dearborn is perfect for that, offering customizable menus with vegetarian, vegan, and gluten-free options that will still blow your guests away. Their Rialto Room is ideal spot for a group, with vaulted ceiling, private bar, fresh floral arrangements, burnished mirror panels and crystal chandeliers. You’ll be able to just sit back, enjoy an amazing evening, and take a few deep breaths before the big day.

First Anniversary: arami

You made it through the first year of marriage - Congrats! You deserve a delicious meal that’s zero pressure and all fun. Arami has a menu of sushi and other Asian dishes that are ideal for sharing with your favorite person. But don’t worry - if you’ve had enough of sharing and want your own maki with no shared bites, they have plenty of those too. Celebrate this first big milestone with some sake with their team!

BIG Anniversary: Oriole

If you’ve made it to five, ten, twenty or more years together, you deserve something extra special. Oriole has long been a foodie-favorite and after it’s post-pandemic revamp, it’s truly a must-try for a one-of-a-kind date night. Congrats on the milestone and enjoy a meal you’ll be talking about for the next five or ten years!

“We Need to Talk” Spot: Club Lucky

Is there really a good place for a break-up? No. But if you must break a heart, you might as well bring them to a place where they can dig into a big bowl of pasta and sip down a giant martini after you have “the talk.” The team at Club Lucky are super welcoming and the atmosphere is cozy AF. Book an early table before the dinner crowds arrive and be gentle.

“We Never Liked Them Anyway - Let’s Go Out” Newly Single Spot: Hubbard Inn

We honestly never liked them anyway! We swear! So celebrate new single-dom with a night on the town baby 🕺💃 Hubbard Inn has multiple levels for dancing, drinks, and getting over a heartbreak. Bring your pals and have the night of your life! Then, head out to the rest of River North for even more fun - we also recommend Joy District and Bub City right down the block. Who even WANTS to date anyway?! 😉

By Kaleigh Glaza | Market Editor