8 Best Date Ideas In Chicago (That Aren't Cliché And Overdone)

Skip the wine bar. Try these instead.

7 Best Date Ideas In Chicago (That Aren't Cliché And Overdone) Jojo's Milk Bar

Why go on a regular date night when you can turn it into an extraordinary date night? Sure, grabbin' cocktails or a bite to eat is just fine and dandy but sometimes doing the same thing every weekend gets a little tired. A little boring. IIn light of that, we've come up with 6 of the best date night ideas (and in one case, date day idea!) in Chicago to mix it up. So whether you're a foodie, a spaa-ie (a new word we just created) or want a restaurant experience that's simply, well, different — in a good way — we've got you covered. So: happy dating!


1. A beer spa

What is it? The mission of Piva Beer Spa, which is the first and only beer spa in Chicago, is is to utliize beer for other non-drinking purposes: through beer soaks, massages, salt room AKA halotherapy, steam room, sauna, etc. In today's world, it’s become more and more difficult to find an outlet of relaxation; Piva Beer Spa wants to create an experience that'll make you forget those stresses. Sure, you can go to any spa to relax but Piva wants to create a more natural oasis for your mind, body, and spirit. To quote Tina Turner, make their customers feel simply the best.

What to try? The warm couples' beer bath. Yes, you can actually soak in beer (while drinking beer!). Piva's a great date night idea for long-term couples who want to destress, soak away their stresses in a giant tub full of warm beer (sounds strange; in reality: luxuriously relaxing), while nibbling on appetizers and a cold brew — all prepped for you. Imagine the quintessential perfect bath experience, then quadruple it. That's the piva beer bath experience.  



A post shared by Piva (@pivabeerspa) on Dec 7, 2018 at 9:01am PST

Why it's a great date spot? Whether you want to tack on a massage, sauna, steam, facial, or salt room to your beer bath, Piva's extensive couples' packages offer every assortment of pampering you could possibly want. Plus, on cold days and nights in Chicago: what's better?

RELATED: 15 Cute & Inexpensive Date Ideas For You & Your Partner When You're On A Budget



A post shared by Piva (@pivabeerspa) on Nov 9, 2018 at 12:13pm PST

(Piva Beer Spa, $290-$550 for a couples package)

2. A brunch cooking class

What is it? If you have an appetite for learning, a class at The Chopping Block will satisfy your cravings. Their classes are designed for home cooks with busy lifestyles who have a passion for food. They offer intimate hands-on and demonstration classes covering topics from the building blocks of cooking to intensive cooking boot camps. Foodies at every skill level can celebrate food on a culinary adventure led by professional chef instructors.



A post shared by The Chopping Block (@the_chopping_block) on Apr 9, 2019 at 6:32am PDT

What to try? A brunch cooking demo. Evening dates are usually the standard, but why not mix it up and try a morning date, instead? In their Bloody Mary brunch demo (they also offer a bellini brunch), a professional chef will walk you through the ins and outs of making a three-course meal: fried chicken and waffles with tabasco honey butter; spinach salad with apples, bacon and a poached egg; and bananas foster with vanilla bean ice cream. The menus constantly evolve, so check their class schedule to see which menu whets your appetite. Bring questions and a plus-one!



A post shared by The Chopping Block (@the_chopping_block) on Apr 5, 2019 at 9:09am PDT

Why it's a great date spot? In addition to the cooking demo, there's a full DIY bloody mary bar to start your weekend morning off right — and you can take home all the recipes to try at home! (At-home date night next? Who's cooking?)


RELATED: 12 Date Ideas For Couples Who Spend WAAAY Too Much Time On The Couch



A post shared by The Chopping Block (@the_chopping_block) on Apr 11, 2019 at 6:57am PDT

(The Chopping Block, prices vary)

3. A flower-shop-meets-restaurant

What is it? Machine serves a globally-inspired, modern-American menu with an innovative craft cocktail program along with an on-site flower shop. This trio combines to create an approachable neighborhood concept in the heart of Wicker Park. Their team consists of some of the sharpest and untapped minds this city has to offer and every meal, cocktail, bouquet & menu has been thoughtfully engineered for a new dining and drinking experience.



A post shared by Machine Engineered Dine&Drink (@dinemachine) on Apr 23, 2019 at 6:22pm PDT

What to try? The braised pigtails (it's exactly what you think it is; and yes, it's decadent) and any of the 'caged' cocktails, which come with a mini-hammer so that you can 'break' your way through the ice to get to the good stuff. (Delicious and interactive drinks? Uh, yes please!) Plus, the dessert cocktails are better than actual desserts; try the 'breaking brulee' — it's basically creme brulee in drink form.



A post shared by Machine Engineered Dine&Drink (@dinemachine) on Apr 10, 2019 at 4:56pm PDT

Why it's a great date spot? The ambience is insanely romantic — think florals literally embedded in the walls and library lamps adorning the bar — and did we mention that Machine also doubles as a floral shop? And that the world's friendliest florist meanders through the restaurant, offering 6 or 12-stem bouquets, which they'll then place at your tableside? Brilliant date idea.



A post shared by Machine Engineered Dine&Drink (@dinemachine) on Apr 12, 2019 at 1:31pm PDT

(Machine, prices vary)

4. A milk bar

What is it? Milk bars are all the rage and Jojo's, which just opened in Chicago's River North, features over-the-top shakes and pastries including jumbo cookie flights with infused milks and designer pop tarts. As for food, Chef Christine McCabe has enhanced diner classics with the perfect smash burger and overstuffed deli sandwiches. There's also a lively bar scene with a pointed whiskey program and decadent cocktail selection, which flank the first floor bar and 2nd floor playroom — the perfect venue for your next date.



A post shared by JoJo’s Milk Bar (@jojosmilkbar) on Apr 26, 2019 at 4:27pm PDT

What to try? The over-the-top milkshakes, of course. (I mean, just look at them; they sell themselves) We recommend 'The Gold Digger,' which blends caramel, snickerdoodle, rice krispies, dark chocolate, and milk chocolate. Ridiculous-good.



A post shared by JoJo’s Milk Bar (@jojosmilkbar) on Apr 24, 2019 at 4:02pm PDT

Why it's a great date spot? Two straws, one milkshake = the perfect 50s date vibe. Plus, the place is loaded with vintage boardgames (don't miss the skeeball and arcade upstairs) so you get a bit of friendly competition going at the same time.



A post shared by JoJo’s Milk Bar (@jojosmilkbar) on Apr 9, 2019 at 3:40pm PDT

RELATED: 52 Free (!!!) Date Ideas For Every Season

(Jojo's Milk Bar, prices vary)

5. A modern steakhouse

What is it? Maple & Ash is an innovative take on the traditional steakhouse, mixing a modern aesthetic with authentic service to deliver classic wood-fired dishes. With a sumptuous menu crafted by two-Michelin-star Chef Danny Grant and a wine list named "one of the most outstanding in the world" by Wine Spectator, Maple & Ash celebrates every moment — and every type of date.



A post shared by Maple & Ash (@mapleandash) on Apr 28, 2019 at 10:51am PDT

What to try? The steak, of course: there's simply no bad option. We ordered the 28-day dry-aged ribeye. Also of note: the ricotta agnolotti, the seafood tower, the endless (and stunningly impressive) wine list, and for dessert? Save room, because you simply must order the sundae service: it's unlike anything we've ever seen. Imagine three tiers of ice cream, flanked by every imaginable topping from your wildest Willy Wonka dreams. It is something to behold.



A post shared by Maple & Ash (@mapleandash) on Mar 28, 2019 at 5:34pm PDT

Why it's a great date spot? The service is unparalled (any place that greets you with complimentary house cocktails and appetizers is simply working at a different level of service) and the ambience is soft, appealing, and cozy: each table is draped with dramatic candleabras and the lighting is a perfect level of dim moodiness. The knowledge of the waitstaff is also unprecendented; there's no question they can't answer or recommendation they can't give. Maple & Ash isn't just a meal; it's a full sensory experience: take someone very, very special here if you want to truly impress.



A post shared by Maple & Ash (@mapleandash) on Oct 31, 2018 at 5:35pm PDT

(Maple & Ash, prices vary)

6. An art fair

What is it?  Showcasing over 120 artists, The Other Art Fair Chicago will present a variety of immersive installations and works ranging from photography to paintings and sculptures chosen by an expert selection committee. Chicago’s own Little Black Pearl, a non-profit that provides opportunities in art, culture and entrepreneurship to youth across Chicago will serve as the official charity partner. 



A post shared by The Other Art Fair (@theotherartfair) on Apr 25, 2019 at 6:50am PDT

What to try? The Other ArtFair will introduce “Greener Future,” its 2019 global initiative promoting a multifaceted approach to eco-sustainability in the arts. Don't miss it.



A post shared by The Other Art Fair (@theotherartfair) on Apr 26, 2019 at 4:31am PDT

Why it's a great date spot? Because viewing and interpreting art with someone else offers a different perspective — and something to talk about!



A post shared by The Other Art Fair (@theotherartfair) on Apr 25, 2019 at 12:40am PDT

(The Other Art Fair, $15 in advance, $18 at the door, May 16-19)

7. An acoustic performance

Kick back and relax to a special live acoustic performances after work starting May 9th, 2019 at River Roast, a restaurant located on the Chicago River which features stunning city and water views from every seat in the house.



A post shared by River Roast Chicago (@riverroastchi) on Apr 8, 2019 at 9:32am PDT

What to try? River Roast is aptly named: they're known for their roasts and trust us, they don't disappoint: choose from the 'roast of the month' or the evergreen options: whole fish (our favorite!), roast chicken, stuffed vidalia onion, roast beef, prime rib, rack of pork. They're all carved tableside and the portions are ginormous. For dessert? The key lime pie is some of the best we've had outside Florida and it can feed a family.

Why it's a great date spot? Chill vibes. Acoustic ambiance. Water views. It's a recipe for romance...with cold-brewed cocktails, to boot.



A post shared by River Roast Chicago (@riverroastchi) on Mar 26, 2019 at 12:02pm PDT

(River Roast, Thursdays, starting May 9th)

8. A whiskey tasting

Returning to Chicago for its second year, the event, which has also stopped in Los Angeles, Denver, New York, and Austin, WhiskyX aims to deliver a multi-dimensional experience through which those relatively new to whisky can make discoveries while still appealing to aficionados.



A post shared by Whisky Festival (@thewhiskyx) on Apr 14, 2019 at 10:00am PDT

Why it's a great date spot? Whisky tastings from more than 60 long-established and emerging whisky brands. Live music. Local Chicago food trucks. Need we say more?



A post shared by Whisky Festival (@thewhiskyx) on Mar 31, 2019 at 10:01am PDT

(WhiskyX, tickets available here)


Andrea Zimmerman is the editor-at-large at Yourtango. She enjoys reading, traveling, and reading while traveling. She lives in Chicago with her husband and three-legged cat. Follow her @angiecat86 on Instagram.