Whether you’re on your first, fifth, or hundredth date with a person (or hundreds of different first dates), love is an awesome and terrible mystery. It’s not easy to start off on the right foot with someone new or keep the relationship fresh with someone you’ve been with FOREVER. We’re not therapists, but we can help you put together a centralized dating itinerary in each of these 30 Chicago neighborhoods.
Albany Park/North Park/Irving Park
Indulge in a hearty Swedish brunch before hitting the trails
Nosh on Swedish pancakes or Belgian waffles piled with fruit at the Tre Kronor diner, then swing by Beijo de Chocolat, which specializes in hard-to-find Brazilian chocolate, for take-home treats. You’ll want to walk off that breakfast, so continue for a stroll through Ronan Park’s Multicultural Sculpture Park & Healing Garden or the trails around the North Park Village Nature Center. In the evening, dine at Angelo’s Wine Bar (or Ixcateco Grill if you’re looking for a great BYOB spot) followed by BreakRoom Brewery a couple blocks over.
Learn all about the Swedes before a casual dinner and drinks at a local beer hall
For a cultural experience, visit the Swedish American Museum then head over to Simon’s Tavern afterwards for some seasonal glögg (if you’re sticking to the Swedish theme) or George’s Ice Cream & Sweets for a scoop of Fat Elvis ice cream. Evening plans can entail a more intimate Korean dinner for two with sojutini cocktails at Jin Ju or a more laid-back dining experience at Hopleaf, which also hosts food and beer pairings as well as the Tuesday Funk eclectic monthly reading series.
Tour a brewery before picnicking on fried chicken coated in honey butter
Revolution's brewery and tap room offers free tours for groups of up to 30 on a first-come, first-served basis. Get your names in early, then treat your date to a Cross of Gold or two beforehand. For dining in this 'hood, you’ll find the infamous Kuma’s Corner for some of the best burgers in the city (as long as you and your date can withstand the Slayer-grade metal on repeat) or Honey Butter Fried Chicken, where you can grab food to go for a picnic in Brands Park down the street. In the event of an excruciating wait list at either place, pop into Kurowski’s Sausage Shop for a Polish pastry while you wait.
Depart for a romantic helicopter ride above the city or engage with experimental art
You don’t have to snag White Sox tickets to head here. Palmisano Park (also known as “Mount Bridgeport” or Stone Quarry) has 27 acres of paths through wetlands to roam with your Sugar Shack sweets. You’ll even find rotisserie duck for two at gastro-tavern The Duck Inn for dinner and 450+ beers at the eclectic dive Maria’s Packaged Goods and Community Bar. There’s also a burgeoning art scene; check out the Co-Prosperity Sphere for experimental art, film, storytelling, comedy, and music performances, or the Bridgeport Art Center every third Friday, when artists open their creative spaces to show off one-of-a-kind pieces for the public to purchase. Those looking to take their relationship to the next level should consider booking a Chicago Helicopter Experience over the city, but obviously not if your date is terrified of heights.
A friendly WhirlyBall competition followed by hot chocolate (or a cold beer)
Spend the afternoon at WhirlyBall Chicago’s giant complex, which has happy hour specials Sun-Wed, bowling, laser tag, and three courts for that crazy game combining lacrosse, basketball, and bumper cars. Once you’ve worked up an appetite, you deserve some dinner at Presidio followed by dessert next door at the city’s chocolate haven, Mindy's Hot Chocolate. Keep things going strong with more drinks at The Map Room and late-night dancing at Danny’s if you’re staying in the 'hood.
Enjoy the best spot for dim sum and strap in for a rock show
Grab a bubble tea/smoothie from Joy Yee Noodle Shop’s extensive selection before you both explore all that Chinatown Square, the Chinatown Bazaar, and Ping Tom Memorial Park have to offer before a BYOB dinner at Lao Sze Chuan. If you head to this 'hood early on the weekend for traditional dim sum served a la carte at Phoenix, plan for some lazing in the park instead. Later on, Reggies is around the corner for rooftop drinks and/or a rock show.
Scavenge for vintage finds and partake in a monthly supper club
Sometimes the best way to get to know people is by the type of junk they’re willing to put in their apartments. So find some premium junk by exploring vintage wares at the Broadway Antique Market or Edgewater Antique Mall over the weekend. But stopping by Broadway Cellars for a Bloody Mary or Cookies & Carnitas for tacos and a giant ice cream cookie sandwich first would be a wise decision. If your date hasn’t purchased too many creepy clown tchotchkes, you can always move to the dog-friendly Waterfront Cafe or Sauce & Bread Kitchen, which also hosts a monthly Stew Supper Club worth looking into.
A mansion row stroll before fine Italian dining and piano-side sing-a-longs
After passing the old mansions of Lake Shore Dr, sip cocktails fireside like aristocrats from the 1950s in the living room-style Library & Coffee Bar at PUBLIC Chicago. For a lighter, airy aesthetic, follow up with dinner at Tony Mantuano’s Michelin-starred Spiaggia. Close out the night with sing-a-longs at the Zebra Lounge piano bar, or maybe elsewhere...
Hit a wine and beer bar after archery, not before...
Whether you’re a novice or master, Archery Bow Range Chicago is here to make learning the lost art of archery fun. Plus, it might be a chance to impress your date. If you’re less sporty/more artsy, there’s always 30-minute Chicago Hot Glass classes to make a killer paperweight instead. Both are walking distance to the 219-acre Humboldt Park (making out at the Boathouse anyone?). Afterwards, enjoy some vino at Rootstock Wine & Beer Bar, a cozy 50-seat nook peppered with locally painted artwork, then hit up The California Clipper, a classic bar with live music, dim red lighting, and a 70-deep cocktail menu. Or you could dance like a maniac while watching porn, if that’s your jam.
Visit an entire 'hood where learning is sexy
Geek out at the Museum of Science and Industry or spend the afternoon exploring this lush part of the city by starting at Promontory Point. Next, scour the co-op 57th Street Books, wind North to Hyde Park Records if you’re looking to weed out your Tinder date based on musical tastes, and head back South again through the University of Chicago’s gothic quadrangles. At Medici on 57th (BYOB spot!), order the Garbage pizza with sausage, ground beef, pepperoni, AND Canadian bacon (apparently a favorite of President Obama’s). Then hop over to Woodlawn Tap (also known as Jimmy’s in honor of the late owner), which occasionally has live blues and jazz music.
Connect mid-air with flying trapeze classes or bond over robot building
You don’t have to blow all your hard-earned cash on a helicopter ride for an adrenaline rush; just take a flying trapeze class at the Trapeze School and see if your date has the guts to catch you. Ready to unleash your inner nerd? Try building robots together at Robot City Workshop’s BYOB Robot Date Night. Other neighborhood bars feature more low-key date nights like board games at Guthries Tavern, free arcade games at Headquarters Beercade, or bowling at Southport Lanes. This season, Theater Wit’s productions are exploring the intersection of love, technology, and politics.
Overlook the park with rooftop drinks
Meet up at the North Pond Nature Sanctuary and wind your way down through the park down to J. Parker, the bar atop the Hotel Lincoln for aerial views of the lake and cityscape (don’t worry, this rooftop bar has a fire pit and retractable roof). Later, head straight up Lincoln Ave for a concert at Lincoln Hall or West to the iO Theater for free improv shows like Carl & the Passions (or Felt is well worth the $5) on Wednesdays. Spend your late nights at the intimate Chicago B.L.U.E.S. Bar -- on Sundays, your cover here will also get you into Kingston Mines for more acts across the street.
Turn up the heat with a hands-on cooking class
Besides Big Joe’s Friday night turtle racing and a plethora of German-themed bars and activities, there are plenty of options in this 'hood for two, such as 1.5- to two-hour “Dance Basics for Couples” workshops at Old Town School of Folk Music or “The Thrill of the Grill” hands-on cooking classes at The Chopping Block. Should you do choose the Big Joe’s adventure (which you should at some point), be sure to grab seats early and consult the dos and don’ts of turtle racing beforehand.
Don’t miss this food tour featuring Chicago's OG Italian beef
Helmed by experts from Chef Driven Food Tours, the Taylor St walking food tour gives you and your date a chance to explore iconic Little Italy spots like Al’s #1 Italian Beef’s original location, the National Italian American Sports Hall of Fame, Piazza DiMaggio, Mario’s Italian Lemonade (depending on the season), and more. Foodies can also explore other 'hoods through the company’s other 3.5-hour culinary adventures like Pilsen, South Side, Devon Ave, and Uptown. Meet up at the their designated Downtown spot, and they’ll do the driving.
Classic is definitely still cool with booze-filled slushies, hot fudge sundaes, and shuffleboard
For an old-school date night, this 'hood has plenty of options: Parson's Chicken & Fish’s lively patio (which is converted into an ice-skating rink in the winter months) for booze-filled slushies and traditional fried chicken, sundaes in a booth at Margie’s Candies, movies at The Logan Theatre, shuffleboard and martinis at Weegee's Lounge, libations at Scofflaw and Longman & Eagle, and even Tiki cocktails at Lost Lake for retro-vacation vibes. You can even re-enact scenes from old movies at The Whistler for "Movieoke" on Wednesdays.
Pick up all the vital knowledge on our fair city with the architecture tour
Explore Chicago’s history and skyline through the Chicago Architecture Foundation’s First Lady River Cruises (they even have romantic river cruises at night). Thursday evenings (5 to 8pm) are free to Illinois residents at The Art Institute of Chicago, where Terzo Piano is also open for dinner in the Modern Wing (other days of the week it is only open for lunch). Most of the season for free events in Millennium Park is over, but you can still catch movies and performances through November (when you can officially kick off winter at McCormick Tribune Ice Rink instead).
Near North Side
Take a dance class then try out your new moves together at a nightclub
Teach your two left feet to dance by trying one of Chicago Dance’s salsa, swing, or social classes, then head over to Nacional 27 for dinner and salsa dancing or Primary Night Club to test out your newfound “social dancing” skills.
If you like The Moth podcast, you’ll dig the live storytelling at this Chicago joint
Treat your date to a badass Bad Apple burger like the Slow Burn with oatmeal stout-sautéed spicy chilies and onions, bacon, and white cheddar (or just order pizza for delivery from Big Bricks while imbibing at Half Acre) before heading to Martyrs’ for The Moth StorySLAM (some advice for Moth-goers: get in line by 5:30pm if you want to sit; show starts at 8). Alternatively, you could check out the regular burlesque-and-live comedy mash-up at High Hat Club, which was recently deemed the winner of Jeppson’s 2015 best Malort bar contest.
Drop into (or out of) one of Chicago’s famous schools of improvisation
Want to know if your date has the same awesome sense of humor as you? Test your date’s comedic chops at a drop-in improv class at The Second City, or just take your OkCupid date to see a performance like #DateMe: An OkCupid Experiment. Follow it up with brews at the Old Town Pour House (or get your night started there instead).
Observe Mexican artwork then drink at the biggest brewery in town
You could hit up Dusek’s, Punch House, and Thalia Hall for three dates in one night, or you could check out the National Museum of Mexican Art, the community’s street art/murals (like the nearby Damen Ave Pink Line station murals and the mural at Casa Aztlan), go on a taco crawl along the way (Los Tres Dias, Birreria Reyes de Ocotlan, and Carnitas Uruapan), and wash it all down with some limited-release brews at Lagunitas Brewing. On the second Friday of every month, explore the 'hood’s exploding art scene at Chicago Arts District 2nd Fridays Gallery Night.
Mix things up by making the perfect whiskey cocktail for each other at a distillery
Tour, sip, and mix at the whiskey wonderland that is Koval Distillery with cocktail-making and whiskey-specific classes. Once you’ve successfully passed the boozy course, bottled varieties are available to take home at a discount. Bring your booze to the intimate BYOB Goosefoot or sport your newfound whiskey knowledge on the Fountainhead rooftop (or fireside if the booze isn’t keeping you warm enough).
Catch a free concert at one of the nation’s longest-running music studios or take a weird tour of Chicago’s red light district
Did you know you could watch a free taping at the JBTV studio? Musician performances are scheduled during the day and in the evenings any day of the week. Just make sure your date RSVPs separately since yours can only count for one, and show up early. For something a little wilder, go on (warning: NSFW) Weird Chicago’s Red Light District Sex Tour, then grab food and drinks at IO Urban Roofscape above the city or Bridge House Tavern by the river. Later you can break into Double A, a secret speakeasy-style lounge (here’s how).
Check out a commissioned mile of street art then schmooze over libations
During the day, walk along The Mile of Murals, a community-based public art initiative consisting of 10 large-scale works that includes five block-long pieces, three viaducts, and one overpass, or do Loyola Park and Beach’s nearly 2/3-mile trail along Lake Michigan. Then browse the well-stocked shelves and artwork at the eclectic secondhand bookstore, The Armadillo’s Pillow. By then you’ll probably be hungry enough to head South to bopNgrill for one of its ridiculous (and crazy-delicious) burgers and try expertly curated cocktails at the friendly Rogers Park Social. The neighborhood also features performances at Mayne Stage, which was originally a 1912 silent screen Nickelodeon.
Relax under the cabanas at a wine bar all night and hit up a show (if you feel like moving)
Enjoy wine with a variety of artisan cheeses and charcuterie like pork belly on a stick with crispy house-made pancetta and maple mustard under one of Volo Restaurant Wine Bar’s patio cabanas before heading to Scooter’s Frozen Custard for coconut cream pie concretes. Be sure to check Beat Kitchen’s calendar for upcoming concerts (both national touring acts and local bands play there) as well as Chicago Underground Comedy stand-up shows.
View contemporary photography and explore the galaxy in the same day in this 'hood
Explore Columbia College’s free Museum of Contemporary Photography before eating Spanish-influenced charcuterie, paellas, and small plates next door at Mercat a la Planxa, then hit up a blues show at Buddy Guy’s. Alternatively, Spoke & Bird’s expansive patio is a great little spot to house local brews like South Loop Brewing’s Good Ryes Wear Black before getting starry eyed at Adler After Dark.
Dine out at the only place where it’s perfectly acceptable to murder your date
Sign up to be a tourist for the day with Bobby’s Bike Hike’s “Museums and Parks at Sunset” or “City Lights at Night” tour (or, you know, forge a similar path with your own bikes). See Chicago’s skyline and fireworks by boat via Shoreline Sightseeing Company’s lake tour from Navy Pier (or from above with drinks at the Signature Room at the 95th). On a group date, solve a hilarious murder case while feasting at the Dinner Detective murder mystery dinner show, and chug a couple glasses of wine before you’re outed as the prime suspect.
Eat unbeatable gnocchi then hopefully conquer many ping-pong victories at a dive bar
For an under-the-radar date night spot (it’s located in a house-turned-restaurant) and unsurpassable gnocchi, try A Tavola, where Chef Dan Bocik also offers two- to three-hour cooking classes on select Mondays of each month. If weather is still warm, al fresco dining at Homestead on the Roof followed by Black Dog Gelato is a top date contender. Then hang out in the beer garden or bat around a ping-pong ball at one of Chi’s best dive bars, Happy Village. To get your weekend started with a free pre-dinner show, watch The Hoyle Brothers tear it up at the Empty Bottle (or just pay the cover for a later show).
Splurge at a bold, Michelin-starred BYOB restaurant or grab a quick, cheap bowl of the best pho in town before hitting up a late-night jazz show
For a reservations-only BYOB with some impressive accolades (like two Michelin stars in its first 10 months), 42 Grams is a daring, yet wise choice. If scoring tickets is impossible, hit up Argyle for some cheaper eats like Pho 777 for some of the best pho in the city. Then head over to see The Neo-Futurists perform the longest-running show in Chicago in an ever-evolving attempt to perform 30 plays in 60 minutes. If the date is going well, there’s always late-night jazz at the Green Mill Cocktail Lounge...
Bocce and barhopping... then maybe an exclusive underground bedroom?
With its 200-seat outdoor beer garden, Kaiser Tiger is best for daytime hanging over bocce ball and ping-pong (or curling in the frozen tundra months). Later, impress your date at Blackbird with a heavy-handed Allocated Old Fashioned and artfully prepared food that’s actually filling, then bar hop at Lone Wolf, Maude's Liquor Bar, and RM Champagne Salon... or really take it up a notch and make arrangements to go all Fifty Shades of Grey in a sex dungeon.
Wrap up a day on The 606 with some pizza and live karaoke
Explore The 606 before heading to Piece Brewery & Pizzeria for live band karaoke on Saturdays followed by intimate late-night drinks at Violet Hour. On the first Friday of every month, artists at The Flat Iron Arts Building also open their studios to the public as part of an art show from 6 to 10pm with impromptu performances throughout the evening.
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Nicole Bruce is a contributing writer for Thrillist Chicago with a hankering for tacos and art. She’d probably be too terrified to throw herself off a platform 23ft in the air (or trust that you’d really catch her), but she is most curious about building a robot while drinking. Tweet your date ideas to her at @nicoleabruce.