Looking for some of the best date ideas Chicago has to offer?
Chicago is a single man’s playground. The Windy City is the nation’s third largest city, boasts a ratio of 116 unmarried women per 100 unmarried men, and has the second highest number of bars and restaurants per capita among the 50 largest metro areas in the US.
Living in a playground is one thing, knowing how to efficiently get the most out of the toys is another.
If you’re a proponent of MegaDating you know that the initial dating period is the most delicate. To date efficiently, the MegaDating philosophy urges followers to adhere to the following guidelines for the first three dates. This article will categorize dates depending on their juncture.
First Date
First dates should be kept to a one-hour maximum with no more than $20 being spent. This ensures that you’ll have more time and money to spend on other dates should this one not work out.
Second Date
Second dates are active and 100% free. Active dates increase heart rate, help you bond over a shared activity and are great for breaking the touch barrier. They should be free to scare away gold diggers.
Third Date
If she’s lucky enough to make it to a third date show her how special she is by spending big, getting fancy, and making it a night to remember.
The following recommendations come to us from dating coaches, professionals, locals, and from yours truly -a former Chicago resident. Without further foreplay, let’s reveal the top 50 best date ideas in Chicago.
-Recommendation by Lo Najar, Business Coach and Sales Strategist at Lo Najar Coaching
I’ll admit it. Cafe joints can be awkward for first dates. With everyone either reading or pretending to write a novel, a cliche first date question can tear through the silence. Lucky for you, The Wormhole has a few nooks that grant daters the privacy they need for a first date to thrive.
-Recommendation by Sarah Ashley, Chicago Local and Freelance Copywriter
Arguably Chicago’s most eclectic market, Randolph Street Market is a must for a first date. For just two days every month, 100+ vendors flock to Chicago’s most prized market to sell their goods. It’s lively, effervescent with craft beer, and is the ideal spot for a first date. If the crowds prove to be too much, take a brief walk over to the adjacent Union Park.
Both affordable and hipster-friendly, Sawada Coffee is owned by world-renowned barista and 2008 Free Pour Latte Art world champion, Sawada Hiroshi. This industrial warehouse-turned cafe will give you and your date plenty of privacy to toss some awkward first-date questions back and forth.
Nothing quite pairs as well as a pastry and cup of coffee. Loba makes for a relaxing first date location, just be aware of their limited hours. If your schedule allows for it, this would be a great spot for a mid-day mid-week first date.
-Recommendation by Lo Najar, Business Coach and Sales Strategist at Lo Najar Coaching
We don’t normally recommend restaurants for first dates, but we’ll make an exception for restaurants that have killer happy hours. Remember that first dates should be kept under $10. But with some of the best happy hours deals in town (M-Th $3 house beer, $2 Taco Tuesday, etc.) the Broken English Taco Pub is a safe choice. Not only does it fulfill MegaDating guidelines, but with three locations sprinkled across Chicago, it’ll never be an out-of-the-way date spot.
It’s a freakin’ cat cafe, need I say more? The only people that should avoid such a spot are devout dog lovers and people with allergies. Lame people aside, everyone that’s ever been here has loved it.
This is an amazing date idea because you’ll get a chance to play with their 30 or so cats and kittens – that are from the shelter. It’s also advised that you make a reservation before bringing your date to this epic kitty club. Lastly, just make sure to not bring in your cats as it’s currently not allowed. There are plenty of cats you can play with that need some love.
Note from Windy Kitty: “A lot of guys surprise their significant others with this as a date and kitten corner is such a great spot! Bringing someone here is definitely a way to win somebody’s heart.”
Fresh roasted artisanal coffee anyone? Big Shoulders operates out of 6 six different establishments throughout the city. Each cafe has its own unique hours and lack of aesthetic, but for what it lacks in beauty it makes up in quality. This spot is known to both locals and transplants as one of the best coffee joints in Chicago.
You’re jittery, doubts are rushing through your head, and you suddenly have a craving for something sweet and diabetes-inducing. First dates are awkward and stressful by nature. Mitigate those nerves by indulging in a cheat day when you bite into one of the Doughnut Vault’s finest.
Firecakes is a company that’s been in the making since the 1930s when the owner’s great grandfather used to bake backwater donuts called, “firecakes” for loggers in Wisconsin. Taking her to a place she’s surely never been to, to try a bastard donut is a perfect first date idea.
What if I told you that you could support local schools, eat at a place that’s been featured in the Chicago Tribune, and eat a fresh cupcake while on a swing all at the same time? You’ll be so busy enjoying yourself that you’ll completely forget about those first date nerves.
Grandpa Joe created the rainbow cone in 1926. Unsatisfied with the lack of ice cream flavors, Joe and his wife decided to make a host of new flavors. Stack them all together and you get the rainbow cone. Located in Beverly, The Original Rainbow Cone is a great date spot for those seeking to enjoy one of Chicago’s oldest and proudest establishments.
There are few eateries more legendary than Margie’s Candies. Famous actors, ball players, and even Al Capone himself have all stuffed their faces with Margie’s epic ice cream sundae.
Lines out of the door is a solid indication that maybe you should open another ice cream joint. Lines out of both doors indicate the same. Eventually, Jeni’s had so many lines out of so many doors that they decided to open 7 ice cream parlors.
Perhaps Sprinkles might not have the same history as other sweet-tooth eateries, it does have convenience. First dates should typically happen midweek just after work. Sprinkles is open M-S, 9-9.
Locally made, locally consumed. Katherine Anne Confections is the go-to spot for hand-dipped truffles, soft honey caramels, and gourmet marshmallows. Katherine Anne is the last first date spot on our list but it’s certainly worth checking out, especially if you’re already in the Palmer Square barrio.
-Recommendation by Lo Najar, Business Coach and Sales Strategist at Lo Najar Coaching
Remember, second dates are meant to be both active and free. Tell your date to bring her bike so that the two of you can build the foundation of your relationship on being adventurous and healthy.
-Recommendation by April Davis, President and Matchmaker of LUMASearch
Regardless of sun, snow, or catastrophic hail storms, you can be sure that Millenium Park will be buzzing. The park is great for a picnic or for a lovely Sunday afternoon jaunt.
-Recommendation by Lo Najar, Business Coach and Sales Strategist at Lo Najar Coaching
The park is awash with free stuff to do. Yoga is part of the city’s Summer workout series. Every Tuesday and Thursday free yoga classes begin at 7:30 sharp.
-Recommendation by April Davis, President and Matchmaker of LUMASearch
Zoos aren’t for everyone. While some people freak out when they see prairie dogs, others get depressed when they think about how underfed they must be. Know what your date thinks about the zoo before you surprise her with a trip to check out some of the most malnourished animals in all of Chicago.
An aerial skills class in a 100+-year-old church might just be the oddest second date you’ll ever have (right next to turtle racing). At least if you fall from the ceiling and die you won’t have to travel too far to get to heaven.
-Recommendation by April Davis, President and Matchmaker of LUMASearch
You just learned that your left-fielder is going out of town and need a stand-in. Have you ever dated your left-fielder before? It’s kind of awesome. Have your date replace your teammate for a game or two as you two bond over how kickass you are as a team. Winning together is, well, winning. Go get physical.
Seriously though if you haven’t seen Free Solo by now you’re out of the loop. Live out your own free soloing adventure as you scale the walls at Brooklyn Boulders.
Inspired by NY’s Highline, the 606 trail is a great place to chat while taking a scenic, leisurely stroll through Chicago.
Chicago has a ton of beaches. Sure it’s a lake, but you wouldn’t know it when you’re sipping on a craft beer and taking in the view. Have a picnic, bring your dogs, play a little volleyball. Whatever activity you want to engage it, the beach is the perfect place for a second date.
Dude. If she’s into video games and doesn’t already know about this place, you’ve scored. What gamer doesn’t love an establishment whose sole purpose is to appreciate video games.
Maybe even after you hit the video game gallery you can head over to the Museum Of Science And Industry. This is such a great date idea because it gives you two a topic to talk about. Sometimes daters can feel like they’re flailing for a conversational topic to grab onto. This problem is solved when you let science drive the conversation.
Sure it sounds a little pretentious, and you know what, it kind of is. The Smart Museum of Art is a donation-based fine arts museum.
For some reason, axe throwing is becoming popular all over the US. We can probably thank Game Of Thrones for the rise of the craze that has finally hit Chicago. No worries if your lady is just a novice -it’d kind of be badass if she weren’t- you two can act like badasses together.
Jolanda might just be the most popular woman at Big Joe’s. Jolanda’s been around longer than most, rarely wins races, but almost always wins you a free drink. She’s been racing at Big Joe’s every Friday at 9 p.m. for years now. Sure she typically comes in last out of the five turtles in the ring, but at Big Joe’s losers win free drinks. Yeah, it’s weird, but I guarantee you no one has ever said that turtle racing was a bad third date idea.
“It can be difficult in other cities to find something enjoyable to eat, especially if you have very specific food choices, (like vegan, paleo, gluten-free). But in Chicago, you’re in luck – especially at Lula’s Cafe, which is geared towards organic/farm to table.”
-Recommendation by April Davis, President and Matchmaker of LUMASearch
A third date should take place at night, has zero financial and time restrictions, and hopefully culminates in sex. Lula provides quality organic and vegan options in a funky backdrop.
-Recommendation by Lo Najar, Business Coach and Sales Strategist at Lo Najar Coaching
For an upscale dinner head to the rooftop of the Gwen Hotel. The food, rooftop view, and general opulence of this place will make you feel like you’re on vacation. Seem like a solid Chicago date idea, don’t you think?
“Food is a great way to explore passion and sensuality.”
-Recommendation by April Davis, President and Matchmaker of LUMASearch
Should your date be a vegetarian, this is the spot for you. As the door proudly indicates, this diner joint has been meat free since 1983.
-Recommendation by April Davis, President and Matchmaker of LUMASearch
Anyone up for some fresh seafood? Parson’s has got you covered.
-Recommendation by Lo Najar, Business Coach and Sales Strategist at Lo Najar Coaching
Few menus can cover this sort of ground and still be good. Union Sushi lives up to the hype. It might be the only sushi place to call a retrofitted warehouse, but that only adds to its fusion charm.
-Recommendation by April Davis, President and Matchmaker of LUMASearch
If you really want to wow your lady, take her on a mini cruise getaway. Sure it’ll only be for a few hours, but you’ll be offered some of the best views, service, and disparate experiences Chicago has to offer.
-Recommendation by Sarah Ashley, Chicago Local and Freelance Copywriter
It’s weird, I know. But the goal of your third date is to stand out, not play it safe. Woo her by hitting up Chicago’s premier magic venue.
-Recommendation by April Davis, President and Matchmaker of LUMASearch
Sure it’s cheesy, but name me a woman that doesn’t want to live her own version of The Notebook?
-Recommendation by Sarah Ashley, Chicago Local and Freelance Copywriter
Netflix and chill is one thing. Watching a movie in Millennium Park is another. Most everyone wants to watch a movie here though only few have. This year they’ll screen movies such as: Black Panther, Frida, Fences, The Wiz and more.
-Recommendation by April Davis, President and Matchmaker of LUMASearch
Meat on meat on meat. That’s what to expect when you mosey into an Argentine restaurant. This place has a killer combination of food and romance.
-Recommendation by Sarah Ashley, Chicago Local and Freelance Copywriter
No time is more fitting for a fancy French restaurant than a third date. It’s got candles, cutsy lights, and opulent dessert options. You can’t really go wrong with a French restaurant as far as gastronomic foreplay goes.
Canadian PM Justin Trudeau was sighted here just last May. If it’s good enough for the second most important man in Canada (Drake being #1) then I’m sure you and your date will approve.
Are you two just not turned on by the lame Hollywood movies of today? The Music Box Theatre is one of the oldest theaters in Chicago. It exclusively plays movies – that like itself – stand the test of time.
–#43: Adler After Dark Date Night (Northerly Island)
Does looking up at the stars in a planetarium get any more romantic? Sure you could be singing and floating around like Emma Stone and Ryan Gosling, but staying on the ground and gazing up into the never-ending expanse of space is still pretty magical. Galileo would agree.
Tipsy painting, I think yes. Should you two strike up a lasting partnership after this date, painting and sipping on Malbec can become your new shared hobby.
If the Netflix original show, Easy, based entirely in Chicago has taught us anything it’s that you’re bound to run across a beer snob while dating in Chicago. When this happens be sure to bring them to a quality brewery. Malt Row is that brewery.
-Recommendation by April Davis, President and Matchmaker of LUMASearch
The Beauty Bar isn’t for timid dancers. People come here to shake their asses and get down. This place is a strictly third date destination. The dance spot likes to change the music up, so check to see what the DJ is spinning before you go, or don’t and roll with the tempo. Be warned that this place can get both packed and loud. Be sure that your dynamic can stand up against loud music and sweaty dudes.
-Recommendation by Chris and Cathy T, Chicago Locals
Come on now. Wrigley Field is the most outlandish, storied, cursed, ludicrous ballpark in America. It looks like what would happen if Frederick Olmsted designed a stadium.
For just $5 you can see a show every Wednesday-Sunday.
This is perhaps the most original date you two can go on. With shows being brief and cheap you should definitely pair this date spot with a nice dinner if you’re using it as third date idea. The venue is surrounded by dozens of amazing food options (and no I’m not referring to IHOP).
Do you really want to make your new lady a dish but have zero culinary ability?
That’s fine – learn together when you two sign up for a cooking class. As I look at their calendar I see that they currently offer classes on how to make a tart, classic New Orleans dishes, pasta, and chicken fricassee.
The Chopping Block also offers virtual classes. Maybe you want to invite her over for a date night at your house where you two first take a virtual cooking class followed by eating good food and smooches for dessert.
Sounds pretty tasty to me.
Are you and your date the competitive type?
If so, why not put your money where your mouth is and back up those ping-pong skills as you two duke it out at SPIN.
Just book a table and enjoy.
SPIN also has monthly art competitions while DJs spin hip yet aggressive background music – trust me, it’s a vibe.
Now you know where to take your next date in the great city of Chicago. But what if you’ve been out of the dating game for some time? What if you’re a little uneasy about your dating skills? Have you thought about hiring a coach to help you? If so, I’d love to assist you.
Enrolling in our program, Dating Decoded means committing to a complete revamp of your dating skills and strategy, ultimately leading to more dates and a super compatible romantic partner.
Our program is exclusively open to men and is designed to give you the skills you need to succeed in the modern dating scene.
Our program is broken down into four pillars:
If you’re interested in joining my program, feel free and book a new client session with me today. During this intro session we’ll assess your current dating issues and determine if my coaching program is a fit for you.
After three short months, you’ll be implementing MegaDating seamlessly, hacking dating applications, and on your way to finding the romantic partner you’ve been yearning for.
See what our students are saying about us.