Despite the fact that we live in a massive city filled with endless options for things to eat, see, and experience, coming up with fun and interesting date ideas can be insanely difficult. Before you subject your date to another round of “I don’t know, what do you want to do?” texts, check out these 45 actually great Chicago date ideas. We’ve even done the dirty work and sorted them all by which date (first through fifth) you should use them on.

Southport Lanes

FIRST DATE

Head to a free outdoor concert

Millennium Park
Grab a blanket, pack some snacks, bring a bottle of wine, and kick back on the lawn. Outdoor concerts are low-pressure, laid-back, and give you the opportunity to talk and get to know each other better. And, you know, cuddle.

Get your game face on

Lakeview/Wicker Park
Turn up the fun factor by challenging your date to a game. Visit Headquarters Beercade or Emporium for arcade games, or Guthries Tavern for good, old-fashioned board games, all with great beer options.

Go beyond a simple walk at Garfield Park Conservatory

Garfield Park
Take a moment to enjoy the beauty that Chicago has to offer, then learn how to start your career as a beekeeper or get your hands dirty at one of Garfield Park’s compost tutorials. Looking for a bit more nature? Go ahead and visit some of the area's other amazing parks.

Get your hookah on at Samah

Edgewater
It's near impossible not to pick up on the sexy vibes in the dimly lit, curtained-off rooms in one of Chicago's top hookah bars. Also, there’s something about lounging atop pillows on the floor that makes conversation flow easier. Tip: although shisha is quite different from tobacco, make sure your date isn't devoted to maintaining perfectly pink lungs before making any reservations.

Go on an old-school date

Multiple locations
Start off the night at Superdawg and see if your date passes the ketchup test, then make your way over to Southport Lanes -- one of the few bowling alleys left that uses human pinsetters. Finish off the night over hot fudge sundaes at Margie’s Candies and try to snag a seat in the famed "Beatles Booth."

Laugh it up at an improv show

Multiple locations
Between Second City, iO, and The Annoyance, Chicago has no shortage of improv options. Assuming it's not dead baby joke night, this should help break the ice.

Crush your first date nerves at Tropikava Kafe

West Town
First dates are nerve-wracking, and have been known to cause people to drink a bit more than they should on occasion. Lower your inhibitions without the risk of getting sloppy with a cocktail (or kocktail?) at Chicago’s first kava bar. Even if you don’t experience the relaxing, sedative and euphoric properties the kava root is said to have, it’ll give you both the chance to bond over a new experience.

Have fireside whiskeys at Fountainhead

Ravenswood
They've got one of the largest dark-liquor selections in this neighborhood, plus a pretty sweet fireplace. It’s also just formal enough to feel each other out, and just cozy enough to, uh, feel each other out.

Meet at the rink for some ice skating

The Loop
The McCormick Tribune Ice Rink is free to enter and charges only $12 to rent skates. At that price, you can splurge on a boozy hot chocolate at nearby Park Grill Cafe.

Go Baroque with Free Thursdays at the Art Institute of Chicago

The Loop
Skip having to spend money on someone you just met with Free Thursdays at the Art Institute of Chicago (you like free stuff, right?) -- which will both make you seem cultured and give you plenty to talk about. If the date is going well, walk across the street to The Gage to continue the conversation.

Signature Room | Flickr/Erin Nekervis

SECOND DATE

Leave the decision-making up to fate

Multiple locations
See where fate takes you by making decisions based on the flip of a coin. Dinner in River North or Wicker Park? Flip a coin to decide. How will you get there? Heads you’re taking the CTA, tails you’re taking a cab. For every decision you need to make, take turns flipping. This is a fun and playful way to make decisions, not to mention an interesting way to see how spontaneous your date is willing to be.  

Turn up the heat with fondue at Geja’s Café

Lincoln Park
There’s a good reason why Geja’s Café is consistently voted one of the most romantic restaurants in Chicago. From the atmosphere (dark, sexy, and cozy) to the food (would it be *cheesy* if we called it sensual?), Geja’s Café exudes romance. Just be sure to take advantage of the coat check -- the scent of oil will stick to your clothes, and that’s not sexy.

Get your slurp on with ramen at Yusho

Avondale, Hyde Park
Ramen is all the rage right now, and nothing lightens the mood faster than wet noodles hitting your face. The Sunday Noodles program gets you ramen, a drink, and a dessert, all for only $25.

Booze with a view at the Signature Lounge

Near North Side
Chicago has no shortage of skyline views, but the one from the 96th floor of the John Hancock Building at the Signature Lounge (above the restaurant on the 95th) has date written all over it.

Try to break into an underground supper club

Multiple locations
Secret handshakes and last-minute location details -- be a part of one of the many secret supper clubs in and around the city. Some are easier to get into than others, but once you’re in... you’re, uh, in, and it’s totally worth it.

Partake in the majesty of Friday night turtle racing

Lincoln Square
Yes, turtle racing. It all goes down at Big Joe’s every Friday night at 9pm -- shouting and ordering drinks by the pitcher are encouraged.

Reenact scenes from Dirty Dancing at Movieoke

Logan Square
For the not-so-musically-inclined, hit Movieoke at The Whistler on the first Monday of every month, where instead of song lyrics, you'll be quoting your favorite movie scenes on stage. Just stay away from anything from The Notebook or Titanic.

Play with some dogs

Lincoln Park/Uptown
Confirm that your date's not a cat person (deal breaker!) by heading to one of the many dog parks (like Wiggly Field Dog Park in Lincoln Park or Montrose Beach in Uptown) to play fetch.

Catch a show at Lincoln Hall

Lincoln Park
Explore lesser known musical acts every night at this Lincoln Park music venue. An open setting allows for casual standing and an up-close view of the performers.

Catch Jazz Era vibes at Green Mill

Uptown
Hit this old Al Capone haunt for The Paper Machete, free every Saturday at 3pm with comedians and storytellers taking on current events.

Arts n Spirits

THIRD DATE

Have a three-course meal with a twist

Multiple locations
The biggest problem with long meals? By the time you’re done, you tend to feel groggy and too full to move. Instead, mix things up by going to a new spot for every course. Think: cocktails and appetizers at Sable Kitchen & Bar, dinner at Quartino, and dessert at Pierrot Gourmet.

Test your smarts at trivia night

Multiple locations
Put your date to the test by hitting up one of Chicago’s many trivia nights. If you’re good, you may even score yourselves cash or prizes that can be put towards date número quatro.

Flash your pearly whites with a photo-booth tour

Multiple locations
There are a few different bars and hangouts equipped with photo booths to document your date progress. You can start at Schubas (Lakeview), and then go to Quimby’s Bookstore (Wicker Park), Beauty Bar (Noble Square), Empty Bottle (Ukrainian Village), and end at Skylark (East Pilsen). Grab a drink at each spot, hit up the photo booth, and then move on to the next. Don’t forget to have a stack of singles ready.

One-stop dining, boozing, and music at Thalia Hall

Pilsen
A night out at Dusek’s, Punch House, and Thalia Hall is like three dates in one. Start off with oysters at the newly BIB-nominated Dusek’s, then head to an after-dinner show at Thalia Hall, the historic landmark space redesigned and reopened in 2013 by the same owners. Finish off with a nightcap at the downstairs Punch House where, conveniently, the punch has already been spiked.

Explore your inner Monet at Bottle & Bottega

Lakeview
Or other "paint dates" like Soul Impressions or Arts n Spirits, all of which let your creativity flow like BYOB wine. At this point, you’ve gotten to know each other a little better and the atmosphere is still intimate enough that you can chat while painting.

Break out your best moves (or shameless lack thereof) at Danny’s

Bucktown
If you both channeled Michael Jackson growing up, Danny’s -- which offers up all-night dancing with throwbacks to the '80s and '90s -- is a must-visit for testing out your moves and moving your hips a little closer together.

Get starry-eyed at Adler After Dark

South Loop
Attend Adler Planetarium's After Dark event (21+) on the third Thursday of each month to enjoy cocktails and one-of-a-kind views of the Chicago skyline. Bonus: the lights are likely to go off at some point in the date.

Test your knife skills at The Chopping Block

Lincoln Square
Get up close and personal with your food by cooking side-by-side at The Chopping Block. Choose from demonstration classes, interactive classes, or wine classes. They've got some of the cheapest bottles you’ll find in Chicago, and you’ll be sent home with lots of leftovers.

Make it Sunday funday with boozy brunch

Multiple locations
Day drinking leads to night drinking which leads to 2am burritos at Tony’s or Burrito House. Start off with some of these top picks for mimosas and Bloody Marys. If things have been going well, you might even be able to sneak in a midday nap.

Sunday Screenings at The Public Hotel

Near North Side
There are Sunday Screenings every Sunday at 6pm along with a wide array of other interesting events. If you’re lucky, maybe you’ll even be able to take advantage of the Public’s $1 nights.

Waterriders Chicago

FOURTH DATE

Paddle your way through the city

Multiple locations
Showcase your upper-body strength (or lack thereof) by paddling your way through the city by kayak. Wateriders offers a variety of interesting guided tours, including a night tour that explores the city’s seedy past. If you’re leery about cruising along the Chicago River due to that whole “Bubbly Creek” thing, Kayak Chicago offers lake tours that start at North Ave Beach.

Drink in a craft brewery crawl

Multiple locations
Commit to a whole day (and night???) together by organizing a brewery tour, starting at the new Lagunitas Brewery in Pilsen, with a pit stop at Revolution's Avondale brewery and tap room (not to be mistaken for the brewpub). End up in North Center at Half Acre, then jump across the street to Bad Apple for one of the better burgers in the city.

Get sexy with Unbridled at Untitled

River North
This weekly Thursday burlesque-inspired show is a way to test each other’s wild side while getting dressed up for a night of beards, Manhattans, and 1920s throwbacks. Bonus: costume tops are coming off on the stage so you have every right to make out in the corner.

Indulge in a hot chocolate crawl

Multiple locations
Whether you’re warming things up with hot chocolate or prefer your chocolate straight up, this is one date that will give you a chance to cozy up next to one another. Hit up a Chocolate Tour of Chicago or tether your own crawl to Wicker Park/Logan Square spots like XOCO, Mindy’s Hot Chocolate, and Katherine Anne Confections.

Take a hike

Multiple locations
From Starved Rock to trails that include creepy abandoned military bunkers, there’s no shortage of great hiking locations near Chicago. More secluded spots = more chances for you and your date to take a breather in the grass. By, you know, rolling around in the grass... in the most PG-13 sense, of course.  

Pretend to be tourists

The Loop
Every so often, we secretly love doing dorky tourist things. The fourth date is the perfect time to see if your connection can withstand an entire day and crowds of tourists. Visit the Skydeck, stand in line at Garrett, have dinner in Chinatown, and end the night with a cheesy-yet-romantic ride in a horse-drawn carriage.

Get geeky at Robot Date Night

Lakeview
Unleash your inner geek at one of Robot City Workshop’s BYOB Robot Date Nights. For $50 per couple (plus the cost of robot kits), you and your date can build your very own robots and finish the night off with a bit of robot trivia. Bonus: if things don’t work out with the person, you’ll at least always have the robot.

Drink your way along your favorite "L" line

Multiple locations
Follow along with our handy transit bar map, highlighting the best bars near each "L" stop from Downtown to O’Hare and much of the North Side. Grab your Ventra card and work your way down your favorite line -- or, if you’re feeling particularly adventurous, see if you can hit up a few stops on each.

Mackinac Island | Flickr/Jasperdo

FIFTH DATE

Attend “Brew Camp”

Ravenswood
Unlike most of your childhood camp memories, this particular camp is actually fun -- partially because Bobby Finkelstein and his awful toad won’t be there... but we digress. Brew Camp’s Making Beer at Home class will give you and your date a 90-minute crash course in the art of homebrewing. Afterwards, bond over your traumatic camp memories over German beers at nearby Huettenbar.     

Learn the art of couples massage

Loop
Bow-chicka-wow-wowww! Perfect your massage skills by practicing on your date’s scalp, back, and feet. The Love Institute’s couples massage class promises to help you massage better, firmer, more gracefully and intuitively. Before you know it, your date will be putty in your hands.  

Test your ability to survive a "vacation"

Multiple locations
You’ve made it this far, now stock up on Cheetos and pop, load your iPod with road trip-worthy mixes, and hit the road. Whether it’s a day trip to Galena, Milwaukee or the dunes, an overnight trip to a Michigan winery, or a cabin in the woods, getting away from the city can give the two of you time to really get to know each other. If you need some inspiration, here's the 10 best vacation spots within driving distance of Chicago.

Check out the night sky

Midway
You've seen Chicago's epic skyline from the ground, now get a bird’s-eye nighttime view via a Chicago by Night Helicopter Tour. The tickets aren’t cheap, so save this for surefire GF/BF material.

See how well you'd do locked together in a weird room

The Loop
Put your mind to work and try the Room Escape Adventures, where you test your riddle skills (and your date’s ability to communicate and get along with strangers) with the goal to escape a room within 60 minutes.

Find out what your future holds

Multiple locations
Wondering if your love is meant to be? Head to your neighborhood psychic or book a tarot card or reading at a popular joint like Psychic Spiritual Gallery or The Chakra Shoppe.

Have a staycation at a local hotel

Multiple locations
Take turns walking into some of Chicago’s swankiest hotel lobbies with nothing but $150 in hand and some charm to see if you can land a room for the night. Once in, order Champagne and room service and don’t come out until checkout time. Pro tip: most hotels never go to capacity, so you might actually win this one.

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Should these date ideas lead to marriage, Lisa Chatroop fully expects you to name your firstborn child after her. Send her your birth announcements via Twitter: @LisaChatroop or score some dating tips at DailyUrbanista.com.

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