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The Best Unexpected Date Ideas in Chicago
The Best Unexpected Date Ideas in Chicago

The Best Unexpected Date Ideas in Chicago

Say no to boring dates! It’s time to spice things up. 🔥


Published April 14, 2022

Finding that special someone can be tough, but dating itself doesn't have to be boring! Say goodbye to the same old happy hour or dinner date ideas and mix things up with this list of Bucket Listers’ favorite unexpected date ideas in Chicago.

Go to a boozy bowling event

Go to a boozy bowling event

Boozy Bowling Social is a gathering for anyone who is over the dating scene. Mingle with new people over bowling, an open bar, tarot card readings, and group games, all hosted by a charismatic MC. Take the pressure away of meeting new people with this special, socializing event. Come with your friends, bring your wingman, or suggest it to a match on a dating app for a fun first date! 

Location: The Pink Squirrel, 2424 Milwaukee Ave, Chicago, IL 60647

When: Thursday, April 28th 7:00 PM - 12:00 AM and Thursday, May 26th 7:00 PM - 12:00 AM

For more information about bowling at the Pink Squirrel.

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location_on The Pink Squirrel, CHI

Boozy Bowling Social at The Pink Squirrel

$55
  • event 2022-04-28
book

Boozy Bowling Social is a gathering for anyone who is over the dating scene. Mingle with new people over bowling, an open bar, tarot card readings, and group games, all hosted by a charismatic MC. Take the pressure away of meeting new people with this special, socializing event. Come with your friends, bring your wingman, or suggest it to a match on a dating app for a fun first date! 

Location: The Pink Squirrel, 2424 Milwaukee Ave, Chicago, IL 60647

When: Thursday, April 28th 7:00 PM - 12:00 AM and Thursday, May 26th 7:00 PM - 12:00 AM

For more information about bowling at the Pink Squirrel.

Practice your swing at Five Iron Golf

Practice your swing at Five Iron Golf

Whether you and your date are beginners or experienced golfers, there's fun for everyone at Five Iron Golf, an indoor golf simulator with several locations in Chicago. Practice your skills on the virtual driving range or course simulator, or challenge each other to a competition with a selection of other exciting virtual games. 

Locations: 

The Loop:  108 N. State St., Chicago, IL 60602

River North: 609 N. Dearborn St., Chicago, IL 60654

Lincoln Park: coming soon! 

Hours:  Monday - Thursday 6:00 a.m. - 11:00 p.m., Friday 6:00 a.m. - 12:00 a.m., Saturday 8:00 a.m. - 12:00 a.m., Sunday 8:00 a.m. - 10:00 p.m. 

For more information on Five Iron Golf - Loop or River North

Whether you and your date are beginners or experienced golfers, there's fun for everyone at Five Iron Golf, an indoor golf simulator with several locations in Chicago. Practice your skills on the virtual driving range or course simulator, or challenge each other to a competition with a selection of other exciting virtual games. 

Locations: 

The Loop:  108 N. State St., Chicago, IL 60602

River North: 609 N. Dearborn St., Chicago, IL 60654

Lincoln Park: coming soon! 

Hours:  Monday - Thursday 6:00 a.m. - 11:00 p.m., Friday 6:00 a.m. - 12:00 a.m., Saturday 8:00 a.m. - 12:00 a.m., Sunday 8:00 a.m. - 10:00 p.m. 

For more information on Five Iron Golf - Loop or River North

Tour the River or Lake Michigan by Kayak

Tour the River or Lake Michigan by Kayak

Head out for a day on the water together with an exciting kayak tour on the Chicago River or Lake Michigan. Have a day of fun in the sun with one of the afternoon paddles, or choose the Twilight or Sunset tour for a romantic night watching the sunset over the water. If you’re looking for a more festive outing, opt for the Happy Hour paddle, which includes a stop at the Island Party Hut for a tiki party with a complimentary beer! You’ve earned it. 

Locations:

Lakefront Location: 110 N. Lakeshore Dr / Chicago, Il 60601

Riverwalk Location: 435 E. Chicago Riverwalk / Chicago, Il 60601

Hours: Times vary, check schedule for available times 

For more information on Kayak Tours on the River and Lake Michigan.

location_on Various Locations, CHI

Chicago Kayak Tours on the River and Lake Michigan

$45
  • event 2022-06-01
book

Head out for a day on the water together with an exciting kayak tour on the Chicago River or Lake Michigan. Have a day of fun in the sun with one of the afternoon paddles, or choose the Twilight or Sunset tour for a romantic night watching the sunset over the water. If you’re looking for a more festive outing, opt for the Happy Hour paddle, which includes a stop at the Island Party Hut for a tiki party with a complimentary beer! You’ve earned it. 

Locations:

Lakefront Location: 110 N. Lakeshore Dr / Chicago, Il 60601

Riverwalk Location: 435 E. Chicago Riverwalk / Chicago, Il 60601

Hours: Times vary, check schedule for available times 

For more information on Kayak Tours on the River and Lake Michigan.

Laugh the night away at a stand up comedy showcase

Laugh the night away at a stand up comedy showcase

Head to the Laugh Factory, one of Chi-town’s most popular comedy clubs, for an unforgettable night out. With showcases of 5-7 comedians performing every night, from some of the biggest names in comedy to local comedians, you're sure to find a show that will make you laugh until your stomach hurts.

Location: 3175 N Broadway, Chicago, IL 60657 

Hours: Monday/Wednesday/Thursday/Sunday 8:00 - 10:00 PM, Tuesday 7:30 - 9:30 PM, Friday/Saturday 7:30 - 9:30 PM, 9:30 - 11:30 PM, 11:30 PM - 1:30 AM

For more information on Stand-up Comedy at the Laugh Factory.

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Yachti Adventure Tours

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Head to the Laugh Factory, one of Chi-town’s most popular comedy clubs, for an unforgettable night out. With showcases of 5-7 comedians performing every night, from some of the biggest names in comedy to local comedians, you're sure to find a show that will make you laugh until your stomach hurts.

Location: 3175 N Broadway, Chicago, IL 60657 

Hours: Monday/Wednesday/Thursday/Sunday 8:00 - 10:00 PM, Tuesday 7:30 - 9:30 PM, Friday/Saturday 7:30 - 9:30 PM, 9:30 - 11:30 PM, 11:30 PM - 1:30 AM

For more information on Stand-up Comedy at the Laugh Factory.

Have a remarkable night at the Chicago Magic Lounge

Have a remarkable night at the Chicago Magic Lounge

Forget what you know about magic – an evening out at the swanky Chicago Magic Lounge is nothing like the cheesy magicians you probably picture when you hear ‘magic show.’ You’ll head into this lounge slash speakeasy via their super-trendy secret entrance before enjoying a one-of-a-kind performance, with traditional Chicago-style “up-close” magic performed at your table while you groove to the live music on stage. 

Location: 5050 North Clark St., Chicago, IL, 60640

Hours:  Sunday - Wednesday: 5 PM - 11 PM, Thursday: 5 PM - 12 AM, Friday and Saturday 5 PM - 2 AM

For more information on the Chicago Magic Lounge. 

Forget what you know about magic – an evening out at the swanky Chicago Magic Lounge is nothing like the cheesy magicians you probably picture when you hear ‘magic show.’ You’ll head into this lounge slash speakeasy via their super-trendy secret entrance before enjoying a one-of-a-kind performance, with traditional Chicago-style “up-close” magic performed at your table while you groove to the live music on stage. 

Location: 5050 North Clark St., Chicago, IL, 60640

Hours:  Sunday - Wednesday: 5 PM - 11 PM, Thursday: 5 PM - 12 AM, Friday and Saturday 5 PM - 2 AM

For more information on the Chicago Magic Lounge. 

Channel your inner artist at Spray Paint & Sip

Channel your inner artist at Spray Paint & Sip

Show off your creative side during this spray paint ‘n’ sip class, where you’ll learn how to create spray paint art taught by authentic street artists. They’ll teach you the ins and outs of working with spray paint & stencil application, and you'll even leave with your own custom spray paint canvas masterpiece! 

Location: 800 N. Kedzie, Chicago IL 60651

Hours: Times vary, check schedule for full availability 

For more information on Spray Paint ‘n’ Sip classes.

location_on Chicago Kedzie Plaza, IL

Spray Paint ‘n’ Sip series

$35
  • event 2022-06-01
book

Show off your creative side during this spray paint ‘n’ sip class, where you’ll learn how to create spray paint art taught by authentic street artists. They’ll teach you the ins and outs of working with spray paint & stencil application, and you'll even leave with your own custom spray paint canvas masterpiece! 

Location: 800 N. Kedzie, Chicago IL 60651

Hours: Times vary, check schedule for full availability 

For more information on Spray Paint ‘n’ Sip classes.

Take a swan boat cruise in Humboldt Park

Take a swan boat cruise in Humboldt Park

Head to scenic Humboldt Park for a romantic vintage swan boat cruise on the park’s lagoon. After paddling to your heart’s content, grab a bite to eat at the similarly retro-inspired Spinning J Bakery and Soda Fountain, serving up gelato, shakes, and other soda-fountain classics just outside the park. 

Location: 1301 North Humboldt Drive, Chicago, Illinois 60622

Hours: May 28 - Aug 21 Monday – Friday 10:00 a.m. – 8:00 p.m., Saturday, Sunday, and Holidays 9:00 a.m. – 8:00 p.m. 

For more information on Wheel Fun boat rentals in Humboldt Park. 

Head to scenic Humboldt Park for a romantic vintage swan boat cruise on the park’s lagoon. After paddling to your heart’s content, grab a bite to eat at the similarly retro-inspired Spinning J Bakery and Soda Fountain, serving up gelato, shakes, and other soda-fountain classics just outside the park. 

Location: 1301 North Humboldt Drive, Chicago, Illinois 60622

Hours: May 28 - Aug 21 Monday – Friday 10:00 a.m. – 8:00 p.m., Saturday, Sunday, and Holidays 9:00 a.m. – 8:00 p.m. 

For more information on Wheel Fun boat rentals in Humboldt Park. 

Relax & Rejuvenate at AIRE Ancient Baths

Relax & Rejuvenate at AIRE Ancient Baths

Prepare to pamper yourselves at this one-of-a-kind spa in River West, where you and your date will go on a relaxation journey via their signature Ancient Thermal Bath Experience. During your visit, soak away your stresses in the traditional Roman, Greek, and Ottoman-style baths (with temperatures ranging from 102ºF to a chilly 50ºF!), try the aromatherapy steam room, or take a swim in the heated indoor/outdoor pool. Add a couples massage or a wine bath for two for a truly luxurious experience. 

Location: 800 West Superior St., Chicago, IL 60642

Hours: Monday - Friday 9:00 a.m. - 11:00 p.m., Saturday & Sunday 8:00 a.m. - 11:00 p.m. 

For more information on AIRE Ancient Baths.

Prepare to pamper yourselves at this one-of-a-kind spa in River West, where you and your date will go on a relaxation journey via their signature Ancient Thermal Bath Experience. During your visit, soak away your stresses in the traditional Roman, Greek, and Ottoman-style baths (with temperatures ranging from 102ºF to a chilly 50ºF!), try the aromatherapy steam room, or take a swim in the heated indoor/outdoor pool. Add a couples massage or a wine bath for two for a truly luxurious experience. 

Location: 800 West Superior St., Chicago, IL 60642

Hours: Monday - Friday 9:00 a.m. - 11:00 p.m., Saturday & Sunday 8:00 a.m. - 11:00 p.m. 

For more information on AIRE Ancient Baths.

Stroll along the 16th Street Mural Wall

Stroll along the 16th Street Mural Wall

For a fun and free date idea, take a stroll down the 16th Street Mural wall, a two-mile embankment covered with more than fifty ever-changing murals painted by top street artists. After you’ve worked up an appetite with your adventure, stop by one of the Pilsen neighborhood’s many bars or restaurants to discuss your favorite murals over a bite to eat with your date. 

Location: 922 W. 16th St., Chicago, IL 60608 - the wall runs from 16th Street from Halsted Street west to Western Avenue

Hours:  Open 24/7

For more information on the 16th Street Mural Wall. 

For a fun and free date idea, take a stroll down the 16th Street Mural wall, a two-mile embankment covered with more than fifty ever-changing murals painted by top street artists. After you’ve worked up an appetite with your adventure, stop by one of the Pilsen neighborhood’s many bars or restaurants to discuss your favorite murals over a bite to eat with your date. 

Location: 922 W. 16th St., Chicago, IL 60608 - the wall runs from 16th Street from Halsted Street west to Western Avenue

Hours:  Open 24/7

For more information on the 16th Street Mural Wall. 

Cozy up to kittens at Catcade

Cozy up to kittens at Catcade

Arcade games and cute cats galore? Hello, perfect date spot! At this arcade slash lounge slash animal rescue, you and your date can challenge each other to a few rounds of classic arcade games like Pacman – and even if you lose, you can console yourself with a cuddly kitten! As a bonus, all the cats are available for adoption, so if you fall in love with a furry friend, they might just come home with you! Reservations are highly recommended. 

Location: 1235 W Belmont Ave, Chicago, IL 60657

Hours: Monday 12:00 - 6:00 p.m., Tuesday & Wednesday closed, Thursday - Saturday 12:00 - 8:00 p.m., Sunday 11:00 a.m. - 6:00 p.m. 

For more information on Catcade.

Arcade games and cute cats galore? Hello, perfect date spot! At this arcade slash lounge slash animal rescue, you and your date can challenge each other to a few rounds of classic arcade games like Pacman – and even if you lose, you can console yourself with a cuddly kitten! As a bonus, all the cats are available for adoption, so if you fall in love with a furry friend, they might just come home with you! Reservations are highly recommended. 

Location: 1235 W Belmont Ave, Chicago, IL 60657

Hours: Monday 12:00 - 6:00 p.m., Tuesday & Wednesday closed, Thursday - Saturday 12:00 - 8:00 p.m., Sunday 11:00 a.m. - 6:00 p.m. 

For more information on Catcade.

Take a trip down the rabbit hole to an Alice in Wonderland cocktail experience

Take a trip down the rabbit hole to an Alice in Wonderland cocktail experience

You and your date will find a topsy-turvy world of fun with this epic Alice in Wonderland immersive cocktail experience. As you journey through this whimsical rabbit hole, you’ll create two bespoke Wonderland cocktails, solve riddles and challenges, paint the roses red, and even try your luck eating your very own “Eat Me” cake. This is one tea party you will NOT want to miss. 

Location: 2442 N Clark St, Chicago, Illinois, United States, 60614

Hours:  Times vary, check schedule for availability 

For more information on the Alice in Wonderland experience.

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Yachti Adventure Tours

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You and your date will find a topsy-turvy world of fun with this epic Alice in Wonderland immersive cocktail experience. As you journey through this whimsical rabbit hole, you’ll create two bespoke Wonderland cocktails, solve riddles and challenges, paint the roses red, and even try your luck eating your very own “Eat Me” cake. This is one tea party you will NOT want to miss. 

Location: 2442 N Clark St, Chicago, Illinois, United States, 60614

Hours:  Times vary, check schedule for availability 

For more information on the Alice in Wonderland experience.

Enjoy a “cheese-y” dinner at Geja’s Cafe

Enjoy a “cheese-y” dinner at Geja’s Cafe

For a unique, interactive dinner experience, head to Geja’s Cafe to share a lavish fondue meal together. Here you can choose from a variety of options ranging from a classic swiss-gruyere cheese fondue all the way up to decadent options like beef tenderloin, cold water lobster tail, and scallops. For dessert, definitely don’t skip the cafe’s famous Belgian chocolate fondue, served tableside with marshmallows. 

Location: 340 W Armitage Ave, Chicago, IL 60614

Hours: Monday - Thursday 5:00 - 9:00 p.m., Friday 5:00 - 10:00 p.m., Saturday 4:00 - 10:00 p.m., Sunday 4:00 - 9:00 p.m.

For more information on Geja’s Cafe.

For a unique, interactive dinner experience, head to Geja’s Cafe to share a lavish fondue meal together. Here you can choose from a variety of options ranging from a classic swiss-gruyere cheese fondue all the way up to decadent options like beef tenderloin, cold water lobster tail, and scallops. For dessert, definitely don’t skip the cafe’s famous Belgian chocolate fondue, served tableside with marshmallows. 

Location: 340 W Armitage Ave, Chicago, IL 60614

Hours: Monday - Thursday 5:00 - 9:00 p.m., Friday 5:00 - 10:00 p.m., Saturday 4:00 - 10:00 p.m., Sunday 4:00 - 9:00 p.m.

For more information on Geja’s Cafe.

Enjoy a secret omakase experience hidden in a swanky hotel

Enjoy a secret omakase experience hidden in a swanky hotel

Tucked away in an upscale suite in Hotel Lincoln is Sushi Suite, a speakeasy-style omakase experience waiting to welcome discerning sushi connoisseurs. Once you find the suite, a private sushi chef will whip up a 17-piece omakase tasting for a dining experience you won’t forget! You can even add on a craft cocktail flight, with curated libations sure to pair perfectly with the chef’s sushi masterpieces. 

Location: 1816 N Clark St, Chicago, IL 60614

Hours:  Monday, Wednesday - Sunday 5:00 PM –11:15 PM, Closed Tuesday

For more information on Sushi Suite 202.

Tucked away in an upscale suite in Hotel Lincoln is Sushi Suite, a speakeasy-style omakase experience waiting to welcome discerning sushi connoisseurs. Once you find the suite, a private sushi chef will whip up a 17-piece omakase tasting for a dining experience you won’t forget! You can even add on a craft cocktail flight, with curated libations sure to pair perfectly with the chef’s sushi masterpieces. 

Location: 1816 N Clark St, Chicago, IL 60614

Hours:  Monday, Wednesday - Sunday 5:00 PM –11:15 PM, Closed Tuesday

For more information on Sushi Suite 202.

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