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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 September 29, 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.

Experience a Night of Mind-Blowing Magic

Experience a Night of Mind-Blowing Magic

Take your date to a magic show! Magic at Lulu's is a weekly Thursday night magic show featuring magicians Mike O’Donnell and Edd Fairman. Find yourself experiencing a night filled with mind-blowing magic, themed cocktails, and a la carte food options. 

Location: Storyville: 712 N Clark St, Chicago, IL 60654

When: Thursdays through November 17. Two sessions:

7:00 PM - 8:30 PM (Featuring magician Edd Fairman)

9:30 PM - 11:00 PM (Featuring magician Mike O’Donnell)

For more information on Storyville Magic Shows at Lulu's.

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Immersive King Tut

location_on Lighthouse ArtSpace Chicago, CHI

Immersive King Tut

From$36 $29 19% off
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Take your date to a magic show! Magic at Lulu's is a weekly Thursday night magic show featuring magicians Mike O’Donnell and Edd Fairman. Find yourself experiencing a night filled with mind-blowing magic, themed cocktails, and a la carte food options. 

Location: Storyville: 712 N Clark St, Chicago, IL 60654

When: Thursdays through November 17. Two sessions:

7:00 PM - 8:30 PM (Featuring magician Edd Fairman)

9:30 PM - 11:00 PM (Featuring magician Mike O’Donnell)

For more information on Storyville Magic Shows at Lulu's.

Watch a Drive-In Movie

Watch a Drive-In Movie

You and your date will love cozying up during a nostalgic drive-in movie date. Movies rotate on a weekly basis at the Pilsen location, with previous highlights including “Star Wars: A New Hope,” “Grease,” and “The Sandlot.” 

Location: 2343 S. Throop Street, Chicago, IL 60608

For more information on Chicago drive-in movies.

location_on ChiTown Futbol, CHI

ChiTown Drive-In New Movies Announced

$33
  • event 2022-05-27
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You and your date will love cozying up during a nostalgic drive-in movie date. Movies rotate on a weekly basis at the Pilsen location, with previous highlights including “Star Wars: A New Hope,” “Grease,” and “The Sandlot.” 

Location: 2343 S. Throop Street, Chicago, IL 60608

For more information on Chicago drive-in movies.

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.

Take a Chicago Street Art Tour and Workshop

Take a Chicago Street Art Tour and Workshop

Spend the day with your date discovering stunning murals and creating your own artwork. The experience starts with a 90-minute bus tour through some Chicago neighborhoods, on the hunt for hidden and not-so-hidden artwork. 

You will learn more about local artists and have the opportunity to snag some photos when making stops along the way. After wrapping up the tour portion, return back to home base at The Graff, where you will have the opportunity to put your own skills to test with an interactive workshop guided by one of our artists

Where: The Graff: 3525 W Grand Ave, Chicago, IL 60651

For more information on Chicago street art tours.

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Blank Mason Candle Bar - Pour & Sip

location_on Blank Mason Candle Bar, CHI

Blank Mason Candle Bar - Pour & Sip

From$50 $45 10% off
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Spend the day with your date discovering stunning murals and creating your own artwork. The experience starts with a 90-minute bus tour through some Chicago neighborhoods, on the hunt for hidden and not-so-hidden artwork. 

You will learn more about local artists and have the opportunity to snag some photos when making stops along the way. After wrapping up the tour portion, return back to home base at The Graff, where you will have the opportunity to put your own skills to test with an interactive workshop guided by one of our artists

Where: The Graff: 3525 W Grand Ave, Chicago, IL 60651

For more information on Chicago street art tours.

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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Sushi Making Classes

location_on Various Locations, CHI

Sushi Making Classes

$59 $56 5% OFF
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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

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.

location_on Laugh Factory, CHI

Stand Up Comedy Tickets

From$20 $10 50% off
  • event 2022-06-01
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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. 

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.

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 Various locations, IL

Spray Paint ‘n’ Sip series

From$40 $35 13% off
  • event 2022-06-01
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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. 

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.

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Stand Up Comedy Tickets

location_on Laugh Factory, CHI

Stand Up Comedy Tickets

From$20 $10 50% off
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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.

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. 

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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