What we’re about
Windy City Connections will be putting together events for 20-30 somethings that focus on one thing: Meeting people and having fun. Well, that's kind of two things...Our group will live by the motto "A good time is all about who you share it with". And I want YOU to help us organize events too! Have an idea for one, email me (Ben, the group Organizer) and we'll get it set up!
We'll be organizing groups to do things like happy hours, trivia nights, visit museums, go to comedy shows, do simple get-togethers, play in intramural sports leagues and more! So if you're fresh in town (welcome!), are looking to make some new friends, and/or simply just want to spice things up and do something other than sitting in a bar with the same ol' folks, we're gonna be that spice.
I also run S3 Simply Social Sports Leagues (s3leagues.com), which offers THE BEST coed rec sports leagues in the city. Sure I'm biased, but the sweet thing is they really are amazing. These leagues allow you to join by yourself or with friends and we create teams by age group for anyone aged 21-42, with post-game festivities at a near-by bar.
My leagues welcome all skill levels too! Rather than a one time event, they last 5-8 weeks and allow you to foster stronger relationships as you come together every week during the season. Being new to town myself years ago, I made all my best friends by joining a coed softball team. I knew I could make it better, and now many years later with tens of thousands of past alum, tons of new friends made, couples formed, and several marriages! I'll be posting these leagues to the group as well.
Sometimes the best connections come from simply expanding your social circle and getting out more. This is our goal, and we're excited to see you at an event or league!
Cheers,
Ben
This August & September, join us for a season of Simply Social fun! There's absolutely nothing better than participating in a recreational, all-skill levels welcome intramural league! It's so nice getting to know new people in a really laid back way over the length of a season, playing games and then over drinks at your walkable league sponsor bar afterwards with all teams.
We've got Kickball, 16" Softball, Beach Volleyball, Singles Skeeball (for singles!) and Family Feud Trivia. They're all a blast!
REGISTER TO JOIN US by yourself or with friends and get placed on a team for the season! Want to participate but can't make it to every game? No problem! We put extra players on every team for this very reason.
NOTE: I'VE GOT A LOT OF DIFFERENT FALL LEAGUES THAT RUN FROM AUGUST-OCTOBER AND PLAY SUNDAY-FRIDAY ALL OVER THE CITY! THE DATE AND LOCATION SHOWN FOR THIS MEETUP EVENT ARE JUST A PLACEHOLDER. CHECK OUT MY WEBSITE FOR THE FULL LEAGUE OPTIONS, DETAILS & TO REGISTER FOR A SUPER FUN SEASON!! https://s3leagues.com/fall-leagues
**Send me a DM if you have any questions and I'll get back to you right away!**
WHY JOIN S3 SIMPLY SOCIAL SPORTS LEAGUES?
I started S3 Leagues 16 years ago in an effort to create more social, welcoming leagues that focus on having fun and meeting new people. Since then, over 97,000 past players (yeah that many lol) have experienced what makes them so great and popular!
Hanging out with the same group week after week for 5-7 weeks makes it pretty effortless to build lasting relationships. That's the best part :)
ALL SKILL LEVELS ARE WELCOME, aka no experience required! Simply register by yourself or with friends and I'll put you with others around your age for the season. Then before we start I'll email EVERYTHING you need to know for the season including your teammate info, the full schedule, how/where we play and TONS more!
FULL DETAILS & REGISTRATION: https://s3leagues.com/fall-leagues
GET $20 OFF 16" SOFTBALL OR KICKBALL PLAYER FEES W/ PROMO CODE 'MEETUPHOOKUP' - PLAY FOR ONLY $45-75!
PLUS GIRLS GET 50% OFF 16" SOFTBALL - PLAY FOR ONLY $32-47!
Promo codes cannot be used for Beach Volleyball ($65-70), Singles Skeeball ($65) and Family Feud Trivia ($35) which are cheap for everyone.
IF YOU'VE GOT A FULL TEAM TO SIGN UP, EMAIL BEN@S3LEAGUES.COM (THAT'S ME!) TO REGISTER AND MAKE IT EVEN CHEAPER PER PLAYER!
I hope you let me show you what makes S3 Simply Social Sports Leagues so popular and exciting. I guarantee it'll be a unique experience unlike anything you've ever been a part of :)
Please send me a message if you have any questions!
Cheers,
Ben
Upcoming events (4+)
See all- Register to join our Summer Coed Softball, Kickball and Beach Volleyball Teams!Leagues played at various locations in Chicago. See specific leagues for where the games are played!, Chicago, IL
When Summer finally arrives in Chicago, it's our goal to be outside enjoying the weather as much as possible. And there's absolutely nothing better than joining a social intramural league! It's a blast getting to know new people playing games and then also over drinks at your league sponsor bar that all teams walk to (or we play in a bar)!
Hanging out with the same group week after week for 5-7 weeks makes it pretty effortless to build lasting relationships over the duration of the season. That's the best part :)
In these leagues, ALL SKILL LEVELS ARE WELCOME (no experience required) and we can place anyone aged 21-42 on a team. Simply register by yourself or with friends and I'll put you with others around your age for the season.
Want to get on a team but can't make it to every game? No problem! We put extra players on every team for this very reason.
REGISTER TO JOIN US as we MEETUP for some coed, recreational level (ALL skill levels welcome) "Simply Social" sports leagues!
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GET $20 OFF 16" SOFTBALL OR KICKBALL PLAYER FEES W/ PROMO CODE 'MEETUPHOOKUP' -- *PLUS GIRLS GET 50% OFF 16" SOFTBALL!Play 7 weeks of softball or kickball for only $37-$80!! Price depends on the league. And 5-week Beach Volleyball seasons are cheap at only $65-70!
*********************NOTE: THE DATE AND LOCATION SHOWN FOR THIS MEETUP EVENT ARE JUST A PLACEHOLDER. CHECK OUT MY WEBSITE HERE FOR THE FULL LEAGUE OPTIONS, DETAILS AND TO REGISTER FOR A FUN SEASON!!
LEAGUES INCLUDE:
- 5-7 Week Season (varies by league)
- We buy your team some beer each week! (in most leagues)
- Team player shirt in your requested size! (in most leagues)
- Food and drink specials at your sponsor bar!
- Team victory bar parties for multiple league champs!
GET $20 OFF 16" SOFTBALL OR KICKBALL PLAYER FEES W/ PROMO CODE 'MEETUPHOOKUP' -- *PLUS GIRLS GET 50% OFF 16" SOFTBALL!
SEE ALL LEAGUE OPTIONS, FULL DETAILS & REGISTRATION HERE
I hope you let me show you what makes S3 Simply Social Sports Leagues so popular and exciting. I guarantee it'll be a unique experience unlike anything you've ever been a part of!
Over 97,000 past players (yeah that many haha) have had a blast since I started running these leagues 15 years ago :)
Please send me a message if you have any questions.
Cheers,
Ben - Play Sunday Funday All Levels Softball & Kickball! Get placed on a coed team!Stanton Park, Chicago, IL
Let's MEETUP on Sunday Fundays this summer! When the weather in Chicago is absolutely perfect, there's nothing better than playing in one of my coed, recreational level intramural leagues! For the past 15 years, people have been signing up for my leagues because we offer not only a super fun outdoor activity, but also create an environment where meeting people is just as important as the games!
What's best is that my "Simply Social" leagues always get super nice, super friendly people to sign up, not overly competitive folks. Hanging out with the same group week after week for 7 weeks makes it effortless to build lasting relationships. That really is the best part :)
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TONS OF PEOPLE JOIN BY THEMSELVES OR WITH A FRIEND OR A FEW TO GET PLACED ON A TEAM OF OTHERS AROUND THEIR AGE!
*Want to get placed on a team but can't make it to every game? No problem! We put extra players on every team for this very reason.
SUNDAY KICKBALL FULL DETAILS & REGISTRATION
SUNDAY SOFTBALL FULL DETAILS & REGISTRATIONPLAY 7 WEEKS FOR JUST $75 W/ PROMO CODE 'MEETUPHOOKUP'! ALSO, GIRLS PLAY 16" SOFTBALL FOR ONLY $47 W/ PROMO CODE 'SOFTBALLGIRLS'!
OR EMAIL BEN@S3LEAGUES.COM (THAT'S ME!) TO REGISTER A FULL TEAM FOR A BIG DISCOUNT - IT'S ONLY $965 FOR A TEAM OF UP TO 20 PLAYERS!
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FULL LEAGUE DETAILS:
*Don't pay attention to the RSVP #. People find out about and join these leagues from many places and they always fill up fast!
Before the season starts, you'll get an email with TONS of important info including your teammates' names and emails, the full schedule, how we play, sponsor bar location more.
FIRST GAMES: Sunday, June 29th. Games played 1:00-4:30 pm and your team's game time rotates weekly.
LENGTH: 7 Weeks. Top half and bottom half ranked teams play in their own separate playoffs & all teams make it in! Winners get prizes to our sponsor bar Sully's House (3 blocks from the field).
LOCATION: Stanton Park (off Halsted between North & Division). There's a free parking lot right next to the fields! All teams walk to the same post-game sponsor bar to hang out after playing!
SUNDAY KICKBALL FULL DETAILS & REGISTRATION
SUNDAY SOFTBALL FULL DETAILS & REGISTRATIONPLAY 7 WEEKS FOR JUST $75 W/ PROMO CODE 'MEETUPHOOKUP'! ALSO, GIRLS PLAY 16" SOFTBALL FOR ONLY $47 W/ PROMO CODE 'SOFTBALLGIRLS'!
Please message me if you have any questions at all! I hope to see you there on opening day!
Cheers, Ben
- The Dramatic Improv FestivalCity Lit Theater, Chicago, IL
The Dramatic Improv Festival returns to Chicago from Thursday, July 10 through Sunday, July 13, 2025, offering a unique exploration of emotionally grounded and narratively rich improvisational theatre.
Hosted by Theatre Momentum and held at City Lit Theater (1020 W Bryn Mawr Ave), the festival brings together an international lineup of performers and instructors for four days of performances, workshops, and collaborative events.
The Dramatic Improv Festival is wholly dedicated to the art of grounded and dramatic improvisation. This year’s program features:
- Over 25 ensembles performing across four nights
- Workshops led by acclaimed instructors from around the world
- An insta-team performance ensemble assembled during the festival
Performances begin at 7:00 PM Thursday, July 10, and continue nightly through Sunday. Workshops will be offered Friday through Sunday. Tickets are $15 per show, and workshops range from $30 to $55. Festival passes and tickets are available at dramaticimprovfest.com.
- $5 First Fridays Stand Up Comedy Shows at Chicago's best venue!Laugh Factory, Chicago, IL
IMPORTANT UPDATE: Our July shows will be held on the Second Friday of July because the First Friday is July 4th and Laugh Factory is closed!
Get your tickets to shows on Friday, July 11th below!The Laugh Factory in Lakeview (Broadway & Belmont) is open for comedy and we all could use some laughs! We always get A LOT of people to attend these shows. Often times over 100 Meetup members!
If you attend by yourself or with friends and want to be seated in the Meetup group section, simply request this when you check in at the ticket booth! Then just say hi to those around you :)
Every First Friday of the month we get $5 TICKETS to their shows at 7:00, 9:15 & 11:30 pm. They're ALWAYS hilarious!
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Get your $5 tickets ASAP before the quantity they give us get sells out. And with our "laugh or get a refund" policy (that has never in 4 years been requested), I know you'll enjoy your MUCH NEEDED night out! This event is posted in lots of different Meetup groups, so the RSVP # won't show how many are actually attending.
READ THE DESCRIPTION OF EACH SHOW AND GET YOUR $5 TIX HERE: https://tinyurl.com/firstfridayslaughfactory
*You can purchase tickets for several people and multiple shows this night through the link. No physical tickets will be issued. Your name will be on a list at the door and all tickets will be under the purchaser's name. Groups of up to 6 people can be sat together if arriving together.
Please Note: These shows are for ages 18+ w/ ID. If you show up after start time you will not be able to enter. There is a 2 drink minimum per person per show (non-alcoholic or alcoholic). Drinks are reasonably priced, and a comedy show is funnier with a few drinks, so this shouldn't be an issue with how cheap our tickets are :) Also, an 18% service fee (aka gratuity) will be applied to all drink tabs at payment to be given directly to service staff.
No refunds or exchanges but tickets can be transferred.
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Is there parking? Street parking and some garages are available throughout the area. However, public transit, ridesharing apps, and taxi services are highly encouraged.
What is the dress code? There is no dress code. Be comfortable!
READ THE DESCRIPTION OF EACH SHOW AND GET YOUR $5 TIX HERE: https://tinyurl.com/firstfridayslaughfactory
Enjoy the laughter!
-Ben
