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- 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
- Our 12th Annual AMAZING River Tubing BYOB Float Trip w/ All You Can Eat Taco BarRiverside Rentals, Winamac, IN
Grab your floaties and coolers and JOIN US on our 12th annual float trip! Hang out with 2 busloads (110 people!) of fun-loving and friendly Meetup folks for THE BEST day trip EVERRRRR!
This trip is an amazing way to get out of the city and onto tubes floating down a river with a drink in hand under the warm summer sun. You just can't beat it :) And these trips sell out REALLY early, so save your spots here right away!
THE TRIP INCLUDES OUR DELICIOUS ALL YOU CAN EAT TACO BAR LUNCH! After a float and some drinks, there's nothing better than chowing down on an all you can eat taco bar lunch! This includes hard and soft shells, ground beef, shredded chicken, lettuce, tomato, shredded cheese, sour cream, rice, and chips & salsa!! Yummmmmmm.
We go on this trip 2 different dates. One on Saturday, July 19th and another on Saturday, August 16th. Sign up for the one that works best for you! They're both a blast. REGISTER HERE!
It's only $88 to attend! Well actually $91.73 because we have to pay a $3.73 processing fee per ticket. We have a lot of costs to cover which is why the event costs this much, and the cost of our buses went up this year. But trust me, it's worth it for how much fun you'll have this day! It really will be THE BEST day of your summer!
THE TRIP INCLUDES:
- Round trip coach bus transportation. We ride in super nice buses, aka way more expensive, but worth it! They've got bathrooms and TVs (to watch movies there/back!) for a higher level of comfort.
- Your personal float tube. Tubes that hold your cooler can be shared and purchased for $10 cash upon arrival. Each cooler tube can hold 2 large standard sized coolers so you can share with others.
- Lunch. ALL YOU CAN EAT taco bar when we get out of the river after floating.
The event in a nutshell:
- Show up to the bus with your own BYOB cooler and snacks.
- We drive ~2 hours into Indiana watching movies, then arrive at the river and float with Riverside Rentals.
- Grab our tubes and float/drink/chat/relax for ~3 hours.
- Get out of the river and chow down on all you can eat tacos.
- Board the bus and head back to sweet home Chicago!
The Schedule:
*All times are listed in Chicago time (Central Standard Time)9:15 am SHARP - Buses Depart Chicago
(meet on the NW corner of Sheffield and Fullerton, you'll see big coach buses and we'll check you in)12:00 pm - Buses arrive at the river and we float!
3:30 pm - Float ends at the tubing place, get out, eat lunch, freshen up and finish your drinks.
4:30-5:00 pm - Head back to Chicago
(drop off at the same place we started the day)~6:30-7:00 pm - Arrive in Chicago
A COUPLE FINAL THINGS:
- You can leave anything you'd like on the bus while we're floating. They'll be locked and waiting for us right when we get out.
- No hard liquor allowed. No exceptions. No glass containers.
- Drinking alcohol isn't allowed on the bus rides.
- DO NOT sign up for this trip if you plan to get drunk. We will all get a nice buzz going on the trip but don't need anyone being irresponsible.
I look forward to enjoying the day with everyone! Please send me a message if you have any questions at all.
Cheers,
Ben - $5 First Fridays Stand Up Comedy Shows at Chicago's best venue!Laugh Factory, Chicago, IL
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!
--------------------------------
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.
--------------------------------
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
