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Summer is on its way and in Chicago that means we can finally emerge from our deeply dug caverns filled with Velveeta encrusted flannel pajamas and overdue Redbox sleeves and finally enjoy the real world again. That’s what we tell ourselves, but like most Chicagoans we end up sitting by the open living room window and watching all the normal folks finding fun things to do outside while we wonder when the sun’s going to go down so we can do a marathon of Archer without that pesky glare.

Not this summer, says CitySwarm, a Chicago-based event startup making sure you step out of your apartment at least once a month. Offering a variety of social events throughout the year focusing on young professionals, CitySwarm organizes fun and unique events that members only have to pay a flat fee to gain access to, including happy hours, city tours, sporting events, and much more.

I sat down with CitySwarm founder Lindsay Saewitz, who was nice enough to not ask about the crusty pajamas I forgot to change out of before I left the house.

What is the backstory behind CitySwarm Chicago?

I got into event planning with my local alumni association. I got elected onto the board and started planning all of these events specifically for young professionals living here in Chicago. After doing that for a while I really enjoyed it and I decided that I wanted to leave the other company I was working for to do it full time.



Two years ago I thought, Why not try to take that concept of planning these group events and create something a little bit broader? I wanted to make something where anyone can come, something that was a way to get people out and explore all these cool things that we have here in Chicago.

What are some of your favorite events around Chicago?

I really like a lot of the active events in the summer like sailing on Lake Michigan, paddle boarding, and kayaking on the Chicago River. I think people really like to get active in the summer.

I also really like events that have a theme. I love our Apple Orchard Day event. People get all dressed up in plaid shirts and cowboy hats and really get into the spirit. Any event where people are really embracing it and dressing up, those are really fun.

How do you choose the events for CitySwarm?

I think first and foremost, whenever I’m conceptualizing a new event, I try to throw the event out there on Facebook or Twitter to get a feel if people are interested. If I get a few people saying they think it sounds like fun then I know it has potential.

Proximity is a big thing. It also has to be at a certain price point where the vendors are willing to discount it in exchange for the marketing value. It has to have either something that is unique and special or something that we can build a package around to make it a unique experience.



Why do you think people fail to take advantage of all the activities going on around Chicago?

I think in general people are just really busy; everyone’s working long hours. I think a lot of it just has to do with the hassle of having to research and organize. I’ve been in Chicago since graduation and until I’d started this company I hadn’t really done any of these things before. It takes a certain sense of urgency to get people to go out and do it.

It’s very easy to fall into a day-to-day routine, and people welcome the opportunity to break that routine and do something different.

What has been your most successful event to date?

One event that definitely does stick out we’ve already done twice now. It’s the kickoff to our Summer Patio Series, which is basically a series of six different happy hours that last throughout the summer. We pick six different bars that have really nice outdoor space. I think it’s successful because it’s that first time when it’s finally warm out and people are itching to get outside.



What are some upcoming CitySwarm events?

Next week is the Cubs Spring Fling at a bar near Wrigley where guests get a full meal, a beer, and a ticket to the baseball game. Another event I’m working on for the end of April is a Margarita Crawl; this is something that I haven’t seen done at all. It’s going to be an event leading up to Cinco de Mayo where we take a trolley tour to three different locations and get margaritas at each one. I think that will be a really cool event.

What advice would you give to any beginning entrepreneurs out there?

I think it’s really important to have a support system. Whether you’re a solo founder, like myself, or part of a larger team I think it’s a really great idea to befriend some other people that are in the same position as you and build that support network so you can help each other. It’s important to build support in the form of mentors and find people that can help you along the way.



What’s next for CitySwarm Chicago?

That’s a great question, as we’re trying to figure out the answer for ourselves at this point. We’re two years in and going on year three. Up until this point our growth has been very organic.

We’ve doubled our users year over year and I think that trend will continue. It’s just a matter now of figuring out if we want to keep growing at a slow pace or potentially try to do something to accelerate it. That could involve partnering with some other organizations. I guess we’ll see.


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