5 Chicago companies offering flexible vacation to help employees recharge

by Andreas Rekdal
March 17, 2017

Of course you can't actually take unlimited vacation (or so we've been told), but offering ample time off is still a great way to make sure your best people get a chance to recharge. These Chicago companies offer flexible PTO policies to help employees bring their a-game every day. 



What they do: UpRight Law delivers consumer legal services directly to your living room. By making it cheaper and more convenient to hire a lawyer, the Chicago-based tech startup is on a mission to close the access gap to America’s legal system.

Official policy: Unlimited PTO

Other awesome perks: UpRight Law’s employees have the option to participate in a student loan repayment program, in addition to perks like intramural sports teams, a free pantry and tap room, happy hours, and a video game room. If you're looking for a way to give back to the local community alongside your coworkers, UpRight offers opportunities for that too.




What they do: Finding an apartment or house you love is one thing, but the neighborhood in which it is located can often be just as important. By matching real estate listings with quality content about the surrounding community, Neighborhoods.com helps consumers get the best of both worlds.

Official policy: Flexible policies both for vacations and for working from home

Other cool perks: In addition to a matching 401(k), casual dress code and opportunities to work from home, Neighborhoods.com’s employees enjoy cold-brew coffee and craft beer on tap. The company offers secure bike storage, but there are also commuter benefits available and a nearby Metra station — in case your perfect neighborhood is further away.




What they do: Pandera Labs leverages analytics and solid product design fundamentals to create custom enterprise software. Its team also partners with other companies in joint ventures to build software products. The company just launched in Chicago — and is already growing in a big way.

Official policy: Unlimited vacation

Other awesome perks: In addition to unlimited vacation, employees enjoy great health care, regular team outings, happy hours, volunteer opportunities and plenty of space for learning.




What they do: A leading digital agency, One North partners with companies and organizations to provide digital brand experiences, including creative services, digital strategy, application development and managed hosting. And the company prides itself on its tight-knit team.

Official policy: Five weeks of paid time off each year, including vacation, personal time, sick time and company holidays

Other cool perks: The employer-matched 401(k) and flexible health plans helps employees gain peace of mind. One North’s building has a gym with discounted memberships and a Glazed & Infused donut shop in the lobby to help you make up for it (or was it the other way around?).




What they do: FastModel Sports creates software for the the world’s best basketball coaches and athletes. Its FastDraw play diagramming software is used by the entire NBA, most D1 college teams and thousands of high school and youth teams.

Official policy: Unlimited flexible time off policy

Other cool perks: Besides getting to work in a sports-driven culture, employees at FastModel get a 401(k) with a guaranteed 3 percent match, generous insurance coverage for themselves and their families, and a training and conference budget. The company also hosts frequent Ping Pong and Pop-A-Shot tournaments in its Magnificent Mile headquarters.



Images via Shutterstock and listed companies.

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