2022 Chicago Companies With The Best Benefits

Chicago has minted eight unicorn startups valued at over $1 billion just in the first half of 2021 alone. The Windy City is on track for explosive growth in the tech sector as Big Tech moves more headquarters to the Midwest and startups bloom around them. 

While there are tons of tech and startup jobs in Chicago, talent is looking for more than a seat of the fastest rocket ship: they’re looking for a purpose and new types of employee benefits. 

Workplace wellness plans, a healthy work environment, and flexible time off or remote startup jobs often top the list of what talent is looking for in the best employee benefits. A 401k, competitive compensation, and health insurance are still important parts of employee benefit packages, but if you’re looking for a startup job that offers modern benefits, we got your back. 

We’ve rounded up some of the best benefits from Chicago startups with a future-forward culture. 

Mid-sized Chicago Startups with the Best Benefits

1. Clearcover

A startup based in Chicago and Detroit that hires remotely, Clearcover is changing how we buy car insurance using technology and affordable, efficient pricing. Clearcover invests in DEI programs, is remote friendly, and has a strong emphasis on mental health and community. 

Clearcover Benefits:

• Equity

• Mental wellness program

• Remote friendly

• Mentorship programs

2. Vouch

Vouch is an insurtech company based in San Francisco with an office in Chicago. Their platform offers business insurance for high-growth companies. Vouch itself is a high-growth company, having just raised $90 million with a $550 million valuation. On top of competitive pay and insurance, Vouch has some additional great employee benefits and perks.

Vouch Benefits:

• Parental leave

• Unlimited PTO

• Wellness allowance

• Technology allowance

• Monthly Doordash credits

3. Chowbus

Not sure how no one thought of this before now, but Chowbus is one of those genius ideas that seems inevitable in hindsight. It’s an app that helps you order quality Asian food, and that’s it. Every company and restaurant featured on Chowbus is hand-picked down to the meal to ensure quality is all you can choose from. Chowbus prides themselves on their highly diverse management team. 

Chowbus Benefits:

• Health insurance

• Continuing education stipend

• Some meals provided

• Equity

• Unlimited vacation

Get alerted when new Chicago startup jobs drop on in the Purpose Jobs community. Subscribe to the weekly newsletter for top startup news and tech jobs.

4. Mediafly

A sales enablement and content management company focused on marketing, technology, and customer experience, Mediafly is one of a new crop of marketing startups leveraging technology. With that new focus comes a new culture of modern benefits. We love the inclusion of an on-site gym, the tuition reimbursement, and offering of a sabbatical, all of which can make a big difference in employees’ lives physically and financially.

Mediafly Benefits: 

• Family medical leave

• Flexible work schedule

• Remote work friendly

• Health insurance

• Disability insurance

• Life insurance 

• On-site gym

• Stocked kitchen, some meals provided

• Job training and development

• Tuition reimbursement

• 401k match

• Employee stock purchase program

• Generous PTO

• Sabbatical

5. Mastery Logistics Systems

If you love a startup that dedicates time for innovation, Mastery Logistics Systems might be a fit. They not only respect work-life balance but actually give you time during your day to work on new ideas. Mastry Logistics Systems is in the logistics and shipping tech industry, an ecosystem Chicago was born to disrupt.

Mastery Logistics Systems Benefits: 

• Health insurance

• Disability insurance

• 401k match

• Bonuses

• Unlimited vacation

5. Provi

Provi is an e-commerce software startup that serves the alcoholic beverage buying space. Simply put, they have created the easiest way for the beverage buying industry to order alcohol.

Provi Benefits:

• Family medical leave

• Flexible work schedule

• Generous parental leave

• Remote work friendly

• Dedicated DEI staff

• Mean gender pay gap below 10%

• Unconscious bias training

• Wellness programs

• Mental health benefits

• Continuing education stipend

• Job training and conferences

• Equity

• Bonuses

• Generous PTO

• Paid volunteer time

Small Chicago Startups with the Best Benefits

1. KPI Sense

One of the fastest growing startups in the nation, KPI Sense is a Chicago-based solution for SaaS startup finances. KPI Sense has beer on tap, happy hours, and an open office floorplan. If collaboration and friends outside of work is your thing, KPI might be a great fit.

KPI Sense Benefits:

• Wellness programs

• Health insurance

• Mental health program

• Equity

• Performance bonuses

• Flexible and remote work

• Generous PTO

2. PatientIQ

PatientIQ is a data-driven startup that has created a platform shared by medical providers, researchers, and industry partners to drive better patient outcomes. Those of you on the software side of things might like to know PatientIQ works with paired programming. Patient IQ also has a documented equal pay policy and diversity manifesto. 

Patient IQ Benefits: 

• Health insurance

• 401k

• Equity

• Remote work friendly

• Flexible work schedule

• Some meals provided

• Job training and conferences

• Bonuses

• Generous PTO

• Unlimited vacation

3. 86 Repairs

While many startups are addressing new technology for the restaurant industry, 86 Repairs is handling something that often goes overlooked: equipment repairs and maintenance. With a remote-friendly culture that embraces anyone who can do their job within 3 hours of the Eastern time zone, this is a cool startup to work for. 86 Repairs is now hiring out of Chicago, Grand Rapids, MI, Atlanta, and New York. 

86 Repairs Benefits: 

• Health insurance

• Flex spending account for family and child care

• 401k match

• Unlimited PTO 

• Generous parental and sick leave

• “Check Please” dining benefit, where the company pays for you to eat at 86 Repairs’ customers’ restaurants

4. ThreeFlow

Here’s a cool concept: Not only is Chicago startup ThreeFlow a company with great employee benefits; it’s their entire mission to change how employers provide benefits. Their enterprise software allows benefits brokers and insurance carriers to manage the entire placement process in one system. ThreeFlow is an unusual startup in that it has created an entirely new category of software. Pretty cool way to get in at the start of a new type of service.

ThreeFlow Benefits:

• Equity

• Health insurance

• 401k

• Generous PTO

• Parental leave 

• Home office stipend

5. Homethrive

Homethrive is another cool concept that leverages technology in a new way. This startup has created a program to match home caregivers with dedicated support to help them care for a loved one. 

Homethrive Benefits:

• Flexible work schedule

• Generous parental leave

• Remote work friendly

• Health insurance

• Some meals provided

• Job training and conferences

• 401k match

• Bonuses

6. EarlyBird

Enter another really cool idea: EarlyBird is an investing platform that allows loved ones besides parents to invest in a child’s financial future. It’s a simple app, but is backed by financial institutions you can trust. EarlyBird describes their culture as transparent, fun-loving, and collaborative, and an impactful organization with a purpose. Sign us up for that.

EarlyBird Benefits:

• Equity

• Flexible PTO

• Health insurance

• Health insurance

• Bonuses

• Unlimited vacation

Looking for more startup jobs? Discover top startup and tech jobs across the Midwest.

7. CoPilot

CoPilot joins the fray of online car buying startups, but with a unique twist. It’s not just a tool to buy a car and have it delivered. CoPilot acts as your own personal car buying expert, so you don’t have to be one. CoPilot is another great startup with fantastic benefits and an on-site gym. The world of work is looking more appealing by the day, and we hope more companies follow suit.

CoPilot Benefits: 

• Health insurance

• Family medical leave

• Life insurance

• On-site gym

• Equity

• 401k

• Generous PTO

8. Upfront

Upfront is a Chicago healthtech startup whose mission is to help patients get the right care they need using a custom platform to help individuals find the right providers and interact with them via their preferred method. As Upfront will tell you, they are in healthtech, so they don’t mess around when it comes to taking care of their own people with health insurance. This looks like a startup that takes care of its own as well as it takes care of its customers.

Upfront Benefits: 

• Health insurance

• Equity

• 401k

• Flexible PTO

• Remote work friendly

• Commuter benefits and flexible spending account

• Some meals provided

• Free gym 

9. Rheaply

We just love the new startups coming out of Chicago, for the value they create and the culture they’re cultivating. Rheaply is a startup focused on resource management to help large organizations better manage their assets. Rheaply has cultivated a DEI-friendly culture and even offers unconscious bias training. They have an on-site gym, have team workouts together, and volunteer together in the local community.

Rheaply Benefits: 

• Health insurance

• Unconscious bias training

• On-site gym

• Team workouts

• Job training

10. Ocient

Love big data and data analysis? Ocient out of Chicago enables rapid analysis and management of the world’s largest data sets. They also offer mentorship, remote work, equity, and unlimited vacation. A dream for those who love working in big data.

Ocient Benefits:

• Remote work friendly

• Unlimited vacation

• Equity

• Mentorship and job training 

• Family medical leave

• Flexible work schedule

• Generous parental leave

• Health insurance

• 401k

11. Leaf Trade

Leaf Trade is at the intersection of e-commerce and the growing cannabis industry. The LeafTrade platform manages orders, fulfillment, and payments for an industry known for complex and evolving industry regulations. LeafTrade even has dedicated DEI staff and programs. 

LeafTrade Benefits: 

• Health insurance

• Disability insurance

• Life insurance

• Equity

• 401k

• Employee stock purchase program

• Unlimited PTO

• Generous parental leave

• Dog-friendly office

• Remote work friendly

• Flexible work schedule

• Job training and conferences

• Bonuses

12. Forager

Want another cool startup in the logistics tech space? Forager manages cross-border shipping. Forager also has dedicated DEI staff. With wellness programs and mental health benefits on top of that, we’re super impressed. 

Forager Benefits:

• Family medical leave

• Generous parental leave

• Health insurance

• Disability insurance

• Life insurance

• Wellness programs

• Mental health benefits

• Some meals provided

• 401k

• Equity

• Bonuses

• Generous PTO

13. Cooler Screens

If you want to work for a startup whose tech is as futuristic as their benefits, Cooler Screens is, well, the coolest. They design screens for in-store shopping experiences to make the way we shop in store as easy and compelling as the way we shop on our phones. 

Cooler Systems Benefits:

• Generous PTDisability insurance

• 529 college savings

• 401k

• Generous parental leave

• Remote work program

• On-site gym

• Some meals provided

• Job development training

• Equity

• Bonuses

14. BigTime Software

BigTime Software is a downtown Chicago Loop startup that focuses on helping you recoup your most valuable asset: time. BigTime Software has DEI staff and programs, and a culture that’s all about cross-functional training and collaboration. 

BigTime Software Benefits: 

• Health insurance

• Generous PTO

• 401k match

• Some meals provided

• Family medical leave

• Generous parental leave

• Remote work program

• Disability insurance

• Life insurance

• On-site gym

• Job training and conferences

• 401k match

• Charitable contribution match

• Bonuses

Want to be the first to know when new Chicago startup jobs drop on Purpose Jobs? Subscribe to our weekly newsletter to get the top startup news and jobs sent straight to your inbox.

Looking for more top companies with the best benefits? Check out other hiring startups with great perks from around the Midwest.

Companies with the Best Benefits: Ann Arbor

Companies with the Best Benefits: Cincinnati

Companies with the Best Benefits: Chicago

Companies with the Best Benefits: Columbus

Companies with the Best Benefits: Detroit

Companies with the Best Benefits: Indianapolis

Companies with the Best Benefits: Milwaukee

Companies with the Best Benefits: Pittsburgh

Companies with the Best Benefits: Remote