How to Find Remote Jobs in Wicker Park (Chicago, IL)

How to Find Remote Jobs in Wicker Park (Chicago, IL)

Wicker Park is one of Chicago’s trendiest neighborhoods — a creative, lively area full of cafés, boutiques, and music venues. It’s also become a hub for digital professionals, freelancers, and remote workers who want the perfect balance of productivity and inspiration. If you live in Wicker Park and want to land a remote job, this guide will walk you through everything you need to know.

🏙️ Why Wicker Park is Ideal for Remote Work

Wicker Park combines Chicago's cultural vibrancy with a relaxed, neighborhood vibe. It's walkable, bike-friendly, and packed with work-friendly spaces. Whether you're in tech, design, writing, or customer success, it's a great launchpad for a remote career.

💼 In-Demand Remote Jobs in Wicker Park

  • Marketing: Content creation, email marketing, social media.
  • Tech: Web development, data analysis, cybersecurity.
  • Customer Support: Remote support agents and account managers.
  • Sales: SDRs, remote account executives, SaaS sales.
  • Education: Virtual instructors and curriculum designers.

🌐 Best Job Boards for Remote Listings

Need help with these? Check out our guides to Indeed, LinkedIn, and ZipRecruiter.

📍 Local Spots to Work Remotely in Wicker Park

  • The Wormhole Coffee: Retro-themed and full of remote workers.
  • Fairgrounds Coffee & Tea: Spacious, with a variety of drinks and strong Wi-Fi.
  • Filter Café: Cozy with great food and coffee.
  • Second Shift Coworking: Full-service coworking space near Logan Square.
  • Free Range Office: Boutique coworking just a short walk from the neighborhood.

📬 Cold Emailing Tips to Stand Out

One of the fastest ways to get interviews is to reach out directly to hiring managers. Here's how:

  1. Search LinkedIn for team leads or hiring managers in your target company.
  2. Use tools like Hunter.io or Clearbit to find their email.
  3. Write a concise intro: who you are, why you’re interested, and how you can help.
  4. Attach your resume and a link to your portfolio or LinkedIn profile.

📄 Optimize Your Resume for Remote Roles

  • Include “Remote” in your job titles (e.g., “Marketing Manager (Remote)”).
  • List remote tools and platforms (Slack, Zoom, Jira, etc.).
  • Show measurable impact (e.g., “Generated 50 qualified leads/month”).

🤝 Local Networking & Remote Work Events

  • 1871 Chicago: Chicago's startup incubator offering remote-focused workshops.
  • Built In Chicago: Events and job boards for tech professionals.
  • Creative Mornings Chicago: Free talks for creatives and freelancers.
  • Remote Work Meetups: Search Meetup.com for virtual-friendly events in Chicago.

🗓️ A Sample Day Working Remotely in Wicker Park

  • 8:00 AM – Morning coffee + emails at The Wormhole
  • 10:00 AM – Deep work block at Free Range Office
  • 1:00 PM – Lunch break at Big Star Tacos
  • 2:00 PM – Virtual interview from home
  • 4:00 PM – Respond to job leads and send follow-ups
  • 6:00 PM – Attend Built In Chicago happy hour

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🚀 Final Thoughts

Wicker Park is one of the best neighborhoods in Chicago to live and work remotely. With the right approach — and a little persistence — you can land a job that fits your lifestyle and professional goals. Keep applying, stay connected locally, and let your resume do the talking.

Want more neighborhood tips? Explore our guides to Midtown Atlanta or Capitol Hill, Seattle.