Thanks to its balance of culture, affordability, and thriving co-working scene, Chicago is becoming a bit of a hotspot for digital nomads. While most of us associate the Second City with deep dish pizzas, skyscrapers, and its passionate sports fans, if you look a little closer, you’ll see an incredible metropolis that offers a mix of historic charm, modern workspaces, and plenty of downtime options for those who like to work hard and play hard!

If you’re thinking of living and working in Chicago for a period, then read on to discover how to make the most of your time here, how to boost your productivity, and how to live, work, and play to the fullest in the Second City.

Where to Stay in Chicago: Tips for Digital Nomads

As you can imagine, there are plenty of hotels in Chicago, but not every one of them can accommodate the needs of a digital nomad! Your best bet is to always begin your search with cheap hotel deals in Chicago, and potentially look for accommodation that offers extended stays or even aparthotels that offer services such as laundry, desk spaces, and even kitchenettes. Choosing to visit during the off-season, which is winter through early spring, means you might also get a discount on your stay.

The best areas to stay are dependent on your specific needs; however, digital nomads may find that downtown areas such as The Loop are close to major attractions and coworking hubs, while areas such as Wicker Park, Logan Square, and the River North offer a good balance of nightlife, restaurants, and trendier spots.

Coworking Spaces and Work-Friendly Cafés

Maintaining high productivity levels is essential as a digital nomad, so having access to a workspace that supports your specific requirements is key. As you can expect from a great city like Chicago, you’re truly spoilt for choice. Here are our recommendations for working in Chicago.

Coworking Hubs: There are plenty of international and national coworking hubs across the city. All offering professional setups with reliable high-speed internet, printing facilities, conference rooms, and networking opportunities. These are ideal if you’re someone who prefers working in a more traditional or structured environment, whether you’re meeting clients, networking, or just have deadlines to meet.

Local Independent Spots: You’ll also find an abundance of independent coworking hubs, many with a community-like feel that is ideal for collaborators and creatives alike. If you prefer more of an intimate setting rather than a corporate feel, then you’ll appreciate the atmosphere in places like Platform and Free Range Office.

Here are some tips for choosing your next coworking space:

• Don’t just take their word for it; always check Wi-Fi speeds on reviews
• If it’s a long stay in Chicago, then consider picking up a membership at your chosen coworking space
• Minimize commuting stress by choosing a space that is near your accommodation.

Getting Around

Getting around Chicago easily is another essential element of meeting your full potential as a digital nomad in the Windy City. Reducing commuting time can help keep your stress levels low and give you more time to enjoy what the city has to offer when you’re away from your spreadsheets, invoices, and daily tasks.

• Try public transport: CTA ‘L’ trains and buses make it easy to get around without a car. It doesn’t take long to get used to the routes and the stops!
• Cycling: If you want to inject some fitness into your daily routine, then hiring a bike or bringing your own along for your trip is an eco-friendly way to get moving.
• Walking: Chicago is very walkable, particularly in neighborhoods such as Wicker Park. Just remember to check the weather forecast. Chicago’s winters are brutal, and the summers are warm and humid!

How to Spend Your Downtime

Working hard is one thing, but playing hard is what Chicago does best! With so much to see and do, there’s something for everyone to enjoy in this beautiful and incredibly diverse city. Whether you want to focus on the nightlife and entertainment side of things, you want to get out and about in nature, or you want to immerse yourself in the art and culture of the city, you’ll be spoilt for choice. Here are our top picks.

Entertainment and Nightlife:

• The Jazz Clubs: Chicago is known for its jazz scene, so you can expect jazz clubs and speakeasy-style venues throughout the city.
• Comedy shows: The Second City in Old Town is world-famous for improv and sketch comedy, having launched the careers of countless comedians. It’s a must for a fun night out.
• Rooftop bars: The city skyline is stunning from above. Spots like Cindy’s Rooftop and LondonHouse offer cocktails with panoramic views. Perfect for unwinding after work or networking with other creatives.

Outdoor Adventures:

• Lake Michigan: Stretching 18 miles along Lake Michigan, the Lakefront Trail is perfect for running, biking, rollerblading, or just strolling with lake views.
• Parks and gardens: Grant Park, Millennium Park, and Lincoln Park provide walking paths, public art, and green spaces for relaxation or a lunchtime picnic. Perfect for winding down after a busy day, or catching your breath between meetings.

Culture & Museums:

• Art Institute of Chicago: One of the oldest and largest art museums in the U.S., home to masterpieces like Grant Wood’s American Gothic and iconic Impressionist collections. Perfect for a few hours of inspiration and quiet reflection after a day of work.
• Museum of Contemporary Art (MCA): Showcases cutting-edge contemporary art, often including installations, multimedia exhibits, and interactive pieces. Great for creatives looking for fresh ideas or simply a dose of modern culture.

Final Thoughts…

With so much to see and do, it’s easy to see why Chicago pulls in so many digital nomads each year. It’s a much underrated gem that is the perfect blend of affordability, culture, and a great working infrastructure. With the right balance of working, planning, and spontaneity, Chicago can feel like a second home that brings out the best in your work ethic and productivity.