Work-Friendly Cafes in Chicago: Start your journey in the bustling city of Chicago, where there are plenty of cafes and co-working spaces with strong Wi-Fi to get your work done. Some spots to check out:
- The Wing (downtown Chicago) - A modern co-working space with amenities for remote workers.
- Sawada Coffee (West Loop) - A cozy spot with excellent coffee and reliable Wi-Fi.
- The Coffee Studio (Andersonville) - Great for working on the go, with tasty brews and a relaxed atmosphere.
- WeWork (various locations) – If you need a more formal co-working space, WeWork offers great amenities and is scattered around the city.
Exploring Downtown Chicago: When you’re not working, take advantage of the city’s many iconic attractions. Visit Millennium Park and check out the famous Cloud Gate sculpture (aka The Bean). You can also stroll along the Chicago Riverwalk or visit museums like the Art Institute of Chicago.

Get Your Route 66 Start: The Route 66 Visitor Center in Chicago is a perfect first stop. Learn about the history of Route 66 and get maps, guides, and tips on the road ahead. It's a nice mix of culture and history, and you'll find inspiration for your digital nomad adventure.

Joliet Area Historical Museum: Take a break from work to dive into Joliet’s history. The museum showcases the area’s industrial past and features exhibits about the city’s role in Route 66. It's an easy stop with great Wi-Fi in the nearby cafes.
Work in Joliet: The town has local coffee shops like Rialto Square Coffee and The Foundry Coffeehouse which are good for both productivity and unwinding.

Gemini Giant: As a digital nomad, you might appreciate quirky roadside attractions like the Gemini Giant, a giant fiberglass astronaut outside the Launching Pad Drive-In. A great photo op and a fun, relaxing stop in between work sessions.
Local Cafes: Small towns like Wilmington often have charming, quiet cafes perfect for work. The Iron House Café is a cozy spot to plug in and get some work done.

Pontiac-Oakland Automobile Museum: Stop here for a dose of automotive history. Pontiac is filled with murals, historic landmarks, and antique stores that provide a mix of work breaks and inspiration.
Work in Pontiac: The Café 110 is an inviting space for remote workers, offering good Wi-Fi and a comfortable environment for digital nomads to get some work done.

Abraham Lincoln Sites: As you make your way through Illinois, a stop in Lincoln is a must. Explore the Abraham Lincoln Presidential Library and Museum, where you can learn about the life and legacy of one of America’s most famous presidents. It’s not only educational but also provides a nice mental break.
Wi-Fi-Friendly Places: The Mill is a popular café in Lincoln, great for grabbing a coffee and staying connected.

Abraham Lincoln Presidential Library & Museum: Another stop for history lovers! After working in Springfield’s many cafes or co-working spaces, take time to visit this museum dedicated to Lincoln’s legacy.
Digital Nomad-Friendly Spots:
- Coffee Connection: A local favorite for coffee and quick Wi-Fi.
- The Incubator: A co-working space that supports entrepreneurs and digital nomads in the Springfield area.

Route 66 Park: This small park offers a relaxing environment for remote workers looking for a peaceful break. Take a walk, stretch your legs, or enjoy the tranquility while thinking about your next project.
Work-Friendly Cafes: There are quaint local cafes perfect for remote work, such as The Olde Towne Café, which is an ideal spot for digital nomads to find peace and focus.

The Edwardsville Arts Center: Take time to explore the local arts scene. The center often has exhibits and events that are a nice mix of culture and relaxation, perfect for unwinding after a workday.
Co-working Spots: If you need a co-working space, The Foundry is located nearby and provides reliable Wi-Fi, comfortable seating, and a productive environment.

Work and Play in St. Louis: St. Louis is just across the Illinois border and offers a huge array of co-working spaces and local cafés with strong Wi-Fi. While in the area, take time to visit the Gateway Arch and Museum of Westward Expansion.
Digital Nomad-Friendly Spaces: T-REX is a tech-focused co-working space perfect for digital nomads. There are also plenty of coffee shops like Sump Coffee and Café Ventana that provide great Wi-Fi and a quiet atmosphere for working.

Shawnee National Forest: If you’re looking for a nature break, take a detour to Shawnee National Forest. This is a great place to refresh your mind with outdoor hikes and stunning views. After work, take a walk on the Garden of the Gods trail for some stunning rock formations and scenic overlooks.
Pere Marquette State Park: A tranquil retreat where you can recharge, reflect, and get inspired. The park offers beautiful hiking trails, and if you need a moment of quiet to clear your mind, this is the perfect place.

Plan Work-Friendly Stops: Check ahead for reliable Wi-Fi at cafes and co-working spaces, especially in smaller towns. Use platforms like Nomad List to check for digital nomad-friendly places.
Flexibility is Key: As a digital nomad, you’ll want to maintain a flexible schedule. Illinois offers a great mix of cultural stops, historical landmarks, and small-town charm—perfect for blending work with exploration.
Embrace Slow Travel: Take your time exploring each of these towns. Illinois offers small, peaceful stops that allow you to balance your work with relaxation and discovery.

Wandering Souls