1-Month trip to Chicago, IL with Remote Year

Discover the best of the Midwest with our community of remote explorers. Stroll the Magnificent Mile between meetings. Taste deep-dish pizza with new friends at lunch. And after work? Listen to live music at Millenium Park, catch fireworks at Navy Pier, or relax at Oak Street Beach. Bring your job and we’ll handle the rest!

Comfortable Accommodation Leader & Local Team 24/7 Access to Workspace Curated Local Experiences Ground Transportation Health & Safety Support COMMUNITY

Traveling the world is incredible, but traveling alongside a vibrant global community – now that’s unforgettable. Over the past 6 years, we’ve helped 4,000+ passionate adventurers find their go-to adventure buddies, business partners, and even love connections while on the road. Everything we do revolves around community. We can’t wait for you to join ours.

People of color 21-77 age range 14% LGTBQ+ Meet one of our Community Leaders

Born in Guadalajara, Mexico, Florencia has a deep love for her home culture, country, and tacos. Inspired to see the world and connect with others, she joined Remote Year as a Community Leader. From a young age her passion for art, architecture, and connection, fueled her curiosity to visit new cities and meet new people. In Chicago, you’ll have a Community Leader (like Florencia) as well as a local City Manager to help make sure your month is seamless and unforgettable.

ACCOMMODATIONSYour home is the perfect base for exploring the best Chicago has to offer. Minutes away from the famous Magnificent Mile, Oak Street beach, and dozens of the city’s best restaurants, museums, stores, and landmarks, you’ll always have an exciting day awaiting you in the Windy City. You will have the option to select a private room or share a room or dorm with fellow program participants. If you are sharing a room, you can specify a roommate or let us match you with someone. Pricing is adjusted to match the room type you select. Participant Rating Centrally Located Safe & Secure

Plenty of unique and fun activities to choose from that also support local communities and businesses. The magic of this program is that all the participants are still working while exploring a new area. I’m already planning my next Remote Year trip. Highly recommend.

Jamie, 1-month Trip

This is how everyone should travel and I’ve never felt happier to be a part of this vibrant community. I can’t thank Remote Year enough for all of the experiences and people i’ve met along the way. It’s been life changing.

Theresa, 1-month Trip

Jamie, 1-month Trip

Theresa, 1-month Trip

Jamie, 1-month Trip WORKSPACESYour state-of-the-art coworking space is just moments away from where you’ll be staying! Ride the elevator down to a space designed to foster your career. Remote Year’s workspace provides reliable wifi, 24/7 access, and private meeting room access. For an afternoon pick me up, the space is also home to a cafe library and local events aimed to bring the local community together through arts, tech, and culture. Centrally Located 24/7 Access Reliable WIFI EXPERIENCES

Zoom through Lake Michigan in a speedboat. Get a bird’s eye city view from 103 floors up when you stand on the ledge of the Chicago Skydeck. Spend an afternoon spotting sharks in the Shedd Aquarium or see renowned pieces at the Art Institute. After work, uncover hidden speakeasies through unmarked doors. It’s time to discover what makes Chicago one of the best big cities to live in the United States.

Experience the Chicago skyline from the water. Kayak along the Chicago River while taking in the city’s historic bridges and soaring skyscrapers. Visit the primary hub of Chicago’s Chinese community, filled with restaurants, shops, and incredible East-Asian style architecture. Enjoy rock climbing, at Chicago’s first and only climbing park. With custom-designed sculptural rocks and boulders, you’re bound to have an adventure. Fly across the waters of Lake Michigan on this high-speed, Seadog Cruise. Get ready for sharp twists and turns, as you speed across the lake. Spot murals by local artists like JC Rivera, Hebru Brantley, The Yok, and Sheryo, as you stroll across 16th Street, home to Chicago’s street art. Experience the Chicago skyline from the water. Kayak along the Chicago River while taking in the city’s historic bridges and soaring skyscrapers. Visit the primary hub of Chicago’s Chinese community, filled with restaurants, shops, and incredible East-Asian style architecture. Enjoy rock climbing, at Chicago’s first and only climbing park. With custom-designed sculptural rocks and boulders, you’re bound to have an adventure. Fly across the waters of Lake Michigan on this high-speed, Seadog Cruise. Get ready for sharp twists and turns, as you speed across the lake. Spot murals by local artists like JC Rivera, Hebru Brantley, The Yok, and Sheryo, as you stroll across 16th Street, home to Chicago’s street art. Experience the Chicago skyline from the water. Kayak along the Chicago River while taking in the city’s historic bridges and soaring skyscrapers. Visit the primary hub of Chicago’s Chinese community, filled with restaurants, shops, and incredible East-Asian style architecture. Enjoy rock climbing, at Chicago’s first and only climbing park. With custom-designed sculptural rocks and boulders, you’re bound to have an adventure. Fly across the waters of Lake Michigan on this high-speed, Seadog Cruise. Get ready for sharp twists and turns, as you speed across the lake. DATES

90% of Remote Year travelers say our programs changed their life. How will we change yours?

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