Canada to Chicago Movers
Cross-Border Moving Services from Quebec to Illinois
Relocating from Montreal to Chicago brings you from historic charm to a world-class metropolis known for its architecture, industry, and vibrant neighborhoods. Whether you’re headed to a downtown high-rise, a brownstone in Lincoln Park, or a family home in the suburbs, Waypoint handles every detail of your move with care and precision.
Long-Distance Moves Built Around Your Needs
Moving across the border isn’t just about distance, it’s about crossing into a new country with different customs, rules, and city infrastructure. Our team specializes in Canada-to-U.S. relocations, creating a plan based on your timeline, household size, and the specific requirements of Chicago’s diverse neighborhoods.

From customs paperwork to driveway access in older neighborhoods, we coordinate it all before moving day.
Why Our Montreal to Chicago Moves Stand Out
Chicago has its own pace and parking rules, we plan every step to fit the city’s layout, your building’s requirements, and your personal schedule.
Durable Packing and Careful Handling
We use high-strength materials designed for long hauls, protecting your belongings from weather shifts, bumps on the interstate, and handling at the border. Antiques, artwork, and electronics get custom crating.
Navigation on Both Sides
Our Montreal-based team handles pickup and documentation, while our Chicago delivery partners are experts in building access, local regulations, and unloading logistics.
Transportation That Fits Your Situation
We offer direct truck transport, consolidated shipping for smaller moves, and optional holding time if your move-in date is flexible.
What to Know When Moving to Chicago from Montreal
Cross-border moves require more than just a truck, they demand planning, paperwork, and familiarity with U.S. city logistics.
Delivery Planning for Chicago Neighborhoods
From narrow alleys in Wicker Park to loading docks in the Loop, we customize your delivery to match your address. We assist with permits, elevator bookings, and entry coordination.
Border and Customs Coordination
You’ll need a valid passport, immigration paperwork (e.g., visa or work permit), and a detailed itemized inventory. We prepare everything, submit forms, and follow up with U.S. Customs to clear your shipment.
Optional Storage and Flexible Delivery
Not ready to move in? We can hold your items at secure facilities in either Montreal or Chicago and deliver when the timing is right.
Services for Montreal to Chicago Relocations
Whether you’re moving for a job, school, or lifestyle change, our services cover the full journey across the border.
Customized Move Coordination
Every plan is built around your schedule, property type, and shipment size.
Full Insurance Coverage
Protect your belongings during long-distance transit with coverage options for full replacement value.
Complete Customs Handling
We handle customs clearance documentation so you don’t face delays at the border.
FAQs About Moving from Montreal to Chicago
If you don't find the answers you're looking for, please reach out to us directly!
What makes Chicago moves different from other U.S. cities?
Chicago’s permit-based parking, weather changes, and dense downtown access points require specific delivery timing and documentation, we handle all of it for you.
Do I need to be present when my items cross the border?
No, we manage the process with your documentation and can transport your shipment without you being physically present.
Can you move items into high-rise apartments downtown?
Absolutely. We coordinate with building managers to secure elevator reservations, insurance documents, and approved access routes.
How long does the move take?
Most moves from Montreal to Chicago take 2–5 days depending on border clearance, transport method, and delivery access.
Do you offer weekend or evening deliveries?
Yes, we work with your building’s policies to offer flexible delivery scheduling that works for your move-in date.
