Chicago
United States
Montreal
Canada
Chicago
Montreal
💰 Budget
🛡️ Safety
Chicago
Tourist areas of Chicago (Loop, River North, Magnificent Mile, Museum Campus, Lincoln Park, Wicker Park) are generally safe. Gun violence affects specific neighborhoods on the South and West sides that tourists have no reason to visit. Petty crime like phone theft occurs on the "L" and in crowded areas.
Montreal
Montreal is one of the safest large cities in North America. Violent crime rates are very low and most neighborhoods are safe to walk day and night. Petty crime (pickpocketing, bike theft) is the main concern, particularly in tourist areas and during festivals.
⭐ Ratings
🌤️ Weather
Chicago
Chicago has a humid continental climate with extreme seasonal swings. Winters are brutally cold with wind chill off Lake Michigan, while summers are hot and humid. Spring and fall are glorious but brief. The lake creates its own microclimate — it can be 5-10 degrees cooler lakeside in summer.
Montreal
Montreal has a humid continental climate with extreme seasonal variation. Winters are long and severely cold with heavy snowfall, while summers are warm and humid. The city fully embraces each season — winter festivals, spring sugar shacks, summer terrasses, and spectacular autumn foliage.
🚇 Getting Around
Chicago
Chicago has an excellent public transit system run by the CTA (Chicago Transit Authority). The "L" (elevated/subway) train and bus network cover most of the city. A Ventra card works on all CTA and Pace buses. Driving downtown is stressful and parking is expensive — transit is the way to go.
Walkability: Downtown Chicago is very walkable and mostly flat. The Loop, Magnificent Mile, Museum Campus, and Riverwalk are easily covered on foot. Neighborhoods like Wicker Park, Lincoln Park, and Pilsen are pleasant to explore by foot. In winter, walking can be treacherous on icy sidewalks.
Montreal
Montreal has a reliable public transit system operated by the STM. The Metro (subway) has four lines, supplemented by an extensive bus network. The new REM (Reseau express metropolitain) light rail connects the airport and suburbs. BIXI bike-share is excellent in warmer months. The OPUS card works across all STM services.
Walkability: Montreal is very walkable in the central neighborhoods. The Plateau, Mile End, Old Montreal, and downtown are best explored on foot. The Underground City (RESO) connects 33 km of tunnels linking malls, Metro stations, and buildings — invaluable in winter. Bring good boots in winter for icy sidewalks.
The Verdict
Choose Chicago if...
you want the Midwest's flagship — Art Institute, deep-dish pizza, Chicago River Architecture Cruise, The Bean, blues bars, and lakefront bike trails
Choose Montreal if...
you want North America's most European city — Old Montreal cobbles, bagels, poutine, Mile End, Jazz Fest, and ski Tremblant 90 minutes north
Chicago
Montreal