Chicago vs Montreal: Which City is Better to Visit?
The verdict
Chicago and Montreal finish level overall — pick by what you value most below.
Both Chicago and Montreal offer unique and captivating experiences. Chicago excels in architecture and cultural attractions, while Montreal shines with its blend of European charm, efficient transportation, and outdoor activities. The choice between these cities depends on personal preferences for either a bustling American metropolis or a bilingual Canadian city with a European flair.
Montreal is notably cheaper across housing, entertainment and overall costs; Chicago costs substantially more, especially accommodation. Chicago has more moderate spring and autumn but harsher winters and humid summers; Montreal offers longer warm-season comfort with clearer skies mid-summer.
Best for well-rounded travelers — Montreal edges ahead overall.
Overall scores are editorial ratings out of 10; category winners come from the per-category scores below. The overall scores tie and no conclusion breaks it.
Overall scores
Category by category
| Category | Chicago | Montreal | Edge |
|---|---|---|---|
| Architecture and Urban LandscapeComparison of iconic buildings, skylines, and urban planning | 9 | 8 | Chicago |
| CuisineAnalysis of local specialties, food scenes, and dining experiences | 9 | 9 | Even |
| Cultural AttractionsComparison of museums, festivals, and cultural experiences | 9 | 8 | Chicago |
| TransportationEvaluation of public transit systems, walkability, and ease of getting around | 8 | 9 | Montreal |
| Outdoor ActivitiesComparison of parks, recreational areas, and outdoor experiences | 8 | 9 | Montreal |
Architecture and Urban Landscape: the details
Chicago
- Iconic skyline featuring Willis Tower and John Hancock Center
- Frank Lloyd Wright's Robie House and other Prairie School designs
- Millennium Park with Cloud Gate (The Bean) sculpture
Montreal
- Mix of French Colonial and modern architecture in Old Montreal
- Notre-Dame Basilica, a stunning example of Gothic Revival style
- Olympic Stadium with its distinctive inclined tower
Cuisine: the details
Chicago
- Famous deep-dish pizza at Lou Malnati's and Giordano's
- Chicago-style hot dogs from Portillo's or The Wieners Circle
- High-end dining scene including Alinea and Girl & the Goat
Montreal
- Iconic poutine from La Banquise or Au Pied de Cochon
- Montreal-style bagels from St-Viateur or Fairmount
- Smoked meat sandwiches at Schwartz's Deli
Cultural Attractions: the details
Chicago
- Art Institute of Chicago, home to an extensive Impressionist collection
- Field Museum of Natural History featuring Sue, the T-Rex
- Annual Chicago Blues Festival, the largest free blues festival in the world
Montreal
- Montreal Museum of Fine Arts, Canada's oldest art museum
- Just For Laughs Festival, the world's largest comedy festival
- Montreal International Jazz Festival, attracting over 2 million visitors annually
Transportation: the details
Chicago
- Extensive 'L' train system covering most of the city
- Comprehensive bus network
- Divvy bike-sharing program
Montreal
- Efficient Metro system known for its distinctive rubber-tired trains
- Extensive bus network including 24-hour routes
- BIXI bike-sharing system with over 700 stations
Outdoor Activities: the details
Chicago
- 18-mile Lakefront Trail along Lake Michigan
- Lincoln Park, home to a free zoo and conservatory
- Chicago Riverwalk for scenic strolls and boat tours
Montreal
- Mount Royal Park, designed by Frederick Law Olmsted
- La Fontaine Park with its picturesque lake and recreational facilities
- Lachine Canal for cycling, kayaking, and paddle boarding
Who should pick which
Chicago vs Montreal: Which Should You Visit?
Both Chicago and Montreal are popular travel destinations, but they offer very different experiences. Whether you’re planning a quick getaway or a longer trip, understanding how they compare on weather, cost, things to do, and cultural depth helps you pick the right one for your travel style and budget.
Weather and Best Time to Visit
Chicago has more moderate spring and autumn but harsher winters and humid summers; Montreal offers longer warm-season comfort with clearer skies mid-summer.
Chicago: Best months are May, September. ≈20 °F to 79 °F.
Montreal: Best months are June, July, August. ≈-13 °C to 26 °C.
Chicago: Best months are May, September. ≈20 °F to 79 °F.
Montreal: Best months are June, July, August. ≈-13 °C to 26 °C.
Weather winner: montreal
Cost of Travel and Daily Budget
Montreal is notably cheaper across housing, entertainment and overall costs; Chicago costs substantially more, especially accommodation.
much higher rents (~81–114 % above Montreal)
much higher rents (~81–114 % above Montreal)
Chicago ~20 % higher cost of living overall, with housing & entertainment up 80–110 %
Sources: {‘name’: ‘Numbeo cost of living comparison’, ‘url’: ‘https://www.numbeo.com/cost-of-living/compare_cities.jsp?city1=Montreal&city2=Chicago%2C+IL&country1=Canada&country2=United+States’}, {‘name’: ‘Expatistan cost of living data’, ‘url’: ‘https://www.expatistan.com/cost-of-living/comparison/montreal/chicago’}
Budget winner: montreal
Things to Do and Activities
Chicago features world-famous large-scale music and cultural festivals; Montreal hosts renowned jazz and culinary winter festivals.
Activities winner: chicago
Culture, Heritage, and Local Life
Montreal blends deep francophone heritage and culinary creativity across seasons; Chicago combines architectural legacy and vibrant contemporary music venues.
Culture winner: montreal
The Bottom Line: Chicago or Montreal?
Montreal takes the edge in 3 out of 4 categories. However, both destinations have distinct strengths, and the best choice depends on your priorities.
Consider visiting Chicago if you prioritize cultural depth. Choose Montreal if affordability matters more to you.
Travel tips
- Consider visiting Chicago in late spring or early fall for pleasant weather and fewer crowds.
- For Montreal, summer offers the best weather and numerous festivals, but winter can be magical if you enjoy cold-weather activities.
- Purchase a Chicago CityPASS or Montreal Attraction Pass for savings on major attractions.
- Learn basic French phrases for Montreal to enhance your experience, although English is widely spoken.
Frequently asked questions
Which city is more expensive, Chicago or Montreal?
Generally, Chicago tends to be more expensive than Montreal, particularly for accommodation and dining. However, costs can vary depending on factors like exchange rates and specific neighborhoods.
Is it easy to get around Chicago and Montreal without a car?
Both cities have excellent public transportation systems, making it easy to get around without a car. Montreal's Metro and extensive bike lanes give it a slight edge in terms of ease of navigation for visitors.
What are the must-try foods in each city?
In Chicago, don't miss deep-dish pizza, Chicago-style hot dogs, and Italian beef sandwiches. In Montreal, be sure to try poutine, Montreal-style bagels, and smoked meat sandwiches.
The two side by side
Chicago
United States
The Windy City, known for its stunning architecture, deep-dish pizza, and vibrant arts scene
- Willis Tower
- Millennium Park
- Deep-dish pizza
- Chicago-style hot dogs
- January: 30
- February: 35
- March: 50
- April: 65
- May: 80
- June: 90
- July: 100
- August: 95
- September: 85
- October: 75
- November: 55
- December: 70
Montreal
Canada
A bilingual metropolis blending European charm with North American modernity
- Old Montreal
- Mount Royal
- Poutine
- Montreal-style bagels
- January: 30
- February: 35
- March: 45
- April: 60
- May: 75
- June: 90
- July: 100
- August: 95
- September: 80
- October: 70
- November: 40
- December: 50
