Toronto vs Chicago: Which is the Superior Lakeside City in 2024?

Key Takeaways

  • Explore two iconic lakeside cities: Toronto and Chicago, with unique cultural attractions, diverse dining experiences, reliable public ransportation options and stunning outdoor spaces.

  • Consider job opportunities & cost of living in each city as well as safety & healthcare when deciding which suits you best.

  • Both offer unforgettable landmarks plus a range of festivals and events to experience their unique heritage!

Toronto and Chicago: City Overview

Toronto, the largest and most populous city in Canada, is a bustling metropolis known for its stunning skyline and multicultural vibrancy. In contrast, Chicago, the United States’ third-largest most populated city, is world famous for its remarkable architecture and diverse culture. Both of these major cities are situated along the shores of the Great Lakes, offering magnificent lake views and skylines that are sure to leave you in awe.

When it comes to sports, both cities have a strong presence. Toronto is a hotbed for professional sports teams, boasting popular teams such as the Toronto Raptors of the NBA, the Toronto Maple Leafs of the NHL, and the Toronto Blue Jays of the MLB. Chicago boasts its famous teams, including the Chicago Bulls (NBA), Chicago Cubs (MLB), Chicago Bears (NFL) and Chicago Fire FC (MLS). You’ll never be short of sports events to attend in either city.

Iconic landmarks also abound in both metropolises. Toronto’s skyline is dominated by the CN Tower, an architectural marvel that offers breathtaking views of the city and beyond. In Chicago, the Willis Tower (formerly Sears Tower) and tall buildings stands out as a significant part of the city’s skyline and history. These landmarks are not only attractive to tourists but also provide a sense of identity and pride for their respective cities.

Weather Comparison: Toronto vs Chicago

Comparing Toronto and Chicago’s climates reveals they both undergo temperature extremes and seasonal shifts.

Chicago experiences a significant variation in temperature throughout the year. July is the hottest month with an average high of 83°F and low of 71°F, while January is the coldest month with an average low of 22°F and high of 33°F. Rainfall is spread throughout the year in Chicago, with June being the wettest month with an average rainfall of 3.5 inches. February is the snowiest month in Chicago with an average snowfall of 3.2 inches.

Toronto experiences a range of temperatures throughout the year. The hottest month is July, with an average high temperature of 77°F and a low of 63°F. The coldest month is January, with an average low temperature of 18°F and a high of 30°F. Rain occurs throughout the year in Toronto, with the most rainfall happening in September, with an average of 2.1 inches. On the other hand, February is the month with the most snowfall in Toronto, with an average snowfall of 3.5 inches.

For sunshine and rainfall, Chicago usually enjoys more sunlight during the spring and fall seasons, whereas Toronto tends to receive more rainfall in October. Despite these differences, both cities offer a range of indoor and outdoor activities all year round, ensuring you’ll never run out of things to do, no matter the weather.

Cultural Attractions

Cultural Attractions and Differences

When it comes to cultural attractions, both Toronto and Chicago have a lot to offer. From world-class museums to iconic landmarks, each city provides a unique experience that reflects its history, diversity, and creativity.

Cultural Attractions in Chicago

Art Institute of Chicago: Home to an extensive collection of artworks spanning thousands of years, this museum is a must-visit for art enthusiasts.

Millennium Park: A modern public space that hosts a variety of public places and events and is famous for the Cloud Gate sculpture, also known as "The Bean."

Museum of Science and Industry: A vast museum offering hands-on exhibits, perfect for families and anyone interested in science and technology.

Navy Pier: A lively boardwalk with amusement rides, shops, restaurants, food, and entertainment options.

Chicago Architecture River Cruise: A guided tour that takes you through the city’s impressive skyline and architectural wonders.

Cultural Attractions in Toronto


Royal Ontario Museum: Featuring a wide array of art, culture, and natural history exhibits, it’s the largest museum in Canada.

Art Gallery of Ontario: Home to more than 90,000 works of art, making it one of the most distinguished art museums in North America.

CN Tower: Toronto’s most iconic landmark, offering panoramic views of the city.

Distillery District: A pedestrian-only village dedicated to arts, culture, and entertainment, set in charming 19th-century buildings.

Toronto Islands: A set of small islands providing a quick escape from big city of life, with recreational activities and great views of Toronto’s skyline.

Both Chicago and Toronto offer rich cultural experiences and a high standard of living, but they also come with their own sets of challenges. In both cities, you can immerse yourself in diverse culinary experiences that reflect the multiculturalism of great city and their populations. From Toronto’s unique fusion cuisine like Peameal bacon sandwiches and sushi pizza to Chicago’s classic deep-dish pizza, there’s a dish to suit every palate.

Dining Experiences: Toronto's Kensington Market vs Chicago's Lincoln Park

Speaking of Food, Visiting Toronto’s Kensington Market or Chicago’s Lincoln Park neighborhood will transport you into a world of diverse dining options and culinary scenes. Kensington Market in Toronto is an eclectic neighborhood with over 240 unique businesses ranging from fine dining to family-run establishments with a cult following. You can savor Jamaican, Italian, German, and Mexican cuisines, to name a few.

Kensington Market Atmosphere

Kensington Market has a bohemian and artsy vibe. The neighborhood is bustling, with colorful murals, vintage shops, and a diverse population. The area has a strong sense of community and embraces an inclusive and multicultural spirit.

Attractions and Offerings

  • Diverse Cuisine

  • Vintage Shops

  • Festivals and Events

On the other hand, Lincoln Park in Chicago offers a variety of dining experiences, from casual eateries to upscale establishments, serving American, Italian, Mexican, and Asian cuisines. Some highly-rated restaurants in this neighborhood include The Purple Pig, The Publican, Avec, and Girl & the Goat. No matter your preference, both cities promise unforgettable dining experiences that will leave you craving for more.

Lincoln Park Atmosphere

Lincoln Park is upscale and lively, with tree-lined streets, elegant brownstones, and a youthful vibe due to its proximity to DePaul University. The neighborhood balances urban energy with lush green spaces.

Attractions and Offerings

  • Lincoln Park: The neighborhood’s namesake, a large public park featuring zoos, museums, and outdoor activities.

  • High-End Shopping: Lincoln Park offers a range of boutique shops and high-end retailers.

  • Nightlife: The area has a vibrant bar and club scene, attracting young professionals and students.

  • Cultural Institutions: Home to various theaters, art galleries, and music venues.

While both neighborhoods offer rich cultural experiences, they cater to different lifestyles and preferences. Kensington Market is more bohemian, diverse, and eclectic, embracing an artsy and inclusive atmosphere. It is perfect for those who appreciate a vibrant street life, unique shops, and a strong sense of community.

Lincoln Park, on the other hand, is more upscale and polished, offering elegant living, green spaces, and a bustling nightlife. It suits those who prefer a more refined urban experience with access to high-end amenities.

Ultimately, choosing between the two would depend on your personal preferences, whether you are drawn to the inclusive and artistic vibe of Kensington Market or the upscale and vibrant energy of Lincoln Park.


Public Transportation: Toronto's TTC vs Chicago's CTA

Efficient public transportation systems make it relatively easy for young people to navigate both Toronto and Chicago. In Toronto, the Toronto Transit Commission (TTC) operates:

  • Buses

  • Subways

  • Streetcars

  • Paratransit services

This makes it simple to get around the city. The TTC’s mission is to set up, manage, and maintain the local passenger transportation system in Toronto.

Chicago boasts the Chicago Transit Authority (CTA), the second-largest public transportation system in the United States, which runs buses and trains throughout the city and 40 surrounding suburbs. CTA provides:

  • Buses

  • ‘L’ Trains (Elevated and Subway) Express Buses

  • Night Owl Service: The CTA provides 24-hour service

  • Paratransit Services

  • Bike & Ride: Bicycles are allowed on CTA trains and buses

With both cities offering reliable public transit and transportation options, you can conveniently explore their neighborhoods and attractions without the need for a car. Comparing the public transportation systems of Toronto's TTC and Chicago's CTA reveals some strengths and challenges. The TTC boasts a diverse range of public transit options, but it often faces overcrowding and accessibility issues.

On the other hand, the CTA has an extensive network, iconic ‘L’ trains, and overall reliability that stand out, although its aging infrastructure is a concern. Both systems are essential for urban connectivity, shaping the daily commute for millions of people and emphasizing the need for continuous investment and improvement in public transportation to enhance city living.

Job Opportunities and Cost of Living

Both Toronto and Chicago are major economic hubs with diverse job markets, but they offer distinct experiences in terms of employment opportunities and the cost of living.

Job Opportunities

  • Diverse Economy: Strong sectors include finance, technology, and media.

  • Tech Boom: Known as a growing tech hub, often dubbed the "Silicon Valley of the North."

  • Global Business Hub: Home to many multinational corporations, providing a range of job opportunities.

  • Trading and Commerce: A historical leader in commodities trading and financial services.

  • Manufacturing and Logistics: Hosts a significant manufacturing industry and is a major transport hub.

  • Healthcare and Education: Has a robust healthcare sector and numerous higher education institutions.

Cost of Living

  • Housing: The real estate market is known for high prices, especially in the downtown area; however, it is slightly cheaper than in Chicago.

  • Taxes: Generally, higher taxes, including sales tax and income tax.

  • Utilities and Services: Comparable to other major cities, though higher than many US cities.

  • Housing: More Expensive than Toronto overall, but prices can be high in sought-after neighborhoods.

  • Taxes: Lower income taxes than in Toronto, but the sales tax and property tax is among the highest in the US.

  • Utilities and Services: Generally lower than in Toronto, with heating costs a consideration due to harsh winters.
    Toronto offers a dynamic job market particularly strong in the tech and financial sectors, but this comes with a higher cost of living, reflected in housing and taxes. Chicago, while facing higher unemployment rates, presents diverse opportunities in trading, manufacturing, and healthcare, and is more expensive in terms of housing and general living expenses. Job seekers will weigh these factors differently based on individual priorities, professional fields, and lifestyle preferences.

Education: York University vs Northwestern University

Programs and Specialization:
  • Chicago: Offers specialized programs such as International Baccalaureate (IB), STEM, and fine arts. The city is known for having some highly competitive and top-ranked schools.

  • Toronto: Provides a range of programs including French immersion, arts-focused schools, and specialized science and technology programs. Toronto is also known for its multicultural and inclusive educational environment.

Both Toronto and Chicago are home to prestigious educational institutions, providing opportunities for higher learning and personal growth. In Toronto, you’ll find institutions such as the University of Toronto, York University, and Ryerson University.

In Chicago, you have access to schools like Northwestern University, the University of Chicago, and Loyola University Chicago. Northwestern University, in particular, is renowned for its comprehensive research programs, interdisciplinary approach, and outstanding undergraduate opportunities. Ultimately, the choice of location of university will depend on your academic interests and career goals.

Outdoor Spaces: Toronto's Lake Ontario vs Chicago's Lakefront


Toronto and Chicago provide scenic outdoor spaces perfect for recreational activities and relaxation. In Toronto, Lake Ontario provides a stunning waterfront with activities such as patio-hopping, swimming, sailing, and stand-up paddleboarding. Additionally, you can explore and visit the Toronto Island Park, which offers beach activities, hiking, and an amusement park called Centreville.

Chicago is one of the great lake cities, and its Lakefront is equally breathtaking, boasting popular parks like Millennium Park, Lincoln Park, and Grant Park. You can enjoy activities such as biking, running, swimming, and kayaking along the shores of Lake Michigan. Whether you’re a nature lover or a city dweller, the outdoor spaces in both cities provide a perfect escape from the urban jungle.

Nightlife and Entertainment

As the day turns to night, Toronto and Chicago burst into life, offering vibrant nightlife and a plethora of entertainment choices. You’ll find a plethora of bars, clubs, and live music venues to choose from in both cities. Sports enthusiasts can also catch a game of their favorite teams, such as the Toronto Raptors or the Chicago Bulls, to make their night even more exciting.

If comedy is more your style, don’t miss out on Chicago’s famous Second City, a comedy club where legends like Dan Aykroyd, John Candy, and John Belushi got their start. Whether you prefer dancing the night away or enjoying a laid-back evening with friends, both Toronto and Chicago have something to offer for everyone. However, overall, it's tough to beat the nightlife of Chicago.

Safety and Healthcare

When selecting a city for residence, safety and healthcare should be significant considerations. In terms of safety, Toronto is generally considered safer than Chicago, with a safety score of 57.05 compared to Chicago’s 33.98 on the Numbeo index. It is important to note that safety scores can vary based on specific areas in both cities since they are both large.

As for healthcare, Toronto offers free healthcare to most residents, while the quality of healthcare in Chicago is high but expensive. Access to medical care and emergency services is crucial for overall well-being, so weighing these factors when deciding between the two cities is essential.

Festivals and Events

Toronto and Chicago host a variety of festivals and events throughout the year, celebrating their rich cultural heritage. Some popular events in Toronto include:

  • Toronto International Film Festival

  • Pride Toronto

  • Toronto Christmas Market

  • Caribbean Carnival

Similarly, Chicago is home to events such as:

  • the Chicago International Film Festival

  • the Chicago Blues Festival

  • Lollapalooza

  • the Chicago Jazz Festival

No matter which multicultural city you choose, you’ll have countless more opportunities to immerse yourself in cultural celebrations and create lasting memories in the city center.

Conclusion: Choosing Between Toronto and Chicago

Choosing between Toronto and Chicago greatly depends on personal preferences and lifestyle requirements in determining the ideal lakeside city.

Some factors to consider when making this decision include:

  • Welcoming community

  • Levels of violence

  • Property taxes

  • Multiculturalism

  • Healthy lifestyle

  • Access to green spaces

These factors make both Toronto and Chicago an attractive choice for many.

Both Chicago and Toronto also offer their own unique charm, architectural beauty, food scene and vibrant culture. Ultimately, the choice is yours to make, and we hope this comparison has provided you with a good bit of valuable insights to help you make an informed decision.


In conclusion, both Toronto and Chicago are unique and vibrant lakeside cities, each offering a range of attractions, experiences, and opportunities. While Toronto may be the better choice for some due to its safety, free healthcare, and multiculturalism, others may prefer Chicago for its architecture, nightlife, and iconic landmarks. Weigh your priorities and preferences to make the best choice for your next adventure or permanent move.

Frequently Asked Questions

Q: Is Toronto comparable to Chicago?

A: Toronto is an incredibly friendly city, with lower property taxes and a cost of living that's 7.4% less expensive than Chicago. It is also highly multicultural and has a healthy lifestyle. Overall, Toronto is comparable to Chicago.

Q: Is Toronto or Chicago bigger city?

A: Toronto is larger than Chicago, with Toronto boasting a population of 2.93 million compared to Chicago's estimated 2.697 million. Already Canada's largest city, Toronto's population has grown to surpass the population of the third-largest city in the United States.

Q: What are some popular sports teams in both Toronto and Chicago?

A: Both Toronto and Chicago have many popular sports teams, such as the Toronto Raptors (NBA), Toronto Maple Leafs (NHL), Toronto Blue Jays (MLB), Chicago Bulls (NBA), Chicago Cubs (MLB), and Chicago Fire FC (MLS).

Q: What are the iconic landmarks in Toronto and Chicago?

A: Toronto's iconic CN Tower and Chicago's iconic Willis Tower are both awe-inspiring landmarks defining the respective skylines of these two cities.

Q: What is the minimum wage in both cities?

A: In Toronto, the minimum wage is $16.55 CAD per hour, and in Chicago it's $15.80 USD (21.13 CAD) per hour.

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