Chicago vs New York: Which City is Better to Visit?
The verdict
New York wins overall (9.2 vs 8.6 out of 10), taking 3 of 5 categories.
While both cities offer incredible urban experiences, New York edges out Chicago due to its unparalleled cultural offerings, diverse food scene, and extensive public transportation system. However, Chicago's stunning architecture and more manageable size make it an excellent alternative for those seeking a slightly less overwhelming city experience.
Chicago is significantly more affordable across accommodation, groceries and rent—overall cost of living substantially lower than New York. New York City offers slightly milder winters and a clearer warm-season window, while Chicago endures colder, cloudier winters and a shorter comfortable stretch; New York’s more extended temperate season gives it the edge.
Best for well-rounded travelers — New York edges ahead overall.
Overall scores are editorial ratings out of 10; category winners come from the per-category scores below. The overall pick is the higher overall score.
Overall scores
Category by category
| Category | Chicago | New York | Edge |
|---|---|---|---|
| Architecture and SkylineComparison of iconic buildings, architectural styles, and city views | 9 | 9 | Even |
| Food SceneAnalysis of culinary offerings, local specialties, and dining experiences | 9 | 10 | New York |
| Cultural AttractionsComparison of museums, theaters, and cultural experiences | 8 | 10 | New York |
| Parks and Green SpacesEvaluation of urban parks, recreational areas, and outdoor activities | 9 | 8 | Chicago |
| TransportationOverview of public transit systems, walkability, and ease of getting around | 8 | 9 | New York |
Architecture and Skyline: the details
Chicago
- Willis Tower (formerly Sears Tower) – 110-story skyscraper with Skydeck
- John Hancock Center – 100-story skyscraper with 360 Chicago Observation Deck
- Frank Lloyd Wright's Robie House – Prairie School masterpiece
New York
- Empire State Building – 102-story Art Deco skyscraper
- One World Trade Center – tallest building in the Western Hemisphere
- Chrysler Building – iconic Art Deco landmark
Food Scene: the details
Chicago
- Deep-dish pizza at Lou Malnati's or Giordano's
- Chicago-style hot dogs at Portillo's
- Fine dining at Alinea (3 Michelin stars)
New York
- New York-style pizza at Joe's Pizza or Lombardi's
- Bagels and lox at Russ & Daughters
- Diverse cuisine in neighborhoods like Chinatown and Little Italy
Cultural Attractions: the details
Chicago
- Art Institute of Chicago – home to iconic works like American Gothic
- Chicago Symphony Orchestra – world-renowned classical music venue
- The Second City – legendary comedy club and school
New York
- Metropolitan Museum of Art – one of the world's largest art museums
- Broadway theater district – home to world-class musicals and plays
- Museum of Modern Art (MoMA) – influential modern art collection
Parks and Green Spaces: the details
Chicago
- Millennium Park – 24.5-acre park featuring Cloud Gate (The Bean) sculpture
- Lincoln Park – 1,200-acre park with a free zoo and conservatory
- The 606 – elevated park and trail system
New York
- Central Park – 843-acre urban oasis in Manhattan
- High Line – elevated linear park built on a former New York Central Railroad spur
- Prospect Park – 526-acre park in Brooklyn designed by Olmsted and Vaux
Transportation: the details
Chicago
- Chicago 'L' – elevated rapid transit system
- Metra commuter rail for suburbs
- Divvy bike-sharing program
New York
- Extensive subway system operating 24/7
- Iconic yellow taxis and ride-sharing services
- Citi Bike bike-sharing program
Who should pick which
Chicago vs New York: Which Should You Visit?
Both Chicago and New York 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
New York City offers slightly milder winters and a clearer warm-season window, while Chicago endures colder, cloudier winters and a shorter comfortable stretch; New York’s more extended temperate season gives it the edge.
Chicago: Best months are may, sept. winter highs around 38 °F; summer highs 72–79 °F.
New York: Best months are mid-june to early july, early aug to late sept. annual range ~28 °F to 85 °F.
Chicago: Best months are may, sept. winter highs around 38 °F; summer highs 72–79 °F.
New York: Best months are mid-june to early july, early aug to late sept. annual range ~28 °F to 85 °F.
Weather winner: new york
Cost of Travel and Daily Budget
Chicago is significantly more affordable across accommodation, groceries and rent—overall cost of living substantially lower than New York.
much higher housing and rent prices
much higher housing and rent prices
overall cost of living ~50% higher in New York than Chicago
Sources: {‘name’: ‘Numbeo cost of living comparison Chicago vs New York’, ‘url’: ‘https://www.numbeo.com/cost-of-living/compare_cities.jsp?city1=Chicago%2C+IL&city2=New+York%2C+NY&country1=United+States&country2=United+States’}, {‘name’: ‘Apartments.com cost of living overview’, ‘url’: ‘https://www.apartments.com/cost-of-living/new-york-ny-vs-chicago-il/’}
Budget winner: chicago
Things to Do and Activities
New York offers a denser lineup of globally renowned annual events; Chicago has strong local festivals but less international notoriety.
Activities winner: new york
Culture, Heritage, and Local Life
New York brings unmatched global cultural dynamism, from design fairs to iconic parades; Chicago offers rich arts in a more concentrated, accessible way.
Culture winner: new york
The Bottom Line: Chicago or New York?
New York 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 lower costs. Choose New York if outdoor activities matters more to you.
Travel tips
- Consider purchasing a Chicago CityPASS or New York CityPASS for savings on major attractions.
- In Chicago, take an architecture river cruise for stunning views of the skyline.
- In New York, use the subway for efficient travel between boroughs and major attractions.
- Visit Chicago's Magnificent Mile for shopping, and New York's Fifth Avenue for luxury brands.
- Try to avoid visiting either city during the harsh winter months unless you're prepared for cold weather.
Frequently asked questions
Which city is more expensive, Chicago or New York?
Generally, New York is more expensive than Chicago, particularly for accommodation and dining. However, both cities can be pricey compared to other U.S. destinations, and costs can vary depending on neighborhood and travel style.
When is the best time to visit Chicago and New York?
Late spring (May-June) and early fall (September-October) are ideal for both cities, offering pleasant weather and fewer crowds. Summer is peak tourist season, while winters can be harsh, especially in Chicago with its infamous wind chill.
Is it possible to visit both Chicago and New York in one trip?
Yes, it's possible to visit both cities in one trip. They are connected by frequent flights (about 2 hours) and overnight trains. However, to fully experience each city, it's recommended to spend at least 3-4 days in each location.
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
New York
United States
The Big Apple, a global hub of culture, finance, and entertainment
- Statue of Liberty
- Times Square
- Broadway shows
- Central Park
- January: 45
- February: 50
- March: 65
- April: 75
- May: 85
- June: 95
- July: 100
- August: 98
- September: 90
- October: 80
- November: 70
- December: 95
