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Chicago or New York? An honest comparison
The short answer
Pick New York for a first US city trip: Broadway, the Met, the skyline and endless neighbourhoods. Pick Chicago for a calmer, cleaner big city with superb architecture, the lakefront and easier logistics. Mid-range costs are close (about €275 in Chicago vs €281 in New York per person per day), with Chicago slightly cheaper.
Chicago: suits families, friends and repeat visitors who want architecture, museums and a big city without the chaos.
New York: suits first-timers, couples, friends and solo travellers who want Broadway, museums and constant energy.
Side by side
| Chicago | New York | |
|---|---|---|
| Mid-range day* | €277 US$312 local | €284 $319 local |
| Budget day* | €139 | €156 |
| Value for money | ●●●●●Slightly cheaper, but taxes and hotels are high. | ●●●●●Expensive rooms; cheap slices and street food help. |
| Crowds (5 = calm) | ●●●●●Busy in summer, but rarely overwhelming. | ●●●●●Times Square, the Statue of Liberty and museums are packed. |
| Food | ●●●●●Italian beef, deep-dish pizza and strong neighbourhood food. | ●●●●●Every cuisine, from pizza slices to Flushing dumplings. |
| Nightlife | ●●●●●Blues, jazz and bars in Wicker Park and River North. | ●●●●●Broadway, live music and bars open until 4 am. |
| Family-friendly | ●●●●●Lakefront museums, aquarium, free zoo and beaches. | ●●●●●Huge museums and parks; crowds and subway stairs tire kids. |
| Getting around | ●●●●●L trains and buses; downtown easy on foot. | ●●●●●24-hour subway and walkable grid. |
| Best months | year-round, see below | May |
| Warmest / coolest | Jun 27°C / Jan 1°C | Jul 30°C / Jan 5°C |
| Known for | Willis Tower, Millennium Park, Navy Pier, The Art Institute of Chicago | Empire State Building, Broadway shows, Brooklyn Bridge, world-class museums |
* Per person per day with two sharing a room: bed, food, sights and local transport, from our Chicago and New York day-cost tables (approximate 2026 prices; other currencies converted at recent rates). Ratings are our editorial judgement.
Which one should you pick?
Pick Chicago if…
- You've already seen New York.
- Architecture is your main interest.
- You're travelling with young children.
- you want a lake beach in the city.
Pick New York if…
- It's your first big US city.
- you want Broadway and the Met.
- you like a city that never stops.
- you want to eat your way through many cuisines.
Weather month by month
| Month | Chicago high / rainy days | New York high / rainy days |
|---|---|---|
| Jan | 1°C · 10 | 5°C · 11 |
| Feb | 1°C · 9 | 6°C · 11 |
| Mar | 9°C · 11 | 11°C · 10 |
| Apr | 15°C · 14 | 16°C · 11 |
| May | 20°C · 10 | 21°C · 9 |
| Jun | 27°C · 10 | 26°C · 11 |
| Jul | 27°C · 12 | 30°C · 14 |
| Aug | 27°C · 12 | 29°C · 14 |
| Sep | 24°C · 10 | 25°C · 11 |
| Oct | 17°C · 15 | 19°C · 10 |
| Nov | 10°C · 5 | 12°C · 8 |
| Dec | 5°C · 11 | 9°C · 11 |
Average daily high and number of rainy days. Copernicus ERA5, 2021–2023.
What you will eat
Chicago
Italian beef · Chicago-style hot dog · Deep-dish pizza · Tavern-style pizza · Maxwell Street Polish · Jibarito
Where: Chinatown (Wentworth Avenue and Chinatown Square), Pilsen and Little Village, Argyle Street and Andersonville, Devon Avenue
New York
New York slice · Bagel with cream cheese · Pastrami on rye · Halal cart chicken and rice · Dumplings and roast pork buns · Cannoli
Where: Chinatown and Little Italy (Manhattan), Lower East Side and Essex Market, Chelsea Market, Flushing (Queens)
Doing both in one trip
8 days: 5 in New York + 3 in Chicago
New York first, since most transatlantic flights land there, then fly to Chicago and return home from O'Hare.
Getting between them: Direct flight about 2 h 15, plus airport time; Amtrak's overnight Lake Shore Limited takes roughly 19–20 hours. Check current timetables. Distance about 1,146 km as the crow flies. Check current timetables.
- Day 1–5: New York — Manhattan skyline, the Met and MoMA, Brooklyn Bridge, a Broadway show, food in Chinatown and Flushing.
- Day 6: Fly to Chicago; architecture river cruise.
- Day 7: Art Institute and Millennium Park.
- Day 8: Willis Tower or a lakefront bike ride, deep-dish pizza, fly home.
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Common questions
Is Chicago or New York cheaper?
Chicago is slightly cheaper on mid-range numbers: about €275 per person per day against roughly €281 in New York. The difference is small, and hotels in both cities are expensive. New York has more cheap food options, from pizza slices to food carts, while many Chicago sights and the lakefront parks are free.
How do I get from New York to Chicago?
Flying is easiest: about 2 h 15 between New York's airports and O'Hare or Midway, with frequent flights. Amtrak's Lake Shore Limited runs overnight and takes roughly 19–20 hours. Driving is about 1,300 km, usually split over two days. Check current timetables.
Which city has better architecture?
Chicago is the birthplace of the skyscraper, and its architecture river cruise is one of the best tours in the US. New York has the more famous skyline, with the Empire State, Chrysler and One World Trade Center, but Chicago offers more variety in a compact downtown.
Which is better for a first-time visit to the US?
New York, for most people. It's the city in the films, with more famous sights, and direct flights from almost everywhere. Chicago is easier and calmer, so it suits a second trip or those who want a big city without the crowds. With a week or more, combine both.