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New York City vs Chicago: which is better, and when to go
New York City is at its best in May and Chicago in May. Below, the two cities side by side: weather, crowds and prices in every month, and what each does better across the year.
By Daan · Last reviewed October 2026
New York City and Chicago
At a glance
| New York City | Chicago | |
|---|---|---|
| Best month | May (9/10) | May (9/10) |
| Warmest month | July, 29°C | July, 27°C |
| Coolest month | January, 4°C | January, -1°C |
| Quietest month | January (Low) | January (Very Low) |
| Busiest month | July (High) | July (Extremely High) |
| Cheapest month | January ($) | January ($$) |
Which one should you choose?
Choose New York City for
- a milder coolest month (January highs around 4°C, against -1°C)
- quieter months across the year on average
- a calmer peak month
- lower prices across the year on average
- more going on through the year (events and festivals)
Choose Chicago for
- a gentler warmest month (July highs around 27°C, against 29°C)
Month by month
Average high, crowds and prices for each month, and which city comes out ahead overall. Open a month for the full comparison.
| Month | New York City | Chicago | Ahead |
|---|---|---|---|
| January | 4°C · Low · $ | -1°C · Very Low · $$ | New York City |
| February | 6°C · Low · $ | 1°C · Very Low · $$ | New York City |
| March | 10°C · Moderate · $$ | 6°C · Low-Moderate · $$ | New York City |
| April | 17°C · Moderate · $$ | 12°C · Moderate · $$$ | New York City |
| May | 22°C · Moderate · $$ | 19°C · Moderate · $$$ | Close |
| June | 26°C · High · $$$ | 25°C · Moderate-High · $$$$ | New York City |
| July | 29°C · High · $$$ | 27°C · Extremely High · $$$$$ | New York City |
| August | 28°C · High · $$$ | 26°C · Extremely High · $$$$$ | New York City |
| September | 25°C · High · $$$ | 23°C · Moderate · $$$ | New York City |
| October | 18°C · Moderate · $$ | 16°C · Moderate · $$$ | Close |
| November | 12°C · Moderate · $$ | 8°C · Low · $$ | New York City |
| December | 7°C · Very high · $$$$ | 2°C · Moderate · $$$ | New York City |
FAQ
New York City or Chicago?
Is New York City or Chicago better?
Both are at their best in May, so the choice comes down to what you want from the trip. See which city suits you in the table below.
When is the best time to visit New York City and Chicago?
New York City: May. Chicago: May.
Which is cheaper, New York City or Chicago?
New York City is cheaper on average across the year.