Chicago: cheap flights and the best time to go
Architecture boat tours, museums and deep-dish pizza. Illinois · Cities, Family
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Cheapest round trip
Safety level
U.S. U.S. destination: no State Department travel advisory
The State Department's travel advisories
Levels: 1 Exercise normal precautions · 2 Exercise increased caution · 3 Reconsider travel · 4 Do not travel. Read the advisory before you book; it can change. Checked 2026-10-07.
Best time to go
For the weather: September, October, April (highs of 62–82°F, not too much rain). With fares from your airport, the best months weigh weather 60% and price 40%.
| Month | High | Low | Rain | Cheapest round trip from JFK |
|---|---|---|---|---|
| January | 33°F | 20°F | 1.5 in | … |
| February | 37°F | 22°F | 1.5 in | … |
| March | 48°F | 32°F | 2.1 in | … |
| April (a best month) | 60°F | 42°F | 3.6 in | … |
| May | 71°F | 52°F | 4.4 in | … |
| June | 81°F | 62°F | 4.0 in | … |
| July | 85°F | 68°F | 3.4 in | … |
| August | 83°F | 67°F | 4.1 in | … |
| September (a best month) | 77°F | 59°F | 2.7 in | … |
| October (a best month) | 63°F | 47°F | 3.6 in | … |
| November | 50°F | 36°F | 2.1 in | … |
| December | 37°F | 25°F | 1.9 in | … |
Typical daily high and low and total rain, 1991–2020: NOAA NCEI GHCN-Daily, station CHICAGO MIDWAY AP (15 km away). ★ = the best three months. Fares are the cheapest found for trips leaving that month in the next year.