Cheap Flights to Chicago
$208 round trip from New Yorkseen Aug 20 · 24–27 Oct
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Overview
Flying to Chicago
Country
United States
Region
North America
Airport
ORD
Cheapest month we saw
October ($173)
Fares by month
When is it cheapest to fly to Chicago?
Cheapest round trip we observed from New York, in USD, across the 7 months we hold fares for. Months we have not seen a fare for are not shown — they are not months without flights.
Climate
Weather in Chicago, month by month
The warmest month in Chicago is August, at an average high of 82°F; the coolest is January at 30°F. May brings the most rain.
| Month | High | Low | Rain |
|---|---|---|---|
| January | 30°F | 21°F | 2.0 in |
| February | 30°F | 21°F | 1.9 in |
| March | 39°F | 28°F | 3.1 in |
| April | 55°F | 43°F | 3.8 in |
| May | 64°F | 52°F | 3.9 in |
| June | 73°F | 63°F | 3.5 in |
| July | 81°F | 70°F | 3.1 in |
| August | 82°F | 70°F | 2.8 in |
| Septemberthis month | 75°F | 63°F | 3.4 in |
| October | 59°F | 50°F | 2.4 in |
| November | 46°F | 37°F | 3.3 in |
| December | 36°F | 27°F | 2.4 in |
Ten-year average (2015–2024) of measured daily observations, not a brochure estimate.
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Good to know
Flying to Chicago — your questions answered
- How much is a round trip flight to Chicago?
- The cheapest round trip we currently hold is $208 from New York (seen Aug 20 · 24–27 Oct). Across the 7 months we hold fares for, October is the cheapest month we have seen, at $173, and April the dearest at $247. These are prices a live search returned, not a standing offer, and they move daily.
- When is it warm in Chicago?
- August is the warmest month in Chicago, averaging a daily high of 82°F, and 3 of the 12 months average 75°F or warmer. The coolest is January at 30°F. These are ten-year averages (2015–2024) of measured observations, not estimates.
- What is the weather like in Chicago in September?
- In September, Chicago averages a daily high of 75°F and an overnight low of 63°F; about 3.4 inches of rain fall across the month. Ten-year measured averages — an individual week can differ.
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