Chicago is at its best from May to June and September to October.
It is busiest and priciest in June to September.
Here is every month at a glance, the dates to plan around, and flights from five Indian cities.
Chicago month by month
Average highs and lows, rain, the season and what's on, for the next twelve months.
| Month | Weather | Season | What's on |
|---|---|---|---|
| October 2026Best weather | 17° / 8°rainy spells, 113 mm | Shoulder | Dussehra |
| November 2026 | 9° / 1°some rain, 56 mm | Shoulder | DiwaliThanksgiving |
| December 2026 | 3° / -4°some rain, 61 mm | Shoulder | Christmas and New Year |
| January 2027 | 0° / -8°some rain, 63 mm | Off-season | Christmas and New YearRepublic Day weekend |
| February 2027 | 3° / -6°some rain, 56 mm | Off-season | Bitter winter: often -10°C or colder with wind chill, and snowstorms can ground... |
| March 2027 | 9° / -1°rainy spells, 94 mm | Off-season | HoliGood Friday weekend |
| April 2027 | 14° / 3°rainy spells, 99 mm | Shoulder | Indian summer holidays |
| May 2027Best weather | 20° / 10°rainy spells, 125 mm | Shoulder | Indian summer holidays |
| June 2027Best weather | 27° / 16°rainy spells, 118 mm | Peak | Indian summer holidays |
| July 2027 | 28° / 19°rainy spells, 145 mm | Peak | Fourth of JulyStudent rush |
| August 2027 | 27° / 18°rainy spells, 93 mm | Peak | Student rush |
| September 2027Best weather | 24° / 15°rainy spells, 90 mm | Peak | Late spring and early autumn: mild and comfortable. |
Dates to plan around
Festivals, holidays and closures in Chicago, and the Indian holiday rushes that raise fares.
- 20 OctDussehraDussehra falls on Tuesday 20 Oct: many take the Monday off for a four-day weekend, so short trips abroad cost more that week.
- 6–10 NovDiwaliDiwali (Lakshmi Puja on Sunday 8 Nov): the busiest travel week of the autumn. Fares out of India rise, and short trips to Dubai, Bangkok and Singapore book up.
- 25–29 NovThanksgivingThanksgiving (Thursday 26 Nov): the busiest travel days of the US year fall around it, and many shops close on the day.
- 19 Dec – 3 JanChristmas and New YearThe priciest fortnight of the year to fly out of India: school holidays, Christmas and New Year all at once. Book early or go just before or after.
- 23–26 JanRepublic Day weekendRepublic Day falls on Tuesday 26 Jan: take the Monday off and it's a four-day weekend, so short trips abroad book up.
- 22–23 MarHoliHoli (22-23 Mar) and Good Friday (26 Mar) fall in the same week, a favourite week for short trips abroad, so fares rise.
- 26–28 MarGood Friday weekendGood Friday (26 Mar) makes a long weekend in India, just after Holi.
- 15 Apr – 15 Jun · expectedIndian summer holidaysSchool holidays (roughly mid-April to mid-June, varying by state): outbound family travel peaks and fares climb, especially to the Gulf, Southeast Asia and Europe.
- 3–5 JulFourth of JulyIndependence Day falls on a Sunday, so Monday 5 Jul is the holiday: fireworks, and busy roads and airports.
- 20 Jul – 31 Aug · expectedStudent rushThousands of Indian students fly out for autumn intakes, so fares from India to the US, UK, Canada, Australia and Europe peak from late July through August.
- 27–31 OctDiwaliDiwali (Lakshmi Puja on Friday 29 Oct): the busiest travel week of the autumn. Fares out of India rise, and short trips abroad book up.
Flights to Chicago from India
The cheapest fare our scanner has seen from each city in the last two weeks. Open a route to price every month live.
Good to know
When is the best time to visit Chicago?
The best weather in Chicago is from May to June and September to October. Late spring and early autumn: mild and comfortable. Peak season, with the most visitors and the highest hotel prices, is June to September. The quietest months are January to March.
When is Chicago most crowded?
Peak season is June to September, when stays cost the most and the sights are busiest.
What is the cheapest way to fly to Chicago from India?
Of the Indian cities we track, Bangalore has the lowest fare right now: ₹77,171 (return, 14 nights) for Wed 10 Feb.
How hot does Chicago get?
The hottest month is July, with average highs of 28°C; the coolest nights come in January, around -8°C.