United States and Canada · United States
Cheap flights to Chicago
Architecture boat tours on the river, deep-dish pizza and a lakefront lined with beaches and parks.
- Best weather
- Jun to Sep
- Warmest
- Jul, 30°C
- Airports
- ORD, MDW
Best time to visit Chicago
The best time to visit Chicago for the weather is from June to September, when daytime highs average 25 to 30°C (77 to 86°F) and there's some rain.
There's no real wet season: rain is spread through the year, with the most in May (about 12 rainy days) and the least in February.
The warmest month is July, with highs around 30°C (85°F); the coolest is January, at around 0°C (33°F) by day and -7°C (20°F) at night.
Chicago weather by month
Average daytime highs, overnight lows and rain for each month.
| Month | High | Low | Rain | What it's like |
|---|---|---|---|---|
| January | 0°C 33°F | -7°C 20°F | 12 rainy days | Cold with some rain |
| February | 3°C 37°F | -5°C 23°F | 9 rainy days | Cold with some rain |
| March | 9°C 48°F | 0°C 32°F | 11 rainy days | Cold with some rain |
| April | 16°C 60°F | 5°C 42°F | 12 rainy days | Cool with some rain |
| May | 22°C 71°F | 11°C 52°F | 12 rainy days | Mild and wet |
| June Best | 27°C 81°F | 17°C 63°F | 11 rainy days | Warm with some rain |
| July Best | 30°C 85°F | 20°C 68°F | 10 rainy days | Warm with some rain |
| August Best | 28°C 83°F | 19°C 67°F | 9 rainy days | Warm with some rain |
| September Best | 25°C 76°F | 15°C 59°F | 8 rainy days | Warm with some rain |
| October | 18°C 64°F | 8°C 47°F | 11 rainy days | Mild with some rain |
| November | 10°C 50°F | 2°C 35°F | 10 rainy days | Cold with some rain |
| December | 3°C 38°F | -4°C 25°F | 11 rainy days | Cold with some rain |
Long-term averages from Chicago (Midway International Airport), 1991–2020. The weather on your dates will vary.
Flying to Chicago
Farepop finds fares to Chicago O'Hare International Airport (ORD) and Chicago Midway International Airport (MDW). These are the closest airports Farepop watches in each region, as the crow flies; with stops, the trip is longer.
| From | Closest airports |
|---|---|
| Australia | Brisbane 14,300 km · about 18.5 hours non-stop Sydney 14,900 km · about 19 hours non-stop |
| New Zealand | Auckland 13,200 km · about 17 hours non-stop Wellington 13,400 km · about 17.5 hours non-stop |
| United States | Washington 590 mi · about 1.5 hours non-stop Atlanta 610 mi · about 1.5 hours non-stop |
| Canada | Toronto 700 km · about 1.5 hours non-stop Montréal 1,200 km · about 2 hours non-stop |
| United Kingdom | Belfast 3,600 mi · about 8 hours non-stop Glasgow 3,700 mi · about 8 hours non-stop |
| Europe | Cork 5,800 km · about 8 hours non-stop Dublin 5,900 km · about 8 hours non-stop |
How Farepop finds cheap flights to Chicago
Compared with the usual price
Every fare is compared with what the same route usually costs for the same trip length and dates. Around busy holidays we use quieter neighbouring months, so a peak price never passes for a saving.
At least 25% below
A deal is at least 25% below the usual price for those dates, and a good fare at least 20%. Full-service airlines selling at budget prices, and travel agents undercutting the airline, are labelled as such.
Checked twice, then again
Fares are checked again on their exact dates before you hear about them, and regularly after. Ones that no longer qualify are withdrawn.
You book direct
Farepop doesn't sell tickets. Tap a deal and book with the airline or travel site; always check the final price, baggage and conditions before you pay.
The full rules are in our savings methodology.
Chicago: questions
When is the best time to visit Chicago?
For the weather, from June to September, when daytime highs average around 28°C. These are long-term averages from Chicago (Midway International Airport), 1991–2020.
Does it rain a lot in Chicago?
Chicago has no distinct wet season. May is usually the wettest month, with about 12 rainy days.
Which airport do you fly into for Chicago?
Farepop finds fares to Chicago O'Hare International Airport (ORD) and Chicago Midway International Airport (MDW).
How can I find cheap flights to Chicago?
Be flexible with your dates and let the fares come to you. Farepop watches flights from your home airports and alerts you when a trip to Chicago costs at least 25% less than it usually does for those dates, so you can book before the fare goes.
More places like Chicago
Fly to Chicago for less.
Android coming soon