Direct flights to Chicago | Cheapflights

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Best time to book a flight to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago with our price prediction graph.

Estimated return price

Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Reviews of airlines flying non-stop to Chicago

Read reviews from past customers who have flown Air New Zealand, Qantas Airways, andUnited Airlines to the United States. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.

Air New Zealand

8.0

Very Good

Reviews

1 / 20

6.0

Good

Anonymous,Jul 2025

AKL - SFO

Flight was delayed an hour. We had just flown Air NZ on a 12- hour flight from AKL so the extra delay on this connecting flight wasn’t welcomed.

Air New Zealand

8.0

Very Good

Air New Zealand

8.0

Very Good

Reviews

1 / 20

6.0

Good

Anonymous,Jul 2025

AKL - SFO

Flight was delayed an hour. We had just flown Air NZ on a 12- hour flight from AKL so the extra delay on this connecting flight wasn’t welcomed.

7.5

Good

Air New Zealand

8.0

Very Good

Reviews

1 / 20

6.0

Good

Anonymous,Jul 2025

AKL - SFO

Flight was delayed an hour. We had just flown Air NZ on a 12- hour flight from AKL so the extra delay on this connecting flight wasn’t welcomed.

United Airlines

7.4

Good

Air New Zealand

8.0

Very Good

Reviews

1 / 20

6.0

Good

Anonymous,Jul 2025

AKL - SFO

Flight was delayed an hour. We had just flown Air NZ on a 12- hour flight from AKL so the extra delay on this connecting flight wasn’t welcomed.

American Airlines

7.2

Good

Air New Zealand

8.0

Very Good

Reviews

1 / 20

6.0

Good

Anonymous,Jul 2025

AKL - SFO

Flight was delayed an hour. We had just flown Air NZ on a 12- hour flight from AKL so the extra delay on this connecting flight wasn’t welcomed.

7.1

Good

Air New Zealand

8.0

Very Good

Reviews

1 / 20

6.0

Good

Anonymous,Jul 2025

AKL - SFO

Flight was delayed an hour. We had just flown Air NZ on a 12- hour flight from AKL so the extra delay on this connecting flight wasn’t welcomed.

Temperature and rainfall in Chicago by month

CHI

Temperature

-5 - 23 °C

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 23.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -5.0 C).

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