Direct flights to Chicago | Cheapflights

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 Singapore Airlines, Air New Zealand, andQantas Airways 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.

Singapore Airlines

8.1

Very Good

Reviews

1 / 20

6.0

Good

Pierre,Apr 2025

MLE - SIN

3 boarding pass checkpoints at the gate. Long line before boarding. Poor leg room in economy.. Flight crew rounds practically non existent during flight.

Singapore Airlines

8.1

Very Good

Singapore Airlines

8.1

Very Good

Reviews

1 / 20

6.0

Good

Pierre,Apr 2025

MLE - SIN

3 boarding pass checkpoints at the gate. Long line before boarding. Poor leg room in economy.. Flight crew rounds practically non existent during flight.

Air New Zealand

8.0

Very Good

Singapore Airlines

8.1

Very Good

Reviews

1 / 20

6.0

Good

Pierre,Apr 2025

MLE - SIN

3 boarding pass checkpoints at the gate. Long line before boarding. Poor leg room in economy.. Flight crew rounds practically non existent during flight.

7.5

Good

Singapore Airlines

8.1

Very Good

Reviews

1 / 20

6.0

Good

Pierre,Apr 2025

MLE - SIN

3 boarding pass checkpoints at the gate. Long line before boarding. Poor leg room in economy.. Flight crew rounds practically non existent during flight.

United Airlines

7.4

Good

Singapore Airlines

8.1

Very Good

Reviews

1 / 20

6.0

Good

Pierre,Apr 2025

MLE - SIN

3 boarding pass checkpoints at the gate. Long line before boarding. Poor leg room in economy.. Flight crew rounds practically non existent during flight.

American Airlines

7.2

Good

Singapore Airlines

8.1

Very Good

Reviews

1 / 20

6.0

Good

Pierre,Apr 2025

MLE - SIN

3 boarding pass checkpoints at the gate. Long line before boarding. Poor leg room in economy.. Flight crew rounds practically non existent during flight.

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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