Find United Airlines(UA) flights from Singapore to Chicago

At the moment, several airlines serve connecting flights from Singapore to Chicago, including: United Airlines EVA Air All Nippon Airways Cathay Pacific Selected airlines are based on historical data collected from flight bookings made by users on Trip.com within the last 90 days.

By analyzing data from all airlines on the Trip.com flight calendar, it looks like the best time to book a flight from Singapore to Chicago is around 40 days (6 weeks) in advance, and the best time to fly is usually on Tuesday, Wednesday, and Saturday. Tuesday typically offers the cheapest flights for departure, while Saturday offers the best return deals.

The cheapest months to fly from Singapore to Chicago is November, when demand for travel is lower.

After crunching the numbers on our September flight calendar, it's currently cheapest to fly from Singapore to Chicago on September 29, 2026 with Air Canada, with prices starting at US$484.

You can land at any one of the following hubs in Chicago: Chicago Midway International Airport (MDW), O'Hare International Airport (ORD), and Chicago Rockford International Airport (RFD). Flying from Singapore Changi Airport to O'Hare International Airport (SIN-ORD) is by far the most common option on this route.

The time difference between Chicago and Singapore is 14h.

Tickets can only be changed or canceled if permitted by airline policy. To submit a change or cancellation request, go to the flight bookings page, select the option to change or cancel your booking, choose the relevant passengers and segment, and submit a request. Please note that additional charges may apply according to the airline ticket policy. However, if the flight has been rescheduled and you would like to change or cancel your ticket, you can submit an involuntary cancellation request. For more details about change and cancellation policies, please check the customer support pages.