Cheap flights from Chicago to Singapore (ORD to SIN) from $881

Book at the right time: For international flights, aim to book 6–10 weeks ahead. Last-minute fares on Chicago to Singapore are rarely cheap, and prices spike sharply within 2 weeks of departure.

Shift your dates by a day or two: Mid-week departures (Tuesday–Wednesday) are almost always cheaper than weekend flights. Even shifting by one day can make a meaningful difference.

Weigh up connecting flights: Connecting flights on Chicago to Singapore can be 20–40% cheaper than direct options. If you have time to spare, it's worth comparing.

Factor in baggage fees: Low-cost carriers on this route often advertise attractive base fares but charge separately for checked luggage. Always compare the all-in price — a $20 cheaper fare plus $50 baggage fee is no saving. ANA and Air Canada may have different inclusions, so check each airline's fare conditions.

Search in private browsing: Some booking sites use cookies to track repeat searches and may show higher prices after multiple lookups. Use an incognito or private window — or just use Booked AI, which pulls live prices without any tracking markup.

Compare two one-ways against a return: On some international routes, booking a one-way with one airline and the return with another can undercut a standard return ticket — especially if a budget carrier covers one direction. Check both options with the flexible dates calendar above.

The cheapest flights from Chicago to Singapore start from $881, with typical prices ranging from $881 to $1,169.

The typical flight time from Chicago to Singapore is approximately 23 hours and 10 minutes.

Airlines operating this route include ANA, Air Canada, Air India, Alaska Airlines, American Airlines, Asiana Airlines, British Airways, Cathay Pacific, Delta Air Lines, EVA Air.