AirHint found the following cheapest return flights from Chicago (MDW) to Singapore (SIN) in December 2025 (see full year).

Return flights

29 Dec - 19 Jan	Air France
25 Dec - 03 Jan	Delta
25 Dec - 04 Jan	Delta
20 Dec - 10 Jan	Delta
11 Dec - 31 Dec	Delta
22 Dec - 04 Jan	Delta
24 Dec - 04 Jan	Delta
11 Dec - 01 Jan	Delta
20 Dec - 04 Jan	Delta
21 Dec - 04 Jan	Delta
24 Dec - 03 Jan	Delta
07 Dec - 13 Dec	Porter Airlines (Canada) Ltd

Also check the deals for one-way flights from Chicago to Singapore in December.

The deals are updated regularly. The prices may go up as tickets are purchased by other travellers. Only the cheapest flights are offered. Select a price to book and secure these cheap prices.

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Cheapest return flights from Chicago to Singapore in December from $1898

Return flights