Cheapest return flights from Chicago to Singapore in May from $1256

Best time to book flights for Chicago (MDW) to Singapore (SIN) flights at AirHint

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

Return flights

06 May - 13 May Delta
12 May - 22 May Delta
19 May - 23 May Delta
18 May - 22 May Delta
18 May - 25 May Delta
17 May - 24 May Delta
18 May - 31 May Delta
16 May - 23 May Delta
15 May - 20 May Delta
28 May - 09 Jun Air France
23 May - 30 May Delta

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

Skyscanner

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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