AirHint found the following cheapest return flights from Chicago (MDW) to Tokyo (NRT) in May 2026 (see full year).

Return flights

01 May - 12 May	Porter Airlines (Canada) Ltd
30 May - 13 Jun	WestJet
01 May - 15 May	WestJet
10 May - 17 May	WestJet
15 May - 29 May	WestJet
20 May - 30 May	WestJet
21 May - 26 May	WestJet
20 May - 31 May	WestJet
09 May - 24 May	WestJet
13 May - 05 Jun	WestJet
23 May - 02 Jun	WestJet
22 May - 02 Jun	WestJet
16 May - 02 Jun	WestJet
15 May - 02 Jun	WestJet
18 May - 02 Jun	WestJet
19 May - 03 Jun	WestJet
14 May - 02 Jun	WestJet
28 May - 12 Jun	Korean Air

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

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.

Book a cheap hotel in Tokyo

Cheap car rent in Tokyo

Cheapest return flights from Chicago to Tokyo in May from $1356

Return flights