Tokyo to Chicago (HND–MDW) — Airlines, Schedules & Connections

Japanese passport holders can enter the United States for up to 90 days under the Visa Waiver Program (VWP) with an approved ESTA (Electronic System for Travel Authorization). Apply at esta.cbp.dhs.gov at least 72 hours before departure. ESTA costs $21, is valid for 2 years, and allows multiple entries. You cannot extend a VWP stay or change immigration status. For stays beyond 90 days, apply for a B-1/B-2 visa at the US Embassy in Tokyo ($185 application fee).

ESTA asks for passport details, employment information, and security questions. Approval is usually instant but can take up to 72 hours. At US immigration, CBP officers may ask about your trip purpose, length of stay, and accommodation. Global Entry ($100, valid 5 years) gives you automated kiosks at major airports, skipping the main immigration line. Apply at ttp.cbp.dhs.gov and interview at the US Embassy Tokyo or at a US airport on arrival.

Direct flights from Tokyo Narita and Haneda to major US cities run 8 to 13 hours depending on the destination. ANA, JAL, United, Delta, American, Hawaiian Airlines, and Zipair operate dozens of daily frequencies. Los Angeles is about 10 hours, New York about 13 hours. The US uses the US dollar, trading at roughly 0.0065 USD per JPY. No vaccination requirements. Mobile Passport Control (MPC) app is an alternative to Global Entry for faster processing at 30+ US airports, free to use.

Keikyu Line from Shinagawa reaches Haneda in 13 minutes (¥310). Tokyo Monorail from Hamamatsucho takes 15–22 minutes (¥500). Both run frequently from 5am to midnight. Haneda's central location makes it by far the most convenient Tokyo airport.Taxis from central Tokyo cost ¥3,500–5,500 depending on destination and traffic. Limousine buses serve major hotels and stations (¥600–1,100). Ride-shares (GO, S.RIDE) are growing in Japan. The airport is 14km from central Tokyo, significantly closer than Narita.