Tokyo tower illuminated at dusk with city skyline
35% below the usual fare
Exit Row · Boarding passSeat 14C

Cheap flights ChicagoTokyo

From
CHIChicago
To
TYOTokyo
Travel
May 2027
Flight
1 stop, one way

Fare from Chicago

US$438

Usually about US$672

-35%vs the usual price

Get the dates and the link

Price seen 29 Oct 2026 · fares change fast and can sell out

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People walking on road near well-lit buildings
Jezael Melgoza / Unsplash
Aerial photography of red tower surrounded by buildings during daytime
Jaison Lin / Unsplash

Why go

Tokyo.

Neon nights, quiet shrines and the best food you'll ever eat.

Best timeLate March for cherry blossom, November for autumn colour.

  • Big city
  • Food
  • Nightlife
  • Luxury

Three things to do

  1. Day trip to Nikko or Kamakura
  2. Shibuya and Shimokitazawa at night
  3. Sushi breakfast near Toyosu market
Distance
10,141 km
Flight
1 stop
Trip
One way

Make it a trip.

Also boarding from Chicago.

Every deal from Chicago

Prices are the cheapest fare we found from Chicago, in USD, for one adult, and can change when you click. Some links are affiliate links: they never change which deals we send or what you pay. How we make money.