This one honestly surprised me. There are very limited flights from Chicago to Tokyo for $675 roundtrip on Air Canada for travel in December. For context, this route is usually $1,200+, and it’s not uncommon to see it push even higher during the winter.
If Japan has been on your radar, this is one of those “book first, figure the details out later” kind of prices.
A Simple 5-Day December Itinerary Around Tokyo
December is such an underrated time to be in Japan — clear skies, crisp air, holiday lights everywhere, and the crowds are way lighter than cherry blossom season. Here’s an easy 5-day plan if you grab this fare.
Day 1 — Shibuya + Shinjuku
Ease into the city:
Check out Shibuya Crossing and Shibuya Sky for the big rooftop views
Wander through Shinjuku’s Omoide Yokocho + Golden Gai
Warm up with a bowl of ramen (Ichiran or Afuri are great starters)
Day 2 — Tokyo Midtown Lights + Roppongi
December means the city goes all-in on holiday illuminations.
Walk through the Midtown and Roppongi light displays
Stop for coffee and dessert in Aoyama or Nogizaka
End the night at Tokyo Tower lit up for the holidays
Day 3 — Asakusa + Tokyo Skytree
A classic Tokyo day.
Visit Senso-ji, one of the most photogenic spots in the city
Snack your way down Nakamise Street
Head up Tokyo Skytree for big views of a winter skyline
Day 4 — Day Trip to Hakone or Kamakura
Your choice depending on the vibe:
Hakone: Hot springs, mountain air, and views of Mt. Fuji
Kamakura: Coastal temples, the Great Buddha, and easy hiking trails
Both are perfect December day trips — cool weather, fewer crowds, great photos.
Day 5 — Tsukiji Market + Ginza
A fun last day:
Fresh sushi and street snacks in Tsukiji
Explore Ginza’s holiday windows and shops
Pick up gifts and snacks inside Tokyo Station before heading home
The Flights
