Tokyo is a must-visit destination, offering a unique mix of rich culture, modern attractions, and world-class dining. If Japan is on your travel bucket list, now is a great time to plan your trip.
Pointrs Seat Radar has found award flight availability from Chicago to Tokyo between February and April 2027, including Economy, Business, and First Class options across multiple airline programs. Travel during Japan’s transition from winter to spring and take advantage of excellent redemption opportunities.
Once you've secured your flight, save even more with exclusive hotel deals through Pointrs Travel Hotels. Check the latest availability with Pointrs Seat Radar and book before these award seats disappear.
JET OFF TO JAPAN FROM CHICAGO!
We've found 752 seats for Feb-Apr 2027, including 80 in first class!
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✈️ Chicago to Tokyo
Economy Return with ANA (non-stop) for only 50,000 Airline Miles - Save 100,000 miles!
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✈️ Chicago to Tokyo
Economy Return with Japan Airlines (non-stop) for only 62,000 Airline Miles - Save 104,000 miles!
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✈️ Chicago to Tokyo
Economy Return with United Airlines (non-stop) for only 50,000 Airline Miles - Save 100,000 miles!
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✈️ Chicago to Tokyo
Economy Return with ANA (non-stop) for only 50,000 Airline Miles - Save 100,000 miles!
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✈️ Chicago to Tokyo
Economy Return with Japan Airlines (non-stop) for only 62,000 Airline Miles - Save 104,000 miles!
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✈️ Chicago to Tokyo
First Return with Japan Airlines (non-stop) for only 160,000 Airline Miles - Save 220,000 miles!
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✈️ Chicago to Tokyo
First Return with Japan Airlines (non-stop) for only $3,012 - Save up to $10,388!
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SAVE EVEN MORE WITH POINTRS TRAVEL!
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Found your flight? Now save up to 50% on hotels and travel extras worldwide with Pointrs Travel VIP!
Check out the savings on these hotels in Tokyo and much more!
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Superior King Room with 1 King Bed
2 Guests, Room Only
Non-refundable
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Twin Standard with 2 Single Beds
2 Guests, Room Only
Free cancellation before 25 Feb 2027
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Standard Twin with 2 Single Beds
2 Guests, Room Only
Non-refundable
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Standard Double room with garden view and 1 Full Double Bed
2 Guests, Room Only
Non-refundable
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*Prices as of 09 Jul 2026 for check-in 3 Mar 2027
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Pointrs subscribers get VIP access for just $1 per year, unlocking super-exclusive deals you won’t find elsewhere.
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