Europe pick1 stop
ORDChicago
LISLisbon
Round trip from$398
Travel windowNov 5–13, 2026
Eight nights for tiled streets, late dinners and Atlantic light.
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Chicago flight deals.
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Scanning fares from ORDLooking for unusually good prices and useful travel windows.
ORDChicago
LISLisbon
Deal found$398
Nov 5–13, 2026 · 1 stop
Long-haul steal1 stop
ORDChicago
HNDTokyo
Round trip from$684
Travel windowJan 18–27, 2027
Nine nights of neon, ramen counters and crisp winter mornings.
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ORDChicago
MEXMexico City
Round trip from$287
Travel windowOct 22–26, 2026
Four days for galleries, tacos and a very good reason to take Friday off.
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ORDChicago
SJUSan Juan
Round trip from$241
Travel windowFeb 6–11, 2027
Trade the lakefront wind for five warm nights by the Caribbean.
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