Cheap International Flights from Chicago in November
Fares shown are modelled estimates, not live quotes.
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November Travel Tip
Black Friday deals hit in mid-November. Great for Caribbean and South America.
Best Destinations from Chicago in November
ORD → MTY
Monterrey
Mexico
Est. $111
round trip
~4h flight time
ORD → CUN
Cancun
Mexico
Est. $122
round trip
~4h flight time
ORD → MEX
Mexico City
Mexico
Est. $142
round trip
~4h flight time
ORD → GDL
Guadalajara
Mexico
Est. $146
round trip
~4h flight time
ORD → PVR
Puerto Vallarta
Mexico
Est. $150
round trip
~5h flight time
ORD → SJD
Los Cabos
Mexico
Est. $152
round trip
~5h flight time
ORD → SVQ
Seville
Spain
Est. $353
round trip
~9h flight time
ORD → VCE
Venice
Italy
Est. $392
round trip
~10h flight time
ORD → NRT
Tokyo
Japan
Est. $579
round trip
~14h flight time
Best Regions from Chicago in November
Related Reading
Frequently Asked Questions
What are the cheapest destinations from Chicago in November?
In November, some of the most affordable destinations from Chicago include Monterrey (est. $111 RT), Cancun (est. $122 RT), Mexico City (est. $142 RT). Prices vary by booking window.
Is November cheap to fly from Chicago?
Black Friday deals hit in mid-November. Great for Caribbean and South America.
How far ahead should I book flights from Chicago in November?
For November departures from Chicago, booking 6–10 weeks in advance typically yields the best fares. For peak months like July and December, book 3–4 months early. Fare reviews and notifications are paused during the provider migration.
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