Cheap International Flights from Chicago in October
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October Travel Tip
October is excellent for Europe and Asia. Weather great, prices down.
Best Destinations from Chicago in October
ORD → MTY
Monterrey
Mexico
Est. $111
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 → OPO
Porto
Portugal
Est. $331
round trip
~9h flight time
ORD → LHR
London
United Kingdom
Est. $332
round trip
~9h flight time
ORD → LIS
Lisbon
Portugal
Est. $336
round trip
~9h flight time
ORD → FAO
Faro
Portugal
Est. $346
round trip
~9h flight time
ORD → CDG
Paris
France
Est. $348
round trip
~9h flight time
ORD → MAD
Madrid
Spain
Est. $352
round trip
~9h flight time
Best Regions from Chicago in October
Related Reading
Frequently Asked Questions
What are the cheapest destinations from Chicago in October?
In October, some of the most affordable destinations from Chicago include Monterrey (est. $111 RT), Mexico City (est. $142 RT), Guadalajara (est. $146 RT). Prices vary by booking window.
Is October cheap to fly from Chicago?
October is excellent for Europe and Asia. Weather great, prices down.
How far ahead should I book flights from Chicago in October?
For October 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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