Cheap International Flights from Chicago in September
Fares shown are modelled estimates, not live quotes.
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September Travel Tip
A strong month for Europe. Shoulder season starts and prices often ease from peak.
Best Destinations from Chicago in September
ORD → DUB
Dublin
Ireland
Est. $308
round trip
~8h flight time
ORD → GLA
Glasgow
United Kingdom
Est. $308
round trip
~8h flight time
ORD → EDI
Edinburgh
United Kingdom
Est. $311
round trip
~8h flight time
ORD → MAN
Manchester
United Kingdom
Est. $321
round trip
~9h flight time
ORD → BHX
Birmingham
United Kingdom
Est. $325
round trip
~9h 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 → AMS
Amsterdam
Netherlands
Est. $345
round trip
~9h flight time
Best Regions from Chicago in September
Related Reading
Frequently Asked Questions
What are the cheapest destinations from Chicago in September?
In September, some of the most affordable destinations from Chicago include Dublin (est. $308 RT), Glasgow (est. $308 RT), Edinburgh (est. $311 RT). Prices vary by booking window.
Is September cheap to fly from Chicago?
A strong month for Europe. Shoulder season starts and prices often ease from peak.
How far ahead should I book flights from Chicago in September?
For September 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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