Chicago to South American cities from only $290 roundtrip

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Cheap flights from Chicago to South American cities from only $290 roundtrip with Copa Airlines.

Fly to:
Cartagena: $290
Bogota: $292
Cali: $307-$328
Guayaquil: $374
Manaus: $499

DEPART:
Chicago, USA

ARRIVE:
Cartagena/Bogota/Cali, Colombia
Guayaquil, Ecuador
Manaus, Brazil

RETURN:
Chicago, USA

DATES:
Availability from September to November 2025

Example dates:

Chicago – Cartagena: $290
9th-16th Sep
10th-17th Sep
12th-19th Sep
16th-23rd Sep
6th-13th Oct
7th-14th Oct
10th-17th Oct
11th-18th Oct
12th-19th Oct
17th-24th Oct
18th-25th Oct
20th-27th Oct
21st-28th Oct
22nd-29th Oct
24th-31st Oct
29th Oct – 5th Nov
30th Oct – 6th Nov
1st-8th Nov
2nd-9th Nov
3rd-10th Nov
7th-14th Nov
8th-15th Nov
9th-16th Nov
10th-17th Nov
11th-18th Nov
12th-19th Nov
13th-20th Nov

Chicago – Bogota: $292
3rd-10th Sep
4th-11th Sep
8th-15th Sep
9th-16th Sep
10th-17th Sep
12th-19th Sep
16th-23rd Sep
17th-24th Sep
19th-26th Sep
23rd-30th Sep
24th Sep – 1st Oct
26th Sep – 3rd Oct
29th Sep – 6th Oct
30th Sep – 7th Oct
6th-13th Oct
7th-14th Oct
8th-15th Oct
10th-17th Oct
15th-22nd Oct
16th-23rd Oct
18th-25th Oct
20th-27th Oct
21st-28th Oct
22nd-29th Oct
23rd-30th Oct
24th-31st Oct
25th Oct – 1st Nov
26th Oct – 2nd Nov
27th Oct – 3rd Nov
28th Oct – 4th Nov
29th Oct – 5th Nov
30th Oct – 6th Nov
1st-8th Nov
2nd-9th Nov
3rd-10th Nov
4th-11th Nov
6th-13th Nov
7th-14th Nov
9th-16th Nov
10th-17th Nov
11th-18th Nov
12th-19th Nov
13th-20th Nov

Chicago – Cali: $307-$328
8th-15th Sep
10th-17th Sep
12th-19th Sep
15th-22nd Sep
16th-23rd Sep
17th-24th Sep
22nd-29th Sep
24th Sep – 1st Oct
26th Sep – 3rd Oct
29th Sep – 6th Oct
3rd-10th Oct
8th-15th Oct
20th-27th Oct
21st-28th Oct
28th Oct – 4th Nov
5th-12th Nov
12th-19th Nov
17th-24th Nov

Chicago – Guayaquil: $374
26th Sep – 3rd Oct
27th Sep – 4th Oct
29th Sep – 6th Oct
7th-14th Oct
8th-15th Oct
10th-17th Oct
15th-22nd Oct
6th-13th Nov
7th-14th Nov
8th-15th Nov
10th-17th Nov
11th-18th Nov
12th-19th Nov
14th-21st Nov
16th-23rd Nov
17th-24th Nov
18th-25th Nov

Chicago – Manaus: $499
3rd-10th Sep
10th-17th Sep
12th-19th Sep
17th-24th Sep
19th-26th Sep
24th Sep – 1st Oct
28th Sep – 5th Oct
30th Sep – 7th Oct
7th-14th Oct
8th-15th Oct
9th-16th Oct
10th-17th Oct
11th-18th Oct
12th-19th Oct
14th-21st Oct
15th-22nd Oct
16th-23rd Oct
18th-25th Oct
19th-26th Oct
20th-27th Oct
21st-28th Oct
22nd-29th Oct
25th Oct – 1st Nov
26th Oct – 2nd Nov
27th Oct – 3rd Nov
28th Oct – 4th Nov
29th Oct – 5th Nov
31st Oct – 7th Nov
1st-8th Nov
2nd-9th Nov
3rd-10th Nov
4th-11th Nov
7th-14th Nov
9th-16th Nov
10th-17th Nov
11th-18th Nov
14th-21st Nov
15th-22nd Nov
16th-23rd Nov
18th-25th Nov

and more…

STOPS:
Panama City

AIRLINES:
Copa Airlines