Cheap trips from Chicago
A week under $1,000 from Chicago.
From Chicago, 10 destinations fit a full week under $1,000, airfare plus seven days on the ground. It starts at Mérida, about $585 all in. $1,000 also reaches Cartagena, Puerto Vallarta and San José. Just over the line: Tbilisi at $1,021.
Prices updated 2026-06-07.
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Every week under $1,000 from Chicago
- Mérida, Mexicoflight $235 + $50/day for a week$585
- Guatemala City, Guatemalaflight $295 + $45/day for a week$610
- Oaxaca, Mexicoflight $269 + $55/day for a week$654
- Mexico City, Mexicoflight $257 + $65/day for a week$712
- Medellín, Colombiaflight $415 + $50/day for a week$765
- Bogotá, Colombiaflight $393 + $55/day for a week$778
- San Juan, Puerto Ricoflight $138 + $100/day for a week$838
- Cartagena, Colombiaflight $320 + $75/day for a week$845
- Puerto Vallarta, Mexicoflight $250 + $90/day for a week$880
- San José, Costa Ricaflight $417 + $80/day for a week$977