Arajet's Lowest Priced Flights from Chicago, United States from US$249*!
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1 Passenger
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Tickets for Our Most Popular Flights from Chicago
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US$
Chicago (ORD)to
Sao Paulo (GRU)03/12/2025 - 28/12/2025
From
US$1,493
Seen: 1 hour ago
Round-trip
Economy
Chicago (ORD)to
Punta Cana (PUJ)22/12/2025 - 03/01/2026
From
US$1,409
Seen: 1 day ago
Round-trip
Economy
*Additional fees and charges for optional products and services may apply. More details on https://www.arajet.com/en/baggage
Best Deals for flight from Chicago
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From | To | Fare Type | Dates | Price |
|---|---|---|---|---|
| Chicago (ORD) | Sao Paulo (GRU) | Round-trip / Economy | 05/01/2026 - 25/01/2026 | From US$1,240 Seen: 11 hrs ago |
| Chicago (ORD) | Punta Cana (PUJ) | Round-trip / Economy | 01/04/2026 - 28/04/2026 | From US$249 Seen: 1 day ago |
| Chicago (ORD) | Cancun (CUN) | Round-trip / Economy | 02/03/2026 - 31/03/2026 | From US$389 Seen: 2 hrs ago |
| Chicago (ORD) | Mexico City (NLU) | Round-trip / Economy | 07/01/2026 - 25/01/2026 | From US$441 Seen: 1 hour ago |
*Additional fees and charges for optional products and services may apply. More details on https://www.arajet.com/en/baggage