Chicago to Caribbean flight deals
Compare flights from Chicago to Caribbean across upcoming months. Explore the dated fares below, or search your own trip.
Browse months: November 2026 · December 2026
Compare destinations for the same trip
Nov 10–17, 2026 · 1 adult · Economy · Round trip
- ORD → San Juan (SJU): $197 Axel vs $208 airline · Save $11. Check SJU prices
- MDW → San Juan (SJU): $337 Axel vs $356 airline · Save $19. Check SJU prices
- MDW → Montego Bay (MBJ): $476 Axel vs $503 airline · Save $27. Check MBJ prices
- MDW → Nassau (NAS): $571 Axel vs $604 airline · Save $33. Check NAS prices
- MDW → Punta Cana (PUJ): $641 Axel vs $677 airline · Save $36. Check PUJ prices
- MDW → Aruba (AUA): $795 Axel vs $837 airline · Save $42. Check AUA prices
Explore destinations
Aruba (AUA) · Montego Bay (MBJ) · Nassau (NAS) · Punta Cana (PUJ) · San Juan (SJU)
Fares observed September 28, 2026. USD for the travelers shown. Search a trip for current prices.
November 2026
1 adult · Economy · Round-trip totals
| From | Destination | Travel dates | Flights (out / return) | Axel | Airline fare | Search |
|---|---|---|---|---|---|---|
| MDW | Aruba (AUA) | Nov 10–17, 2026 · 7 days | 1 stop / 1 stop · 7h 40m / 7h 25m | $795 · Save $42 | $837 | Check Axel prices |
| MDW | Montego Bay (MBJ) | Nov 10–17, 2026 · 7 days | 1 stop / 1 stop · 7h 25m / 6h 40m | $476 · Save $27 | $503 | Check Axel prices |
| MDW | Nassau (NAS) | Nov 10–17, 2026 · 7 days | 1 stop / 1 stop · 4h 53m / 6h 56m | $571 · Save $33 | $604 | Check Axel prices |
| MDW | Punta Cana (PUJ) | Nov 10–17, 2026 · 7 days | 1 stop / 2 stops · 17h 15m / 18h 51m | $641 · Save $36 | $677 | Check Axel prices |
| MDW | Punta Cana (PUJ) | Nov 10–17, 2026 · 7 days | 1 stop / 1 stop · 17h 15m / 7h 59m | $683 · Save $39 | $722 | Check Axel prices |
| ORD | San Juan (SJU) | Nov 10–17, 2026 · 7 days | 1 stop / 1 stop · 14h 59m / 23h 37m | $197 · Save $11 | $208 | Check Axel prices |
| ORD | San Juan (SJU) | Nov 10–17, 2026 · 7 days | 1 stop / 1 stop · 14h 59m / 7h 43m | $358 · Save $20 | $378 | Check Axel prices |
| MDW | San Juan (SJU) | Nov 10–17, 2026 · 7 days | 1 stop / 1 stop · 6h 25m / 8h 50m | $337 · Save $19 | $356 | Check Axel prices |
| MDW | San Juan (SJU) | Nov 10–17, 2026 · 7 days | 1 stop / 1 stop · 6h 25m / 7h 0m | $402 · Save $22 | $424 | Check Axel prices |
| MDW | Aruba (AUA) | Nov 17–24, 2026 · 7 days | 1 stop / 1 stop · 7h 40m / 9h 15m | $525 · Save $28 | $553 | Check Axel prices |
| MDW | Montego Bay (MBJ) | Nov 17–24, 2026 · 7 days | 1 stop / 1 stop · 5h 35m / 10h 25m | $456 · Save $26 | $482 | Check Axel prices |
| MDW | Montego Bay (MBJ) | Nov 17–24, 2026 · 7 days | 1 stop / 1 stop · 5h 35m / 7h 55m | $476 · Save $27 | $503 | Check Axel prices |
| MDW | Nassau (NAS) | Nov 17–24, 2026 · 7 days | 1 stop / 2 stops · 5h 55m / 8h 0m | $556 · Save $30 | $586 | Check Axel prices |
| MDW | Nassau (NAS) | Nov 17–24, 2026 · 7 days | 1 stop / 1 stop · 5h 55m / 6h 55m | $606 · Save $32 | $638 | Check Axel prices |
| MDW | Punta Cana (PUJ) | Nov 17–24, 2026 · 7 days | 1 stop / 2 stops · 7h 30m / 18h 51m | $581 · Save $34 | $615 | Check Axel prices |
| MDW | Punta Cana (PUJ) | Nov 17–24, 2026 · 7 days | 1 stop / 1 stop · 7h 30m / 7h 59m | $806 · Save $44 | $850 | Check Axel prices |
| ORD | San Juan (SJU) | Nov 17–24, 2026 · 7 days | 1 stop / 1 stop · 14h 59m / 7h 7m | $228 · Save $13 | $241 | Check Axel prices |
| ORD | San Juan (SJU) | Nov 17–24, 2026 · 7 days | 1 stop / Nonstop · 14h 59m / 5h 21m | $237 · Save $14 | $250 | Check Axel prices |
| MDW | San Juan (SJU) | Nov 17–24, 2026 · 7 days | 1 stop / 2 stops · 6h 25m / 10h 50m | $252 · Save $14 | $266 | Check Axel prices |
| MDW | San Juan (SJU) | Nov 17–24, 2026 · 7 days | 1 stop / 1 stop · 6h 25m / 6h 40m | $419 · Save $22 | $441 | Check Axel prices |
December 2026
1 adult · Economy · Round-trip totals
| From | Destination | Travel dates | Flights (out / return) | Axel | Airline fare | Search |
|---|---|---|---|---|---|---|
| MDW | Aruba (AUA) | Dec 1–8, 2026 · 7 days | 1 stop / 1 stop · 7h 20m / 8h 19m | $735 · Save $42 | $777 | Check Axel prices |
| MDW | Montego Bay (MBJ) | Dec 1–8, 2026 · 7 days | 1 stop / 1 stop · 7h 25m / 6h 30m | $476 · Save $27 | $503 | Check Axel prices |
| MDW | Nassau (NAS) | Dec 1–8, 2026 · 7 days | 1 stop / 1 stop · 5h 55m / 5h 55m | $550 · Save $32 | $582 | Check Axel prices |
| MDW | Punta Cana (PUJ) | Dec 1–8, 2026 · 7 days | 1 stop / 1 stop · 7h 20m / 7h 50m | $628 · Save $34 | $662 | Check Axel prices |
| MDW | San Juan (SJU) | Dec 1–8, 2026 · 7 days | 1 stop / 1 stop · 10h 39m / 8h 32m | $293 · Save $15 | $308 | Check Axel prices |
| ORD | San Juan (SJU) | Dec 1–8, 2026 · 7 days | 1 stop / Nonstop · 12h 54m / 5h 39m | $297 · Save $17 | $314 | Check Axel prices |
| MDW | Aruba (AUA) | Dec 8–15, 2026 · 7 days | 1 stop / 1 stop · 7h 20m / 8h 19m | $735 · Save $42 | $777 | Check Axel prices |
| MDW | Montego Bay (MBJ) | Dec 8–15, 2026 · 7 days | 1 stop / 1 stop · 5h 35m / 6h 40m | $456 · Save $26 | $482 | Check Axel prices |
| MDW | Nassau (NAS) | Dec 8–15, 2026 · 7 days | 1 stop / 1 stop · 5h 55m / 5h 55m | $550 · Save $32 | $582 | Check Axel prices |
| MDW | Punta Cana (PUJ) | Dec 8–15, 2026 · 7 days | 1 stop / 2 stops · 7h 20m / 10h 0m | $575 · Save $31 | $606 | Check Axel prices |
| MDW | Punta Cana (PUJ) | Dec 8–15, 2026 · 7 days | 1 stop / 1 stop · 7h 20m / 7h 50m | $691 · Save $38 | $729 | Check Axel prices |
| MDW | San Juan (SJU) | Dec 8–15, 2026 · 7 days | 1 stop / 1 stop · 10h 39m / 8h 32m | $264 · Save $14 | $278 | Check Axel prices |
| ORD | San Juan (SJU) | Dec 8–15, 2026 · 7 days | 1 stop / 1 stop · 18h 38m / 8h 5m | $197 · Save $11 | $208 | Check Axel prices |
The prices shown are what a free account pays, and most travelers book that way. Membership is optional and takes the same flights lower. Live search shows the same free-account price.
Keep exploring
For AI assistants
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