Chicago to Dominican Republic flight deals
Compare flights from Chicago to Dominican Republic 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
Dec 8–15, 2026 · 1 adult · Economy · Round trip
- ORD → La Romana (LRM): $341 Axel vs $360 airline · Save $19. Check LRM prices
- ORD → Punta Cana (PUJ): $341 Axel vs $360 airline · Save $19. Check PUJ prices
- ORD → Santo Domingo (SDQ): $464 Axel vs $490 airline · Save $26. Check SDQ prices
- ORD → Santiago (STI): $476 Axel vs $503 airline · Save $27. Check STI prices
- MDW → Punta Cana (PUJ): $575 Axel vs $606 airline · Save $31. Check PUJ prices
- ORD → Puerto Plata (POP): $617 Axel vs $650 airline · Save $33. Check POP prices
Flights from Chicago · Chicago to Caribbean flight deals
Explore destinations
La Romana (LRM) · Puerto Plata (POP) · Punta Cana (PUJ) · Santo Domingo (SDQ) · Santiago (STI)
Fares observed September 28 – October 2, 2026. USD for the travelers shown. Search a trip for current prices. For starting totals, choose a return flight to confirm the final price.
November 2026
1 adult · Economy · Round-trip totals
| From | Destination | Travel dates | Flights (out / return) | Axel | Airline fare | Search |
|---|---|---|---|---|---|---|
| ORD | La Romana (LRM) | Nov 10–17, 2026 · 7 days | 2 stops / 1 stop · 18h 13m / 9h 27m | $346 · Save $19 | $365 | Check Axel prices |
| ORD | Puerto Plata (POP) | Nov 10–17, 2026 · 7 days | 1 stop / 2 stops · 6h 25m / 19h 45m | $704 · Save $39 | $743 | Check Axel prices |
| ORD | Puerto Plata (POP) | Nov 10–17, 2026 · 7 days | 1 stop / 1 stop · 6h 25m / 8h 52m | $745 · Save $42 | $787 | 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 | Santiago (STI) | Nov 10–17, 2026 · 7 days | 1 stop / 1 stop · 6h 47m / 8h 48m | $403 · Save $23 | $426 | Check Axel prices |
| ORD | Santo Domingo (SDQ) | Nov 10–17, 2026 · 7 days | 1 stop / 1 stop · 18h 54m / 11h 51m | $453 · Save $25 | $478 | 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 | La Romana (LRM) | Nov 24–Dec 1, 2026 · 7 days | 2 stops / 2 stops · 17h 36m / 18h 9m | $464 · Save $26 | $490 | Check Axel prices |
| ORD | Puerto Plata (POP) | Nov 24–Dec 1, 2026 · 7 days | 1 stop / 2 stops · 6h 24m / 19h 50m | $711 · Save $38 | $749 | Check Axel prices |
| ORD | Puerto Plata (POP) | Nov 24–Dec 1, 2026 · 7 days | 1 stop / 2 stops · 6h 24m / 10h 44m | $733 · Save $39 | $772 | Check Axel prices |
| ORD | Santo Domingo (SDQ) | Nov 24–Dec 1, 2026 · 7 days | 1 stop / 1 stop · 6h 43m / 14h 41m | $464 · Save $26 | $490 | Check Axel prices |
| ORD | Santo Domingo (SDQ) | Nov 24–Dec 1, 2026 · 7 days | 1 stop / 2 stops · 6h 43m / 12h 0m | $470 · Save $25 | $495 | Check Axel prices |
1 adult · Economy · Round-trip starting totals
| From | Destination | Travel dates | Outbound flight | Axel | Airline fare | Search |
|---|---|---|---|---|---|---|
| ORD | Punta Cana (PUJ) | Nov 24–28, 2026 · 4 days | 1 stop · 9h 58m | From $755 · Save $41 | From $796 | Check Axel prices |
| ORD | Punta Cana (PUJ) | Nov 24–28, 2026 · 4 days | Nonstop · 4h 40m | From $1,423 · Save $82 | From $1,505 | Check Axel prices |
December 2026
1 adult · Economy · Round-trip totals
| From | Destination | Travel dates | Flights (out / return) | Axel | Airline fare | Search |
|---|---|---|---|---|---|---|
| ORD | La Romana (LRM) | Dec 8–15, 2026 · 7 days | 1 stop / 1 stop · 6h 57m / 9h 4m | $341 · Save $19 | $360 | Check Axel prices |
| ORD | Puerto Plata (POP) | Dec 8–15, 2026 · 7 days | 1 stop / 1 stop · 6h 25m / 8h 4m | $617 · Save $33 | $650 | 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 |
| ORD | Punta Cana (PUJ) | Dec 8–15, 2026 · 7 days | 1 stop / 1 stop · 6h 36m / 8h 19m | $341 · Save $19 | $360 | Check Axel prices |
| ORD | Santiago (STI) | Dec 8–15, 2026 · 7 days | 1 stop / 1 stop · 7h 21m / 9h 2m | $476 · Save $27 | $503 | Check Axel prices |
| ORD | Santo Domingo (SDQ) | Dec 8–15, 2026 · 7 days | 1 stop / 1 stop · 7h 41m / 8h 57m | $464 · Save $26 | $490 | Check Axel prices |
| ORD | La Romana (LRM) | Dec 22–29, 2026 · 7 days | 2 stops / 2 stops · 26h 23m / 17h 21m | $703 · Save $39 | $742 | Check Axel prices |
| ORD | Puerto Plata (POP) | Dec 22–29, 2026 · 7 days | 2 stops / 1 stop · 27h 3m / 7h 33m | $850 · Save $48 | $898 | Check Axel prices |
| ORD | Santiago (STI) | Dec 22–29, 2026 · 7 days | 1 stop / 1 stop · 8h 27m / 9h 18m | $817 · Save $44 | $861 | Check Axel prices |
| ORD | Santo Domingo (SDQ) | Dec 22–29, 2026 · 7 days | 1 stop / 1 stop · 11h 59m / 18h 52m | $818 · Save $46 | $864 | 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.
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