Cheap Flights from Chicago, IL to Santo Domingo from $442
On Cheapflightsplus.com you will find 21 connecting flights from Chicago to Santo Domingo. You can compare airfare deals from 4 airlines and multiple travel sites from $442, book and save on cheap plane tickets and last minute offers. Also check out CHI-SDQ flight schedule to find best flight time, convenient departure and arrival airports.
Find One-Way and Round-Trip Chicago to Santo Domingo Flight Deals
To find the cheapest one way airline ticket select the date with the lowest price on the calendar below and click «Find Flights».
To search for round-trip flight deals click on the link «Check prices for return flights» and select the date of the return flight.
Cheapest flights in November: $442 (one-way), $758 (round-trip).
Direct flights
Check prices for return flight
Best Flights from Chicago to Santo Domingo Today
Take a look at the list of non stop flights and flights with layovers from Chicago to Santo Domingo with the lowest price of $442. Take a look at the list of flights with layovers from Chicago to Santo Domingo from $442. There’re no direct flights. The fastest connecting flight – 21h 25m.
| Price | Departure | Arrival | Flight Duration | Airline | Flight |
|---|---|---|---|---|---|
| from $442 | 19:46 Chicago O'Hare International | 09:15+2 дня Santo Domingo La Isabela Int | 35h 29m layover 9h 16m - Miami 20h 18m - Port-au-Prince | Spirit Airlines | NK158 NK951 Q48451 |
| from $453 | 05:00 Chicago O'Hare International | 13:30+1 день Santo Domingo La Isabela Int | 30h 30m layover 2h 38m - Miami 20h 50m - Aruba | Spirit Airlines | NK2 NK885 Y2172 |
| from $486 | 13:44 Chicago O'Hare International | 12:30+2 дня Santo Domingo La Isabela Int | 44h 46m layover 13h 49m - San Juan 24h 10m - Saint Martin | Spirit Airlines | NK172 3M107 Y2162 |
| from $487 | 08:30 Chicago O'Hare International | 13:30+2 дня Santo Domingo La Isabela Int | 51h 0m layover 25h 0m - Miami 18h 56m - Aruba | Spirit Airlines | NK1986 NK885 Y2172 |
| from $527 | 16:20 Chicago O'Hare International | 13:30+2 дня Santo Domingo La Isabela Int | 43h 10m layover 17h 7m - Miami 18h 56m - Aruba | Spirit Airlines | NK1 NK885 Y2172 |
| from $552 | 05:00 Chicago O'Hare International | 13:30+1 день Santo Domingo La Isabela Int | 30h 30m layover 2h 32m - Miami 20h 50m - Aruba | Spirit Airlines | NK19 NK885 Y2172 |
| from $599 | 14:28 Chicago O'Hare International | 13:45+2 дня Santo Domingo La Isabela Int | 45h 17m layover 13h 17m - Miami 24h 50m - Willemstad | Spirit Airlines | NK717 AD8787 Y2152 |
| from $606 | 13:50 Chicago O'Hare International | 12:30+2 дня Santo Domingo La Isabela Int | 44h 40m layover 13h 50m - San Juan 24h 10m - Saint Martin | Spirit Airlines | NK491 3M107 Q48439 |
| from $618 | 13:35 Chicago O'Hare International | 16:00+1 день Santo Domingo La Isabela Int | 24h 25m layover 10h 35m - Bogota 5h 10m - Willemstad | Avianca | AV263 AV8374 W1809 |
| from $682 | 11:15 Chicago Midway | 13:30+2 дня Santo Domingo La Isabela Int | 48h 15m layover 19h 28m - Toronto 20h 52m - Aruba | Porter Airlines | PD2388 WS2198 Y2172 |
| from $717 | 13:54 Chicago O'Hare International | 13:45+2 дня Santo Domingo La Isabela Int | 45h 51m layover 12h 49m - Panama City 24h 25m - Willemstad | Compania Panamena de Aviacion | CM229 CM288 Q48435 |
| from $725 | 13:44 Chicago O'Hare International | 12:30+2 дня Santo Domingo La Isabela Int | 44h 46m layover 13h 49m - San Juan 24h 10m - Saint Martin | Spirit Airlines | NK172 3M107 Q48439 |
| from $731 | 12:55 Chicago Midway | 12:30+2 дня Santo Domingo La Isabela Int | 45h 35m layover 17h 53m - Toronto 20h 14m - Saint Martin | Porter Airlines | PD2388 WS2276 Q48439 |
| from $747 | 17:35 Chicago Midway | 13:30+2 дня Santo Domingo La Isabela Int | 41h 55m layover 13h 8m - Toronto 20h 52m - Aruba | Porter Airlines | PD2394 WS2198 Y2172 |
| from $838 | 14:05 Chicago O'Hare International | 13:30+1 день Santo Domingo La Isabela Int | 21h 25m layover 10h 10m - Bogota 2h 30m - Aruba | Avianca | AV263 AV242 Y2172 |
| from $1059 | 13:35 Chicago O'Hare International | 13:45+1 день Santo Domingo La Isabela Int | 22h 10m layover 10h 35m - Bogota 2h 55m - Willemstad | Avianca | AV263 AV92 Y2152 |
Show all tickets
*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on May 11, 2025
Flight Schedule Chicago (Illinois) to Santo Domingo
Full flight schedule will help you in detecting at what time planes fly from Chicago to Santo Domingo. You can also specify the concrete flights and airlines on the route and how long the flight actually is. Use the calendar for today, tomorrow or other specific date as some flights are available only on certain days of the week.
| Departure | Arrival | Flight Details | Flight Duration | Price |
|---|---|---|---|---|
|
05:00 — 13:30
+1 day
|
05:00 — 09:09
NK2
Spirit Airlines
Chicago — Miami
2h 38m stop
11:47 — 15:40
NK885
Spirit Airlines
Miami — Aruba
20h 50m stop
12:30 — 13:30
Y2172
Y2
Aruba — Santo Domingo
|
30h 30m including layover |
Find flight
from$453 |
|
|
05:00 — 13:30
+1 day
|
05:00 — 09:00
NK19
Spirit Airlines
Chicago — Miami
2h 32m stop
11:46 — 15:40
NK885
Spirit Airlines
Miami — Aruba
20h 50m stop
12:30 — 13:30
Y2172
Y2
Aruba — Santo Domingo
|
30h 30m including layover |
Find flight
from$552 |
|
|
06:54 — 09:15
+2 days
|
06:54 — 13:10
CM236
Compania Panamena de Aviacion
Chicago — Panama City
20h 50m stop
10:00 — 13:00
S6409
Salmon Air
Panama City — Port-au-Prince
18h 30m stop
07:30 — 09:15
Q48451
Q4
Port-au-Prince — Santo Domingo
|
48h 21m including layover |
Find flight
from$1688 |
|
|
08:30 — 13:30
+2 days
|
08:30 — 12:37
NK1986
Spirit Airlines
Chicago — Miami
25h stop
13:37 — 17:34
NK885
Spirit Airlines
Miami — Aruba
18h 56m stop
12:30 — 13:30
Y2172
Y2
Aruba — Santo Domingo
|
51h including layover |
Find flight
from$487 |
|
|
10:42 — 13:45
+2 days
|
10:42 — 15:00
NK1
Spirit Airlines
Chicago — Miami
17h stop
08:00 — 11:55
AD8787
Azul
Miami — Willemstad
24h 50m stop
12:45 — 13:45
Q48435
Q4
Willemstad — Santo Domingo
|
49h 3m including layover |
Find flight
from$624 |
|
|
11:15 — 13:30
+2 days
|
11:15 — 13:57
PD2388
Porter Airlines
Chicago — Toronto
19h 28m stop
09:25 — 15:38
WS2198
WestJet
Toronto — Aruba
20h 52m stop
12:30 — 13:30
Y2172
Y2
Aruba — Santo Domingo
|
48h 15m including layover |
Find flight
from$682 |
|
|
12:55 — 12:30
+2 days
|
12:55 — 15:37
PD2388
Porter Airlines
Chicago — Toronto
17h 53m stop
09:30 — 15:17
WS2276
WestJet
Toronto — Saint Martin
20h 14m stop
11:30 — 12:30
Q48439
Q4
Saint Martin — Santo Domingo
|
45h 35m including layover |
Find flight
from$731 |
|
|
13:35 — 16:00
+1 day
|
13:35 — 20:25
AV263
Avianca
Chicago — Bogota
10h 35m stop
07:00 — 09:50
AV8374
Avianca
Bogota — Willemstad
5h 10m stop
15:00 — 16:00
W1809
W1
Willemstad — Santo Domingo
|
24h 25m including layover |
Find flight
from$618 |
|
|
13:35 — 13:45
+1 day
|
13:35 — 20:25
AV263
Avianca
Chicago — Bogota
10h 35m stop
07:00 — 09:50
AV92
Avianca
Bogota — Willemstad
2h 55m stop
12:45 — 13:45
Y2152
Y2
Willemstad — Santo Domingo
|
22h 10m including layover |
Find flight
from$1059 |
|
|
13:35 — 13:45
+1 day
|
13:35 — 20:25
AV263
Avianca
Chicago — Bogota
10h 35m stop
07:00 — 09:50
AV92
Avianca
Bogota — Willemstad
2h 55m stop
12:45 — 13:45
Q48435
Q4
Willemstad — Santo Domingo
|
22h 10m including layover |
Find flight
from$1234 |
|
|
13:44 — 12:30
+2 days
|
13:44 — 20:21
NK172
Spirit Airlines
Chicago — San Juan
13h 49m stop
10:10 — 11:20
3M107
Gulfstream International Airlines
San Juan — Saint Martin
24h 10m stop
11:30 — 12:30
Y2162
Y2
Saint Martin — Santo Domingo
|
44h 46m including layover |
Find flight
from$486 |
|
|
13:44 — 12:30
+2 days
|
13:44 — 20:21
NK172
Spirit Airlines
Chicago — San Juan
13h 49m stop
10:10 — 11:20
3M107
Gulfstream International Airlines
San Juan — Saint Martin
24h 10m stop
11:30 — 12:30
Q48439
Q4
Saint Martin — Santo Domingo
|
44h 46m including layover |
Find flight
from$725 |
|
|
13:50 — 12:30
+2 days
|
13:50 — 20:20
NK491
Spirit Airlines
Chicago — San Juan
13h 50m stop
10:10 — 11:20
3M107
Gulfstream International Airlines
San Juan — Saint Martin
24h 10m stop
11:30 — 12:30
Q48439
Q4
Saint Martin — Santo Domingo
|
44h 40m including layover |
Find flight
from$606 |
|
|
13:54 — 13:45
+2 days
|
13:54 — 20:22
CM229
Compania Panamena de Aviacion
Chicago — Panama City
12h 49m stop
09:11 — 12:20
CM288
Compania Panamena de Aviacion
Panama City — Willemstad
24h 25m stop
12:45 — 13:45
Q48435
Q4
Willemstad — Santo Domingo
|
45h 51m including layover |
Find flight
from$717 |
|
|
14:05 — 13:30
+1 day
|
13:35 — 20:25
AV263
Avianca
Chicago — Bogota
10h 10m stop
07:05 — 10:00
AV242
Avianca
Bogota — Aruba
2h 30m stop
12:30 — 13:30
Y2172
Y2
Aruba — Santo Domingo
|
21h 25m including layover |
Find flight
from$838 |
|
|
14:28 — 13:45
+2 days
|
14:28 — 18:43
NK717
Spirit Airlines
Chicago — Miami
13h 17m stop
08:00 — 11:55
AD8787
Azul
Miami — Willemstad
24h 50m stop
12:45 — 13:45
Y2152
Y2
Willemstad — Santo Domingo
|
45h 17m including layover |
Find flight
from$599 |
|
|
16:20 — 13:30
+2 days
|
16:20 — 20:30
NK1
Spirit Airlines
Chicago — Miami
17h 7m stop
13:37 — 17:34
NK885
Spirit Airlines
Miami — Aruba
18h 56m stop
12:30 — 13:30
Y2172
Y2
Aruba — Santo Domingo
|
43h 10m including layover |
Find flight
from$527 |
|
|
17:11 — 13:45
+2 days
|
17:11 — 21:26
NK158
Spirit Airlines
Chicago — Miami
10h 34m stop
08:00 — 11:55
AD8787
Azul
Miami — Willemstad
24h 50m stop
12:45 — 13:45
Q48435
Q4
Willemstad — Santo Domingo
|
42h 34m including layover |
Find flight
from$650 |
|
|
17:35 — 13:30
+2 days
|
17:35 — 20:17
PD2394
Porter Airlines
Chicago — Toronto
13h 8m stop
09:25 — 15:38
WS2198
WestJet
Toronto — Aruba
20h 52m stop
12:30 — 13:30
Y2172
Y2
Aruba — Santo Domingo
|
41h 55m including layover |
Find flight
from$747 |
|
|
19:46 — 09:15
+2 days
|
19:46 — 23:54
NK158
Spirit Airlines
Chicago — Miami
9h 16m stop
09:10 — 11:12
NK951
Spirit Airlines
Miami — Port-au-Prince
20h 18m stop
07:30 — 09:15
Q48451
Q4
Port-au-Prince — Santo Domingo
|
35h 29m including layover |
Find flight
from$442 |
|
|
19:46 — 13:30
+2 days
|
19:46 — 23:54
NK158
Spirit Airlines
Chicago — Miami
11h 52m stop
11:46 — 15:40
NK885
Spirit Airlines
Miami — Aruba
20h 50m stop
12:30 — 13:30
Y2172
Y2
Aruba — Santo Domingo
|
39h 44m including layover |
Find flight
from$549 |
|
*Departure and arrival times - local. Updated on May 11, 2025
Flight Information
Below we will explain in detail what the flights cost on the destination from Chicago to Santo Domingo depends on and how to choose the most interesting flight option for you.
Distance between Chicago and Santo Domingo is 3113 miles. Time difference between the cities is 2h. Airplanes depart 05:00 to 19:46 from 7 Chicago airports and arrive 05:00 to 19:46 to 3 Santo Domingo airports. Average flight time is 43h 10m.
- The fastest flight 21h 25m
- Average flight time 43h 10m
- The earliest flight 05:00
- The latest flight 19:46
- Distance 1935 ml
The cheapest months to travel to Santo Domingo are november (from 442 $), february (from 453 $), january (from 486 $).
The most expensive months are december (from 623 $), january (from 486 $), february (from 453 $).
What is the lowest airfare Chicago to Santo Domingo?
The cheapest plane ticket found by our users is $442. This airfare is for economy class on one-way NK158 flight by Spirit Airlines for November 12, 2024 which leaves O'Hare International in Chicago at 19:46 am and arrives at Santo Domingo La Isabela Int at 09:15.
Economy class
$442
Business class
?
First class
?
Popular Airlines on the Route
The flight Chicago — Santo Domingo is served by 4 regular airlines and 2 low-cost airlines. Most of the flights on this route are operated by Porter Airlines - 3 departures per week at the price of from $ 682 . And the most expensive tickets are offered by Compania Panamena de Aviacion airline - from $ 1688.
Direct flights
There’re no direct flights on this route. Try flights with stops.
Connecting Flights
There are 21 flights with layovers on the route. The fastest connecting flight is AV263 by Avianca takes 21h 25m and the cheapest is NK158 by Spirit Airlines for $442.
- PD - Porter Airlinesfrom $682Find
- AV - Aviancafrom $618Find
- CM - Compania Panamena de Aviacionfrom $717Find
- NK - Spirit Airlinesfrom $442Find
See more connecting flights
Airports
You can fly from Chicago to Santo Domingo from 7 airports (O'Hare International, Midway, Dupage County, Chicago FSS, Merrill C Meigs (closed), Pal-Waukee, Chicago NAS).
Chicago airports
- O'Hare International-ORDfrom $442Find
- Midway-MDWfrom $682Find
- Dupage County-DPAFind
- Chicago FSS-CHIFind
- Merrill C Meigs (closed)-CGXFind
- Pal-Waukee-PWKFind
- Chicago NAS-NOHFind
Santo Domingo airports
- La Isabela Int-JBQFind
- Las Americas-SDQFind
- Santo Domingo Herrera-HEXFind
Airplanes
There are flights to Santo Domingo from Chicago by 4 airlines that use 0 aircraft brands. They range from huge modern airplanes to small-sized.
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Top International Destinations from Chicago
Our state-of-the art metasearch will definitely provide you with the best airfare on international flights. We’re proud to partner with many reliable travel suppliers located outside the US what gives us an opportunity to offer the most competitive prices on far destinations.
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How to book a plane ticket yourself?
- Fill in the search parameters — cities of departure and destination, departure and return dates and click «Find flights»
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- Click «Buy» when you are ready — our system will redirect you to the site that sells the selected flight ticket.
- Fill in all passenger and payment information — passport and contact information, please double check all passengers’ names and make a payment for your itinerary.
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