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Cheap flights from Chicago O'Hare Intl Airport to Santiago de los Caballeros from $146

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago O'Hare Intl Airport to Santiago de los Caballeros departing on 1/1. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Chicago O'Hare Intl Airport to Santiago de los Caballeros

Cheap round-trip flights

Enter your travel dates to find the best prices.
Spirit Airlines Logo
1:34 pm - 2:42 amORD-STI
11h 08m2 stops
Spirit Airlines Logo
3:43 am - 11:08 amSTI-ORD
9h 25m1 stop
$307Spirit Airlines
Find Deal
Thu, Dec 4 - Tue, Dec 9
Spirit Airlines Logo
4:21 pm - 2:42 amORD-STI
8h 21m1 stop
Spirit Airlines Logo
3:43 am - 11:08 amSTI-ORD
9h 25m1 stop
$308Spirit Airlines
Find Deal
Thu, Dec 4 - Tue, Dec 9
Multiple Airlines Logo
4:01 pm - 2:42 amORD-STI
32h 41m2 stops
Multiple Airlines Logo
3:43 am - 11:08 amSTI-ORD
9h 25m1 stop
$335Multiple Airlines
Find Deal
Wed, Dec 3 - Tue, Dec 9
American Airlines Logo
7:00 am - 3:32 pmORD-STI
6h 32m1 stop
American Airlines Logo
4:33 pm - 12:30 amSTI-ORD
9h 57m1 stop
$389American Airlines
Find Deal
Mon, Jan 19 - Wed, Jan 28
Multiple Airlines Logo
6:15 pm - 12:22 pmORD-STI
16h 07m2 stops
Multiple Airlines Logo
3:43 am - 11:14 amSTI-ORD
9h 31m1 stop
$397Multiple Airlines
Find Deal
Mon, Dec 1 - Tue, Dec 30
JetBlue Logo
6:04 am - 3:15 pmORD-STI
7h 11m1 stop
JetBlue Logo
11:06 pm - 11:49 amSTI-ORD
14h 43m1 stop
$398JetBlue
Find Deal
Sun, Mar 1 - Thu, Mar 5
American Airlines Logo
8:10 am - 10:56 pmORD-STI
12h 46m1 stop
American Airlines Logo
6:20 am - 3:56 pmSTI-ORD
11h 36m2 stops
$402American Airlines
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Tue, Nov 25 - Tue, Dec 2
JetBlue Logo
7:00 am - 11:26 amORD-STI
26h 26m1 stop
JetBlue Logo
12:52 pm - 9:52 pmSTI-ORD
11h 00m1 stop
$419JetBlue
Find Deal
Wed, Dec 3 - Wed, Dec 10
Delta Logo
1:30 pm - 11:27 pmORD-STI
8h 57m1 stop
Delta Logo
6:00 am - 5:37 pmSTI-ORD
12h 37m1 stop
$458Delta
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Wed, Mar 18 - Thu, Mar 26
Delta Logo
6:45 am - 12:53 amORD-STI
16h 08m2 stops
Delta Logo
6:35 am - 5:45 pmSTI-ORD
13h 10m1 stop
$474Delta
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Sun, Mar 1 - Thu, Mar 5

American Airlines flights from Chicago O'Hare Intl Airport to Santiago de los Caballeros

Our best American Airlines deals on Chicago O'Hare Intl Airport to Santiago de los Caballeros flight tickets
American Airlines
Jan 19
ORD7:00 amChicago O'Hare Intl
6h 32m
1 stop
STI3:32 pmSantiago de los Caballeros
Jan 28
STI4:33 pmSantiago de los Caballeros
9h 57m
1 stop
ORD12:30 amChicago O'Hare Intl
$389
Find similar
American Airlines
Nov 25
ORD8:10 amChicago O'Hare Intl
12h 46m
1 stop
STI10:56 pmSantiago de los Caballeros
Dec 2
STI6:20 amSantiago de los Caballeros
11h 36m
2 stops
ORD3:56 pmChicago O'Hare Intl
$402
Find similar
American Airlines
Dec 1
ORD10:25 amChicago O'Hare Intl
10h 31m
1 stop
STI10:56 pmSantiago de los Caballeros
Dec 31
STI6:00 amSantiago de los Caballeros
20h 43m
1 stop
ORD12:43 amChicago O'Hare Intl
$403
Find similar

JetBlue flights from Chicago O'Hare Intl Airport to Santiago de los Caballeros

Our best JetBlue deals on Chicago O'Hare Intl Airport to Santiago de los Caballeros flight tickets
JetBlue
Mar 1
ORD6:04 amChicago O'Hare Intl
7h 11m
1 stop
STI3:15 pmSantiago de los Caballeros
Mar 5
STI11:06 pmSantiago de los Caballeros
14h 43m
1 stop
ORD11:49 amChicago O'Hare Intl
$398
Find similar
JetBlue
Dec 3
ORD7:00 amChicago O'Hare Intl
26h 26m
1 stop
STI11:26 amSantiago de los Caballeros
Dec 10
STI12:52 pmSantiago de los Caballeros
11h 00m
1 stop
ORD9:52 pmChicago O'Hare Intl
$419
Find similar
JetBlue
Mar 1
ORD12:41 pmChicago O'Hare Intl
6h 59m
1 stop
STI9:40 pmSantiago de los Caballeros
Mar 4
STI4:35 amSantiago de los Caballeros
9h 13m
1 stop
ORD11:48 amChicago O'Hare Intl
$440
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago O'Hare Intl Airport to Santiago de los Caballeros that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated November 6, 2025.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Santiago de los Caballeros that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Thu 12/4

1:34 pm-2:42 am

2 stops11h 08m

Santiago de los Caballeros

Tue 12/9

3:43 am-11:08 am

1 stop9h 25m

$307

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Thu 12/4

4:21 pm-2:42 am

1 stop8h 21m

Santiago de los Caballeros

Tue 12/9

3:43 am-11:08 am

1 stop9h 25m

$308

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Wed 12/3

4:01 pm-2:42 am

2 stops32h 41m

Santiago de los Caballeros

Tue 12/9

3:43 am-11:08 am

1 stop9h 25m

$335

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Mon 1/19

7:00 am-3:32 pm

1 stop6h 32m

Santiago de los Caballeros

Wed 1/28

4:33 pm-12:30 am

1 stop9h 57m

$389

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Mon 12/1

6:15 pm-12:22 pm

2 stops16h 07m

Santiago de los Caballeros

Tue 12/30

3:43 am-11:14 am

1 stop9h 31m

$397

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Sun 3/1

6:04 am-3:15 pm

1 stop7h 11m

Santiago de los Caballeros

Thu 3/5

11:06 pm-11:49 am

1 stop14h 43m

$398

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Tue 11/25

8:10 am-10:56 pm

1 stop12h 46m

Santiago de los Caballeros

Tue 12/2

6:20 am-3:56 pm

2 stops11h 36m

$402

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Wed 12/3

7:00 am-11:26 am

1 stop26h 26m

Santiago de los Caballeros

Wed 12/10

12:52 pm-9:52 pm

1 stop11h 00m

$419

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Wed 3/18

1:30 pm-11:27 pm

1 stop8h 57m

Santiago de los Caballeros

Thu 3/26

6:00 am-5:37 pm

1 stop12h 37m

$458

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Sun 3/1

6:45 am-12:53 am

2 stops16h 08m

Santiago de los Caballeros

Thu 3/5

6:35 am-5:45 pm

1 stop13h 10m

$474

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Santiago de los Caballeros from

How to get the cheapest flight ticket from Chicago O'Hare Intl Airport to Santiago de los Caballeros

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Santiago de los Caballeros?

The cheapest month to fly to Santiago de los Caballeros from Chicago O'Hare Intl Airport is in October. Flight prices, which tend to average around $356, are often lower during this time because this is during the off-season. If you aren’t able to travel to Santiago de los Caballeros during the month of October, then flying in February is also cheap. Prices for this month can be found on momondo for an average of $416.

What is the cheapest day to depart on your flight to Santiago de los Caballeros?

The cheapest day to depart from Chicago O'Hare Intl Airport to Santiago de los Caballeros is on a Tuesday when prices can be found for as low as $425. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Chicago O'Hare Intl Airport to Santiago de los Caballeros for around $683.

What is the cheapest time of day to depart on your flight to Santiago de los Caballeros?

Our data shows that the cheapest Chicago O'Hare Intl Airport to Santiago de los Caballeros flights are usually those with departure times in the afternoon. Our users have found flights to Santiago de los Caballeros in the afternoon for as low as $393. In the morning is when there is more demand to fly to Santiago de los Caballeros, so prices are often more expensive at around $564 per ticket.

How have Chicago O'Hare Intl Airport to Santiago de los Caballeros flight prices changed over time?

When to book flights from Chicago O'Hare Intl Airport to Santiago de los Caballeros

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago O'Hare Intl Airport to Santiago de los Caballeros according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago O'Hare Intl Airport to Santiago de los Caballeros (ORD to STI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago O'Hare Intl Airport to Santiago de los Caballeros

Direct flights

None
There are no direct flights from Chicago O'Hare Intl Airport to Santiago de los Caballeros. There are no popular flight routes from Chicago O'Hare Intl Airport to Santiago de los Caballeros.
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  • How far is Chicago O'Hare Intl to Santiago de los Caballeros by plane?

    There are 1852.8 mi between Chicago O'Hare Intl and Santiago de los Caballeros. 6h 32m is a normal flight duration for this route.

  • When did momondo last update prices for flights from Chicago O'Hare Intl Airport to Santiago de los Caballeros Airport?

    Prices for flights from Chicago O'Hare Intl Airport to Santiago de los Caballeros Airport are refreshed on a daily basis.

  • How many operators does momondo search for flights from Chicago O'Hare Intl Airport to Santiago de los Caballeros Airport?

  • How old do you have to be to fly from Chicago O'Hare Intl Airport to Santiago de los Caballeros Airport?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago O'Hare Intl Airport to Santiago de los Caballeros Airport.

  • What documentation or ID do you need to fly to Santiago de los Caballeros Airport?

    The travel and health documents required for your trip to Santiago de los Caballeros Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Santiago de los Caballeros Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular airline from Chicago O'Hare Intl Airport to Santiago de los Caballeros?

Best airlines flying from Chicago O'Hare Intl Airport to Santiago de los Caballeros

Compare and see reviews for airlines that fly from Chicago O'Hare Intl Airport to Santiago de los Caballeros with momondo
Airline
Rating
Free Cancellation
Price
United AirlinesPriceFrom $226Free CancellationRating
7.4
9,003 reviews
Search United Airlines flights
Spirit AirlinesPriceFrom $298Free CancellationRating
6.3
8,114 reviews
Search Spirit Airlines flights
DeltaPriceFrom $356Free CancellationRating
7.9
8,004 reviews
Search Delta flights
JetBluePriceFrom $391Free CancellationRating
7.2
2,907 reviews
Search JetBlue flights
American AirlinesPriceFrom $395Free CancellationRating
7.2
11,042 reviews
Search American Airlines flights

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Santiago de los Caballeros?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Chicago to Santiago de los Caballeros for you.

Can I find flights from Chicago to Santiago de los Caballeros with flexible booking policies on momondo?

Flights from Chicago to Santiago de los Caballeros with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Chicago to Santiago de los Caballeros?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Chicago to Santiago de los Caballeros.

I’m not ready to book a flight from Chicago to Santiago de los Caballeros right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Chicago to Santiago de los Caballeros flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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