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Cheap flights from Chicago O'Hare Intl Airport to Santiago de los Caballeros from $187

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 11/19. 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
3:21 pm - 2:42 amORD-STI
9h 21m1 stop
Spirit Airlines Logo
3:43 am - 11:14 amSTI-ORD
9h 31m1 stop
$283Spirit Airlines
Find Deal
Sat, Dec 6 - Fri, Dec 12
Multiple Airlines Logo
11:42 am - 5:06 pmORD-STI
27h 24m1 stop
Multiple Airlines Logo
6:18 pm - 7:29 pmSTI-ORD
27h 11m1 stop
$306Multiple Airlines
Find Deal
Sun, Jan 25 - Wed, Feb 11
Spirit Airlines Logo
8:41 am - 5:06 pmORD-STI
6h 25m1 stop
Spirit Airlines Logo
6:18 pm - 9:23 amSTI-ORD
17h 05m1 stop
$314Spirit Airlines
Find Deal
Mon, Jan 12 - Mon, Feb 2
Spirit Airlines Logo
3:21 pm - 2:42 amORD-STI
9h 21m1 stop
Spirit Airlines Logo
3:43 am - 11:14 amSTI-ORD
9h 31m1 stop
$318Spirit Airlines
Find Deal
Fri, Dec 5 - Thu, Dec 11
Multiple Airlines Logo
5:05 am - 5:06 pmORD-STI
10h 01m1 stop
Multiple Airlines Logo
6:18 pm - 7:29 pmSTI-ORD
27h 11m1 stop
$321Multiple Airlines
Find Deal
Wed, Jan 21 - Wed, Feb 11
Spirit Airlines Logo
3:21 pm - 2:42 amORD-STI
9h 21m1 stop
Spirit Airlines Logo
3:43 am - 11:14 amSTI-ORD
9h 31m1 stop
$326Spirit Airlines
Find Deal
Sat, Dec 6 - Sat, Dec 13
Multiple Airlines Logo
5:20 am - 5:06 pmORD-STI
33h 46m2 stops
Multiple Airlines Logo
6:18 pm - 7:29 pmSTI-ORD
27h 11m1 stop
$333Multiple Airlines
Find Deal
Fri, Jan 23 - Wed, Feb 11
Delta Logo
1:30 pm - 11:54 pmORD-STI
8h 24m1 stop
Delta Logo
6:35 am - 5:37 pmSTI-ORD
13h 02m1 stop
$358Delta
Find Deal
Thu, Jan 22 - Fri, Feb 6
JetBlue Logo
2:05 pm - 12:23 amORD-STI
8h 18m1 stop
JetBlue Logo
4:10 am - 1:10 pmSTI-ORD
11h 00m1 stop
$398JetBlue
Find Deal
Sat, Jan 17 - Fri, Jan 30
Delta Logo
10:35 am - 11:54 pmORD-STI
11h 19m2 stops
Delta Logo
6:35 am - 8:38 pmSTI-ORD
16h 03m2 stops
$402Delta
Find Deal
Sun, Jan 18 - Sat, Jan 31

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

Our best Spirit Airlines deals on Chicago O'Hare Intl Airport to Santiago de los Caballeros flight tickets
Spirit Airlines
Dec 6
ORD3:21 pmChicago O'Hare Intl
9h 21m
1 stop
STI2:42 amSantiago de los Caballeros
Dec 12
STI3:43 amSantiago de los Caballeros
9h 31m
1 stop
ORD11:14 amChicago O'Hare Intl
$283
Find similar
Spirit Airlines
Jan 12
ORD8:41 amChicago O'Hare Intl
6h 25m
1 stop
STI5:06 pmSantiago de los Caballeros
Feb 2
STI6:18 pmSantiago de los Caballeros
17h 05m
1 stop
ORD9:23 amChicago O'Hare Intl
$314
Find similar
Spirit Airlines
Dec 5
ORD3:21 pmChicago O'Hare Intl
9h 21m
1 stop
STI2:42 amSantiago de los Caballeros
Dec 11
STI3:43 amSantiago de los Caballeros
9h 31m
1 stop
ORD11:14 amChicago O'Hare Intl
$318
Find similar

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

Our best Delta deals on Chicago O'Hare Intl Airport to Santiago de los Caballeros flight tickets
Delta
Jan 22
ORD1:30 pmChicago O'Hare Intl
8h 24m
1 stop
STI11:54 pmSantiago de los Caballeros
Feb 6
STI6:35 amSantiago de los Caballeros
13h 02m
1 stop
ORD5:37 pmChicago O'Hare Intl
$358
Find similar
Delta
Jan 18
ORD10:35 amChicago O'Hare Intl
11h 19m
2 stops
STI11:54 pmSantiago de los Caballeros
Jan 31
STI6:35 amSantiago de los Caballeros
16h 03m
2 stops
ORD8:38 pmChicago O'Hare Intl
$402
Find similar
Delta
Oct 29
ORD7:10 amChicago O'Hare Intl
10h 56m
2 stops
STI7:06 pmSantiago de los Caballeros
Nov 12
STI6:40 amSantiago de los Caballeros
14h 11m
2 stops
ORD6:51 pmChicago O'Hare Intl
$425
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 October 22, 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

Sat 12/6

3:21 pm-2:42 am

1 stop9h 21m

Santiago de los Caballeros

Fri 12/12

3:43 am-11:14 am

1 stop9h 31m

$283

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Sun 1/25

11:42 am-5:06 pm

1 stop27h 24m

Santiago de los Caballeros

Wed 2/11

6:18 pm-7:29 pm

1 stop27h 11m

$306

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Mon 1/12

8:41 am-5:06 pm

1 stop6h 25m

Santiago de los Caballeros

Mon 2/2

6:18 pm-9:23 am

1 stop17h 05m

$314

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Fri 12/5

3:21 pm-2:42 am

1 stop9h 21m

Santiago de los Caballeros

Thu 12/11

3:43 am-11:14 am

1 stop9h 31m

$318

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Wed 1/21

5:05 am-5:06 pm

1 stop10h 01m

Santiago de los Caballeros

Wed 2/11

6:18 pm-7:29 pm

1 stop27h 11m

$321

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Sat 12/6

3:21 pm-2:42 am

1 stop9h 21m

Santiago de los Caballeros

Sat 12/13

3:43 am-11:14 am

1 stop9h 31m

$326

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Fri 1/23

5:20 am-5:06 pm

2 stops33h 46m

Santiago de los Caballeros

Wed 2/11

6:18 pm-7:29 pm

1 stop27h 11m

$333

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Thu 1/22

1:30 pm-11:54 pm

1 stop8h 24m

Santiago de los Caballeros

Fri 2/6

6:35 am-5:37 pm

1 stop13h 02m

$358

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Sat 1/17

2:05 pm-12:23 am

1 stop8h 18m

Santiago de los Caballeros

Fri 1/30

4:10 am-1:10 pm

1 stop11h 00m

$398

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Sun 1/18

10:35 am-11:54 pm

2 stops11h 19m

Santiago de los Caballeros

Sat 1/31

6:35 am-8:38 pm

2 stops16h 03m

$402

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 14 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 25m 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
8,990 reviews
Search United Airlines flights
Spirit AirlinesPriceFrom $298Free CancellationRating
6.3
8,098 reviews
Search Spirit Airlines flights
DeltaPriceFrom $356Free CancellationRating
7.9
7,981 reviews
Search Delta flights
JetBluePriceFrom $391Free CancellationRating
7.2
2,908 reviews
Search JetBlue flights
American AirlinesPriceFrom $395Free CancellationRating
7.2
11,028 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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