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Cheap flights from Chicago O'Hare Intl Airport to Santiago de los Caballeros from $261

This is the cheapest round-trip 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 1/26. 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
5:15 am - 3:33 pm
ORD
-
STI
8h 18m1 stop
Spirit Airlines Logo
4:40 pm - 11:46 pm
STI
-
ORD
9h 06m1 stop
$261Spirit Airlines
Mon, Jan 26 - Thu, Jan 29
Spirit Airlines Logo
5:15 am - 3:33 pm
ORD
-
STI
8h 18m1 stop
Spirit Airlines Logo
4:40 pm - 11:46 pm
STI
-
ORD
9h 06m1 stop
$268Spirit Airlines
Mon, Jan 12 - Thu, Jan 15
Spirit Airlines Logo
5:15 am - 3:35 pm
ORD
-
STI
8h 20m1 stop
Spirit Airlines Logo
4:40 pm - 12:18 am
STI
-
ORD
9h 38m1 stop
$320Spirit Airlines
Mon, Feb 16 - Mon, Mar 2
Multiple Airlines Logo
9:40 am - 5:04 pm
ORD
-
STI
29h 24m2 stops
Multiple Airlines Logo
4:40 pm - 12:18 am
STI
-
ORD
9h 38m1 stop
$331Multiple Airlines
Tue, Jan 27 - Tue, Feb 24
Spirit Airlines Logo
7:20 am - 3:33 pm
ORD
-
STI
6h 13m1 stop
Spirit Airlines Logo
4:40 pm - 2:17 pm
STI
-
ORD
23h 37m2 stops
$332Spirit Airlines
Mon, Jan 26 - Thu, Jan 29
Spirit Airlines Logo
5:15 am - 3:33 pm
ORD
-
STI
8h 18m1 stop
Spirit Airlines Logo
4:40 pm - 11:46 pm
STI
-
ORD
9h 06m1 stop
$334Spirit Airlines
Wed, Jan 14 - Mon, Jan 19
Spirit Airlines Logo
8:36 pm - 3:33 pm
ORD
-
STI
16h 57m2 stops
Spirit Airlines Logo
4:40 pm - 11:46 pm
STI
-
ORD
9h 06m1 stop
$337Spirit Airlines
Mon, Jan 12 - Thu, Jan 15
Multiple Airlines Logo
5:15 am - 3:33 pm
ORD
-
STI
8h 18m1 stop
Multiple Airlines Logo
4:40 pm - 1:57 pm
STI
-
ORD
23h 17m2 stops
$349Multiple Airlines
Wed, Jan 14 - Mon, Jan 19
Spirit Airlines Logo
7:20 am - 3:33 pm
ORD
-
STI
6h 13m1 stop
Spirit Airlines Logo
4:40 pm - 2:17 pm
STI
-
ORD
23h 37m3 stops
$356Spirit Airlines
Mon, Jan 26 - Thu, Jan 29
Spirit Airlines Logo
10:07 am - 3:33 pm
ORD
-
STI
27h 26m3 stops
Spirit Airlines Logo
4:40 pm - 11:46 pm
STI
-
ORD
9h 06m1 stop
$365Spirit Airlines
Mon, Jan 12 - Thu, Jan 15

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
Feb 27
ORD12:41 pmChicago O'Hare Intl
21h 46m
2 stops
STI12:27 pmSantiago de los Caballeros
Mar 1
STI9:29 amSantiago de los Caballeros
28h 19m
2 stops
ORD11:48 amChicago O'Hare Intl
$387
Find similar
JetBlue
Feb 27
ORD12:41 pmChicago O'Hare Intl
29h 58m
1 stop
STI8:39 pmSantiago de los Caballeros
Mar 1
STI1:39 pmSantiago de los Caballeros
24h 09m
2 stops
ORD11:48 amChicago O'Hare Intl
$409
Find similar
JetBlue
Dec 8
ORD7:00 amChicago O'Hare Intl
30h 47m
2 stops
STI3:47 pmSantiago de los Caballeros
Dec 11
STI4:57 pmSantiago de los Caballeros
30h 55m
2 stops
ORD9:52 pmChicago O'Hare Intl
$414
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
Feb 5
ORD7:01 amChicago O'Hare Intl
11h 33m
1 stop
STI8:34 pmSantiago de los Caballeros
Feb 9
STI6:39 amSantiago de los Caballeros
14h 10m
2 stops
ORD6:49 pmChicago O'Hare Intl
$389
Find similar
Delta
Feb 7
ORD10:29 amChicago O'Hare Intl
12h 21m
1 stop
STI12:50 amSantiago de los Caballeros
Feb 11
STI6:38 amSantiago de los Caballeros
8h 36m
1 stop
ORD1:14 pmChicago O'Hare Intl
$398
Find similar
Delta
Dec 6
ORD7:00 amChicago O'Hare Intl
10h 32m
1 stop
STI7:32 pmSantiago de los Caballeros
Dec 11
STI8:57 pmSantiago de los Caballeros
15h 17m
2 stops
ORD10:14 amChicago O'Hare Intl
$450
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 December 4, 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

Mon 1/26

5:15 am-3:33 pm

1 stop8h 18m

Santiago de los Caballeros

Thu 1/29

4:40 pm-11:46 pm

1 stop9h 06m

$261

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Mon 1/12

5:15 am-3:33 pm

1 stop8h 18m

Santiago de los Caballeros

Thu 1/15

4:40 pm-11:46 pm

1 stop9h 06m

$268

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Mon 2/16

5:15 am-3:35 pm

1 stop8h 20m

Santiago de los Caballeros

Mon 3/2

4:40 pm-12:18 am

1 stop9h 38m

$320

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Tue 1/27

9:40 am-5:04 pm

2 stops29h 24m

Santiago de los Caballeros

Tue 2/24

4:40 pm-12:18 am

1 stop9h 38m

$331

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Mon 1/26

7:20 am-3:33 pm

1 stop6h 13m

Santiago de los Caballeros

Thu 1/29

4:40 pm-2:17 pm

2 stops23h 37m

$332

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Wed 1/14

5:15 am-3:33 pm

1 stop8h 18m

Santiago de los Caballeros

Mon 1/19

4:40 pm-11:46 pm

1 stop9h 06m

$334

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Mon 1/12

8:36 pm-3:33 pm

2 stops16h 57m

Santiago de los Caballeros

Thu 1/15

4:40 pm-11:46 pm

1 stop9h 06m

$337

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Wed 1/14

5:15 am-3:33 pm

1 stop8h 18m

Santiago de los Caballeros

Mon 1/19

4:40 pm-1:57 pm

2 stops23h 17m

$349

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Mon 1/26

7:20 am-3:33 pm

1 stop6h 13m

Santiago de los Caballeros

Thu 1/29

4:40 pm-2:17 pm

3 stops23h 37m

$356

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Mon 1/12

10:07 am-3:33 pm

3 stops27h 26m

Santiago de los Caballeros

Thu 1/15

4:40 pm-11:46 pm

1 stop9h 06m

$365

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

Fastest flight time

7h 13m

Direct flights

None
The fastest flight from Chicago O'Hare Intl Airport to Santiago de los Caballeros takes 7h 13m
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.
Search flight deals

  • 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 13m 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 $215Free CancellationRating
7.4
9,066 reviews
Search United Airlines flights
Spirit AirlinesPriceFrom $298Free CancellationRating
6.3
8,157 reviews
Search Spirit Airlines flights
DeltaPriceFrom $356Free CancellationRating
7.9
8,011 reviews
Search Delta flights
JetBluePriceFrom $391Free CancellationRating
7.2
2,899 reviews
Search JetBlue flights
American AirlinesPriceFrom $437Free CancellationRating
7.2
11,047 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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