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Cheap flights from Chicago to Santiago de los Caballeros from $155

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 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 to Santiago de los Caballeros

Cheap round-trip flights

Spirit Airlines Logo
7:43 pm - 10:38 amORD-STI
13h 55m1 stop
Spirit Airlines Logo
11:43 am - 6:38 pmSTI-ORD
7h 55m1 stop
$308Spirit Airlines
Find Deal
jue., oct. 9 - lun., oct. 27
Spirit Airlines Logo
4:53 pm - 10:38 amORD-STI
16h 45m1 stop
Spirit Airlines Logo
11:43 am - 1:03 amSTI-ORD
14h 20m1 stop
$317Spirit Airlines
Find Deal
vie., oct. 10 - vie., oct. 31
Spirit Airlines Logo
7:43 pm - 10:38 amORD-STI
13h 55m1 stop
Spirit Airlines Logo
12:43 pm - 6:38 pmSTI-ORD
7h 55m1 stop
$331Spirit Airlines
Find Deal
vie., oct. 31 - lun., nov. 3
JetBlue Logo
7:00 am - 10:58 pmORD-STI
13h 58m1 stop
JetBlue Logo
1:35 pm - 9:33 pmSTI-ORD
9h 58m1 stop
$397JetBlue
Find Deal
dom., mar. 1 - jue., mar. 5
American Airlines Logo
12:02 pm - 8:51 pmORD-STI
6h 49m1 stop
American Airlines Logo
4:35 pm - 7:21 amSTI-ORD
16h 46m2 stops
$400American Airlines
Find Deal
dom., nov. 2 - mié., nov. 5
Delta Logo
7:00 am - 11:54 pmORD-STI
14h 54m2 stops
Delta Logo
6:35 am - 5:37 pmSTI-ORD
13h 02m1 stop
$402Delta
Find Deal
dom., mar. 1 - jue., mar. 5
Delta Logo
10:40 am - 7:11 pmORD-STI
7h 31m1 stop
Delta Logo
8:31 pm - 12:40 pmSTI-ORD
17h 09m2 stops
$420Delta
Find Deal
jue., oct. 2 - vie., oct. 10
United Airlines Logo
12:00 pm - 11:51 pmORD-STI
9h 51m1 stop
United Airlines Logo
6:00 am - 1:14 pmSTI-ORD
9h 14m1 stop
$441United Airlines
Find Deal
mié., nov. 19 - dom., nov. 23
American Airlines Logo
9:06 pm - 12:27 pmORD-STI
14h 21m2 stops
American Airlines Logo
1:14 pm - 11:03 amSTI-ORD
22h 49m1 stop
$442American Airlines
Find Deal
jue., oct. 2 - vie., oct. 10
JetBlue Logo
6:45 am - 7:34 pmORD-STI
11h 49m1 stop
JetBlue Logo
4:41 am - 8:52 pmSTI-ORD
18h 11m1 stop
$452JetBlue
Find Deal
vie., oct. 31 - dom., nov. 2

United Airlines flights from Chicago to Santiago de los Caballeros

Our best United Airlines deals on Chicago to Santiago de los Caballeros flight tickets
United Airlines
Nov 19
ORD12:00 pmChicago O'Hare Intl
9h 51m
1 stop
STI11:51 pmSantiago de los Caballeros
Nov 23
STI6:00 amSantiago de los Caballeros
9h 14m
1 stop
ORD1:14 pmChicago O'Hare Intl
$441
Find similar
United Airlines
Sep 24
ORD6:00 amChicago O'Hare Intl
8h 12m
1 stop
STI3:12 pmSantiago de los Caballeros
Oct 3
STI2:07 pmSantiago de los Caballeros
8h 19m
1 stop
ORD9:26 pmChicago O'Hare Intl
$553
Find similar

Spirit Airlines flights from Chicago to Santiago de los Caballeros

Our best Spirit Airlines deals on Chicago to Santiago de los Caballeros flight tickets
Spirit Airlines
Oct 9
ORD7:43 pmChicago O'Hare Intl
13h 55m
1 stop
STI10:38 amSantiago de los Caballeros
Oct 27
STI11:43 amSantiago de los Caballeros
7h 55m
1 stop
ORD6:38 pmChicago O'Hare Intl
$308
Find similar
Spirit Airlines
Oct 10
ORD4:53 pmChicago O'Hare Intl
16h 45m
1 stop
STI10:38 amSantiago de los Caballeros
Oct 31
STI11:43 amSantiago de los Caballeros
14h 20m
1 stop
ORD1:03 amChicago O'Hare Intl
$317
Find similar
Spirit Airlines
Oct 31
ORD7:43 pmChicago O'Hare Intl
13h 55m
1 stop
STI10:38 amSantiago de los Caballeros
Nov 3
STI12:43 pmSantiago de los Caballeros
7h 55m
1 stop
ORD6:38 pmChicago O'Hare Intl
$331
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago 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 septiembre 17, 2025.
Use the filters below to find and compare flights from Chicago 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

jue. 10/9

7:43 pm-10:38 am

1 stop13h 55m

Santiago de los Caballeros

lun. 10/27

11:43 am-6:38 pm

1 stop7h 55m

$308

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

vie. 10/10

4:53 pm-10:38 am

1 stop16h 45m

Santiago de los Caballeros

vie. 10/31

11:43 am-1:03 am

1 stop14h 20m

$317

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

vie. 10/31

7:43 pm-10:38 am

1 stop13h 55m

Santiago de los Caballeros

lun. 11/3

12:43 pm-6:38 pm

1 stop7h 55m

$331

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

dom. 3/1

7:00 am-10:58 pm

1 stop13h 58m

Santiago de los Caballeros

jue. 3/5

1:35 pm-9:33 pm

1 stop9h 58m

$397

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

dom. 11/2

12:02 pm-8:51 pm

1 stop6h 49m

Santiago de los Caballeros

mié. 11/5

4:35 pm-7:21 am

2 stops16h 46m

$400

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

dom. 3/1

7:00 am-11:54 pm

2 stops14h 54m

Santiago de los Caballeros

jue. 3/5

6:35 am-5:37 pm

1 stop13h 02m

$402

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

jue. 10/2

10:40 am-7:11 pm

1 stop7h 31m

Santiago de los Caballeros

vie. 10/10

8:31 pm-12:40 pm

2 stops17h 09m

$420

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

mié. 11/19

12:00 pm-11:51 pm

1 stop9h 51m

Santiago de los Caballeros

dom. 11/23

6:00 am-1:14 pm

1 stop9h 14m

$441

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

jue. 10/2

9:06 pm-12:27 pm

2 stops14h 21m

Santiago de los Caballeros

vie. 10/10

1:14 pm-11:03 am

1 stop22h 49m

$442

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

vie. 10/31

6:45 am-7:34 pm

1 stop11h 49m

Santiago de los Caballeros

dom. 11/2

4:41 am-8:52 pm

1 stop18h 11m

$452

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 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 is in September. Flight prices, which tend to average around $293, 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 September, then flying in August is also cheap. Prices for this month can be found on momondo for an average of $392.

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

The cheapest day to depart from Chicago 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 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 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.

When to book flights from Chicago to Santiago de los Caballeros

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago 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 to Santiago de los Caballeros (CHI to STI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Santiago de los Caballeros

Direct flights

None
There are no direct flights from Chicago to Santiago de los Caballeros. There are no popular flight routes from Chicago to Santiago de los Caballeros.
Search flight deals

  • How far is Chicago to Santiago de los Caballeros by plane?

    The distance between Chicago and Santiago de los Caballeros is about 1838.3 mi. 6h 25m is a normal flight duration for this route.

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

    Prices for flights from Chicago to Santiago de los Caballeros Airport were last updated today.

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

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

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago 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 to Santiago de los Caballeros?

Best airlines flying from Chicago to Santiago de los Caballeros

Compare and see reviews for airlines that fly from Chicago to Santiago de los Caballeros with momondo
Airline
Rating
Free Cancellation
Price
United AirlinesPriceFrom $215Free CancellationRating
7.4
8,926 reviews
Search United Airlines flights
JetBluePriceFrom $391Free CancellationRating
7.2
2,914 reviews
Search JetBlue flights
American AirlinesPriceFrom $395Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
DeltaPriceFrom $412Free CancellationRating
7.9
7,961 reviews
Search Delta flights

Why use momondo?

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

It is quick and easy to find Chicago to Santiago de los Caballeros flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Santiago de los Caballeros that suits 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 provides multiple filters to help you find the best flight to Santiago de los Caballeros from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

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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