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Cheap flights from Chicago to Santiago de los Caballeros from $174

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 11/16. 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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Cheap round-trip flights

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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
$334Spirit Airlines
Find Deal
Mon, Feb 2 - Mon, Feb 9
Spirit Airlines Logo
3:26 pm - 2:42 amORD-STI
9h 16m1 stop
Spirit Airlines Logo
1:01 pm - 8:01 pmSTI-ORD
9h 00m1 stop
$335Spirit Airlines
Find Deal
Fri, Dec 5 - Sat, Dec 13
American Airlines Logo
12:07 pm - 9:46 pmORD-STI
7h 39m1 stop
American Airlines Logo
4:33 pm - 11:08 pmSTI-ORD
8h 35m1 stop
$388American Airlines
Find Deal
Mon, Jan 19 - Wed, Jan 28
Multiple Airlines Logo
5:20 am - 5:06 pmORD-STI
33h 46m2 stops
Multiple Airlines Logo
6:18 pm - 9:23 amSTI-ORD
17h 05m1 stop
$390Multiple Airlines
Find Deal
Mon, Feb 2 - Mon, Feb 9
JetBlue Logo
12:41 pm - 2:44 amORD-STI
12h 03m1 stop
JetBlue Logo
11:06 pm - 11:49 amSTI-ORD
14h 43m1 stop
$398JetBlue
Find Deal
Sun, Mar 1 - Thu, Mar 5
Delta Logo
7:05 am - 8:34 pmORD-STI
11h 29m2 stops
Delta Logo
6:39 am - 9:04 pmSTI-ORD
16h 25m2 stops
$402Delta
Find Deal
Mon, Feb 2 - Mon, Feb 9
Multiple Airlines Logo
10:00 am - 2:42 amORD-STI
14h 42m2 stops
Multiple Airlines Logo
3:43 am - 3:42 pmSTI-ORD
13h 59m1 stop
$427Multiple Airlines
Find Deal
Tue, Dec 16 - Mon, Dec 22
American Airlines Logo
8:20 am - 10:56 pmORD-STI
12h 36m2 stops
American Airlines Logo
6:20 am - 3:56 pmSTI-ORD
11h 36m2 stops
$438American Airlines
Find Deal
Tue, Nov 25 - Tue, Dec 2
JetBlue Logo
1:45 pm - 9:58 pmORD-STI
7h 13m1 stop
JetBlue Logo
10:01 am - 10:59 pmSTI-ORD
13h 58m1 stop
$464JetBlue
Find Deal
Sat, Apr 11 - Sat, Apr 18
Delta Logo
10:35 am - 12:53 amORD-STI
12h 18m2 stops
Delta Logo
6:35 am - 5:45 pmSTI-ORD
13h 10m1 stop
$474Delta
Find Deal
Sun, Mar 1 - Thu, Mar 5

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
Feb 2
ORD8:41 amChicago O'Hare Intl
6h 25m
1 stop
STI5:06 pmSantiago de los Caballeros
Feb 9
STI6:18 pmSantiago de los Caballeros
17h 05m
1 stop
ORD9:23 amChicago O'Hare Intl
$334
Find similar
Spirit Airlines
Dec 5
ORD3:26 pmChicago O'Hare Intl
9h 16m
1 stop
STI2:42 amSantiago de los Caballeros
Dec 13
STI1:01 pmSantiago de los Caballeros
9h 00m
1 stop
ORD8:01 pmChicago O'Hare Intl
$335
Find similar
Spirit Airlines
Dec 16
ORD3:26 pmChicago O'Hare Intl
9h 16m
1 stop
STI2:42 amSantiago de los Caballeros
Dec 22
STI3:43 amSantiago de los Caballeros
16h 56m
1 stop
ORD6:39 pmChicago O'Hare Intl
$371
Find similar

American Airlines flights from Chicago to Santiago de los Caballeros

Our best American Airlines deals on Chicago to Santiago de los Caballeros flight tickets
American Airlines
Jan 19
ORD12:07 pmChicago O'Hare Intl
7h 39m
1 stop
STI9:46 pmSantiago de los Caballeros
Jan 28
STI4:33 pmSantiago de los Caballeros
8h 35m
1 stop
ORD11:08 pmChicago O'Hare Intl
$388
Find similar
American Airlines
Nov 25
ORD8:20 amChicago O'Hare Intl
12h 36m
2 stops
STI10:56 pmSantiago de los Caballeros
Dec 2
STI6:20 amSantiago de los Caballeros
11h 36m
2 stops
ORD3:56 pmChicago O'Hare Intl
$438
Find similar
American Airlines
Feb 16
ORD12:32 pmChicago O'Hare Intl
7h 32m
1 stop
STI10:04 pmSantiago de los Caballeros
Mar 2
STI8:00 amSantiago de los Caballeros
17h 07m
1 stop
ORD11:07 pmChicago O'Hare Intl
$440
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 November 3, 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

Mon 2/2

8:41 am-5:06 pm

1 stop6h 25m

Santiago de los Caballeros

Mon 2/9

6:18 pm-9:23 am

1 stop17h 05m

$334

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Fri 12/5

3:26 pm-2:42 am

1 stop9h 16m

Santiago de los Caballeros

Sat 12/13

1:01 pm-8:01 pm

1 stop9h 00m

$335

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Mon 1/19

12:07 pm-9:46 pm

1 stop7h 39m

Santiago de los Caballeros

Wed 1/28

4:33 pm-11:08 pm

1 stop8h 35m

$388

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Mon 2/2

5:20 am-5:06 pm

2 stops33h 46m

Santiago de los Caballeros

Mon 2/9

6:18 pm-9:23 am

1 stop17h 05m

$390

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Sun 3/1

12:41 pm-2:44 am

1 stop12h 03m

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

Mon 2/2

7:05 am-8:34 pm

2 stops11h 29m

Santiago de los Caballeros

Mon 2/9

6:39 am-9:04 pm

2 stops16h 25m

$402

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Tue 12/16

10:00 am-2:42 am

2 stops14h 42m

Santiago de los Caballeros

Mon 12/22

3:43 am-3:42 pm

1 stop13h 59m

$427

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Tue 11/25

8:20 am-10:56 pm

2 stops12h 36m

Santiago de los Caballeros

Tue 12/2

6:20 am-3:56 pm

2 stops11h 36m

$438

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Sat 4/11

1:45 pm-9:58 pm

1 stop7h 13m

Santiago de los Caballeros

Sat 4/18

10:01 am-10:59 pm

1 stop13h 58m

$464

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Sun 3/1

10:35 am-12:53 am

2 stops12h 18m

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 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 $251, 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.
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  • 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 $226Free CancellationRating
7.4
8,997 reviews
Search United Airlines flights
Spirit AirlinesPriceFrom $298Free CancellationRating
6.3
8,115 reviews
Search Spirit Airlines flights
DeltaPriceFrom $356Free CancellationRating
7.9
8,002 reviews
Search Delta flights
JetBluePriceFrom $391Free CancellationRating
7.2
2,907 reviews
Search JetBlue flights
American AirlinesPriceFrom $395Free CancellationRating
7.2
11,038 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?

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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