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Cheap flights from Chicago to Santiago de los Caballeros from $135

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 10/14. 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
8:12 pm - 9:15 amORD-STI
12h 03m1 stop
Spirit Airlines Logo
12:10 pm - 10:48 pmSTI-ORD
11h 38m1 stop
$257Spirit Airlines
Find Deal
Tue, Aug 19 - Tue, Sep 30
Spirit Airlines Logo
6:44 pm - 11:05 amORD-STI
15h 21m1 stop
Spirit Airlines Logo
12:10 pm - 10:48 pmSTI-ORD
11h 38m1 stop
$271Spirit Airlines
Find Deal
Sat, Sep 13 - Sat, Sep 20
Spirit Airlines Logo
6:44 pm - 11:05 amORD-STI
15h 21m1 stop
Spirit Airlines Logo
12:10 pm - 10:48 pmSTI-ORD
11h 38m1 stop
$319Spirit Airlines
Find Deal
Fri, Sep 19 - Tue, Sep 23
Delta Logo
1:00 pm - 12:34 amORD-STI
10h 34m1 stop
Delta Logo
6:11 am - 7:00 pmSTI-ORD
13h 49m2 stops
$375Delta
Find Deal
Fri, Sep 19 - Tue, Sep 23
Delta Logo
7:00 am - 7:11 pmORD-STI
11h 11m1 stop
Delta Logo
6:11 am - 5:45 pmSTI-ORD
12h 34m1 stop
$377Delta
Find Deal
Tue, Sep 16 - Tue, Sep 23
American Airlines Logo
7:03 pm - 12:27 pmORD-STI
16h 24m2 stops
American Airlines Logo
1:29 pm - 10:26 pmSTI-ORD
9h 57m1 stop
$381American Airlines
Find Deal
Thu, Sep 4 - Tue, Sep 9
American Airlines Logo
5:00 am - 12:27 pmORD-STI
6h 27m1 stop
American Airlines Logo
1:29 pm - 10:26 pmSTI-ORD
9h 57m1 stop
$443American Airlines
Find Deal
Tue, Sep 16 - Wed, Sep 24
JetBlue Logo
6:45 am - 6:04 pmORD-STI
10h 19m1 stop
JetBlue Logo
5:15 am - 12:10 pmSTI-ORD
7h 55m1 stop
$448JetBlue
Find Deal
Mon, Sep 15 - Wed, Sep 24
Logo
5:16 pm - 12:51 pmORD-STI
18h 35m2 stops
Logo
10:20 am - 7:07 pmSTI-ORD
9h 47m1 stop
$452
Find Deal
Sun, Aug 17 - Thu, Aug 21
JetBlue Logo
1:36 pm - 2:16 amORD-STI
11h 40m1 stop
JetBlue Logo
3:44 am - 9:48 pmSTI-ORD
19h 04m1 stop
$467JetBlue
Find Deal
Wed, Oct 22 - Wed, Oct 29

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
Aug 19
ORD8:12 pmChicago O'Hare Intl
12h 03m
1 stop
STI9:15 amSantiago de los Caballeros
Sep 30
STI12:10 pmSantiago de los Caballeros
11h 38m
1 stop
ORD10:48 pmChicago O'Hare Intl
$257
Find similar
Spirit Airlines
Sep 13
ORD6:44 pmChicago O'Hare Intl
15h 21m
1 stop
STI11:05 amSantiago de los Caballeros
Sep 20
STI12:10 pmSantiago de los Caballeros
11h 38m
1 stop
ORD10:48 pmChicago O'Hare Intl
$271
Find similar
Spirit Airlines
Sep 19
ORD6:44 pmChicago O'Hare Intl
15h 21m
1 stop
STI11:05 amSantiago de los Caballeros
Sep 23
STI12:10 pmSantiago de los Caballeros
11h 38m
1 stop
ORD10:48 pmChicago O'Hare Intl
$319
Find similar

Delta flights from Chicago to Santiago de los Caballeros

Our best Delta deals on Chicago to Santiago de los Caballeros flight tickets
Delta
Sep 19
ORD1:00 pmChicago O'Hare Intl
10h 34m
1 stop
STI12:34 amSantiago de los Caballeros
Sep 23
STI6:11 amSantiago de los Caballeros
13h 49m
2 stops
ORD7:00 pmChicago O'Hare Intl
$375
Find similar
Delta
Sep 16
ORD7:00 amChicago O'Hare Intl
11h 11m
1 stop
STI7:11 pmSantiago de los Caballeros
Sep 23
STI6:11 amSantiago de los Caballeros
12h 34m
1 stop
ORD5:45 pmChicago O'Hare Intl
$377
Find similar
Delta
Sep 19
ORD7:00 amChicago O'Hare Intl
11h 11m
1 stop
STI7:11 pmSantiago de los Caballeros
Sep 22
STI8:40 pmSantiago de los Caballeros
14h 30m
2 stops
ORD10:10 amChicago O'Hare Intl
$385
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 July 31, 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

Tue 8/19

8:12 pm-9:15 am

1 stop12h 03m

Santiago de los Caballeros

Tue 9/30

12:10 pm-10:48 pm

1 stop11h 38m

$257

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Sat 9/13

6:44 pm-11:05 am

1 stop15h 21m

Santiago de los Caballeros

Sat 9/20

12:10 pm-10:48 pm

1 stop11h 38m

$271

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Fri 9/19

6:44 pm-11:05 am

1 stop15h 21m

Santiago de los Caballeros

Tue 9/23

12:10 pm-10:48 pm

1 stop11h 38m

$319

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Fri 9/19

1:00 pm-12:34 am

1 stop10h 34m

Santiago de los Caballeros

Tue 9/23

6:11 am-7:00 pm

2 stops13h 49m

$375

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Tue 9/16

7:00 am-7:11 pm

1 stop11h 11m

Santiago de los Caballeros

Tue 9/23

6:11 am-5:45 pm

1 stop12h 34m

$377

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Thu 9/4

7:03 pm-12:27 pm

2 stops16h 24m

Santiago de los Caballeros

Tue 9/9

1:29 pm-10:26 pm

1 stop9h 57m

$381

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Tue 9/16

5:00 am-12:27 pm

1 stop6h 27m

Santiago de los Caballeros

Wed 9/24

1:29 pm-10:26 pm

1 stop9h 57m

$443

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Mon 9/15

6:45 am-6:04 pm

1 stop10h 19m

Santiago de los Caballeros

Wed 9/24

5:15 am-12:10 pm

1 stop7h 55m

$448

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Sun 8/17

5:16 pm-12:51 pm

2 stops18h 35m

Santiago de los Caballeros

Thu 8/21

10:20 am-7:07 pm

1 stop9h 47m

$452

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Wed 10/22

1:36 pm-2:16 am

1 stop11h 40m

Santiago de los Caballeros

Wed 10/29

3:44 am-9:48 pm

1 stop19h 04m

$467

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 $373, 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 $397.

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

Best Price Found

$135

Fastest flight time

6h 27m

Direct flights

None

Airports in Santiago de los Caballeros

1 airport
The best one-way flight to Santiago de los Caballeros from Chicago in the past 72 hours is $135. The best round-trip flight deal from Chicago to Santiago de los Caballeros found on momondo in the last 72 hours is $257.
The fastest flight from Chicago to Santiago de los Caballeros takes 6h 27m
There are no direct flights from Chicago to Santiago de los Caballeros. Popular non-direct routes for this connection are Chicago Midway Airport - Santiago de los Caballeros Airport and Chicago O'Hare Intl Airport - Santiago de los Caballeros Airport.
There is 1 airport near Santiago de los Caballeros: Santiago de los Caballeros (STI)
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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 27m 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
8,900 reviews
Search United Airlines flights
JetBluePriceFrom $343Free CancellationRating
7.2
2,914 reviews
Search JetBlue flights
DeltaPriceFrom $345Free CancellationRating
8.0
7,981 reviews
Search Delta flights
American AirlinesPriceFrom $395Free CancellationRating
7.2
10,000 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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