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Cheap flights from Chicago to Santiago de los Caballeros from $195

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 7/30. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Chicago to Santiago de los Caballeros

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
6:00 am - 5:46 pm
ORD
-
STI
10h 46m
1 stop
Delta Logo
6:40 am - 5:34 pm
STI
-
ORD
12h 54m
1 stop
$426Delta
Wed, Oct 28 - Tue, Nov 10
JetBlue Logo
2:35 pm - 11:51 pm
ORD
-
STI
8h 16m
1 stop
JetBlue Logo
3:55 pm - 11:44 pm
STI
-
ORD
8h 49m
1 stop
$428JetBlue
Fri, Oct 9 - Sat, Oct 17
Delta Logo
7:05 am - 5:46 pm
ORD
-
STI
9h 41m
2 stops
Delta Logo
6:40 am - 5:34 pm
STI
-
ORD
12h 54m
1 stop
$431Delta
Wed, Oct 28 - Tue, Nov 10
JetBlue Logo
6:00 am - 1:27 pm
ORD
-
STI
6h 27m
1 stop
JetBlue Logo
3:49 pm - 11:31 pm
STI
-
ORD
8h 42m
1 stop
$436JetBlue
Mon, Sep 28 - Fri, Oct 2
JetBlue Logo
6:00 am - 1:27 pm
ORD
-
STI
6h 27m
1 stop
JetBlue Logo
3:49 pm - 11:31 pm
STI
-
ORD
8h 42m
1 stop
$438JetBlue
Thu, Sep 17 - Wed, Sep 30
American Airlines Logo
7:05 pm - 12:10 pm
ORD
-
STI
16h 05m
1 stop
American Airlines Logo
7:00 am - 4:05 pm
STI
-
ORD
11h 05m
2 stops
$441American Airlines
Wed, Oct 28 - Tue, Nov 10
American Airlines Logo
6:59 am - 2:35 pm
ORD
-
STI
6h 36m
1 stop
American Airlines Logo
7:00 am - 11:30 pm
STI
-
ORD
17h 30m
1 stop
$449American Airlines
Wed, Aug 19 - Sun, Aug 23
American Airlines Logo
4:00 pm - 12:10 pm
ORD
-
STI
19h 10m
1 stop
American Airlines Logo
7:00 am - 4:05 pm
STI
-
ORD
11h 05m
2 stops
$451American Airlines
Wed, Oct 28 - Tue, Nov 10
American Airlines Logo
9:56 am - 8:03 pm
ORD
-
STI
9h 07m
2 stops
American Airlines Logo
7:00 am - 11:30 pm
STI
-
ORD
17h 30m
1 stop
$454American Airlines
Wed, Aug 19 - Sun, Aug 23
American Airlines Logo
7:05 pm - 12:10 pm
ORD
-
STI
16h 05m
1 stop
American Airlines Logo
7:00 am - 4:05 pm
STI
-
ORD
11h 05m
2 stops
$471American Airlines
Wed, Oct 28 - Tue, Nov 10

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JetBlue flights from Chicago to Santiago de los Caballeros

Our best JetBlue deals on Chicago to Santiago de los Caballeros flight tickets
JetBlue
Sep 2
ORD7:00 amChicago O'Hare Intl
7h 01m
1 stop
STI3:01 pmSantiago de los Caballeros
Sep 16
STI3:49 pmSantiago de los Caballeros
8h 42m
1 stop
ORD11:31 pmChicago O'Hare Intl
$416
JetBlue
Oct 9
ORD2:35 pmChicago O'Hare Intl
8h 16m
1 stop
STI11:51 pmSantiago de los Caballeros
Oct 17
STI3:55 pmSantiago de los Caballeros
8h 49m
1 stop
ORD11:44 pmChicago O'Hare Intl
$428
JetBlue
Oct 9
ORD2:35 pmChicago O'Hare Intl
8h 16m
1 stop
STI11:51 pmSantiago de los Caballeros
Oct 17
STI3:55 pmSantiago de los Caballeros
8h 49m
1 stop
ORD11:44 pmChicago O'Hare Intl
$431

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
Sep 2
ORD5:00 amChicago O'Hare Intl
14h 03m
1 stop
STI8:03 pmSantiago de los Caballeros
Sep 16
STI3:15 pmSantiago de los Caballeros
17h 27m
2 stops
ORD7:42 amChicago O'Hare Intl
$441
American Airlines
Aug 19
ORD6:59 amChicago O'Hare Intl
6h 36m
1 stop
STI2:35 pmSantiago de los Caballeros
Aug 23
STI7:00 amSantiago de los Caballeros
17h 30m
1 stop
ORD11:30 pmChicago O'Hare Intl
$449
American Airlines
Oct 28
ORD4:00 pmChicago O'Hare Intl
19h 10m
1 stop
STI12:10 pmSantiago de los Caballeros
Nov 10
STI7:00 amSantiago de los Caballeros
11h 05m
2 stops
ORD4:05 pmChicago O'Hare Intl
$451

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 June 21, 2026.
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

Cheapest round-trip

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Wed 10/28

6:00 am-5:46 pm

1 stop10h 46m

Santiago de los Caballeros

Tue 11/10

6:40 am-5:34 pm

1 stop12h 54m

$426

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Fri 10/9

2:35 pm-11:51 pm

1 stop8h 16m

Santiago de los Caballeros

Sat 10/17

3:55 pm-11:44 pm

1 stop8h 49m

$428

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Wed 10/28

7:05 am-5:46 pm

2 stops9h 41m

Santiago de los Caballeros

Tue 11/10

6:40 am-5:34 pm

1 stop12h 54m

$431
Quickest round-trip

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Mon 9/28

6:00 am-1:27 pm

1 stop6h 27m

Santiago de los Caballeros

Fri 10/2

3:49 pm-11:31 pm

1 stop8h 42m

$436

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Thu 9/17

6:00 am-1:27 pm

1 stop6h 27m

Santiago de los Caballeros

Wed 9/30

3:49 pm-11:31 pm

1 stop8h 42m

$438

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Wed 10/28

7:05 pm-12:10 pm

1 stop16h 05m

Santiago de los Caballeros

Tue 11/10

7:00 am-4:05 pm

2 stops11h 05m

$441

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Wed 8/19

6:59 am-2:35 pm

1 stop6h 36m

Santiago de los Caballeros

Sun 8/23

7:00 am-11:30 pm

1 stop17h 30m

$449

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Wed 10/28

4:00 pm-12:10 pm

1 stop19h 10m

Santiago de los Caballeros

Tue 11/10

7:00 am-4:05 pm

2 stops11h 05m

$451

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Wed 8/19

9:56 am-8:03 pm

2 stops9h 07m

Santiago de los Caballeros

Sun 8/23

7:00 am-11:30 pm

1 stop17h 30m

$454

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Wed 10/28

7:05 pm-12:10 pm

1 stop16h 05m

Santiago de los Caballeros

Tue 11/10

7:00 am-4:05 pm

2 stops11h 05m

$471

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 November. Flight prices, which tend to average around $206, 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 November, then flying in June is also cheap. Prices for this month can be found on momondo for an average of $239.

Can stopping save me money on Chicago to Santiago de los Caballeros flights?

You could potentially save up to 31% on your flight if you consider stops on a Chicago to Santiago de los Caballeros flight.

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

Fastest flight time

6h 27m

Direct flights

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

Frequently asked questions about flying from Chicago to Santiago de los Caballeros

  • 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
DeltaPriceFrom $239Free CancellationRating
7.8
8,422 reviews
Search Delta flights
JetBluePriceFrom $255Free CancellationRating
7.1
2,993 reviews
Search JetBlue flights
American AirlinesPriceFrom $407Free CancellationRating
7.1
11,735 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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