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Cheap flights from Chicago to Santiago de los Caballeros from $188

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 6/27. 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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0 bags

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Find the cheapest flights from Chicago to Santiago de los Caballeros

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
8:00 pm - 9:54 am
ORD
-
STI
12h 54m
1 stop
Frontier Logo
11:09 am - 6:47 pm
STI
-
ORD
8h 38m
1 stop
$432Frontier
Mon, Jun 8 - Sun, Jun 14
Spirit Airlines Logo
5:05 am - 2:12 pm
ORD
-
STI
8h 07m
1 stop
Spirit Airlines Logo
3:17 pm - 11:15 pm
STI
-
ORD
8h 58m
1 stop
$449Spirit Airlines
Sat, May 16 - Sat, May 23
Multiple Airlines Logo
7:52 pm - 9:54 am
ORD
-
STI
13h 02m
1 stop
Multiple Airlines Logo
3:52 pm - 11:59 pm
STI
-
ORD
9h 07m
1 stop
$463Multiple Airlines
Sat, Jun 20 - Sat, Jul 4
Spirit Airlines Logo
5:10 am - 2:45 pm
ORD
-
STI
8h 35m
1 stop
Spirit Airlines Logo
3:52 pm - 11:59 pm
STI
-
ORD
9h 07m
1 stop
$466Spirit Airlines
Sat, Jun 20 - Sat, Jul 4
Spirit Airlines Logo
5:10 am - 2:45 pm
ORD
-
STI
8h 35m
1 stop
Spirit Airlines Logo
3:52 pm - 11:59 pm
STI
-
ORD
9h 07m
1 stop
$476Spirit Airlines
Sat, Jun 20 - Sat, Jul 4
Spirit Airlines Logo
5:10 am - 2:45 pm
ORD
-
STI
8h 35m
1 stop
Spirit Airlines Logo
3:52 pm - 11:59 pm
STI
-
ORD
9h 07m
1 stop
$483Spirit Airlines
Sat, Jun 20 - Sat, Jul 4
American Airlines Logo
6:55 am - 9:13 pm
ORD
-
STI
13h 18m
2 stops
American Airlines Logo
7:04 am - 5:09 pm
STI
-
ORD
11h 05m
1 stop
$492American Airlines
Tue, May 26 - Thu, Jun 11
Delta Logo
12:59 pm - 12:59 am
ORD
-
STI
11h 00m
1 stop
Delta Logo
6:00 am - 5:11 pm
STI
-
ORD
12h 11m
1 stop
$495Delta
Tue, May 26 - Thu, Jun 11
Spirit Airlines Logo
5:10 am - 2:45 pm
ORD
-
STI
8h 35m
1 stop
Spirit Airlines Logo
3:52 pm - 11:59 pm
STI
-
ORD
9h 07m
1 stop
$498Spirit Airlines
Sat, Jun 20 - Fri, Jun 26
Delta Logo
12:59 pm - 12:59 am
ORD
-
STI
11h 00m
1 stop
Delta Logo
6:00 am - 6:29 pm
STI
-
ORD
13h 29m
2 stops
$500Delta
Tue, May 26 - Thu, Jun 11

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
May 16
ORD5:05 amChicago O'Hare Intl
8h 07m
1 stop
STI2:12 pmSantiago de los Caballeros
May 23
STI3:17 pmSantiago de los Caballeros
8h 58m
1 stop
ORD11:15 pmChicago O'Hare Intl
$449
Spirit Airlines
Jun 20
ORD5:10 amChicago O'Hare Intl
8h 35m
1 stop
STI2:45 pmSantiago de los Caballeros
Jul 4
STI3:52 pmSantiago de los Caballeros
9h 07m
1 stop
ORD11:59 pmChicago O'Hare Intl
$466
Spirit Airlines
Jun 20
ORD5:10 amChicago O'Hare Intl
8h 35m
1 stop
STI2:45 pmSantiago de los Caballeros
Jul 4
STI3:52 pmSantiago de los Caballeros
9h 07m
1 stop
ORD11:59 pmChicago O'Hare Intl
$476

Delta flights from Chicago to Santiago de los Caballeros

Our best Delta deals on Chicago to Santiago de los Caballeros flight tickets
Delta
May 26
ORD12:59 pmChicago O'Hare Intl
11h 00m
1 stop
STI12:59 amSantiago de los Caballeros
Jun 11
STI6:00 amSantiago de los Caballeros
12h 11m
1 stop
ORD5:11 pmChicago O'Hare Intl
$495
Delta
May 26
ORD12:59 pmChicago O'Hare Intl
11h 00m
1 stop
STI12:59 amSantiago de los Caballeros
Jun 11
STI6:00 amSantiago de los Caballeros
13h 29m
2 stops
ORD6:29 pmChicago O'Hare Intl
$500
Delta
May 26
ORD12:59 pmChicago O'Hare Intl
11h 00m
1 stop
STI12:59 amSantiago de los Caballeros
Jun 11
STI6:00 amSantiago de los Caballeros
12h 11m
1 stop
ORD5:11 pmChicago O'Hare Intl
$510

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 May 5, 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

Mon 6/8

8:00 pm-9:54 am

1 stop12h 54m

Santiago de los Caballeros

Sun 6/14

11:09 am-6:47 pm

1 stop8h 38m

$432
Quickest round-trip

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Sat 5/16

5:05 am-2:12 pm

1 stop8h 07m

Santiago de los Caballeros

Sat 5/23

3:17 pm-11:15 pm

1 stop8h 58m

$449

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Sat 6/20

7:52 pm-9:54 am

1 stop13h 02m

Santiago de los Caballeros

Sat 7/4

3:52 pm-11:59 pm

1 stop9h 07m

$463

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Sat 6/20

5:10 am-2:45 pm

1 stop8h 35m

Santiago de los Caballeros

Sat 7/4

3:52 pm-11:59 pm

1 stop9h 07m

$466

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Sat 6/20

5:10 am-2:45 pm

1 stop8h 35m

Santiago de los Caballeros

Sat 7/4

3:52 pm-11:59 pm

1 stop9h 07m

$476

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Sat 6/20

5:10 am-2:45 pm

1 stop8h 35m

Santiago de los Caballeros

Sat 7/4

3:52 pm-11:59 pm

1 stop9h 07m

$483

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Tue 5/26

6:55 am-9:13 pm

2 stops13h 18m

Santiago de los Caballeros

Thu 6/11

7:04 am-5:09 pm

1 stop11h 05m

$492

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Tue 5/26

12:59 pm-12:59 am

1 stop11h 00m

Santiago de los Caballeros

Thu 6/11

6:00 am-5:11 pm

1 stop12h 11m

$495

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Sat 6/20

5:10 am-2:45 pm

1 stop8h 35m

Santiago de los Caballeros

Fri 6/26

3:52 pm-11:59 pm

1 stop9h 07m

$498

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Tue 5/26

12:59 pm-12:59 am

1 stop11h 00m

Santiago de los Caballeros

Thu 6/11

6:00 am-6:29 pm

2 stops13h 29m

$500

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 typical price of a round-trip flight between Chicago and Santiago de los Caballeros?

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 $212.

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 36m

Direct flights

None
The fastest flight from Chicago to Santiago de los Caballeros takes 6h 36m
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 36m 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
Spirit AirlinesPriceFrom $298Free CancellationRating
6.3
8,633 reviews
Search Spirit Airlines flights
DeltaPriceFrom $356Free CancellationRating
7.9
8,459 reviews
Search Delta flights
American AirlinesPriceFrom $445Free CancellationRating
7.1
11,670 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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