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Cheap flights from Chicago to Santiago de los Caballeros from $139

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 4/5. 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.
Spirit Airlines Logo
8:16 pm - 2:33 pm
ORD
-
STI
16h 17m
1 stop
Spirit Airlines Logo
2:46 am - 5:15 pm
STI
-
ORD
15h 29m
1 stop
$266Spirit Airlines
Sat, Mar 7 - Sun, Mar 15
Spirit Airlines Logo
7:05 am - 2:35 pm
ORD
-
STI
6h 30m
1 stop
Spirit Airlines Logo
3:40 pm - 11:41 pm
STI
-
ORD
9h 01m
1 stop
$282Spirit Airlines
Mon, Apr 20 - Sat, Apr 25
Spirit Airlines Logo
8:16 pm - 2:33 pm
ORD
-
STI
16h 17m
1 stop
Spirit Airlines Logo
2:46 am - 11:17 am
STI
-
ORD
9h 31m
1 stop
$287Spirit Airlines
Sat, Mar 7 - Sun, Mar 15
Spirit Airlines Logo
5:15 am - 2:35 pm
ORD
-
STI
8h 20m
1 stop
Spirit Airlines Logo
3:40 pm - 11:41 pm
STI
-
ORD
9h 01m
1 stop
$302Spirit Airlines
Mon, Jun 1 - Wed, Jun 3
Spirit Airlines Logo
5:15 am - 2:35 pm
ORD
-
STI
8h 20m
1 stop
Spirit Airlines Logo
3:40 pm - 11:41 pm
STI
-
ORD
9h 01m
1 stop
$306Spirit Airlines
Wed, Apr 22 - Sat, Apr 25
Spirit Airlines Logo
8:16 pm - 3:35 pm
ORD
-
STI
17h 19m
1 stop
Spirit Airlines Logo
3:41 pm - 11:47 pm
STI
-
ORD
9h 06m
1 stop
$308Spirit Airlines
Fri, Mar 6 - Mon, Mar 9
Multiple Airlines Logo
6:36 pm - 2:33 pm
ORD
-
STI
18h 57m
1 stop
Multiple Airlines Logo
3:43 pm - 5:15 pm
STI
-
ORD
26h 32m
1 stop
$309Multiple Airlines
Tue, Mar 10 - Sun, Mar 15
Delta Logo
9:35 am - 11:54 pm
MDW
-
STI
13h 19m
2 stops
Delta Logo
8:40 pm - 12:29 pm
STI
-
MDW
16h 49m
2 stops
$561Delta
Tue, Mar 17 - Mon, Mar 30
Delta Logo
9:34 am - 1:34 am
MDW
-
STI
14h 00m
2 stops
Delta Logo
9:59 pm - 12:46 pm
STI
-
MDW
16h 47m
2 stops
$1,159Delta
Mon, Feb 16 - Mon, Mar 2
Delta Logo
9:34 am - 1:34 am
MDW
-
STI
14h 00m
2 stops
Delta Logo
9:59 pm - 12:46 pm
STI
-
MDW
16h 47m
2 stops
$1,199Delta
Mon, Feb 16 - Mon, Mar 2

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
Mar 7
ORD8:16 pmChicago O'Hare Intl
16h 17m
1 stop
STI2:33 pmSantiago de los Caballeros
Mar 15
STI2:46 amSantiago de los Caballeros
15h 29m
1 stop
ORD5:15 pmChicago O'Hare Intl
$266
Spirit Airlines
Apr 20
ORD7:05 amChicago O'Hare Intl
6h 30m
1 stop
STI2:35 pmSantiago de los Caballeros
Apr 25
STI3:40 pmSantiago de los Caballeros
9h 01m
1 stop
ORD11:41 pmChicago O'Hare Intl
$282
Spirit Airlines
Mar 7
ORD8:16 pmChicago O'Hare Intl
16h 17m
1 stop
STI2:33 pmSantiago de los Caballeros
Mar 15
STI2:46 amSantiago de los Caballeros
9h 31m
1 stop
ORD11:17 amChicago O'Hare Intl
$287

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
Apr 20
ORD7:00 pmChicago O'Hare Intl
16h 23m
1 stop
STI12:23 pmSantiago de los Caballeros
Apr 25
STI1:32 pmSantiago de los Caballeros
11h 53m
1 stop
ORD12:25 amChicago O'Hare Intl
$385
American Airlines
Apr 20
ORD7:00 pmChicago O'Hare Intl
16h 23m
1 stop
STI12:23 pmSantiago de los Caballeros
Apr 25
STI1:32 pmSantiago de los Caballeros
18h 52m
2 stops
ORD7:24 amChicago O'Hare Intl
$389

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 February 6, 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

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Sat 3/7

8:16 pm-2:33 pm

1 stop16h 17m

Santiago de los Caballeros

Sun 3/15

2:46 am-5:15 pm

1 stop15h 29m

$266

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Mon 4/20

7:05 am-2:35 pm

1 stop6h 30m

Santiago de los Caballeros

Sat 4/25

3:40 pm-11:41 pm

1 stop9h 01m

$282

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Sat 3/7

8:16 pm-2:33 pm

1 stop16h 17m

Santiago de los Caballeros

Sun 3/15

2:46 am-11:17 am

1 stop9h 31m

$287

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Mon 6/1

5:15 am-2:35 pm

1 stop8h 20m

Santiago de los Caballeros

Wed 6/3

3:40 pm-11:41 pm

1 stop9h 01m

$302

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Wed 4/22

5:15 am-2:35 pm

1 stop8h 20m

Santiago de los Caballeros

Sat 4/25

3:40 pm-11:41 pm

1 stop9h 01m

$306

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Fri 3/6

8:16 pm-3:35 pm

1 stop17h 19m

Santiago de los Caballeros

Mon 3/9

3:41 pm-11:47 pm

1 stop9h 06m

$308

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Tue 3/10

6:36 pm-2:33 pm

1 stop18h 57m

Santiago de los Caballeros

Sun 3/15

3:43 pm-5:15 pm

1 stop26h 32m

$309

ChicagoSantiago de los Caballeros

MDW - STI

MDWSTI

Chicago Midway

Tue 3/17

9:35 am-11:54 pm

2 stops13h 19m

Santiago de los Caballeros

Mon 3/30

8:40 pm-12:29 pm

2 stops16h 49m

$561

ChicagoSantiago de los Caballeros

MDW - STI

MDWSTI

Chicago Midway

Mon 2/16

9:34 am-1:34 am

2 stops14h 00m

Santiago de los Caballeros

Mon 3/2

9:59 pm-12:46 pm

2 stops16h 47m

$1,159

ChicagoSantiago de los Caballeros

MDW - STI

MDWSTI

Chicago Midway

Mon 2/16

9:34 am-1:34 am

2 stops14h 00m

Santiago de los Caballeros

Mon 3/2

9:59 pm-12:46 pm

2 stops16h 47m

$1,199

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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.

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 13m

Direct flights

None
The fastest flight from Chicago to Santiago de los Caballeros takes 6h 13m
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 13m 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
9,239 reviews
Search United Airlines flights
JetBluePriceFrom $255Free CancellationRating
7.2
2,893 reviews
Search JetBlue flights
Spirit AirlinesPriceFrom $298Free CancellationRating
6.3
8,418 reviews
Search Spirit Airlines flights
DeltaPriceFrom $356Free CancellationRating
7.9
8,149 reviews
Search Delta flights
American AirlinesPriceFrom $437Free CancellationRating
7.2
11,234 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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