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Cheap flights from Chicago O'Hare Intl Airport to Santiago de los Caballeros from $157

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 O'Hare Intl Airport to Santiago de los Caballeros departing on 8/17. 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 O'Hare Intl Airport to Santiago de los Caballeros

Cheap round-trip flights

Enter your travel dates to find the best prices.
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
$370JetBlue
Mon, Sep 21 - Thu, Sep 24
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
$378JetBlue
Mon, Sep 21 - Thu, Sep 24
American Airlines Logo
8:55 pm - 2:15 pm
ORD
-
STI
16h 20m
2 stops
American Airlines Logo
3:15 pm - 7:58 am
STI
-
ORD
17h 43m
2 stops
$383American Airlines
Mon, Sep 21 - Thu, Sep 24
American Airlines Logo
8:55 pm - 2:15 pm
ORD
-
STI
16h 20m
2 stops
American Airlines Logo
3:15 pm - 7:58 am
STI
-
ORD
17h 43m
2 stops
$391American Airlines
Mon, Sep 14 - Wed, Sep 30
American Airlines Logo
2:30 pm - 2:15 pm
ORD
-
STI
22h 45m
1 stop
American Airlines Logo
3:15 pm - 11:32 pm
STI
-
ORD
9h 17m
1 stop
$392American Airlines
Thu, Oct 1 - Sun, Oct 4
American Airlines Logo
2:30 pm - 2:15 pm
ORD
-
STI
22h 45m
1 stop
American Airlines Logo
3:15 pm - 7:27 am
STI
-
ORD
17h 12m
2 stops
$397American Airlines
Thu, Oct 1 - Sun, Oct 4
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
$404JetBlue
Fri, Oct 9 - Sat, Oct 17
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
$412JetBlue
Mon, Sep 21 - Thu, Sep 24
JetBlue Logo
2:35 pm - 11:51 pm
ORD
-
STI
8h 16m
1 stop
JetBlue Logo
4:43 pm - 11:44 pm
STI
-
ORD
9h 01m
1 stop
$438JetBlue
Wed, Oct 28 - Tue, Nov 10
American Airlines Logo
8:37 am - 8:03 pm
ORD
-
STI
10h 26m
1 stop
American Airlines Logo
3:35 pm - 11:30 pm
STI
-
ORD
8h 55m
1 stop
$442American Airlines
Tue, Aug 11 - Tue, Aug 18

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American Airlines flights from Chicago O'Hare Intl Airport to Santiago de los Caballeros

Our best American Airlines deals on Chicago O'Hare Intl Airport to Santiago de los Caballeros flight tickets
American Airlines
Sep 21
ORD8:55 pmChicago O'Hare Intl
16h 20m
2 stops
STI2:15 pmSantiago de los Caballeros
Sep 24
STI3:15 pmSantiago de los Caballeros
17h 43m
2 stops
ORD7:58 amChicago O'Hare Intl
$383
American Airlines
Sep 14
ORD5:00 amChicago O'Hare Intl
8h 15m
1 stop
STI2:15 pmSantiago de los Caballeros
Sep 30
STI3:15 pmSantiago de los Caballeros
17h 43m
2 stops
ORD7:58 amChicago O'Hare Intl
$391
American Airlines
Oct 1
ORD2:30 pmChicago O'Hare Intl
22h 45m
1 stop
STI2:15 pmSantiago de los Caballeros
Oct 4
STI3:15 pmSantiago de los Caballeros
9h 17m
1 stop
ORD11:32 pmChicago O'Hare Intl
$392

JetBlue flights from Chicago O'Hare Intl Airport to Santiago de los Caballeros

Our best JetBlue deals on Chicago O'Hare Intl Airport to Santiago de los Caballeros flight tickets
JetBlue
Sep 21
ORD6:00 amChicago O'Hare Intl
6h 27m
1 stop
STI1:27 pmSantiago de los Caballeros
Sep 24
STI3:49 pmSantiago de los Caballeros
8h 42m
1 stop
ORD11:31 pmChicago O'Hare Intl
$370
JetBlue
Sep 21
ORD6:00 amChicago O'Hare Intl
6h 27m
1 stop
STI1:27 pmSantiago de los Caballeros
Sep 24
STI3:49 pmSantiago de los Caballeros
8h 42m
1 stop
ORD11:31 pmChicago O'Hare Intl
$378
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
$404

momondo Fare Finder

 
Customize your flight search to find flights from Chicago O'Hare Intl Airport 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 1, 2026.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Santiago de los Caballeros that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Mon 9/21

6:00 am-1:27 pm

1 stop6h 27m

Santiago de los Caballeros

Thu 9/24

3:49 pm-11:31 pm

1 stop8h 42m

$370

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Mon 9/21

6:00 am-1:27 pm

1 stop6h 27m

Santiago de los Caballeros

Thu 9/24

3:49 pm-11:31 pm

1 stop8h 42m

$378

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Mon 9/21

8:55 pm-2:15 pm

2 stops16h 20m

Santiago de los Caballeros

Thu 9/24

3:15 pm-7:58 am

2 stops17h 43m

$383

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Mon 9/14

8:55 pm-2:15 pm

2 stops16h 20m

Santiago de los Caballeros

Wed 9/30

3:15 pm-7:58 am

2 stops17h 43m

$391

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Thu 10/1

2:30 pm-2:15 pm

1 stop22h 45m

Santiago de los Caballeros

Sun 10/4

3:15 pm-11:32 pm

1 stop9h 17m

$392

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Thu 10/1

2:30 pm-2:15 pm

1 stop22h 45m

Santiago de los Caballeros

Sun 10/4

3:15 pm-7:27 am

2 stops17h 12m

$397

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

$404

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Mon 9/21

6:00 am-1:27 pm

1 stop6h 27m

Santiago de los Caballeros

Thu 9/24

3:49 pm-11:31 pm

1 stop8h 42m

$412

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Wed 10/28

2:35 pm-11:51 pm

1 stop8h 16m

Santiago de los Caballeros

Tue 11/10

4:43 pm-11:44 pm

1 stop9h 01m

$438

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Tue 8/11

8:37 am-8:03 pm

1 stop10h 26m

Santiago de los Caballeros

Tue 8/18

3:35 pm-11:30 pm

1 stop8h 55m

$442

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 O'Hare Intl Airport 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 O'Hare Intl Airport is in October. Flight prices, which tend to average around $356, 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 October, then flying in February is also cheap. Prices for this month can be found on momondo for an average of $395.

Can stopping save me money on Chicago O'Hare Intl Airport to Santiago de los Caballeros flights?

You could potentially save up to 18% on your flight if you consider stops on a Chicago O'Hare Intl Airport to Santiago de los Caballeros flight.

How have Chicago O'Hare Intl Airport to Santiago de los Caballeros flight prices changed over time?

When to book flights from Chicago O'Hare Intl Airport to Santiago de los Caballeros

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago O'Hare Intl Airport 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 O'Hare Intl Airport to Santiago de los Caballeros (ORD to STI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago O'Hare Intl Airport to Santiago de los Caballeros

Fastest flight time

6h 27m

Direct flights

None
The fastest flight from Chicago O'Hare Intl Airport to Santiago de los Caballeros takes 6h 27m
There are no direct flights from Chicago O'Hare Intl Airport to Santiago de los Caballeros. There are no popular flight routes from Chicago O'Hare Intl Airport to Santiago de los Caballeros.
Search flight deals

Frequently asked questions about flying from Chicago O'Hare Intl Airport to Santiago de los Caballeros

  • How far is Chicago O'Hare Intl to Santiago de los Caballeros by plane?

    There are 1852.8 mi between Chicago O'Hare Intl and Santiago de los Caballeros. 6h 27m is a normal flight duration for this route.

  • When did momondo last update prices for flights from Chicago O'Hare Intl Airport to Santiago de los Caballeros Airport?

    Prices for flights from Chicago O'Hare Intl Airport to Santiago de los Caballeros Airport are refreshed on a daily basis.

  • How many operators does momondo search for flights from Chicago O'Hare Intl Airport to Santiago de los Caballeros Airport?

  • How old do you have to be to fly from Chicago O'Hare Intl Airport to Santiago de los Caballeros Airport?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago O'Hare Intl Airport 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 O'Hare Intl Airport to Santiago de los Caballeros?

Best airlines flying from Chicago O'Hare Intl Airport to Santiago de los Caballeros

Compare and see reviews for airlines that fly from Chicago O'Hare Intl Airport to Santiago de los Caballeros with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $239Free CancellationRating
7.8
8,452 reviews
Search Delta flights
JetBluePriceFrom $255Free CancellationRating
7.1
3,009 reviews
Search JetBlue flights
American AirlinesPriceFrom $407Free CancellationRating
7.1
11,768 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?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Chicago to Santiago de los Caballeros for 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 offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Chicago to Santiago de los Caballeros.

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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