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Cheap flights from Chicago to Santiago de los Caballeros from $202

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 10/28. 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.
JetBlue Logo
7:00 am - 3:01 pmORD  Chicago O'Hare Intl-STI Santiago de los Caballeros
7h 01m1 stop Fort Lauderdale
JetBlue Logo
4:54 pm - 11:44 pmSTI  Santiago de los Caballeros-ORD Chicago O'Hare Intl
7h 50m1 stop Fort Lauderdale
$425JetBlue
Tue, Sep 1 - Fri, Sep 4
American Airlines Logo
6:29 am - 4:03 pmORD  Chicago O'Hare Intl-STI Santiago de los Caballeros
7h 34m1 stop Philadelphia
American Airlines Logo
7:00 am - 3:33 pmSTI  Santiago de los Caballeros-ORD Chicago O'Hare Intl
10h 33m1 stop Miami
$428American Airlines
Tue, Nov 10 - Wed, Dec 9
American Airlines Logo
5:05 am - 2:12 pmORD  Chicago O'Hare Intl-STI Santiago de los Caballeros
8h 07m1 stop Miami
American Airlines Logo
3:12 pm - 12:38 amSTI  Santiago de los Caballeros-ORD Chicago O'Hare Intl
10h 26m1 stop Miami
$428American Airlines
Mon, Oct 26 - Thu, Oct 29
American Airlines Logo
6:29 am - 4:03 pmORD  Chicago O'Hare Intl-STI Santiago de los Caballeros
7h 34m1 stop Philadelphia
American Airlines Logo
7:00 am - 4:15 pmSTI  Santiago de los Caballeros-ORD Chicago O'Hare Intl
11h 15m2 stops Miami Washington, D.C. Reagan-National
$433American Airlines
Tue, Nov 10 - Wed, Dec 9
Delta Logo
1:55 pm - 12:55 amORD  Chicago O'Hare Intl-STI Santiago de los Caballeros
9h 00m1 stop New York John F Kennedy Intl
Delta Logo
2:30 pm - 9:42 pmSTI  Santiago de los Caballeros-ORD Chicago O'Hare Intl
9h 12m1 stop New York John F Kennedy Intl
$450Delta
Tue, Nov 10 - Wed, Dec 9
Delta Logo
8:04 am - 12:55 amORD  Chicago O'Hare Intl-STI Santiago de los Caballeros
14h 51m2 stops Atlanta Hartsfield-Jackson New York John F Kennedy Intl
Delta Logo
9:00 pm - 9:27 amSTI  Santiago de los Caballeros-ORD Chicago O'Hare Intl
14h 27m1 stop New York John F Kennedy Intl
$455Delta
Tue, Nov 10 - Wed, Dec 9
Copa Airlines Logo
3:20 pm - 2:58 pmORD  Chicago O'Hare Intl-STI Santiago de los Caballeros
22h 38m1 stop Panama City Tocumen Intl
Copa Airlines Logo
4:10 pm - 12:57 amSTI  Santiago de los Caballeros-ORD Chicago O'Hare Intl
9h 47m1 stop Panama City Tocumen Intl
$472Copa Airlines
Fri, Oct 9 - Sat, Oct 17
Copa Airlines Logo
3:20 pm - 2:58 pmORD  Chicago O'Hare Intl-STI Santiago de los Caballeros
22h 38m1 stop Panama City Tocumen Intl
Copa Airlines Logo
4:10 pm - 1:59 pmSTI  Santiago de los Caballeros-ORD Chicago O'Hare Intl
22h 49m1 stop Panama City Tocumen Intl
$492Copa Airlines
Fri, Oct 2 - Sat, Oct 10
JetBlue Logo
7:00 am - 3:01 pmORD  Chicago O'Hare Intl-STI Santiago de los Caballeros
7h 01m1 stop Fort Lauderdale
JetBlue Logo
4:54 pm - 11:44 pmSTI  Santiago de los Caballeros-ORD Chicago O'Hare Intl
7h 50m1 stop Fort Lauderdale
$545JetBlue
Tue, Sep 1 - Sat, Sep 5
JetBlue Logo
7:00 am - 3:01 pmORD  Chicago O'Hare Intl-STI Santiago de los Caballeros
7h 01m1 stop Fort Lauderdale
JetBlue Logo
4:54 pm - 11:44 pmSTI  Santiago de los Caballeros-ORD Chicago O'Hare Intl
7h 50m1 stop Fort Lauderdale
$545JetBlue
Mon, Aug 31 - Sat, Sep 5

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Copa Airlines flights from Chicago to Santiago de los Caballeros

Our best Copa Airlines deals on Chicago to Santiago de los Caballeros flight tickets
Copa Airlines
Oct 9
ORD3:20 pmChicago O'Hare Intl
22h 38m
1 stop
STI2:58 pmSantiago de los Caballeros
Oct 17
STI4:10 pmSantiago de los Caballeros
9h 47m
1 stop
ORD12:57 amChicago O'Hare Intl
$472
Copa Airlines
Oct 9
ORD3:20 pmChicago O'Hare Intl
22h 38m
1 stop
STI2:58 pmSantiago de los Caballeros
Oct 17
STI4:10 pmSantiago de los Caballeros
9h 47m
1 stop
ORD12:57 amChicago O'Hare Intl
$492

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
Oct 26
ORD5:05 amChicago O'Hare Intl
8h 07m
1 stop
STI2:12 pmSantiago de los Caballeros
Oct 29
STI3:12 pmSantiago de los Caballeros
10h 26m
1 stop
ORD12:38 amChicago O'Hare Intl
$428
American Airlines
Oct 26
ORD8:55 pmChicago O'Hare Intl
16h 17m
2 stops
STI2:12 pmSantiago de los Caballeros
Oct 29
STI3:12 pmSantiago de los Caballeros
9h 56m
2 stops
ORD12:08 amChicago O'Hare Intl
$433
American Airlines
Sep 22
ORD6:59 amChicago O'Hare Intl
6h 16m
1 stop
STI2:15 pmSantiago de los Caballeros
Oct 6
STI3:12 pmSantiago de los Caballeros
10h 26m
1 stop
ORD12:38 amChicago O'Hare Intl
$448

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 August 7, 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
Quickest round-trip

ChicagoSantiago de los Caballeros

ORD Chicago O'Hare Intl - STI Santiago de los Caballeros

ORDSTI

Chicago O'Hare Intl

Tue 9/1

7:00 am-3:01 pm

1 stop7h 01m

Santiago de los Caballeros

Fri 9/4

4:54 pm-11:44 pm

1 stop7h 50m

$425

ChicagoSantiago de los Caballeros

ORD Chicago O'Hare Intl - STI Santiago de los Caballeros

ORDSTI

Chicago O'Hare Intl

Tue 11/10

6:29 am-4:03 pm

1 stop7h 34m

Santiago de los Caballeros

Wed 12/9

7:00 am-3:33 pm

1 stop10h 33m

$428

ChicagoSantiago de los Caballeros

ORD Chicago O'Hare Intl - STI Santiago de los Caballeros

ORDSTI

Chicago O'Hare Intl

Mon 10/26

5:05 am-2:12 pm

1 stop8h 07m

Santiago de los Caballeros

Thu 10/29

3:12 pm-12:38 am

1 stop10h 26m

$428

ChicagoSantiago de los Caballeros

ORD Chicago O'Hare Intl - STI Santiago de los Caballeros

ORDSTI

Chicago O'Hare Intl

Tue 11/10

6:29 am-4:03 pm

1 stop7h 34m

Santiago de los Caballeros

Wed 12/9

7:00 am-4:15 pm

2 stops11h 15m

$433

ChicagoSantiago de los Caballeros

ORD Chicago O'Hare Intl - STI Santiago de los Caballeros

ORDSTI

Chicago O'Hare Intl

Tue 11/10

1:55 pm-12:55 am

1 stop9h 00m

Santiago de los Caballeros

Wed 12/9

2:30 pm-9:42 pm

1 stop9h 12m

$450

ChicagoSantiago de los Caballeros

ORD Chicago O'Hare Intl - STI Santiago de los Caballeros

ORDSTI

Chicago O'Hare Intl

Tue 11/10

8:04 am-12:55 am

2 stops14h 51m

Santiago de los Caballeros

Wed 12/9

9:00 pm-9:27 am

1 stop14h 27m

$455

ChicagoSantiago de los Caballeros

ORD Chicago O'Hare Intl - STI Santiago de los Caballeros

ORDSTI

Chicago O'Hare Intl

Fri 10/9

3:20 pm-2:58 pm

1 stop22h 38m

Santiago de los Caballeros

Sat 10/17

4:10 pm-12:57 am

1 stop9h 47m

$472

ChicagoSantiago de los Caballeros

ORD Chicago O'Hare Intl - STI Santiago de los Caballeros

ORDSTI

Chicago O'Hare Intl

Fri 10/2

3:20 pm-2:58 pm

1 stop22h 38m

Santiago de los Caballeros

Sat 10/10

4:10 pm-1:59 pm

1 stop22h 49m

$492

ChicagoSantiago de los Caballeros

ORD Chicago O'Hare Intl - STI Santiago de los Caballeros

ORDSTI

Chicago O'Hare Intl

Tue 9/1

7:00 am-3:01 pm

1 stop7h 01m

Santiago de los Caballeros

Sat 9/5

4:54 pm-11:44 pm

1 stop7h 50m

$545

ChicagoSantiago de los Caballeros

ORD Chicago O'Hare Intl - STI Santiago de los Caballeros

ORDSTI

Chicago O'Hare Intl

Mon 8/31

7:00 am-3:01 pm

1 stop7h 01m

Santiago de los Caballeros

Sat 9/5

4:54 pm-11:44 pm

1 stop7h 50m

$545

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 February. Flight prices, which tend to average around $392, 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 February, then flying in March is also cheap. Prices for this month can be found on momondo for an average of $439.

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

You could potentially save up to 9% 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

7h 01m

Direct flights

None
The fastest flight from Chicago to Santiago de los Caballeros takes 7h 01m
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. 7h 01m 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
8,502 reviews
Search Delta flights
JetBluePriceFrom $255Free CancellationRating
7.1
3,030 reviews
Search JetBlue flights
American AirlinesPriceFrom $407Free CancellationRating
7.1
11,881 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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