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Santiago de los Caballeros

$161+ Cheap flights from Chicago (CHI) to Santiago de los Caballeros (STI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 7/28. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — STI
Jul 8 — Jul 151
Tue 7/8
Tue 7/15
1 adult, Economy
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Cheap flight deals from Chicago to Santiago de los Caballeros

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Santiago de los Caballeros (STI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated July 3, 2025.

Round-trip from

$335
(Cheapflightsfares)

One-way from

$161
(SmartFares)

Popular in

December

Cheapest in

September

Average price

$573
From Chicago (CHI) to Santiago de los Caballeros
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One-way flight from Chicago (CHI) to Santiago de los Caballeros
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Highest demand for flights based on searches. 11% potential increase in price ($69 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($22 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Find flight deals from Chicago to Santiago de los Caballeros

Cheapest flights from Chicago to Santiago de los Caballeros
Explore the most affordable flight options available from Chicago to Santiago de los Caballeros. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 3, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/228:12 pmORD - STI
1 stop12h 03mSpirit Airlines
Fri 9/512:10 pmSTI - ORD
1 stop11h 38mSpirit Airlines
Deal found 7/2$335
This Delta deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/107:30 amORD - STI
1 stop10h 08mDelta
Mon 10/209:03 pmSTI - ORD
1 stop14h 01mDelta
Deal found 6/30$423
This American Airlines deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/138:09 amORD - STI
2 stops11h 39mAmerican Airlines
Wed 8/277:00 amSTI - ORD
1 stop15h 25mAmerican Airlines
Deal found 7/3$427
This JetBlue deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/166:45 amORD - STI
1 stop10h 18mJetBlue
Thu 9/253:20 amSTI - ORD
1 stop9h 50mJetBlue
Deal found 7/3$482
This Mytrip deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/109:40 amMDW - STI
3 stops23h 10mMultiple Airlines
Thu 7/1710:55 amSTI - MDW
2 stops23h 46mMultiple Airlines
Deal found 7/1$797
This Delta deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/19:30 amMDW - STI
2 stops13h 56mDelta
Sat 12/66:45 amSTI - MDW
2 stops13h 51mDelta
Deal found 7/1$1,685

Cheapflights 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, Cheapflights users made 2,558,603 searches. Data last updated July 3, 2025.
Use the filters below to find and compare flights from Chicago to Santiago de los Caballeros that are best for you.

Fly from

Chicago

Fly to

Santiago de los Caballeros

Route

Depart

Return

Price

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Fri 8/22

8:12 pm-9:15 am

1 stop12h 03m

Santiago de los Caballeros

Fri 9/5

12:10 pm-10:48 pm

1 stop11h 38m

$335

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Fri 10/10

7:30 am-6:38 pm

1 stop10h 08m

Santiago de los Caballeros

Mon 10/20

9:03 pm-10:04 am

1 stop14h 01m

$423

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Wed 8/13

8:09 am-8:48 pm

2 stops11h 39m

Santiago de los Caballeros

Wed 8/27

7:00 am-9:25 pm

1 stop15h 25m

$427

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Tue 9/16

6:45 am-6:03 pm

1 stop10h 18m

Santiago de los Caballeros

Thu 9/25

3:20 am-12:10 pm

1 stop9h 50m

$482

ChicagoSantiago de los Caballeros

MDW - STI

MDWSTI

Chicago Midway

Mon 12/1

9:30 am-1:26 am

2 stops13h 56m

Santiago de los Caballeros

Sat 12/6

6:45 am-6:36 pm

2 stops13h 51m

$1,685

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Mon 7/28

5:40 pm-9:50 am

1 stop15h 10m

$161

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Tue 10/14

7:00 am-6:38 pm

2 stops10h 38m

$200

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Sun 7/13

4:43 pm-12:51 pm

2 stops19h 08m

$248

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Sun 7/13

5:36 pm-10:03 am

1 stop15h 27m

$260

ChicagoSantiago de los Caballeros

MDW - STI

MDWSTI

Chicago Midway

Sat 7/12

9:12 pm-9:50 am

2 stops35h 38m

$376

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/1

Showing 1-10 of 11 results
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Best time to book a flight from Chicago to Santiago de los Caballeros

Have a flexible travel schedule? Discover the best time to fly to Santiago de los Caballeros from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Santiago de los Caballeros

What is the cheapest month to book a flight from Chicago to Santiago de los Caballeros?

Currently, May is the cheapest month in which you can book a flight from Chicago to Santiago de los Caballeros (average of $347). Flying from Chicago to Santiago de los Caballeros in July is currently the most expensive (average of $629). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to STI?

Find hourly flight availability from Chicago to Santiago de los Caballeros. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 3, 2025.

One of the essential ways to save on airfare from Chicago to Santiago de los Caballeros is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the afternoon could potentially save you up to 31% on airfare.

How much does it cost to fly round-trip from Chicago to Santiago de los Caballeros?

Reviews of airlines servicing Santiago de los Caballeros

Get insights into the airlines that provide service to Santiago de los Caballeros. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Santiago de los Caballeros. Reviews last updated July 3, 2025.
Peruse reviews from past customers who have flown with Delta, United Airlines, and JetBlue from Chicago to Santiago de los Caballeros to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,982 reviews

Boarding

8.2

Crew

8.5

Overall

8.0

Entertainment

7.9

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,982 reviews
Delta
8.0
Very good
7,982 reviews

Boarding

8.2

Crew

8.5

Overall

8.0

Entertainment

7.9

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,861 reviews
Delta
8.0
Very good
7,982 reviews

Boarding

8.2

Crew

8.5

Overall

8.0

Entertainment

7.9

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
JetBlue
7.3
Good
2,916 reviews
Delta
8.0
Very good
7,982 reviews

Boarding

8.2

Crew

8.5

Overall

8.0

Entertainment

7.9

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,982 reviews

Boarding

8.2

Crew

8.5

Overall

8.0

Entertainment

7.9

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Spirit Airlines
6.3
Okay
8,086 reviews
Delta
8.0
Very good
7,982 reviews

Boarding

8.2

Crew

8.5

Overall

8.0

Entertainment

7.9

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

Related info for your journey

Find useful and relevant information for your journey from Chicago to Santiago de los Caballeros. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Santiago de los Caballeros from Chicago?

    For a flight from Chicago to Santiago de los Caballeros, you will be flying into Santiago. Santiago de los Caballeros (STI) is just 6.8 mi from the center of the city. Santiago is the only Santiago de los Caballeros airport and it handles 0 inbound flights from Chicago per day. 4 airlines have flights to Santiago de los Caballeros from Chicago on a regular basis.

  • What are the cheapest airlines flying from Chicago to Santiago de los Caballeros round-trip?

    Currently priced at $335, Spirit Airlines will fly you from Chicago to Santiago de los Caballeros and back. In addition to Spirit Airlines, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from Delta and American Airlines - these airlines can fly you to your destination from $427 and $427, respectively. Users have found that Spirit Airlines is 37% cheaper than the other options available to this destination.

  • What are the cheapest airlines to fly from Chicago to Santiago de los Caballeros one-way?

    For one-way options, check prices for Spirit Airlines. According to our data, you can fly for as low as $161. Users have also found prices from $248 and $304 on Frontier and JetBlue, respectively.

  • Can I find deals for flights from Chicago to Santiago de los Caballeros that include hotel bookings?

    Yes. In addition to deals on Chicago to Santiago de los Caballeros flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Santiago de los Caballeros?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Santiago de los Caballeros.

  • Can I find deals for business class flights from Chicago to Santiago de los Caballeros?

    Yes. Cheapflights offers flight deals from Chicago to Santiago de los Caballeros by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Santiago de los Caballeros?

    Currently, May is the cheapest month in which you can book a flight from Chicago to Santiago de los Caballeros (average of $347). Flying from Chicago to Santiago de los Caballeros in July is currently the most expensive (average of $629). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Top 4 airlines flying from Chicago to Santiago de los Caballeros

Discover the top 4 airlines that operate flights from Chicago to Santiago de los Caballeros. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$226Average$671FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$343Average$472FlexibilityNo cancel feeOn-time62%
DeltaCheapest$345Average$437FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$395Average$772FlexibilityNo cancel feeOn-time71%

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