Cheap flights from Chicago (CHI) to Santiago de los Caballeros (STI) from $157

This is the cheapest one-way flight price, found on 6/5. Prices may vary by date and flight preferences.
CHI — STI
Jun 11 — Jun 181
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.

The best prices from Chicago to Santiago de los Caballeros are usually found in April or February, booked 48 days in advance, depart on a Friday or Thursday and return on a Tuesday

How to find the cheapest flight from Chicago (CHI) to Santiago de los Caballeros (STI)

All the information you need to plan the best CHI to STI flight in 2023: compare Chicago to Santiago de los Caballeros flight prices with the expected peak season, weather and rainfall in Santiago de los Caballeros.

Popular in

December

Cheapest in

April

Round-trip from

$382

One-way from

$237
High demand for flights, 39% potential price rise
Best time to find cheap flights, 25% potential price drop
From Chicago (CHI) to Santiago de los Caballeros
One-way flight from Chicago (CHI) to Santiago de los Caballeros

CHI - STI

Price

$382 - $954

STI

Temperature

73.4 - 80.6 °F

STI

Rainfall

3 - 11.6 inches

Cheap flights from Chicago to Santiago de los Caballeros in June, July 2023

The best prices found for CHI to STI flights for June, July
Check out some of the best flight deals from Chicago to Santiago de los Caballeros in 2023. More deals are always being added, so be sure to check back regularly.

Chicago to Santiago de los Caballeros 2023 flight deals

Cheap flights to Santiago de los Caballeros from Chicago found for this year
Check out some of the best flight deals from Chicago to Santiago de los Caballeros in 2023. More deals are always being added, so be sure to check back regularly.

Cheap Spirit Airlines flights from Chicago to Santiago de los Caballeros

Find some of the cheapest Spirit Airlines flights traveling from Chicago to Santiago de los Caballeros. Deals update often to give you more flight options matching your criteria

Cheap American Airlines flights from Chicago to Santiago de los Caballeros

To aid your search, here are some of the cheapest American Airlines flights we've found from Chicago to Santiago de los Caballeros. Deals frequently update to provide users with more options.

Last minute flights from Chicago to Santiago de los Caballeros

Late deals on return flights to Santiago de los Caballeros from Chicago, departing today and this week
Consider one of these great deals we found on last-minute flights from Chicago to Santiago de los Caballeros. Users should examine the flight details to ensure there are no surprises.

One-way flights to Santiago de los Caballeros from Chicago

The cheapest one-way flights from Chicago to Santiago de los Caballeros
Take a look at some of the best available options we've come across on one-way flights from Chicago to Santiago de los Caballeros. Users needing a return flight from Chicago to Santiago de los Caballeros should utilize the search form above.

Find flights from Chicago to Santiago de los Caballeros within your budget

Use the slider to find flights from Chicago to Santiago de los Caballeros that fit your budget.

Fly from

Any airport

Fly to

Any airport

Budget

$350 - $432

Route

Depart

Return

Price

Chicago O'Hare IntlSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Wed 6/21

2 stops11h 02m

Santiago de los Caballeros

Sun 7/2

1 stop16h 09m

Chicago O'Hare IntlSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Tue 6/20

2 stops17h 59m

Santiago de los Caballeros

Sun 7/2

1 stop16h 09m

Chicago O'Hare IntlSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Tue 6/20

1 stop14h 04m

Santiago de los Caballeros

Sun 7/2

1 stop16h 09m

Chicago O'Hare IntlSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Wed 6/21

2 stops11h 02m

Santiago de los Caballeros

Sat 7/1

1 stop7h 50m

Chicago O'Hare IntlSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Wed 6/21

2 stops11h 02m

Santiago de los Caballeros

Fri 6/30

1 stop16h 09m

Chicago O'Hare IntlSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Wed 9/13

1 stop15h 02m

Santiago de los Caballeros

Fri 9/22

1 stop11h 21m

Chicago O'Hare IntlSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Thu 9/14

2 stops16h 37m

Santiago de los Caballeros

Tue 9/19

2 stops16h 57m

Chicago O'Hare IntlSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Thu 7/6

2 stops28h 47m

Santiago de los Caballeros

Mon 7/10

1 stop7h 50m

Chicago MidwaySantiago de los Caballeros

MDW - STI

MDWSTI

Chicago Midway

Wed 9/13

2 stops17h 14m

Santiago de los Caballeros

Fri 9/22

2 stops21h 23m

Flights are sorted by cheapest first

Deals found on 6/5

Reviews of airlines servicing Santiago de los Caballeros

Read reviews from past customers who have flown Spirit Airlines, American Airlines and Delta from Chicago to Santiago de los Caballeros. 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
2,393 reviews

Crew

8.5

Overall

8.0

Boarding

8.1

Food

7.2

Comfort

7.9

Entertainment

7.8

Reviews

1 / 10

Flights were on time with no delays, luggage arrived with the flight. I know the flights were short, but the only drinks offered were water, tea and coffee. It would’ve been nice to have the option to choose a soda, especially since I was in comfort class. The snacks were very small.

Delta
8.0
Very good
2,393 reviews
Delta
8.0
Very good
2,393 reviews

Crew

8.5

Overall

8.0

Boarding

8.1

Food

7.2

Comfort

7.9

Entertainment

7.8

Reviews

1 / 10

Flights were on time with no delays, luggage arrived with the flight. I know the flights were short, but the only drinks offered were water, tea and coffee. It would’ve been nice to have the option to choose a soda, especially since I was in comfort class. The snacks were very small.

American Airlines
7.3
Good
2,149 reviews
Delta
8.0
Very good
2,393 reviews

Crew

8.5

Overall

8.0

Boarding

8.1

Food

7.2

Comfort

7.9

Entertainment

7.8

Reviews

1 / 10

Flights were on time with no delays, luggage arrived with the flight. I know the flights were short, but the only drinks offered were water, tea and coffee. It would’ve been nice to have the option to choose a soda, especially since I was in comfort class. The snacks were very small.

Spirit Airlines
6.5
Okay
1,064 reviews
Delta
8.0
Very good
2,393 reviews

Crew

8.5

Overall

8.0

Boarding

8.1

Food

7.2

Comfort

7.9

Entertainment

7.8

Reviews

1 / 10

Flights were on time with no delays, luggage arrived with the flight. I know the flights were short, but the only drinks offered were water, tea and coffee. It would’ve been nice to have the option to choose a soda, especially since I was in comfort class. The snacks were very small.

Related info for your journey

Useful info, stats and facts about Chicago to Santiago de los Caballeros flights.

Top 5 airlines flying from Chicago to Santiago de los Caballeros

The chart below displays the airlines Cheapflights users traveling from Chicago to Santiago de los Caballeros choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
AirlineCheapestAverageFlexibilityOn-timeCOVID-19 safety
Spirit AirlinesCheapest$362Average$565FlexibilityNo cancel feeOn-time65%COVID-19 safety
Search Spirit Airlines flights
American AirlinesCheapest$381Average$807FlexibilityNo cancel feeOn-time71%COVID-19 safety
Search American Airlines flights
JetBlueCheapest$417Average$605FlexibilityNo cancel feeOn-time62%COVID-19 safety
Search JetBlue flights
United AirlinesCheapest$420Average$704FlexibilityNo cancel feeOn-time69%COVID-19 safety
Search United Airlines flights
DeltaCheapest$460Average$590FlexibilityNo cancel feeOn-timeN/ACOVID-19 safety
Search Delta flights