Cheap Flights from Chicago (ORD) to Santiago (STI)

Popular airlines from Chicago O'Hare Intl. Airport (ORD) to Cibao Intl. Airport (STI)

Find the cheapest month to fly from Chicago (ORD) to Santiago de los Caballeros (STI)

October is typically the cheapest month to fly

From US$300 - US$711 per traveler.

Frequently asked questions

How much does a flight from O'Hare Intl. Airport (ORD) to Cibao Intl. Airport (STI) cost?
Grab a cheap one-way flight or cheap return flight from O'Hare Intl. Airport (ORD) to Cibao Intl. Airport (STI) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight deals on this route.
What is the cheapest month to fly from O'Hare Intl. Airport (ORD) to Cibao Intl. Airport (STI)?
The cheapest month to fly from ORD to STI is , when there's less demand. Off-peak season is generally when you'll find cheap fares for travel between these airports.
What is the cheapest airline that flies from O'Hare Intl. Airport (ORD) to Cibao Intl. Airport (STI)?
Use the filter tool on Expedia to compare airlines and find the most affordable carrier that'll take you from ORD to STI. Then, sort your results by "Price (lowest to highest)" to score a great deal.
How many flights per day from O'Hare Intl. Airport (ORD) to Cibao Intl. Airport (STI)?
Direct flights from O'Hare Intl. Airport (ORD) to Cibao Intl. Airport (STI) aren't available daily, so you'll have to take a flight with a layover. Explore your options with our filter tool. Enter your travel details and choose either "1 Stop" or "2+ Stops."
What day of the week has the most flights from ORD to STI?
Generally you'll have the most choice when it comes to flights on a Friday. Tuesdays tend to be the quietest.* But this can vary depending on the season, carrier and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from O'Hare Intl. Airport (ORD) to Cibao Intl. Airport (STI)?
Book a flight from O'Hare Intl. Airport (ORD) to Cibao Intl. Airport (STI) that takes off before 3 PM to reduce the risk of cancellations. Departures later than this have a 22% higher chance of being canceled, on average.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from O'Hare Intl. Airport (ORD) to Cibao Intl. Airport (STI) last-minute?
Last-minute fares from ORD to STI are generally more expensive. To secure the best rates, start looking for flights well in advance. That being said, if your travel plans are flexible, you may land a cheap fare just before your departure.
Is it cheaper to book an ORD to STI flight and hotel package?
Opting for an ORD to STI flight and hotel package tends to be cheaper than booking separately. With Expedia, you can enjoy the convenience of organizing your travels in one place. Pick from our wide range of hotels and then add car rentals, activities and flights to your booking. Bundle it all together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from O'Hare Intl. Airport (ORD) to Cibao Intl. Airport (STI)?
If you booked your ORD to STI flight in the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of fare you purchased, additional charges may apply for changes beyond that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, visit our Customer Service portal if you'd like more information.

Travel information

Origin airport
O'Hare Intl.
Destination airport
Cibao Intl.
Distance
1859 mi

Book with confidence

Chicago to Santiago Flights

The cheapest times to fly from Chicago to Santiago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Santiago are during the month of . You can find some of the cheapest flights from Chicago to Santiago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Santiago

Sunday is one of the best days to book for cheap flights from Chicago to Santiago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to Santiago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Santiago in 2025. You can also book with separate airlines for your outbound and return journeys, from one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Santiago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Santiago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Chicago to Santiago Flights

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*Available to One Key members.