Popular airlines from Chicago O'Hare Intl. Airport (ORD) to Santiago Island (RAI-Praia Intl.)
TAP PortugalTAP Portugal
Turkish AirlinesTurkish Airlines
Royal Air MarocRoyal Air Maroc
Swiss International Air LinesSwiss International Air Lines
Ethiopian AirlinesEthiopian Airlines
Be in the knowGet alerts if flight prices drop or rise*
Book smarterSave up to 30% on select hotels after you book a flight*
Cheap Flights from Chicago to Santiago Island (ORD-RAI)
Prices were available within the past 7 days and start at $364 for one-way flights and $784 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Alternative airports near Praia
Prices were available within the past 7 days. Prices and availability are subject to change.
Origin airport | O'Hare Intl. |
|---|---|
Destination airport | Praia Intl. |
Airlines serving | Ethiopian Airlines, Royal Air Maroc, Swiss International Air Lines, TAP Portugal, Turkish Airlines |
Roundtrip price | $783 |
Distance | 4224 mi |
Chicago to Santiago Island Flights
The cheapest times to fly from Chicago to Santiago Island
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 Island are during the month of December. You can find some of the cheapest flights from Chicago to Santiago Island with Expedia's search tool and vast selection of airlines.
The best time to book a flight from Chicago to Santiago Island
Sunday is one of the best days to book for cheap flights from Chicago to Santiago Island: 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 Island
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 Island in 2025. You can also book with separate airlines for your outbound and return journeys, from $364 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 Island 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 Island 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.