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Cheap Flights from Chicago to Santiago

Compare Chicago to Santiago flight deals

Find the cheapest month or even day of the year to fly to Santiago

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Flight deals from Chicago to Santiago

Looking for a cheap last-minute deal or the best return flight from Chicago to Santiago? Find the lowest prices on one-way and return tickets right here.
Santiago.R 1,842 per passenger.Departing Sat, 21 Feb.One-way flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Sat, 21 Feb, arriving in Santiago.Price includes taxes and charges.From R 1,842, select.
Santiago.R 1,853 per passenger.Departing Sun, 1 Mar.One-way flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Sun, 1 Mar, arriving in Santiago.Price includes taxes and charges.From R 1,853, select.
Santiago.R 1,908 per passenger.Departing Thu, 22 Jan.One-way flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Thu, 22 Jan, arriving in Santiago.Price includes taxes and charges.From R 1,908, select.
Santiago.R 2,453 per passenger.Departing Tue, 2 Jun.One-way flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Tue, 2 Jun, arriving in Santiago.Price includes taxes and charges.From R 2,453, select.
Santiago.R 2,664 per passenger.Departing Mon, 11 May.One-way flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Mon, 11 May, arriving in Santiago.Price includes taxes and charges.From R 2,664, select.
Santiago.R 3,487 per passenger.Departing Sat, 18 Apr.One-way flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Sat, 18 Apr, arriving in Santiago.Price includes taxes and charges.From R 3,487, select.
Santiago.R 6,396 per passenger.Departing Sun, 11 Oct.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago O'Hare International on Sun, 11 Oct, arriving in Santiago.Price includes taxes and charges.From R 6,396, select.
Santiago.R 8,527 per passenger.Departing Wed, 1 Jul.One-way flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Wed, 1 Jul, arriving in Santiago.Price includes taxes and charges.From R 8,527, select.

Find the cheapest month to fly from Chicago to Santiago

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago to Santiago flights are currently cheapest in February.
Jan
from R 1,908
Feb
from R 1,842
Mar
from R 1,853
Apr
from R 3,487
May
from R 2,664
Jun
from R 2,453
Jul
from R 8,527
Aug
Find prices
Sep
Find prices
Oct
from R 6,396
Nov
Find prices
Dec
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Chicago to Santiago: Alternative routes

Compare routes from Chicago to Santiago below. You may find an airport to fly into that's cheaper, faster, or easier than Santiago.

Chicago to Santiago: Flight information

The things to know before you go.
Cheapest flight foundR 1,842
Cheapest month to flyFebruary

Finding cheap flights from Chicago to Santiago: Frequently asked questions

The best price we found for a return flight from Chicago to Santiago is R 4,187. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
Currently, there are no airlines that fly direct from Chicago to Santiago. But we found flights with one stop from R 4,187.
As of January 2026, there are no flights flying from Chicago to Santiago.
The cheapest month to fly from Chicago to Santiago is usually February.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Santiago Airport on Saturday, 21 February 2026.
No airlines currently offer direct flights between Chicago and Santiago Airport. Most routes have one or more stops.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Santiago but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Santiago is around 40 days in advance, so don’t leave your flight to the last minute.
The cheapest airline that flies to Santiago is Spirit Airlines .

Travelling from Chicago to Cibao International Airport (STI): What you need to know

  • Put your holiday plans into action by working out where you'll board your flight from Chicago to Cibao International Airport (STI). O'Hare International Airport (ORD) and Chicago Midway International Airport (MDW) are Chicago's main airports.

  • Santiago is one hour ahead of Chicago. Cibao International Airport is located in Santiago, which is in the UTC-4 timezone.

  • Get to the airport on time so you don't miss your flight from Chicago to STI. Be there at least two hours ahead for international flights and an hour early for domestic departures to avoid any last-minute rush.

  • If you're jetting off during a major holiday or other peak period, give yourself extra time. Arrive two hours ahead of domestic flights and up to four hours before international departures. Queues at check-in and security will be longer.

Airports in Chicago

O'Hare International Airport (ORD)

  • Consider adding a stopover to find cheap flights from Chicago to STI. Just uncheck 'Direct flights only' when browsing departures from O'Hare International Airport (ORD). Slip in a stop (and skip the high fares) by flying through one of these popular airports:

    • Miami International Airport (MIA)

    • Fort Lauderdale-Hollywood International Airport (FLL)

    • Luis Munoz Marin International Airport (SJU)

  • Located around 40 kilometres from the centre of Chicago, ORD can be reached in about 35 minutes by car (depending on traffic). The journey on public transport takes roughly 55 minutes.

  • In search of a comfortable hotel near O'Hare International Airport? If you've booked an early flight from Chicago to Cibao International Airport, these stays will put you moments from your departure gate:

  • 74.85% of flights leaving from O'Hare International Airport touch down at their destination on schedule.

  • ORD is located at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • Think about building a stopover into your journey at Miami International Airport (MIA). It's a popular transfer point for flights from Chicago to Cibao International Airport (STI) leaving Chicago Midway International Airport.

  • MDW is about 19 kilometres from central Chicago. It'll take 20 minutes or so to get to the airport in a car from the city centre. Public transport takes approximately 45 minutes.

  • Kick off your holiday early with an additional night away from home. Before catching your Chicago to STI flight, kick back in one of these hotels close to Chicago Midway International Airport:

  • As far as flight punctuality goes, Chicago Midway International Airport has an on-time arrival performance of 77.88%.

  • The street address for MDW is 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • From the centre of Chicago, RFD is around 137 kilometres away. It takes roughly 1 hour 25 minutes to reach the airport by car and 4 hours 15 minutes or so if you're on public transport.

  • Make departure day worry-free — stay close to Chicago Rockford International Airport and know you'll make it to your boarding gate with time to spare. Get comfy at one of these hotels the day before if you're catching an early Chicago to Cibao International Airport flight:

  • Flights departing from RFD make it to their destination as scheduled 76.19% of the time.

  • You'll find Chicago Rockford International Airport at 2 Airport Cir.

About Cibao International Airport (STI)

Getting from Cibao International Airport (STI) to central Santiago

  • Cibao International Airport to the centre of Santiago is about 13 kilometres. If you're renting a car or getting a cab, plan ahead to make your trip as easy as possible. Journey times may vary depending on traffic and the time of day.

  • Travelling by public transport will take you around 1 hour 10 minutes.

How to find the cheapest flights from Chicago to Cibao International Airport (STI)

  • Currently, R 1,842 is the lowest price we've found for a one-way ticket from Chicago to Cibao International Airport. The cheapest price for a return flight is R 4,187. Remember fares may change due to availability at the time of booking.

  • Booking in advance is often the key to finding a cheap flight from Chicago to STI. Prices tend to rise as demand increases, so the closer you get to departure, the more you'll likely spend.

  • Cheap Chicago to Cibao International Airport tickets are easier to find when your dates are flexible. Try using the 'Whole month' search tool to compare fares throughout the month and then fly out on the cheapest day.

  • You don't need to check back in every day to find out if prices have dropped when you set up a Price Alert. We'll let you know when a better deal comes up on plane tickets from Chicago to STI.

  • Tailor your travel plans using filters. Pick your ideal arrival and departure times, total journey duration and airlines. You can also sort your results by 'Fastest,' 'Best' or 'Cheapest' flights from Chicago to Cibao International Airport.

The best time to fly from Chicago to Cibao International Airport (STI)

  • August is when most people book flights from Chicago to Cibao International Airport (STI). Plan your visit to Santiago in May for a more low-key escape.

  • The warmest month in Santiago is August, with temperatures ranging between 21ºC (70ºF) and 33ºC (91ºF). Book your Chicago to STI plane ticket then if that's your ideal forecast.

  • For cooler conditions, look for a cheap ticket from Chicago to Cibao International Airport in January when temperatures are between 16ºC (61ºF) and 29ºC (84ºF).

More about Santiago

  • Start your Santiago trip right by choosing the perfect place to stay. Once you've booked your flight from Chicago to Cibao International Airport, browse our selection of hotels including:

  • Every great adventure has to include a little sightseeing. MTB National Park, Catedral de Santiago Apostol and Baracoa Park are attractions you won't want to skip in Santiago.

Explore more of the Dominican Republic

  • Santo Domingo is just one of the many cities in the Dominican Republic waiting to be explored after you've experienced Santiago. Around 129 kilometres away to the south-east, check out popular attractions including Alcazar de Colon, The Cathedral of the Americas and República Dominicana - Santo Domingod.

  • If you're looking to explore another corner of the Dominican Republic, consider Santo Domingo Este, about 129 kilometres south-east of Santiago. Lago los tres ojos, Los Corales Park and National Aquarium are highlights.

Plan the rest of your trip from Chicago to Santiago

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.