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

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      Compare Chicago to Santiago flight deals

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

      Book the best Santiago fare with no extra fees

      Flight deals from Chicago to Santiago

      Looking for a cheap last-minute deal or the best return flight from Chicago to Santiago Airport? If you want to travel next month, return fares start from £325. Find the lowest prices on one-way and return tickets right here.

      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 September.

      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 found£145
      Cheapest month to flySeptember

      Finding cheap flights from Chicago to Santiago: Frequently asked questions

      The best price we found for a return flight from Chicago to Santiago is £316. 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 £316.
      As of August 2026, there are no flights flying from Chicago to Santiago.
      The cheapest month to fly from Chicago to Santiago is usually September.
      After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Santiago Airport on Monday, 28 September 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 Delta .

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

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

      • Your flight from Chicago to STI won't wait if you're running late, so show up at the airport on time. Arrive up to one hour in advance for domestic flights and two hours ahead when you're flying internationally.

      • Flying during a peak time like July? High seasons (like spring break and New Year) can add another hour at security. Be extra safe and arrive up to four hours ahead of an international flight and two hours before domestic departures.

      Airports in Chicago

      Chicago O'Hare International Airport (ORD)

      • Consider adding a stopover to find cheap flights from Chicago to STI. Just deselect 'Direct flights only' when searching for departures from Chicago O'Hare International Airport (ORD). Break up your trip (and maybe get a better deal) by stopping at one of these popular airports:

        • Miami International Airport (MIA)

        • Fort Lauderdale-Hollywood International Airport (FLL)

        • Luis Munoz Marin International Airport (SJU)

      • Travelling from central Chicago to ORD takes around 45 minutes by public transport. If you ride-share, drive or grab a taxi, you'll cover the 27 kms (17 miles) in 30 minutes or so, depending on traffic.

      • Looking for a convenient hotel close to Chicago O'Hare International Airport? If you're catching an early flight from Chicago to Cibao International Airport, these stays will have you sleeping moments from your check-in counter:

      • Of all flights departing from Chicago O'Hare International Airport, 70% arrive as scheduled at their destination.

      • You'll find ORD 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) departing Chicago Midway International Airport.

      • You can reach MDW from central Chicago in about 25 minutes by car, depending on traffic conditions. The journey on public transport will take roughly 30 minutes to travel the 16 kms (10 miles) or so.

      • Want to enjoy an extra night away before catching your Chicago to STI flight? Kick back in a hotel near Chicago Midway International Airport before your trip officially begins. These stays are calling your name:

      • Chicago Midway International Airport has an on-time performance rate of 76%. This figure highlights how frequently flights that take off from this airport arrive at their destination on time.

      • MDW is located at 5700 South Cicero.

      Chicago Rockford International Airport (RFD)

      • From central Chicago, RFD is around 145 kms (90 miles) away. It'll take you roughly 1 hour 40 minutes to get there by car and 2 hours or so on public transport.

      • Make catching an early Chicago to Cibao International Airport flight the easiest part of your trip. Book a room at one of these accommodation options close to Chicago Rockford International Airport and get to your departure gate with time to spare:

      • Airports have an on-time performance rating that measures how often flights get to their destinations within the expected time frame. At RFD, that figure is 71%.

      • The address of Chicago Rockford International Airport is 2 Airport Cir.

      About Cibao International Airport (STI)

      Getting from Cibao International Airport (STI) to central Santiago

      • Central Santiago is around 16 kms (10 miles) from Cibao International Airport and takes about 25 minutes to reach by car. Explore your options for getting into the city, whether that's with a car hire, taxi or ride-share.

      • It takes roughly 40 minutes when travelling by public transport.

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

      • Currently, £145 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 £316. Remember fares can change due to availability at the time of booking.

      • Don't leave everything to the last minute. You're more likely to walk away with cheap flights from Chicago to STI if you book in advance. Airlines often offer some fantastic early bird rates.

      • If you have some flexibility with your travel dates, use the 'Whole month' tool. It'll show you the cheapest price across the month when searching for your Chicago to Cibao International Airport ticket.

      • Locking in a cheap plane ticket from Chicago to STI is a breeze with Price Alerts. Simply set up one of these automatic alerts and we'll let you know when there's a price drop.

      • Uncover a great deal on a flight from Chicago to Cibao International Airport with the help of the filters. Pick your ideal departure and arrival times, airlines and number of stops. You can also sort your results by 'Fastest,' 'Best' or 'Cheapest.'

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

      • It's time to work out when to book your flight from Chicago to Cibao International Airport (STI). August is the most popular month to visit Santiago. If a slower pace sounds more appealing, think about going in December.

      • When booking your Chicago to STI plane ticket, consider the kind of weather you prefer. August is the warmest month in Santiago, with temperatures ranging from 21ºC to 33ºC.

      • January has temperatures of between 16ºC and 29ºC. Search for cheap tickets from Chicago to Cibao International Airport around that time if you like cooler conditions.

      More about Santiago

      • Once you've booked your flight from Chicago to Cibao International Airport, find a hotel that keeps you close to what you want to see. Make one of these accommodation options your base for exploring Santiago:

      • MTB National Park and Catedral de Santiago Apostol are just the start of the top-rated attractions to add to your Santiago itinerary. Keep the adventure rolling by checking out Monument to the Heroes of the Restoration.

      Explore more of the Dominican Republic

      • Santiago has its own special appeal, but there are so many other corners of the Dominican Republic waiting to be explored. Around 129 kms (80 miles) southeast of Santiago, a trip to Santo Domingo will keep you on the move. Start with leading attractions like Catedral Primada de las Americas, Alcazar de Colon and The Cathedral of the Americas.

      • Around 129 kms (80 miles) southeast of Santiago, Santo Domingo Este is another essential stop in the Dominican Republic. Get a taste of what this destination has to offer at Lago los tres ojos, National Aquarium and La Cueva del Eden.

      Prices shown on this page are estimated lowest prices only. Found in the last 12 days.