Cheap Flights from Chicago to Santiago from $180

Frequently Asked Questions

• What are the cheapest flights from Chicago to Santiago (CHI-STI)?

  Based on Trip.com data, Delta Air Lines offers one-way fares as low as $180 on Cheapest nonstop routes (e.g. ORD to STI on Sat, Oct 3), while American Airlines offers Cheapest nonstop round-trips from $428 departing on Tue, Sep 29 and returning on Tue, Oct 6.

• Which airlines offer flights from Chicago to Santiago?

  At the moment, several airlines serve connecting flights from Chicago to Santiago, including: American Airlines Selected airlines are based on historical data collected from flight bookings made by users on Trip.com within the last 90 days.

• When is the best time to book flights from Chicago to Santiago?

  By analyzing data from all airlines on the Trip.com flight calendar, it looks like the best time to book a flight from Chicago to Santiago is around 40 days (6 weeks) in advance, and the best time to fly is usually on Tuesday, Wednesday, and Saturday. Tuesday typically offers the cheapest flights for departure, while Saturday offers the best return deals.

• How can I find the best deals on flights from Chicago to Santiago?

  To find best deals on flights from Chicago to Santiago, you can use various tools on Trip.com:
  · Be flexible with your travel dates to get the cheapest flight deal. Now the cheapest flight deal is on Sat, Oct 3, with one-way flights priced at just $180.
  · Compare airlines strategically. Budget carriers often provide the lowest base fares, while we found the most affordable airline currently operating on this route is Delta Air Lines.
  · Set up price alerts to easily monitor ticket prices without having to check every day.
  · Check Trip.com flight deals and promo codes frequently.
  · Avoid peak season unless you book very early. It seems the peak season for Santiago travel is around July.
  · Get exclusive promo codes for Trip.com app users.

• When are flight tickets from Chicago (CHI) to Santiago (STI) the cheapest?

  The cheapest months to fly from Chicago to Santiago is November, when demand for travel is lower.

• Which upcoming date is cheapest to fly from Chicago to Santiago on?

  After crunching the numbers on our August flight calendar, it's currently cheapest to fly from Chicago to Santiago on August 27, 2026 with American Airlines, with prices starting at $453.

• Which airports can I fly to for Santiago from Chicago?

  You can land at any one of the following hubs in Santiago, with O'Hare International Airport to Cibao International Airport (ORD-STI) is by far the most common option on this route: Cibao International Airport (STI).

• Is there any time difference between Chicago and Santiago?

  The time difference between Santiago and Chicago is 2h.

• How do I change or cancel my ticket from Chicago to Santiago?

  Tickets can only be changed or canceled if permitted by airline policy. To submit a change or cancellation request, go to the flight bookings page, select the option to change or cancel your booking, choose the relevant passengers and segment, and submit a request. Please note that additional charges may apply according to the airline ticket policy. However, if the flight has been rescheduled and you would like to change or cancel your ticket, you can submit an involuntary cancellation request. For more details about change and cancellation policies, please check the customer support pages.

• What is the average cost of a one-way flight from Chicago to Santiago?

  Based on Trip.com data for flights departing in the next 30 days, the average one-way fare from Chicago to Santiago is $361. Fares vary by travel date, airline and availability.

• How do I book flights from Chicago to Santiago on Trip.com?

  Enter Chicago and Santiago, choose your travel dates and passengers, then compare flights by price, duration and baggage. Select a fare, review the change and cancellation rules, enter traveler details and complete payment to receive your confirmation.