Cheap Flights from Chicago to Santiago Starting at $407
Helping travelers to find the best flight offers
Cheapest flights from Chicago to Santiago
Find the best deals for flights from Chicago to Santiago (Dominican Republic) with a single search — we scan over 700 airlines, 50+ agencies and more than 5 top booking systems to uncover the cheapest fares, best schedules and flexible conditions. Friendly and fast, our metasearch helps you compare options side-by-side so you can book with confidence and get to the Caribbean sooner.
Remember that on average the ideal time to book flights is 2 months before departure!
We carefully collect statistics on the search and pricing of airlines and, based on these data, we make an assumption about future prices. Thus, you can better understand which season is the cheapest to fly from Chicago to Santiago
Airlines operating on route
Direct Flights from Chicago to Santiago
Fly nonstop from Chicago to Santiago (Dominican Republic) for the fastest, most convenient way to get from city to beach — fewer transfers mean more time enjoying your trip and less stress at airports. While connecting options can sometimes be cheaper, direct flights save hours and offer a more comfortable travel experience, so compare prices and book the straight route when time and ease matter most.
Schedule of direct flights from Chicago to Santiago
A direct flight is the easiest way to get to your destination. The following airlines operate non-stop flights from Chicago to Santiago:
Chicago airports overview
Santiago airports overview
Frequently asked questions (FAQ)
Answers to questions about the route that travelers are most interested in.
Special offers and sales on air tickets from Chicago to Santiago
We keep tight track on airlines' pre-holidays sales and other special offers occurences all the time to let you save maximum amount of funds while traveling to your family or just going out on vacation.
Alternative routes
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Cheapest one way flight
$407
United Airlines
1 transfer
1d 0h 41m
12/25/2025
The cheapest one-way flight from Chicago to Santiago departs on 12/25/2025, is operated by United Airlines and costs $407
Cheapest round trip flight
$816
American Airlines
1 transfer
1d 8h 31m
12/24/2025
The cheapest roundtrip flight from Chicago to Santiago departs on 12/24/2025, is operated by American Airlines and costs $816
The fastest flight
1d 0h 41m
Fastest flight from Chicago to Santiago takes 1d 0h 41m
Direct flights
No direct flights
There are no direct flights on this route.
Distance
2970km
Timezone difference
2h
The distance between Chicago and Santiago is 2970km (1841 miles). The time difference between Chicago and Santiago is 2h
Avg Price
You can fly from Chicago to Santiago with United Airlines. It is the only carrier on this route, which makes the choice straightforward. Despite the lack of competition, ticket prices remain affordable: fares start from $407. Our service helps you track price changes, compare by dates, and select the most suitable flight. If you value stability and predictability, flying with United Airlines is a convenient solution. We make it easy to find good deals and ensure a comfortable booking process.
There appear to be no direct flights from Chicago to Santiago at this time.... Well, or something went wrong on our side and we couldn't find anything
Unable to find information about the schedule of direct flights from
Chicago is served mainly by two large airports: O'Hare International (ORD), a major global hub handling numerous international and domestic carriers including United and American, and Midway (MDW), a smaller airport that typically caters to budget and domestic airlines such as Southwest. O'Hare lies about 17 miles northwest of downtown, with CTA Blue Line trains taking roughly 45–55 minutes and fares around $3; taxis or rideshares can run 30–60 minutes depending on traffic and cost more. Midway sits roughly 10 miles southwest, reachable by CTA Orange Line in about 25–35 minutes for a similar fare, or shorter rideshare trips. O'Hare offers extensive connections and amenities but can be busy and sprawling; Midway is often quicker for domestic trips yet has fewer international services and amenities.
How much is the cheapest flight ticket from Chicago to Santiago?
The cheapest flight ticket from Chicago to Santiago according to data for the last 48 hours costs $407
When is the best time to buy air tickets on the route Chicago — Santiago?
Often the best time to buy tickets from Chicago to Santiago is 2 months before departure.
How long does it take to fly from Chicago to Santiago?
The fastest flights from Chicago to Santiago start from 41 minutes in the air.
Which airline can fly direct from Chicago to Santiago?
The following airlines operate direct flights on the route Chicago — Santiago:
We couldn't find any special offers for flights from Chicago to Santiago
Las Américas International Airport (SDQ) serves Santiago as the main international gateway in the Dominican Republic and typically handles a mix of full-service carriers and regional budget airlines; it can be the most convenient option for international arrivals. The airport is about 20–25 km southeast of Santiago’s city center, with taxi rides usually taking 20–40 minutes depending on traffic and costing roughly RD$800–RD$1,500; public buses and shared vans provide cheaper alternatives but can be slower and less predictable. Facilities are generally basic but functional, offering duty-free shops and car rental desks. Pros: straightforward international connections and relatively short transfer times; cons: limited premium lounges and occasional congestion during peak periods.
