CHI - STI

$186 Find Cheap Flights from Chicago to Santiago de los Caballeros

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Santiago de los Caballeros departing on 9/28. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Santiago de los Caballeros

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Santiago de los Caballeros, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Santiago de los Caballeros, as well as popular online travel agencies
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Everything you should know

Cheapest round-trip
$421
Typical prices: $551-$363
JetBlue
Wed 10/28Tue 11/10
ORD - STI • 1 stop
Cheapest one-way
$186
Typical prices: $200-$253
JetBlue
Mon 9/28
ORD - STI • 1 stop
Top airlines
Cheapest • from $421 (round-trip)
Best reviews • 7.1 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between Chicago and Santiago de los Caballeros. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $414 (round-trip)
Shortest trip • 7h 09m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 32% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Santiago de los Caballeros!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Chicago to Santiago de los Caballeros (CHI-STI)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Santiago de los Caballeros that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Santiago de los Caballeros

Wed, Oct 28 - Tue, Nov 10
JetBlue Logo
2:35 pm - 11:51 pm
ORD
-
STI
8h 16m
1 stop
JetBlue Logo
4:43 pm - 11:44 pm
STI
-
ORD
9h 01m
1 stop
$421JetBlue
Mon, Sep 28 - Fri, Oct 2
JetBlue Logo
6:00 am - 1:27 pm
ORD
-
STI
6h 27m
1 stop
JetBlue Logo
3:49 pm - 11:31 pm
STI
-
ORD
8h 42m
1 stop
$426JetBlue
Wed, Oct 28 - Tue, Nov 10
Delta Logo
7:05 am - 5:46 pm
ORD
-
STI
9h 41m
2 stops
Delta Logo
6:40 am - 7:34 pm
STI
-
ORD
14h 54m
2 stops
$431Delta
Fri, Jul 17 - Tue, Jul 21
JetBlue Logo
2:35 pm - 11:51 pm
ORD
-
STI
8h 16m
1 stop
JetBlue Logo
4:54 pm - 11:44 pm
STI
-
ORD
7h 50m
1 stop
$435JetBlue
Tue, Aug 11 - Sat, Aug 15
American Airlines Logo
6:59 am - 8:03 pm
ORD
-
STI
12h 04m
1 stop
American Airlines Logo
3:35 pm - 7:34 am
STI
-
ORD
16h 59m
1 stop
$456American Airlines
Tue, Aug 11 - Sat, Aug 15
American Airlines Logo
6:49 am - 8:03 pm
ORD
-
STI
12h 14m
2 stops
American Airlines Logo
3:35 pm - 7:34 am
STI
-
ORD
16h 59m
1 stop
$461American Airlines
Sat, Sep 5 - Sat, Sep 12
American Airlines Logo
8:49 pm - 12:22 pm
ORD
-
STI
14h 33m
1 stop
American Airlines Logo
3:15 pm - 12:32 am
STI
-
ORD
10h 17m
1 stop
$476American Airlines
Sat, Sep 5 - Sat, Sep 12
American Airlines Logo
8:49 pm - 12:22 pm
ORD
-
STI
14h 33m
1 stop
American Airlines Logo
3:15 pm - 7:58 am
STI
-
ORD
17h 43m
2 stops
$481American Airlines
Tue, Dec 8 - Fri, Dec 25
Delta Logo
10:40 am - 12:55 am
ORD
-
STI
12h 15m
1 stop
Delta Logo
3:40 am - 5:34 pm
STI
-
ORD
15h 54m
1 stop
$485Delta
Wed, Oct 28 - Tue, Nov 10
Delta Logo
5:25 pm - 12:03 pm
MDW
-
STI
17h 38m
2 stops
Delta Logo
6:40 am - 6:37 pm
STI
-
MDW
13h 57m
2 stops
$490Delta
Booking Insights

KAYAK's insights & trends for Chicago to Santiago de los Caballeros flights

Get data-powered insights and trends into flights from Chicago to Santiago de los Caballeros to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Chicago to Santiago de los Caballeros?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago to Santiago de los Caballeros departing in October.

What is the cheapest month to fly from Chicago to Santiago de los Caballeros?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Santiago de los Caballeros, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago to Santiago de los Caballeros is November, where tickets cost $206 (return) on average. On the other hand, the most expensive months are September and January, where the average cost of round-trip tickets is $422 and $397 respectively.

Good to know

Low seasonAugust
Cheapest flight$186
Best time to beat the crowds with an average 27% drop in price.
Most popular time to fly with an average 65% increase in price.
Flight from Chicago O'Hare Airport to Santiago de los Caballeros

When to book flights from Chicago to Santiago de los Caballeros

Are your dates flexible? Find out the best times to travel from Chicago to Santiago de los Caballeros based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Chicago to Santiago de los Caballeros

  • What is the cheapest flight from Chicago to Santiago de los Caballeros?

    In the last 5 days, the lowest price for a flight from Chicago to Santiago de los Caballeros was $186 for a one-way ticket and $421 for a round-trip.

  • Do I need a passport to fly between Chicago and Santiago de los Caballeros?

    Yes, you’ll need a passport to travel to Santiago de los Caballeros from Chicago.

  • Which airports will I be using when flying from Chicago to Santiago de los Caballeros?

    On your way to Santiago de los Caballeros, you’ll fly out from one of these Chicago airports: Chicago Midway or Chicago O'Hare Intl. You’ll be landing at Santiago de los Caballeros.

  • Which aircraft models fly most regularly from Chicago to Santiago de los Caballeros?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Chicago to Santiago de los Caballeros?

    SkyTeam, and oneworld are the airline alliances operating flights between Chicago and Santiago de los Caballeros, with SkyTeam being the most commonly used for this route.

  • How does KAYAK find such low prices on flights from Chicago to Santiago de los Caballeros?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Santiago de los Caballeros.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Santiago de los Caballeros?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Santiago de los Caballeros from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Santiago de los Caballeros?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Santiago de los Caballeros with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Santiago de los Caballeros?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Santiago de los Caballeros from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from Chicago to Santiago de los Caballeros

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Santiago de los Caballeros. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Chicago to Santiago de los Caballeros? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.1
American AirlinesOverall score based on 11668 reviews
7.9Crew
6.8Entertainment
6.4Food
7.5Boarding
7.2Comfort
Airline reviews

I’ve got 31F seat and window seat . My 2 co passengers was AA crew members and they were very rude attitude and when I was going to use bathroom their gestures was very different and awkward and the guy beside me completely occupied the hand rest and I was really uncomfortable

2.0 MediocreGirish, Jun 2026
ORD - DFW
Read more American Airlines reviews

I’ve got 31F seat and window seat . My 2 co passengers was AA crew members and they were very rude attitude and when I was going to use bathroom their gestures was very different and awkward and the guy beside me completely occupied the hand rest and I was really uncomfortable

It was so much better than expected, Ohare is not such a pleasant experience but American Airlines with the new, clean aeroplane and free Wi-Fi was outstanding and the crew so pleasant and helpful.

It wa sort of on time; the cab was left with some trash

My pillow had a shoe print on it, when I asked if I can have another pillow, I was told “I’m sorry but it is one pillow per guest, do YOU want to turn it inside out” to which I responded , no thanks I will go without. This is generally not ok, but For the price tag I paid flying business this is absolutely unacceptable. Hopefully American Airlines can update their accommodations to bedding that is not tossed on the ground and stepped on, or at least have a couple of extra pillows in hand, incase someone had decided to step on the pillows for what ever reason

American Airlines II: Delay Boogaloo. Multiple gate changes, delays, boarded and then MORE delays. I hate to say this won’t matter, but posting stuff about major corporations in 2026 is a post-modern “scream into the void.” Was multiple hours late coming home, so there you go.

Our flight was cancelled while we are on our way to the airport. So, no notice. We were rescheduled to another airline with a 2 hour later takeoff and so arrived at our destination on time. We pre-paid American Airlines $190 to upgrade our seats. No refund. So no use for AA or Kayak.

Terrible, horrible, disappointing- without telling us they changed planes and moved and separated our seats to opposite sides - said they changed seats putting us together - got to airport to find no, they did not - we sat opposing sides of plane - food overly salty to inedible, never saw stewardess but once - it was terrible

The airplane was an old model, the overhead didn’t have enough room for people’s items and made boarding and boarding disappointing and stressful. Crew allowed passengers to bring more than the permitted baggage sizes.

Original flight was on time, then late, then changed gates...4 times. Once our newest plane came in, it was fine.

I almost missed my flight and they helped me out enormously

Everything you need to know for your flight from Chicago to Santiago de los Caballeros

Information on your arrival and departure airports