ORD - STI

$164 Find Cheap Flights from Chicago O'Hare Airport to Santiago de los Caballeros - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from O'Hare Intl to Santiago de los Caballeros departing on 8/17. 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
$356
Typical prices: $498-$522
JetBlue
Mon 9/14Wed 9/30
ORD - STI • 1 stop
Cheapest one-way
$164
JetBlue
Mon 8/17
ORD - STI • 1 stop
Top airlines
Cheapest • from $353 (round-trip)
Best reviews • 7.8 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between O'Hare Intl 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 • 37% 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 O'Hare Intl to Santiago de los Caballeros (ORD-STI)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from O'Hare Intl 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 O'Hare Intl to Santiago de los Caballeros

Mon, Sep 14 - Wed, Sep 30
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
$356JetBlue
Mon, Sep 21 - Thu, Sep 24
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
$368JetBlue
Mon, Sep 14 - Wed, Sep 30
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
$370JetBlue
Mon, Sep 21 - Thu, Sep 24
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
$378JetBlue
Mon, Sep 14 - Wed, Sep 30
American Airlines Logo
5:00 am - 2:15 pm
ORD
-
STI
8h 15m
1 stop
American Airlines Logo
3:15 pm - 7:58 am
STI
-
ORD
17h 43m
2 stops
$379American Airlines
Mon, Sep 21 - Thu, Sep 24
American Airlines Logo
6:00 am - 2:15 pm
ORD
-
STI
7h 15m
1 stop
American Airlines Logo
3:15 pm - 7:58 am
STI
-
ORD
17h 43m
2 stops
$383American Airlines
Mon, Sep 14 - Wed, Sep 30
American Airlines Logo
5:00 am - 2:15 pm
ORD
-
STI
8h 15m
1 stop
American Airlines Logo
3:15 pm - 7:58 am
STI
-
ORD
17h 43m
2 stops
$391American Airlines
Fri, Oct 9 - Sat, Oct 17
JetBlue Logo
2:35 pm - 11:51 pm
ORD
-
STI
8h 16m
1 stop
JetBlue Logo
3:55 pm - 11:44 pm
STI
-
ORD
8h 49m
1 stop
$394JetBlue
Fri, Oct 9 - Sat, Oct 17
JetBlue Logo
2:35 pm - 11:51 pm
ORD
-
STI
8h 16m
1 stop
JetBlue Logo
3:55 pm - 11:44 pm
STI
-
ORD
8h 49m
1 stop
$404JetBlue
Mon, Sep 21 - Thu, Sep 24
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
$412JetBlue
Booking Insights

KAYAK's insights & trends for O'Hare Intl to Santiago de los Caballeros flights

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

What is the cheapest month to fly from Chicago O'Hare Intl Airport 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 O'Hare Intl Airport 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 O'Hare Intl Airport to Santiago de los Caballeros is October, where tickets cost $356 (return) on average. On the other hand, the most expensive months are January and December, where the average cost of round-trip tickets is $745 and $716 respectively.

Good to know

Low seasonJuly
Cheapest flight$164
Best time to beat the crowds but there is an average 18% increase in price.
Most popular time to fly with an average 27% increase in price.
Flight from Chicago O'Hare Airport to Santiago de los Caballeros

When to book flights from O'Hare Intl to Santiago de los Caballeros

Are your dates flexible? Find out the best times to travel from O'Hare Intl 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 Chicago O'Hare Airport to Santiago de los Caballeros flights

  • What is the cheapest flight from Chicago O'Hare Intl Airport to Santiago de los Caballeros?

    In the last 5 days, the lowest price for a flight from Chicago O'Hare Intl Airport to Santiago de los Caballeros was $164 for a one-way ticket and $353 for a round-trip.

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

    Yes, you'll most likely have to show a valid passport before boarding the plane in Chicago O'Hare Airport and on arrival in Santiago de los Caballeros.

  • Which aircraft models fly most regularly from Chicago O'Hare Airport to Santiago de los Caballeros?

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

  • Which airline alliances offer flights from Chicago O'Hare Airport to Santiago de los Caballeros?

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

  • Which is the best airline for flights from Chicago to Santiago de los Caballeros, Delta or American Airlines?

    The two airlines most popular with KAYAK users for flights from Chicago to Santiago de los Caballeros are Delta and American Airlines. With an average price for the route of $446 and an overall rating of 7.8, Delta is the most popular choice. American Airlines is also a great choice for the route, with an average price of $704 and an overall rating of 7.1.

  • How does KAYAK find such low prices on flights from Chicago O'Hare Airport 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 O'Hare Airport 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 O'Hare Airport 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 O'Hare Airport 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 O'Hare Airport 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 O'Hare Airport with another airline. Booking your flights between Chicago O'Hare Airport and STI can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago O'Hare Airport 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 O'Hare Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 3 airlines serving from O'Hare Intl 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 O'Hare Intl 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.
7.8
DeltaOverall score based on 8454 reviews
8.1Boarding
8.5Crew
7.8Comfort
7.2Food
7.8Entertainment
Airline reviews

Very easy to use and convenient, you can perform any action within the same portal

10.0 ExcellentMurat, Apr 2026
ORD - LGA
Read more Delta reviews

Very easy to use and convenient, you can perform any action within the same portal

Okay considering we had weather delays which the Pilot notified us of immediately!

Everything could have benn better. Short fly, no food, no entertainment and no wifi.

Stop changing gates. Stop cancelling flights Stop moving my seat.

The staff was frielndly. The plane was terrible, it was too small and should be decommissioned. There were no back seat screens at all. The only beverages we had a choice from was coffee, tea or water. The only bathroom in the back was behind the flight attendant's jump seat and wasn't working. And I literally felt like I was sitting on top of the guy next to me. It was terribly hot in the plane and we had to sit on the tarmac in Chicago for 1/2 hour due to congestion in Mpls. Wouldn't they have know that before they even boarded us so that we could have sat in comfort in the terminal?

This was one of the worst flights I’ve been on in years. I upgraded to comfort and had such an uncomfortable experience. The person next to me was oversized - which I understand - however, they took up their space and mine. I could only use about 50% of my seat space to not be physically touching this person the entire flight and there was no spatial awareness. I also could not use the seat outlet because their body was obstructing it. It was very inconvenient. Their body kept touching me repeatedly during the flight and I felt very uncomfortable. To pay more for an upgraded space and then not even being able to use it was highly disappointing.

It was very cold because the air conditioner was on high power, and my son got sick.

Horrible. Flight ORD to CGH was okay, but Paris was a nightmare. Old planes, delays, involuntary downgrades, broken planes, terrible communication. CGH to CPT was my worst flight ever.

The boarding process was terrible especially with an indirect flight Chicago to Seattle to San Diego was terrible talking about we overbooked a flight idk if I’d take this airline ever again we got off our flight from Chicago to Seattle and we traveled for business and they told us our connecting flight was over booked and their was no seats asking people to take a delayed next flight and they don’t tell anyone coughing to wear masks seats 30A-B were terrible during the flight no one wants to sit next to people coughing all around I don’t want to be sick traveling for work or get sick anytime it’s very upsetting the staff doesn’t take this stuff serious to tell them to wear masks when they see people coughing and sneezing

Delta airlines charge $ 30,oo US DOLLARS for the check in for a suitcase in the baggage hold

Very turbulent flight, no drinks, very little service, unorganized boarding, gate changed multiple times

The flight was delayed significantly. Communication during the flight was abrupt and caused some panic as we were navigating turbulence. It was also too loud and every announcement felt startling. The flight attendants did not offer any assurances and I felt unsettled most of the flight. The seats, floor and tray table was very dirty. The seat next to me was broken and the passenger sitting there was very uncomfortable. He had a spring in his back and his seat made terrible squeaking noises through the flight.

Significant delays on my trip to Chicago and my trip back to NY

Delayed by 5 hours and I had to wit in the airport for more than 6+ hours.

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.

When I agreed to give up my two seats because of overbooking by the airline, I should have been offered some sort of reward or credit towards a future flight. I was not. It was not until the next day when I mentioned it to a Jet Blue employee that I was advised to call 1-800-JetBlue. So here I am, having done Jet Blue a favor and I had to do the work to find out if I was going to get a credit. Such service

A nightmare. Scheduled flight delayed 2 hours then cancelled because pilot timed out . Unable to find another pilot. Really?! Weather certainly a factor, but JetBlue seemed totally unprepared for the chaos that ensued when flight routes were cancelled. More cancelled flights, finally many of us who had been bumped from other flights were allowed to board a Boston bound plane around 3:00am, delay after delay, sat on tarmac for another half hour while pilot dealt with weight distribution issues (?), arrived in Boston 4:30. Crew were wonderful- same attendants all day and night and they were exhausted. Fortunately for me and my son that Boston was our final destination, not so lucky for many who missed connecting flights.

Complete and total debacle from start to finish. HUGE mistake picking this airline. NEVER again! Rudest staff in the business.

The food took two hours to be delivered to my seat, when I'm on an overnight flight I want to sleep asap after take off

It's not JetBlues fault but there was a smell on the plane (possibly other travelers) and 3 children behind me that never quit whining. Soccor fans that were very loud. Pilot brought the plane down from high altitude quickly, dropping us hu dress of feet at a time. I've never felt that intense of dropping on other airlines (usually fly Southwest Airlines). But I arrived safely and I'm thankful for that.

Seats were great, the staff was great, and the food was about the best I've had on a plane, and is especially the best of any US-based carrier I've flown. Free Wi-Fi was also great.

All the TV screens in my rows was non functional . The map shown for an international route was antiqued..

There was a fowl odour coming from the lavatory the entire flight

The flights are back on time and everything else runs perfectly.

Surly, unhelpful ground staff at JFK. There was a complete lack of empathy—a flawed check-in ordeal caused us to miss our flight. All airlines that I have ever flown would have worked to help me solve the ticket problem. Instead, frontline employees shrugged their shoulders and pointed fingers at us for having made an error. I will do anything to avoid EVER flying on Jet Blue again. It well deserves its low rank among airlines.

Everything you need to know for your flight from O'Hare Intl to Santiago de los Caballeros

Information on your arrival and departure airports