ORD - STI

$161 Find Cheap Flights from Chicago O'Hare Airport 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 O'Hare Intl to Santiago de los Caballeros departing on 4/5. 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
$285
Typical prices: $624-$412
Spirit Airlines
Sat 4/11Mon 4/13
ORD - STI • 1 stop
Cheapest one-way
$148
Typical prices: $155-$186
Spirit Airlines
Sun 4/5
ORD - STI • 1 stop
Top airlines
Cheapest • from $285 (round-trip)
Best reviews • 7.9 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 $443 (round-trip)
Shortest trip • 7h 09m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 43% 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

Sat, Apr 11 - Mon, Apr 13
Spirit Airlines Logo
5:05 am - 2:23 pm
ORD
-
STI
8h 18m
1 stop
Spirit Airlines Logo
2:46 am - 11:17 am
STI
-
ORD
9h 31m
1 stop
$285Spirit Airlines
Tue, Apr 7 - Mon, Apr 13
Multiple Airlines Logo
5:05 am - 2:23 pm
ORD
-
STI
8h 18m
1 stop
Multiple Airlines Logo
3:28 pm - 9:17 pm
STI
-
ORD
30h 49m
1 stop
$336Multiple Airlines
Fri, May 1 - Fri, May 15
Spirit Airlines Logo
5:05 am - 2:02 pm
ORD
-
STI
7h 57m
1 stop
Spirit Airlines Logo
4:15 pm - 11:15 pm
STI
-
ORD
8h 00m
1 stop
$347Spirit Airlines
Sat, Apr 11 - Tue, Apr 14
Spirit Airlines Logo
10:55 am - 2:23 pm
ORD
-
STI
26h 28m
3 stops
Spirit Airlines Logo
3:28 pm - 11:17 pm
STI
-
ORD
8h 49m
1 stop
$351Spirit Airlines
Tue, Apr 7 - Tue, Apr 14
Spirit Airlines Logo
5:05 am - 2:23 pm
ORD
-
STI
8h 18m
1 stop
Spirit Airlines Logo
3:28 pm - 11:17 pm
STI
-
ORD
8h 49m
1 stop
$358Spirit Airlines
Fri, Apr 10 - Sun, Apr 12
Spirit Airlines Logo
4:36 pm - 1:49 am
ORD
-
STI
8h 13m
1 stop
Spirit Airlines Logo
2:46 am - 5:15 pm
STI
-
ORD
15h 29m
1 stop
$371Spirit Airlines
Thu, Apr 9 - Mon, Apr 13
Multiple Airlines Logo
5:05 am - 2:23 pm
ORD
-
STI
8h 18m
1 stop
Multiple Airlines Logo
3:28 pm - 9:17 pm
STI
-
ORD
30h 49m
1 stop
$382Multiple Airlines
Sat, Apr 11 - Tue, Apr 14
Spirit Airlines Logo
10:55 am - 2:23 pm
ORD
-
STI
26h 28m
3 stops
Spirit Airlines Logo
3:28 pm - 8:05 am
STI
-
ORD
17h 37m
2 stops
$385Spirit Airlines
Fri, Apr 10 - Mon, Apr 13
Spirit Airlines Logo
6:10 pm - 1:49 am
ORD
-
STI
6h 39m
1 stop
Spirit Airlines Logo
3:28 pm - 11:17 pm
STI
-
ORD
8h 49m
1 stop
$389Spirit Airlines
Tue, Apr 7 - Sun, Apr 12
Multiple Airlines Logo
9:05 am - 1:49 am
ORD
-
STI
15h 44m
1 stop
Multiple Airlines Logo
2:46 am - 3:17 pm
STI
-
ORD
37h 31m
2 stops
$391Multiple Airlines
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.

How much is a round-trip flight from Chicago O'Hare Intl Airport 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 O'Hare Intl Airport to Santiago de los Caballeros departing in April.

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 February, where tickets cost $332 (return) on average. On the other hand, the most expensive months are July and May, where the average cost of round-trip tickets is $896 and $796 respectively.

Good to know

Low seasonJuly
Cheapest flight$148
Best time to beat the crowds but there is an average 53% increase in price.
Most popular time to fly with an average 22% 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 3 days, the lowest price for a flight from Chicago O'Hare Intl Airport to Santiago de los Caballeros was $148 for a one-way ticket and $285 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 JetBlue?

    The two airlines most popular with KAYAK users for flights from Chicago to Santiago de los Caballeros are Delta and JetBlue. With an average price for the route of $477 and an overall rating of 7.9, Delta is the most popular choice. JetBlue is also a great choice for the route, with an average price of $443 and an overall rating of 7.2.

  • 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 4 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.
7.9
DeltaOverall score based on 8357 reviews
7.8Entertainment
7.9Comfort
8.5Crew
7.2Food
8.1Boarding
Airline reviews

The flight was delayed 90 minutes The Gate was wrong The Restroom on Aircraft was not clean There was a half used water bottle in my seat

2.0 MediocreJames, Mar 2026
BOS - LGA
Read more Delta reviews

The flight was delayed 90 minutes The Gate was wrong The Restroom on Aircraft was not clean There was a half used water bottle in my seat

Delta is always a wonderful experience. A clean plane and the crew is really friendly.

Too many people are taking up space in the overhead bins with their extra piece of luggage. Since they cannot fit their backpacks or extra luggage piece under the seat in front of them, they store it in the overheads and thus taking up room for other passengers. It wasn’t only one or two persons; more like 12 or 13 passengers.

Excellent service, I love the soft blush pink mood lighting on the 767-400ER during meal service. The overhead gasper vents on the 767-400ER were also very strong with a lot of airflow to keep me comfortable on my flight.

This was the worse experience. They delayed our flight twice and we still had to find another flight to get home sooner which was alos delayed. Also, the flight attendant named Ginny on DL9890 leaving at 4:13pm on 3/23/26 was extremely rude.

I love Delta the flight attendants were personable and the flight arrived 1/2 earlier thanks expected. All a plus. The gate agent was a bit flustered but even with that I still had a good experience. Her supervisor assisted me.

Got to fly my favorite plane, the Boeing 767-400ER, to Milan. The soft blush pink mood lighting during meal service was very beautiful and gorgeous. The service was top-notch, and our flights were on time. I highly recommend Delta.

I am still at the Airport! Delayed Delayed and Delyaed

I took seat 15A in anticipation of window seat, there is no window.

The first class flight attendant was awful to everyone. Very rude; no customer service. She should not be working in first class.

Absolutely horrible. Flight was delayed 4 hours and they had no clue what was going on.

Onboard functioning wide-variety entertainment on a budget and having an open pantry is nice. Seats are not comfortable but go provide plenty of legroom for a 6'2" 260lbs man.

Even though the weather made a lot of flights become cancelled Jet Blue made the flight that was supposed to leave at 9 pm and we left at 12:15 am and I was so grateful- Thanks to the Senior Jet Blue Staff who made those decisions

Worst customer service ever experienced on the planet, dirty plane, no communication, and severe delays

Flight cancelled 2 hours prior to boarding. No explanation. No refunds.

Delayed by 1.5 hours. Terrible apologies, half hearted at best. It will be a LONG time until i book w Jet Blue again. Very disappointed.

My check in was stressful. I somehow lost my seat from my original booking, the plane showed no availability/no seat when it was time to check-in. I called and was instructed to try to get a seat at the airport. I asked if it was a full flight and the travel agent said the site showed some seating but was not able to secure one for me. Why not? On my way to the airport the app finally revealed one available seat towards the back of the aircraft that I was able to book. It ended up being an overbooked flight, so glad I wasn't stuck.

Flights with JetBlue from San Diego to Boston are a miserable experience. The flight was delayed about 1.5 hours due to “weather” supposedly but the flights for other airlines left on time so it just have been some kind of weather that only affects JetBlue. I had a small carry on - purse. The crew stored it in a bin 2 rows down from me because they were using the bin next to my seat for other people’s stuff. The TV screen in the emergency row seats does not work. It just was awful from start to finish. When we landed, we had to sit inside the plane for a very long time because the plane had to be moved to a different gate.

They made me check my bag and I didn't need to as there was overhead space available. I paid for a seat towards the front of the plane and it didn't recline. I requested a refund and they declined to give me one.

I have to congratulate Kayak (and Dylan the Chatdeal agent) because because when we decided extended our trip in Florida by two days, there were many direct flights oprions back to Boston available on the Friday we wanted to fly on the JetBlue website, but once I canceled the original JetBlue flight on their website, those direct return options disappeared immediatley! I think it's a game JetBlue plays. . Luckily, I checked Kayak and they had a direct flight that wasn't appearing on JetBlue's website and so I booked it, and we were able to fly home direct through the Kayak booking when JetBlue was offering nothing (even though I have been a True Blue member for 20 years, and also am a Mosaic member). So much for loyalty- their algorithm for booking is like a shell game. JetBlue used to be a good company but now they're worse than anyone. Also I was originally booked this trip to Florida, two months before the departure date, I booked the trip on JetBlue's website and then after the payment part, they said there was a problem and that I needed to do the booking again, so when I immediately went to rebook , the price had gone up 30%! I called them and it sounded like they had heard this so many times before and the guy told me to check back in 10 minutes and the price would be back to where it was when I was booking- it but it never was. How could the price go up 30% in one minute two months before the flight???? They're playing a game with their customers. Anyways, I booked a cheaper flight then at a less convenient time. So fast forward two months the night before the 7 AM flight, they sent me an email at midnight when I was sleeping to let me know that my flight at 7 AM had been canceled. The only thing they offered was a flight that night from from a different airport (Providence) to a different airport in Florida (West Palm Beach) or a flight two days later. No compensation, nothing. They couldn't of tried to get another plane to the Boston airport? They had all night to do it. I passed on their ridiculous options and flew with Delta and it was a great experience. Of course, I had to pay a lot more booking on the same day, but JetBlue doesn't care. I put in a lengthy complaint with the agent who assured me someone would get back to me by email within three days and I haven't heard a thing. JetBlue used to be a good company but now they're among the worst. The only thing they still have is decent legroom, but the corporate bean counters will probably start taking that away too.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

The gate got changed several times and the flight was delayed over an hour. Awful experience

American continues to decline in their customer service and its beyond disappointing.

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

As previously stated the delay I experienced flying from Wichita to Chicago caused a host of issues. When I finally was able to be booked on the last remaining American flight from Chicago to Cincinnati, the gate changed four times with the last change occurring very near the scheduled boarding time. While I didn't have a problem moving from gate to gate, I did notice and make note of others that had mobility issues and had to move each time for the gate change.

Maintenance took a very long time and then we were in a holding pattern. While a one-off maintenance issue is standard, there were delays on both of my flights for this trip based on maintenance issues with the planes, which delayed both flights over 45 minutes. Thankfully, I didn't have any connections but it wasn't an experience that would make me pick AA if I have other options.

No Snacks or Entertainment. The flight was short, snacks should still be given.

See prior comment about how Kayak mishandled my reservation and delayed my arrival by 6 hours.

Boarding delayed 20 minutes for no reason, no wifi, in flight entertainment, or snacks / waters?

They cancelled our flight. 2 hours before we were supposed to take off and offered us nothing! We got our money back and that was it. No other flight to get to our cruise no working with another airline or with us to get there. Terrible customer service, no apology.

We get stuck in the plane when landed during 45min and no communication from the crew People were listening to their phone and music out loud and nobody told them anything I definitely want stop booking spirit flight it is a disaster

Good: It was cheap and they got us to our destination safely. Not so Good: Gates experience with many, many nauseatingly (almost) threatening announcements about bags size and how much they were going to charge us if our bag was too big, even to the point of having a gate agent roaming around through the passengers eyeballing bags size and making people go check their bags in the sizers.

Terrible. The flight was randomly delayed in Chicago causing us to miss our connection and they offered us a flight the next day at 6 am and it would have taken till 345 to get to Pensacola. They didn’t cover any fees. Our bags also supposedly were on the flight to Pensacola and we tried to get them yesterday after driving 6 hours and nobody was available. Worst company ever and will never use them again. Had to pay for a rental. Spirit is claiming in climate weather for the delay but there wasn’t any weather issuesz it’s a bunch of bullshit and I am not happy

Checking in at desk in Chicago was horrible. Person was not friendly never smiled and said my flight was not paid for so I had to give another credit card. Then it ended up that I was charged twice. Then after arriving at my destination had to wait on the phone a long time to speak to a person to fix the double charge! Thank goodness the flight was perfect.

Flight was delayed for 12 h. They should stop overlooking flights.

Horrible we lost a day at the destination. Flight was canceled at 2am left us scrambling for another airline to get us to destination

All of our flights were canceled, though every other airline was flying out and in

it was terrible. flight was cancelled hours before the flight without a given reason and no other booking available .

Spirit Airlines has a reputation for being a terrible, cheap airline, this is why. I took a gamble on them, having never flown with them before, and the flight got cancelled. First they delayed the flight about 4 times before finally canceling it because a flight attendant didn’t show up to work that day. That’s so stupid. When I asked a ticketing agent she said that’s “company policy”. A company policy that inconveniences hundreds of passengers because a single flight attendant didn’t show is ridiculous and inefficient. I will never, ever try flying Spirit Airlines again.

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

Information on your arrival and departure airports