ORD - STI

$136 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 5/5. 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
$276
Overall average: $417
Spirit Airlines
Fri 3/13Sat 3/14
ORD - STI • 1 stop
Cheapest one-way
$136
Typical prices: $194-$252
Multiple Airlines
Tue 5/5
ORD - STI • 1 stop
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
Boston (BOS)
Cheapest • Avg $443 (round-trip)
Boston (BOS)
Shortest trip • 7h 09m (one-way)
Insights
Insights
Insights
Insights
When to travel
October
Cheapest • 40% price drop
December
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

Fri, Mar 13 - Sat, Mar 14
Spirit Airlines Logo
6:10 pm - 1:49 am
ORD
-
STI
6h 39m
1 stop
Spirit Airlines Logo
2:46 am - 11:17 am
STI
-
ORD
9h 31m
1 stop
$276Spirit Airlines
Wed, Mar 11 - Thu, Mar 12
Spirit Airlines Logo
5:15 am - 2:33 pm
ORD
-
STI
8h 18m
1 stop
Spirit Airlines Logo
3:43 pm - 11:17 pm
STI
-
ORD
8h 34m
1 stop
$281Spirit Airlines
Wed, Mar 11 - Fri, Mar 20
Spirit Airlines Logo
5:15 am - 2:33 pm
ORD
-
STI
8h 18m
1 stop
Spirit Airlines Logo
2:46 am - 11:17 am
STI
-
ORD
9h 31m
1 stop
$299Spirit Airlines
Sun, Apr 19 - Thu, Apr 23
Spirit Airlines Logo
5:05 am - 2:22 pm
ORD
-
STI
8h 17m
1 stop
Spirit Airlines Logo
3:27 pm - 12:14 am
STI
-
ORD
9h 47m
1 stop
$312Spirit Airlines
Mon, Mar 23 - Tue, Mar 24
Spirit Airlines Logo
6:10 pm - 1:49 am
ORD
-
STI
6h 39m
1 stop
Spirit Airlines Logo
3:43 pm - 8:25 am
STI
-
ORD
17h 42m
1 stop
$320Spirit Airlines
Wed, May 6 - Fri, May 15
Multiple Airlines Logo
1:27 pm - 2:02 pm
ORD
-
STI
23h 35m
1 stop
Multiple Airlines Logo
3:07 pm - 10:57 pm
STI
-
ORD
8h 50m
1 stop
$334Multiple Airlines
Fri, Mar 13 - Wed, Mar 18
Spirit Airlines Logo
6:10 pm - 1:49 am
ORD
-
STI
6h 39m
1 stop
Spirit Airlines Logo
3:43 pm - 11:17 pm
STI
-
ORD
8h 34m
1 stop
$337Spirit Airlines
Sat, May 9 - Fri, May 15
Multiple Airlines Logo
1:27 pm - 2:02 pm
ORD
-
STI
23h 35m
1 stop
Multiple Airlines Logo
3:07 pm - 10:57 pm
STI
-
ORD
8h 50m
1 stop
$347Multiple Airlines
Thu, May 7 - Fri, May 15
Multiple Airlines Logo
1:27 pm - 2:02 pm
ORD
-
STI
23h 35m
1 stop
Multiple Airlines Logo
3:07 pm - 10:57 pm
STI
-
ORD
8h 50m
1 stop
$350Multiple Airlines
Wed, May 6 - Sun, May 10
Multiple Airlines Logo
1:27 pm - 2:02 pm
ORD
-
STI
23h 35m
1 stop
Multiple Airlines Logo
3:07 pm - 10:57 pm
STI
-
ORD
8h 50m
1 stop
$352Multiple 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.

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 May and July, where the average cost of round-trip tickets is $912 and $896 respectively.

Good to know

Low seasonJuly
Cheapest flight$136
Best time to beat the crowds but there is an average 50% increase in price.
Most popular time to fly with an average 20% 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 $136 for a one-way ticket and $276 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, Star Alliance, 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 United Airlines?

    The two airlines most popular with KAYAK users for flights from Chicago to Santiago de los Caballeros are Delta and United Airlines. With an average price for the route of $437 and an overall rating of 7.9, Delta is the most popular choice. United Airlines is also a great choice for the route, with an average price of $677 and an overall rating of 7.4.

  • 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 5 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 8245 reviews
8.1Boarding
7.8Entertainment
8.5Crew
7.2Food
7.9Comfort
Airline reviews

There’s not much to say about a one hour flight. This is a connection from LA to RNO that I missed the previous night due to a mechanical check delay on my originating flight from JFK to LAX. The short flight itself was fine. Instructions from the pilot and crew were per usual. The coffee was barely lukewarm, which possibly was purposeful so we would down it quickly. Bags were already on carousel upon reaching baggage claim, which was excellent.

10.0 ExcellentGrace, Feb 2026
JFK - LAX
Read more Delta reviews

There’s not much to say about a one hour flight. This is a connection from LA to RNO that I missed the previous night due to a mechanical check delay on my originating flight from JFK to LAX. The short flight itself was fine. Instructions from the pilot and crew were per usual. The coffee was barely lukewarm, which possibly was purposeful so we would down it quickly. Bags were already on carousel upon reaching baggage claim, which was excellent.

Flight was warm for first few hours and quite rough

Seat was extremely hard which made even a short 1 hour 20 minute flight fairly uncomfortable.

Everything was good except wifi and a leaking drink chiller. The floor was all wet and my bag was soaked. Did not notice until debarking. Have not heard back from Delta. Even though this was leg one of an international flight in first class, they denied access to their Sky Club - very disappointing!

The staff was fine. The plane was extremely tight, and I paid for the wifi and it did not work at all. I was actually going to ask for a refund.

two hour delay and the Delta representative on the PA system was unable to understand

An awesome flight crew. FC seat cushion just doesn’t cut it for a 3+ hour flight.

2+hrs delay without any reason provided and a cramped flight

We waited an hour on the runway to get a gate in Orlando

Flight was delayed by 3-hours and their fix was… complimentary pretzels.

This trip did not start off well. The inbound flight was delayed about 20 minutes. Then, after initial onboarding, the passengers had to deplane due to a mechanical problem. That took about 30 minutes to fix and be cleared. Then, reboarding was chaotic. It took a long time to sort passengers and two passengers on standby were ticketed but there was no seat. So, they had to deplane. One of the flight crew was trying to help passengers figure out a place to put their carry-on bags and that took more time. In the end, our scheduled 10:30 am departure did not actually take off until about 12:05 pm CST. The flight itself was long but we got to Houston. Some passengers missed their connecting flights and had to rebook. Not the best of flights I've had.

We were delayed for about an hour from taking off due to traffic control procedures at the destination airport. But once in the air, the flight went well. The crew members were great and provided cabin service despite moderate turbulence during much of the flight.

Short flight, but no drink/snack service. The flights both going and coming were delayed.

Not being stranded in Chicago for her airport to 11:30 tomorrow morning the 3rd

I was fully checked in the prior night and i was unchecked and then didn’t have a seat when I boarded. Instead of an aisle seat, I was out in the middle seat of the very last row of the plane.

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

I understand weather is an issue, but making us chase our plane down at five scheduled gates across three terminals in an airport the size of O'Hare was unfair. They'd have probably been better off to leave gates as TBD until the inbound plane is in final approach instead of running us all over the place. Also, props to the consistently-unprepared ground crew in Richmond for once again leaving my lane parked short of the gate because they couldn't have a crew in place on time with 2 hours notice...

cabin crew was OK, food was OK, the trip from the US to Munich was actually pretty bad comfort wise. Noisy aircraft, lights never dimmed even in Business class (night flight) barely sufficient amenities for the price. I have millions of miles with United but TBH American is gaining ground and Delta has always been marginally better then United although on paper United has more longes and cheaper upgrades.

Essy to get on. The hostess gave very little pop, the plane was late getting in, and we are still waiting for our bags. This sucks. :/

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?

Delayed an hour due to operational issues. Minimal apologies or care for the significant inconvenience caused. Landed at nearly 1am and they still couldn’t find ground staff to get us off the plane promptly.

The aircraft had several problems - from excess fuel to non operational ac. Two hours of delay in Chicago could have been avoided with proper planning and aircraft maintenance.

Crew in Columbia was not prepared for landing. It was a bit of a disaster and getting bags took forever.

We were upgraded to First Class and it was a great flight

We were made to wait in the airport for six hours for a flight that was ultimately canceled.

Both flights were significantly delayed. The flight experience itself was great.

My flight got delayed and eventually canceled, then rescheduled. I and several others had a connection from Boston to Paris and asked several times if we would make it. They assured us we would and then rebooked us mid flight without our consent and closed doors early even though they said they communicated we were a bit delayed. We got stranded in Boston and I opted with being rebooked for a different connection to France since they refused to pay for a Hotel. I've now been in Europe for 5 days and still haven't recieved my bags. There was absolutely no urgency for the fact that I'm in a foreign country with absolutely no change of clothes or any of my medication. Such an overwhelming and frustrating experience.

Automated scanning was slow and somewhat haphazard. Too many people were unfamiliar with the tech and were forced to learn on the fly. The hands off approach of the gate staff made it more uncomfortable. This needs work. Overall the flight and cabin crew were excellent.

The crew for the flight was A+ top notch. They were friendly and professional and made the flight a very relaxing and enjoable.

Rude crew member. She seemed annoyed at me without me saying a single word. Also loudly admonished me for having my bag next to my seat instead of tucked away before landing. Just telling me to put it away and guiding me without giving me a lecture would have been enough.

No included food for a 5 hour flight and the entertainment was only accessible if you had wired headphones (not provided). Otherwise though, great and smooth flying and customer service.

Crew were fantastic and so catering and wonderful! Full score for the entire crew!

Because of weather and mechanical issues our flight was 4 hours late. The only compensation offered to us was a meal voucher to be used only at Boston Airport and only on the day issued. But by the time it was offered to us all the restaurants were closed, so there was no way to use that offer.

Friendly crew, efficient boarding and flight arrived early. Couldn’t ask for a better experience

bought basic spirit fares, add checked bags - like the up front info on website about this. bring your own snacks, buy a soda after TSA security to bring with you, or buy on the plane (limited selection) all in all, a good experience

I cannot effectively rate the food and drink as I had not. Otherwise, the trip was fine. The seats were nice, the crew was fine. They could smile once in a while. They all look like they were mad.

4 hour delay, 2 hours in the airport and then 2 hours on the tarmac. With a flight full of kids it would have been better to leave us in the airport for the delay, it was crying kids chaos on the flight. Miserable. And no apology or airline credit for the significant delay.

Flight was on time with no issues. Price is very competitive. Flight schedule works well for me

They charged late fees for selecting seats (no $0 options). They also changed my gate within the last half hour and are refusing to reimburse my costs to drive across the country with two small children in a rental car.

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