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CHI - STI

$256 Find cheap flights from Chicago to Santiago de los Caballeros

This is the cheapest round-trip 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 5/25. 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
0 bags
Mon 6/3
Mon 6/10

Search 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
In the last 7 days travelers have searched 43,369,418 times on KAYAK, and here is why:

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Cheap flight deals 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 and deals for you by selecting your travel dates.
Choose your dates
6:40 pm - 1:59 amORD-STI
6h 19m1 stop
2:59 am - 9:55 amSTI-ORD
7h 56m1 stop
$256Spirit Airlines
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Sat, May 25 - Fri, May 31
6:40 pm - 1:59 amORD-STI
6h 19m1 stop
2:59 am - 9:55 amSTI-ORD
7h 56m1 stop
$263Spirit Airlines
Find Deal
Sat, May 25 - Sat, Jun 1
6:40 pm - 1:59 amORD-STI
6h 19m1 stop
2:59 am - 4:35 pmSTI-ORD
14h 36m1 stop
$264Spirit Airlines
Find Deal
Tue, May 14 - Fri, May 17
6:40 pm - 1:59 amORD-STI
6h 19m1 stop
3:56 pm - 10:01 amSTI-ORD
19h 05m1 stop
$273Spirit Airlines
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Sat, Jun 1 - Tue, Jun 11
6:45 pm - 12:25 pmORD-STI
16h 40m1 stop
5:10 pm - 9:07 amSTI-ORD
16h 57m1 stop
$355American Airlines
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Sat, May 25 - Sun, Jun 2
5:23 pm - 12:02 pmORD-STI
17h 39m2 stops
6:15 am - 8:11 pmSTI-ORD
14h 56m1 stop
$386Delta
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Sat, May 25 - Sat, Jun 1
6:45 pm - 12:25 pmORD-STI
16h 40m1 stop
2:24 pm - 9:07 amSTI-ORD
19h 43m1 stop
$398American Airlines
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Sat, May 25 - Sun, Jun 2
5:23 pm - 12:02 pmORD-STI
17h 39m2 stops
6:15 am - 7:53 pmSTI-ORD
14h 38m2 stops
$441Delta
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Sat, May 25 - Sat, Jun 1
6:05 pm - 2:46 amORD-STI
7h 41m1 stop
10:17 pm - 8:58 amSTI-ORD
11h 41m1 stop
$529JetBlue
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Thu, Oct 24 - Sun, Oct 27
10:35 am - 1:39 amORD-STI
14h 04m1 stop
1:45 am - 9:51 amSTI-ORD
9h 06m1 stop
$781JetBlue
Find Deal
Fri, Jun 21 - Tue, Jul 30

Flights from Chicago to Santiago de los Caballeros - Travel Insights & Trends

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.

What’s the cheapest day of the week to fly from Chicago to Santiago de los Caballeros?

The average price of all flights from Chicago to Santiago de los Caballeros clicked on KAYAK for each day over the last 12 months.
If your flying dates are flexible, you should consider flying to Santiago de los Caballeros on a Tuesday, as we generally find the cheapest rates on that day for this route. On the other hand, Sunday is the most expensive day to fly from Chicago to Santiago de los Caballeros. For your return ticket, we recommend flying on a Monday and avoiding Wednesdays for the best deals.

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 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 April, where tickets cost $207 on average. On the other hand, the most expensive months are December and July, where the average cost of tickets is $726 and $704 respectively.

How far in advance should I book a flight from Chicago to Santiago de los Caballeros?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Chicago to Santiago de los Caballeros, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price on the flight from Chicago to Santiago de los Caballeros, you should book around 3 days before departure. For the absolute cheapest price, our data suggests you should book 24 days before departure.

Good to know

Low season

August

High season

April

Cheapest flight

$256
Best time to beat the crowds but there is an average 27% increase in price.
Most popular time to fly and prices are also 59% lower on average.
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 3 days, the lowest price for a flight from Chicago to Santiago de los Caballeros was $256 for a round-trip ticket.

  • 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?

    oneworld, and SkyTeam are the airline alliances operating flights between Chicago 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 $469 and an overall rating of 8.0, Delta is the most popular choice. JetBlue is also a great choice for the route, with an average price of $497 and an overall rating of 7.6.

  • 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.

See more FAQs

Top 5 airlines serving 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.
8.0
DeltaOverall score based on 10838 reviews
8.2Boarding
8.0Entertainment
7.9Comfort
7.4Food
8.6Crew
Airline reviews

On time departure, smooth trip, flight attendant told through passengers the gate we would arrive at and the gate our outbound flight was departing from. Early arrival

10.0 ExcellentAllan, May 2024SUN - SLC
Read more about Delta reviews

On time departure, smooth trip, flight attendant told through passengers the gate we would arrive at and the gate our outbound flight was departing from. Early arrival

Checking in at the airport the agent only booked the first keg of my trip and had my checked luggage going to the airport with a layover! Never was issued a boarding pass for the second leg or received sticker fir my checked bag. All was well in the end! Delta agents helped to resolve the situation!!!

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

Big plane, long flight, absolutely no leg room and basically non existent air! I am 5”4’ and always travel Main Cabin, I was miserable on this plane and could barely move when we arrived in Cabo due to the cramped leg area!

From Atlanta to Cabo I would have hoped on a plane that size I would have been able to breathe and wiggle my feet a little! The leg room in that plane is non existent and I am only 5”4’. And the air vent either wasn’t working very well or just could not blow air from the ceiling to the seat area as I was suffocating through the entire flight! And please don’t say I would have been more comfortable in first class because I cannot afford those rates and have always travelled Main Cabin without issues !

The pilots were good. Disappointing when planes don't have electrical ports

I liked the piloting of the aircraft. Very disappointed about lack of electrical ports. Also, although a short flight. there was enough time to hand out snacks to comfort + seats as was done for first class.

I had a wonderful experience flying with delta. The gentleman taking care of us on our flight was so nice, accommodating, and attentive. He always was smiling and giving pins to the kids which made me smile. The flight was quick too and without turbulence. Thank you for the great flying experience.

Delta is one of the best airlines I have flown

Great. Loved that there was WiFi on flight to keep in touch and excellent service of beverages and snacks.

Business class is great. New airplane, very comfortable, better than some of the major airlines I am used to

Terrible. Flight was cancelled due to the weather in the east and sout east(florida). Did not get any compesation of any kind. According to them, it was not under their control so I lost all the money paid for the 2 fairs from Raleigh, NC to Orlando, Fl.

great flight. Pilot was communicative, flight attendants were excellent. Really nice experience except my tv didn’t work.

Overall, the flight was better than the flight I took to go to Florida, which had a bunch of problems. The crew is really nice and the plane was new so it had a small problem when we were on the runway, but the flight itself was great. They even made some time back up, which is always a good thing.

at the time for boarding the lady just call Group A and no other goups and everybody from A to F go inside without the right turn,and when we get in theres no more spsce for carry on , the ones that get in at not correct group from the back occupy our space !!!!! a mess !!!!

There were multiple delays but JetBlue tried to make the boarding and departure process as quick and efficient as possible. The crew was as detached from reality as could be, meaning: not very friendly and just doing things by the numbers.

I had back trouble prior to my flight and everyone was great about helping me.

Jetblue needs to improve on Onboarding as it seems to always be behind on departing. It never leaves on time. I would recommend to have an earlier Onboarding in order to leave on time and respect your customers time as well.

40 minute delay before take off after boarding flight. Bright lights throughout night flight due Issues with light panels. In flight Entertainment nonfunctional

Great! The plane was decently sized and comfortable. The staff was nice and there was great in flight entertainment

Last minute gate change nearly caused us to miss our flight. Change was not announced or displayed in the main board at the old gate. Terrible communication. When we landed we had to wait 20 minutes because there was another plane at the assigned gate. Not the crew’s fault, but adding 20 minutes to a 45 minute flight sucked.

Nothing beats ANA customer service on my opinion. Maybe because of their Japanese culture (and food). Arigatō

delay several times and wait extra long to board. no entertainment service because there are problem for some rows. always encounter some delays for the last flight of the day.

Flight delayed for 2 hours due to a part. The plane sat waiting for boarding for a long time and during final preflight inspection the issue was found. Why not do the preflight inspection sooner if you know the plane is being used?

The flight experience was very good! Especially the United Club!

I was not able to buy food in the flight. They refer to include your Credit card in the APP, and if you are not from USA (i have a credit card form Canada) it is not possible

Aircraft has better leg room than any of United's larger planes. We had requested mobility assistance for this and related flights. United's response to all was superb.

The flight from Ottawa to Chicago took a lot longer due to DC in Ottawa. We got to Chicago and went to our gate to catch our flight. We only had nine minutes I found that very stressful.

Good boarding. Crew started quick with drinks and food. They came around several times for trash which I really liked. Other than turbulence due to storms in the area, flight was great.

It was spectacular. I had basic Economy and was given so much space and their seats lean back so far. Staff was superb, food was superb, everything was superb, Finnair is Fantastic.

Good flights. Departure and arrivals were on time. DFW was a little problematic in that the Skytrain without prior notice bypassed the Echo terminal so that delayed my arrival at my connecting flight.

Because I can’t stand very long in one place, I was allowed to reword.

We were delayed bc ground crew gave the flight crew the wrong paperwork. We taxiied to the runway then back to the gate to get the correct paperwork that no one bothered reviewing the first time we pushed back. Boarding was rude and stressful like it always is. Gate agents and flight attendants are all over 55 years of age, embittered by years of underpayment From AA leading to their passive agressive bitchiness for no reason.

Boarding time was easy & quick. Crew was excellent. In-flight entertainment was great/easy. Seats are too small and not enough room between rows: felt like a sardine/very cramped.

5 hour flight - full flight - not enough room to use my computer - slightly delayed - Admirals club was excellent quality food, drink made up for flight seating. No food offerred on flight, you ahd to prebook.

Excellent- plan was barely populated. I cannot remember a flight where I was able/encouraged to stretch out!

Great flight. Boarding was efficient and quick. On time departure and smooth flight. Flight arrived early at destination. Good experience.

Had technical issue which delayed the flight period. Flight crew knew there was 5 passengers that the connecting flight was within 15 minutes once at the gate. Rather than identify the 5 passengers to assure they got first. The flight attended mentioned it but didn't assist to assure passengers with connecting flights off first. This caused a hardship and our party of 3 missed the connecting flight.

I don't like that I have to pay if I want extra leg room. The seats are so expensive; I sit in normal seats and my legs and knees cramp the entire flight. I never feel comfortable on AA flights.

The crew was not great or professional. It seemed like they didn't really want to be there. A true lack of effort for accommodating customers.

Everything was really good but the seats are not very comfortable.

I paid for WiFi, but it (WiFi) was very very slow, will never take again! Impossible open Utube 😤😤😤

I had no legroom, although I paid for extra legroom. I could barely put my bag in front of my feet and under the seat. The Wi-Fi was horrible. In fact the flight attendant said that they had to reboot it and see if it was going to work and never did.

The guy with severe body odor sat next to me. For the whole duration of the flight it was a torture. The airline should have better policy on limiting people with bad body odor to board the flight. Passengers should not be the ones to endure bad odor for the whole duration of the flight. The airline should be e the one to ensure decent air quality for ever passenger.

Overall it was a miserable experience... I will never fly spirit for more than a 3 hour flight or overnight.

The boarding attendant was slightly rude when I asked about checking our stroller. Made me feel like I was bothering her.

My wife and I are both handicapped and at boarding they upgraded us to a seat closer to the front rather than all the way towards the back. Much appreciated.

Not much seat room, but that was unexpected. But the seat headrest was very uncomfortable.

First the good, everyone was friendly and efficient. Flight was smooth and plane was very clean and new. Now the bad, seats have almost no padding on your behind. I was in exit row so I had tons of leg room for a 6' 2" bean pole with long legs. Everything was extra - water, soda, snacks everything besides oxygen. Ya get what you pay for, and my flight was cheap as you could ever want it, so no worries.

Flights to Santiago de los Caballeros

Destination:

Santiago de los Caballeros (STI)Dominican Republic

Cabin classes: