CHI - STI

$146 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 1/1. 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
$334
Overall average: $416
Spirit Airlines
Mon 2/2Mon 2/9
ORD - STI • 1 stop
Cheapest one-way
$146
Spirit Airlines
Thu 1/1
ORD - STI • 1 stop
Top airlines
Spirit Airlines
Cheapest • from $334 (round-trip)
Delta
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to travel
September
Cheapest • 51% price drop
March
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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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

Mon, Feb 2 - Mon, Feb 9
Spirit Airlines Logo
8:41 am - 5:06 pmORD-STI
6h 25m1 stop
Spirit Airlines Logo
6:18 pm - 9:23 amSTI-ORD
17h 05m1 stop
$334Spirit Airlines
Find Deal
Fri, Dec 5 - Fri, Dec 12
Spirit Airlines Logo
3:26 pm - 2:42 amORD-STI
9h 16m1 stop
Spirit Airlines Logo
3:43 am - 11:08 amSTI-ORD
9h 25m1 stop
$335Spirit Airlines
Find Deal
Mon, Jan 19 - Wed, Jan 28
American Airlines Logo
12:07 pm - 9:46 pmORD-STI
7h 39m1 stop
American Airlines Logo
4:33 pm - 11:08 pmSTI-ORD
8h 35m1 stop
$388American Airlines
Find Deal
Mon, Feb 2 - Mon, Feb 9
Multiple Airlines Logo
5:20 am - 5:06 pmORD-STI
33h 46m2 stops
Multiple Airlines Logo
6:18 pm - 9:23 amSTI-ORD
17h 05m1 stop
$390Multiple Airlines
Find Deal
Sun, Mar 1 - Thu, Mar 5
JetBlue Logo
12:41 pm - 2:44 amORD-STI
12h 03m1 stop
JetBlue Logo
11:06 pm - 11:49 amSTI-ORD
14h 43m1 stop
$398JetBlue
Find Deal
Tue, Nov 25 - Tue, Dec 2
American Airlines Logo
8:10 am - 10:56 pmORD-STI
12h 46m1 stop
American Airlines Logo
6:20 am - 3:56 pmSTI-ORD
11h 36m2 stops
$402American Airlines
Find Deal
Sat, Apr 11 - Sat, Apr 18
JetBlue Logo
1:45 pm - 2:54 amORD-STI
12h 09m1 stop
JetBlue Logo
10:01 am - 10:59 pmSTI-ORD
13h 58m1 stop
$464JetBlue
Find Deal
Sun, Mar 1 - Thu, Mar 5
Delta Logo
10:35 am - 12:53 amORD-STI
12h 18m2 stops
Delta Logo
6:35 am - 5:45 pmSTI-ORD
13h 10m1 stop
$474Delta
Find Deal
Sat, Apr 4 - Fri, Apr 10
Delta Logo
7:30 am - 11:27 pmORD-STI
14h 57m1 stop
Delta Logo
7:41 pm - 10:09 amSTI-ORD
15h 28m1 stop
$503Delta
Find Deal
Tue, Nov 25 - Fri, Nov 28
Multiple Airlines Logo
11:48 am - 12:22 pmORD-STI
22h 34m1 stop
Multiple Airlines Logo
1:17 pm - 12:08 amSTI-ORD
12h 51m2 stops
$514Multiple Airlines
Find Deal
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.

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

The average price of all round-trip flights from Chicago to Santiago de los Caballeros clicked on KAYAK for each day over the last 12 months.

Your flight ticket price will generally be cheaper if you fly to Santiago de los Caballeros on a Tuesday and more expensive on a Saturday. On your return trip to Chicago, you should consider flying back on a Saturday, and avoid Wednesdays for better 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 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 September, where tickets cost $251 (return) on average. On the other hand, the most expensive months are December and May, where the average cost of round-trip tickets is $776 and $680 respectively.

Good to know

Low seasonJanuary
Cheapest flight$146
Best time to beat the crowds with an average 3% drop in price.
Most popular time to fly with an average 30% 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 3 days, the lowest price for a flight from Chicago to Santiago de los Caballeros was $146 for a one-way ticket and $334 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?

    Star Alliance, SkyTeam, and oneworld are the airline alliances operating flights between Chicago and Santiago de los Caballeros, with Star Alliance 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 $545 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 $545 and an overall rating of 7.4.

  • 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 3 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.
7.9
DeltaOverall score based on 8003 reviews
7.3Food
8.2Boarding
7.9Comfort
8.5Crew
7.9Entertainment
Airline reviews

I truly love flying with Delta. They have always treated me with the upmost respect

10.0 ExcellentMAYRA, Nov 2025JFK - MIA
Read more Delta reviews

I truly love flying with Delta. They have always treated me with the upmost respect

Our flight attendant in FIRST CLASS was one of the worst I’ve ever had. She was not at all pleasant, nor particularly good at her service.

Everything went well and was good. Nothing exceptional, but no complaints either. Cheap seats are pretty comfortable.

Staff were friendly and happy. Delta could make sure passengers that don't have the app know of changes. Without Kayak I would not have known about the change of gate or the delay. Kayak was faster to notify me.

They ended up paying for the bag twice, but the counter wouldn't take my baggage receipt. Left it to me to resolve. Not sure how to resolve the issue.

The customer service before board was very rude and when I expressed my concerns about making the connecting flight she laughed and told me I bought the wrong ticket. I explained once it showed the flight was delayed it no longer let me change seats or anything. I was trying to upgrade to make sure I would get to the next gate on time.

Non stop on long haul is the way to go. Great experience

The aircraft interior is old and tired on this aircraft. The entertainment system never worked despite the crews attempt to reset the system.

The flight used a B767 with a very old interior from before 2014. The entertainment system did not work at all during the flight despite attempts to reset the system. It was like they flew this route just to be competitive.

Old plane and old configuration/seats but still comfortable for a morning flight

Excellent flight. Smooth, efficient boarding. Quick flight. Arrived early at STL.

Not the fault of United—weather, reroute around weather, time sitting on tarmac, arrived couple hours late, too late for train into city necessitating a much pricier cab but weather…can’t be helped.

I will never book a flight through Cheap fare. They booked me from Portland Main . And would not give me a refund, so I bought 2 tickets one for 299. From Portland Main to ORD. Then I had to buy a ticket from Oregon PDX to ORD that was another 440. So Just so you know they even told me it was there fault but no refund. Bad bussniess. I did inform United but they said they couldn't help me due to the fact I booked through Cheap Tickets. Never again. And I'm spreding the word. I let everyone know at my 50th class reunion

The flight attendants were rude. Seemed like they didn’t want to be there. Except for one girl that was really nice. Seats are sooooo uncomfortable. They give you a piece of paper and a thin cushion for a pillow and blanket that does nothing. Airlines have gone way downhill, especially United international flights. Food was disguting. Definitely flying ANA next time.

Crew and customer service were excellent. This flight also had plenty of leg room and seat mounted screens for entertainment. A very pleasant flight all around!

It would have been better if the crew has supported my husband's reasons for needing to keep the space clear around his feet, rather than insisting that he put his knapsack in that space.

Subject: Formal Complaint: Discriminatory and Unprofessional Conduct – Request for Immediate Action & Compensation Dear [Airline Customer Relations Team], I am writing to file a formal complaint regarding my recent travel experience with [Airline], which was by far the worst I have ever encountered. What occurred was not only unprofessional, but in several instances discriminatory, unsafe, and unacceptable. On the first leg of my trip, I arrived only four minutes past check-in. Instead of making any attempt to resolve the matter, your representative flatly denied me boarding and made me wait while she attended to passengers who arrived after me. By the time a manager intervened, it was too late to board, costing me time, money, and unnecessary frustration. The second leg of my trip (Chicago–San Francisco) raised even more serious concerns. From the outset, it was apparent that the staff—particularly two attendants—prioritized Caucasian passengers while dismissing African American and minority passengers. • When a Caucasian passenger in the exit row refused to comply with federal safety requirements, I, as a first responder, immediately offered to switch seats and assume the responsibility. My offer was blatantly ignored, and instead, a Caucasian passenger seated further up was chosen. This was discriminatory and deeply insulting, especially as I was actively de-escalating the situation that could have delayed the flight further. • During a lengthy tarmac delay of over 90 minutes, passengers were given conflicting and unreasonable instructions that created unnecessary distress and tension. • Throughout the flight, a visibly intoxicated passenger directly in front of me was disruptive, rude to others, failed to comply with seatbelt and electronic device rules, and yet faced no enforcement from the crew. In stark contrast, I was singled out for repeated compliance checks even though I was following every rule. This unequal treatment was so obvious that multiple passengers around me spoke up in my defense. This pattern of behavior demonstrated a clear lack of professionalism, disregard for passenger safety, and discriminatory treatment. I expect far better from an airline of your stature. As a paying customer subjected to this unacceptable treatment, I am formally requesting: 1. A full investigation into the conduct of the staff on both flights. 2. A written apology acknowledging the discriminatory and unprofessional behavior I endured. 3. Appropriate compensation for the distress, inconvenience, and mishandling of my travel. If this matter is not addressed promptly and thoroughly, I will have no choice but to escalate my complaint further, including filing with the U.S. Department of Transportation and sharing my experience through other channels. I trust [Airline] will take this complaint seriously and provide a timely resolution.

Check in was quick and easy during early hours. Flight was on time, and customer services was a plus.

Once we got in the air the pilot made up some of the time of the delay. So that was really nice.

We had a layover from YVR to Denver. We bought 4 bottles of Absolut Vodka at the YVR Duty Free for $116.20, after going through security and American Customs Pre Clearance at YVR, Vancouver. When we landed in Denver, United put us behind the American Customs as well as TSA again for some reason. We were forced to go through American Customs and TSA again. TSA confiscated our rightfully owned Duty Free Absolut Vodka bottles. Because United incorrectly forced our flight behind American border and TSA again, we missed the connecting flight. After United put us on a later flight, we eventually arrived in Chicago very late, with hardly any sleep. I am looking for compensation from United for our incorrectly confiscated Absolut Vodka bottles worth $116.20, as well as compensation for incorrectly putting us behind American Customs and TSA again, causing us to miss our connecting flight, making us arrive extremely late in Chicago.

We loved the steward on the plane. He made the night enjoyable

The plane was late, when we did board the plane was as cold as a freezer. I was freezing the entire flight, no blankets. Lost miserable flight I’ve ever had.

My wife and I love to travel, so we fly a lot. We've already logged 381,075 miles and with practically every major airline. But this flight was very disappointing. It started off well, with no delays and a new plane. But when lunchtime approached, all that good impression was ruined. Instead of white tablecloths, we were offered small, dark placemats, which, as it turned out, were perfectly adequate for the food. All the food offered—and my wife and I only took fish, and the meat—was not just bad, it was downright disgusting and not heated enough. The same applies to the appetizers. This was the first time in many years of traveling that we've been offered such disgusting food.

Lost luggage stuck no clothes and no word after 2 days leaving on cruise no stuff or clothes

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

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

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