CHI - STI

$144 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 6/3. 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
$289
Overall average: $416
Spirit Airlines
Wed 2/11Wed 2/25
ORD - STI • 1 stop
Cheapest one-way
$144
Typical prices: $409-$509
Spirit Airlines
Wed 6/3
ORD - STI • 1 stop
Top airlines
Spirit Airlines
Cheapest • from $289 (round-trip)
United Airlines
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to travel
September
Cheapest • 54% 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 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

Wed, Feb 11 - Wed, Feb 25
Spirit Airlines Logo
7:20 am - 3:33 pm
ORD
-
STI
6h 13m
1 stop
Spirit Airlines Logo
4:40 pm - 11:47 pm
STI
-
ORD
9h 07m
1 stop
$289Spirit Airlines
Sat, Apr 18 - Sat, Apr 25
Spirit Airlines Logo
7:05 am - 2:35 pm
ORD
-
STI
6h 30m
1 stop
Spirit Airlines Logo
3:40 pm - 11:41 pm
STI
-
ORD
9h 01m
1 stop
$310Spirit Airlines
Wed, Mar 25 - Tue, Mar 31
Spirit Airlines Logo
5:05 am - 2:35 pm
ORD
-
STI
8h 30m
1 stop
Spirit Airlines Logo
2:46 am - 11:21 am
STI
-
ORD
9h 35m
1 stop
$312Spirit Airlines
Mon, Mar 30 - Tue, Apr 7
Spirit Airlines Logo
8:41 pm - 2:35 pm
ORD
-
STI
16h 54m
1 stop
Spirit Airlines Logo
3:43 pm - 11:21 am
STI
-
ORD
20h 38m
1 stop
$319Spirit Airlines
Sun, Feb 8 - Sat, Feb 14
Spirit Airlines Logo
8:43 pm - 3:33 pm
ORD
-
STI
16h 50m
1 stop
Spirit Airlines Logo
4:40 pm - 7:54 am
STI
-
ORD
17h 14m
2 stops
$323Spirit Airlines
Wed, Feb 11 - Wed, Feb 25
Spirit Airlines Logo
7:20 am - 3:33 pm
ORD
-
STI
6h 13m
1 stop
Spirit Airlines Logo
4:40 pm - 11:47 pm
STI
-
ORD
9h 07m
1 stop
$324Spirit Airlines
Tue, Mar 17 - Mon, Mar 30
Multiple Airlines Logo
6:36 pm - 2:35 pm
ORD
-
STI
18h 59m
1 stop
Multiple Airlines Logo
3:43 pm - 7:46 pm
STI
-
ORD
29h 03m
1 stop
$338Multiple Airlines
Sun, Feb 8 - Sat, Feb 14
Delta Logo
9:33 am - 12:50 am
MDW
-
STI
13h 17m
2 stops
Delta Logo
9:59 pm - 12:46 pm
STI
-
MDW
16h 47m
2 stops
$439Delta
Mon, Feb 16 - Mon, Mar 2
Delta Logo
9:34 am - 1:34 am
MDW
-
STI
14h 00m
2 stops
Delta Logo
9:59 pm - 12:46 pm
STI
-
MDW
16h 47m
2 stops
$561Delta
Mon, Feb 16 - Mon, Mar 2
Delta Logo
9:34 am - 1:34 am
MDW
-
STI
14h 00m
2 stops
Delta Logo
9:59 pm - 12:46 pm
STI
-
MDW
16h 47m
2 stops
$771Delta
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 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 $985 and $712 respectively.

Good to know

Low seasonMay
Cheapest flight$144
Best time to beat the crowds but there is an average 31% increase in price.
Most popular time to fly with an average 81% 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 $144 for a one-way ticket and $289 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, United Airlines or American Airlines?

    The two airlines most popular with KAYAK users for flights from Chicago to Santiago de los Caballeros are United Airlines and American Airlines. With an average price for the route of $545 and an overall rating of 7.4, United Airlines is the most popular choice. American Airlines is also a great choice for the route, with an average price of $577 and an overall rating of 7.2.

  • 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 airlines flying 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.
7.4
United AirlinesOverall score based on 9215 reviews
7.7Boarding
7.1Entertainment
6.6Food
7.3Comfort
8.1Crew
Airline reviews

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

8.0 ExcellentAnonymous, Jan 2026
ORD - TPA
Read more United Airlines reviews

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. :/

Not United Airlines' fault. It's ORL airport's fault.

Great flight. On time boarding. Smooth flight and on time arrival at EWR. The flight crew was marvelous and there was a great selection of movies on the entertainment system. Our bags were at the carousel before we got there. Another excellent flight from United.

I liked the snacks and the flight attendants were friendly.

The movies offered were great. Staff were very pleasant and very efficient.

After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.

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 experienced gate changes and a long delay. My seat was dirty when I boarded and I had to use wipes to clean it myself. There was an unpleasant and overpowering cleaning product scent on the plane as well that lingered through the flight.

My carry on baggage was damaged. Entire trip, I had to carry the baggage. When complained to the boarding crew, they got mad at me and still asked me to valet check in the cabin baggage. Rude boarding crew!!!

Crew were all friendly and helpful. It was a short flight so just a beverage service with a cookie. After we were boarded the plane took about 45 minutes to leave the gate but it was New Year’s Eve so not shocking there was some delay. Overall good experience and very grateful.

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

The boarding by groups is pointless. The first two groups worked fine, but almost Noone boarded in goups three thru five leaving the vast majority boarding when group six was called. It defeated the purpose of spreading out the crowd.

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.

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

Information on your arrival and departure airports