CHI - STI

$119 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 2/23. 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
$248
Overall average: $395
Spirit Airlines
Wed 2/4Sat 2/7
ORD - STI • 1 stop
Cheapest one-way
$119
Typical prices: $159-$192
Spirit Airlines
Mon 2/23
ORD - STI • 1 stop
Top airlines
Spirit Airlines
Cheapest • from $261 (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 • 52% price drop
December
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

Wed, Feb 4 - Sat, Feb 7
Spirit Airlines Logo
7:20 am - 3:33 pm
ORD
-
STI
6h 13m1 stop
Spirit Airlines Logo
4:40 pm - 11:47 pm
STI
-
ORD
9h 07m1 stop
$248Spirit Airlines
Wed, Feb 4 - Sat, Feb 7
Spirit Airlines Logo
7:20 am - 3:33 pm
ORD
-
STI
6h 13m1 stop
Spirit Airlines Logo
4:40 pm - 11:47 pm
STI
-
ORD
9h 07m1 stop
$261Spirit Airlines
Wed, Feb 11 - Wed, Feb 18
Spirit Airlines Logo
5:15 am - 3:33 pm
ORD
-
STI
8h 18m1 stop
Spirit Airlines Logo
4:40 pm - 11:47 pm
STI
-
ORD
9h 07m1 stop
$262Spirit Airlines
Fri, Jan 30 - Mon, Feb 2
Spirit Airlines Logo
8:43 pm - 3:33 pm
ORD
-
STI
16h 50m1 stop
Spirit Airlines Logo
4:40 pm - 11:47 pm
STI
-
ORD
9h 07m1 stop
$283Spirit Airlines
Sun, Jan 25 - Sun, Feb 1
Spirit Airlines Logo
5:15 am - 3:33 pm
ORD
-
STI
8h 18m1 stop
Spirit Airlines Logo
4:40 pm - 11:47 pm
STI
-
ORD
9h 07m1 stop
$303Spirit Airlines
Mon, Feb 16 - Mon, Mar 2
Spirit Airlines Logo
7:00 am - 3:35 pm
ORD
-
STI
6h 35m1 stop
Spirit Airlines Logo
4:40 pm - 11:47 pm
STI
-
ORD
9h 07m1 stop
$305Spirit Airlines
Wed, Feb 4 - Sat, Feb 7
Multiple Airlines Logo
7:45 am - 5:04 pm
ORD
-
STI
31h 19m2 stops
Multiple Airlines Logo
4:40 pm - 11:47 pm
STI
-
ORD
9h 07m1 stop
$329Multiple Airlines
Fri, Jan 30 - Tue, Feb 3
Delta Logo
10:48 am - 12:50 am
MDW
-
STI
12h 02m2 stops
Delta Logo
6:38 am - 5:55 pm
STI
-
MDW
13h 17m2 stops
$401Delta
Fri, Jan 30 - Mon, Feb 2
Delta Logo
9:33 am - 12:50 am
MDW
-
STI
13h 17m2 stops
Delta Logo
9:59 pm - 11:59 am
STI
-
MDW
16h 00m2 stops
$402Delta
Mon, Mar 23 - Mon, Mar 30
Delta Logo
5:40 pm - 7:15 pm
MDW
-
STI
24h 35m2 stops
Delta Logo
8:40 pm - 5:54 pm
STI
-
MDW
22h 14m2 stops
$474Delta
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 $915 and $712 respectively.

Good to know

Low seasonMay
Cheapest flight$119
Best time to beat the crowds but there is an average 36% increase in price.
Most popular time to fly with an average 75% 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 $119 for a one-way ticket and $248 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 $564 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 9121 reviews
7.3Comfort
7.7Boarding
6.6Food
8.1Crew
7.1Entertainment
Airline reviews

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...

6.0 GoodRob, Dec 2025
ORD - RIC
Read more United Airlines reviews

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.

Very nice flight love the small aircraft. We had a wonderful flight attendant. Nice to see someone that really enjoys her job. Don't have her name but had a southern accent.

Very thoughtful flight attendant offered me water immediately since I had run to make my connection.

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.

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

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

Information on your arrival and departure airports