CHI - STI

$168 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 4/5. 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
Travelers love KAYAK
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Everything you should know

Cheapest round-trip
$360
Overall average: $471
Spirit Airlines
Thu 4/9Thu 4/16
ORD - STI • 1 stop
Cheapest one-way
$168
Typical prices: $155-$186
Spirit Airlines
Sun 4/5
ORD - STI • 1 stop
Top airlines
Cheapest • from $360 (round-trip)
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between Chicago and Santiago de los Caballeros. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $443 (round-trip)
Shortest trip • 7h 05m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 53% price drop
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

Thu, Apr 9 - Thu, Apr 16
Spirit Airlines Logo
4:36 pm - 1:49 am
ORD
-
STI
8h 13m
1 stop
Spirit Airlines Logo
3:07 pm - 12:24 am
STI
-
ORD
10h 17m
1 stop
$360Spirit Airlines
Wed, Apr 8 - Fri, Apr 10
Spirit Airlines Logo
7:17 am - 2:23 pm
ORD
-
STI
6h 06m
1 stop
Spirit Airlines Logo
2:46 am - 11:17 am
STI
-
ORD
9h 31m
1 stop
$390Spirit Airlines
Tue, Mar 31 - Thu, Apr 9
Spirit Airlines Logo
6:10 pm - 1:49 am
ORD
-
STI
6h 39m
1 stop
Spirit Airlines Logo
3:28 pm - 11:17 pm
STI
-
ORD
8h 49m
1 stop
$391Spirit Airlines
Mon, Apr 6 - Thu, Apr 9
Spirit Airlines Logo
6:10 pm - 1:49 am
ORD
-
STI
6h 39m
1 stop
Spirit Airlines Logo
3:28 pm - 11:17 pm
STI
-
ORD
8h 49m
1 stop
$394Spirit Airlines
Tue, Mar 31 - Wed, Apr 8
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
$395Spirit Airlines
Fri, Apr 10 - Mon, Apr 13
Multiple Airlines Logo
6:10 pm - 2:23 pm
ORD
-
STI
19h 13m
1 stop
Multiple Airlines Logo
3:28 pm - 5:00 pm
STI
-
ORD
26h 32m
2 stops
$396Multiple Airlines
Sun, May 17 - Sat, May 23
Spirit Airlines Logo
5:05 am - 2:02 pm
ORD
-
STI
7h 57m
1 stop
Spirit Airlines Logo
3:07 pm - 12:27 am
STI
-
ORD
10h 20m
1 stop
$425Spirit Airlines
Wed, Apr 15 - Wed, Apr 22
Delta Logo
10:41 am - 12:22 am
MDW
-
STI
12h 41m
2 stops
Delta Logo
6:00 am - 4:26 pm
STI
-
MDW
11h 26m
2 stops
$493Delta
Mon, Apr 27 - Mon, May 4
Delta Logo
9:27 am - 12:22 am
MDW
-
STI
13h 55m
2 stops
Delta Logo
8:59 pm - 12:07 pm
STI
-
MDW
16h 08m
2 stops
$604Delta
Thu, Apr 30 - Thu, May 7
Delta Logo
9:27 am - 12:22 am
MDW
-
STI
13h 55m
2 stops
Delta Logo
6:00 am - 6:33 pm
STI
-
MDW
13h 33m
2 stops
$1,091Delta
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 seasonMarch
Cheapest flight$168
Best time to beat the crowds but there is an average 13% increase in price.
Most popular time to fly with an average 71% 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 $168 for a one-way ticket and $360 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?

    SkyTeam, Star Alliance, and oneworld 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, 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 $662 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 7.1.

  • 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.
7.4
United AirlinesOverall score based on 9431 reviews
7.7Boarding
8.1Crew
7.3Comfort
6.6Food
7.1Entertainment
Airline reviews

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.

4.0 OkayDr. Joseph, Feb 2026
ORD - IAH
Read more United Airlines reviews

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. :/

The gate got changed several times and the flight was delayed over an hour. Awful experience

American continues to decline in their customer service and its beyond disappointing.

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

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.

Absolutely terrible, flight was cancelled and we missed our cruise. Will never fly Spirit again.

Horrendous and unprofessional staff and will never fly spirit again

We get stuck in the plane when landed during 45min and no communication from the crew People were listening to their phone and music out loud and nobody told them anything I definitely want stop booking spirit flight it is a disaster

Good: It was cheap and they got us to our destination safely. Not so Good: Gates experience with many, many nauseatingly (almost) threatening announcements about bags size and how much they were going to charge us if our bag was too big, even to the point of having a gate agent roaming around through the passengers eyeballing bags size and making people go check their bags in the sizers.

Terrible. The flight was randomly delayed in Chicago causing us to miss our connection and they offered us a flight the next day at 6 am and it would have taken till 345 to get to Pensacola. They didn’t cover any fees. Our bags also supposedly were on the flight to Pensacola and we tried to get them yesterday after driving 6 hours and nobody was available. Worst company ever and will never use them again. Had to pay for a rental. Spirit is claiming in climate weather for the delay but there wasn’t any weather issuesz it’s a bunch of bullshit and I am not happy

Checking in at desk in Chicago was horrible. Person was not friendly never smiled and said my flight was not paid for so I had to give another credit card. Then it ended up that I was charged twice. Then after arriving at my destination had to wait on the phone a long time to speak to a person to fix the double charge! Thank goodness the flight was perfect.

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 .

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

Information on your arrival and departure airports