STI - ORD

$213 Find Cheap Flights from Santiago de los Caballeros to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Santiago de los Caballeros to O'Hare Intl departing on 6/10. 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.
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KAYAK searches hundreds of travel sites at once for deals on flights to Chicago O'Hare Intl Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Santiago de los Caballeros to Chicago, 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 Santiago de los Caballeros to Chicago, as well as popular online travel agencies
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Cheap Flight Deals from Santiago de los Caballeros to Chicago (STI-ORD)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Santiago de los Caballeros to Chicago 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.

Recent round-trip flight deals from Santiago de los Caballeros to O'Hare Intl

KAYAK's recommended round-trip deals from the most popular airlines that fly from Santiago de los Caballeros to O'Hare Intl.
Discover the best prices for you by selecting your travel dates on KAYAK.
Spirit Airlines Logo
11:29 am - 11:45 pmSTI-ORD
13h 16m1 stop
Spirit Airlines Logo
4:45 pm - 10:29 amORD-STI
16h 44m1 stop
$443Spirit Airlines
Find Deal
Thu, Jun 12 - Sat, Jun 21
American Airlines Logo
1:35 pm - 10:53 amSTI-ORD
22h 18m1 stop
American Airlines Logo
8:35 pm - 12:20 pmORD-STI
14h 45m2 stops
$444American Airlines
Find Deal
Mon, Sep 15 - Tue, Sep 30
Spirit Airlines Logo
3:53 pm - 11:04 pmSTI-ORD
8h 11m1 stop
Spirit Airlines Logo
5:05 am - 2:48 pmORD-STI
8h 43m1 stop
$475Spirit Airlines
Find Deal
Tue, May 13 - Tue, May 20
Delta Logo
9:20 pm - 12:08 pmSTI-ORD
15h 48m2 stops
Delta Logo
7:00 am - 7:54 pmORD-STI
11h 54m2 stops
$499Delta
Find Deal
Mon, Sep 15 - Tue, Sep 30
 Logo
3:53 pm - 11:04 pmSTI-ORD
8h 11m1 stop
 Logo
9:08 pm - 2:00 pmORD-STI
39h 52m2 stops
Tue, May 13 - Wed, May 21
JetBlue Logo
10:30 am - 6:36 pmSTI-ORD
9h 06m1 stop
JetBlue Logo
6:15 am - 8:30 pmORD-STI
13h 15m1 stop
$572JetBlue
Find Deal
Tue, May 13 - Wed, May 21
JetBlue Logo
5:20 am - 3:04 pmSTI-ORD
10h 44m1 stop
JetBlue Logo
7:31 pm - 9:05 amORD-STI
12h 34m1 stop
$712JetBlue
Find Deal
Wed, May 14 - Sun, May 18
Delta Logo
6:11 am - 6:48 pmSTI-ORD
13h 37m2 stops
Delta Logo
7:00 am - 5:50 pmORD-STI
9h 50m1 stop
$723Delta
Find Deal
Wed, May 14 - Sun, May 18
United Airlines Logo
4:23 pm - 11:37 pmSTI-ORD
8h 14m1 stop
United Airlines Logo
4:46 pm - 1:46 amORD-STI
8h 00m1 stop
$731United Airlines
Find Deal
Sat, Jun 28 - Tue, Jul 29
United Airlines Logo
6:00 am - 1:15 pmSTI-ORD
8h 15m1 stop
United Airlines Logo
6:25 pm - 3:12 pmORD-STI
19h 47m2 stops
$993United Airlines
Find Deal
Tue, May 20 - Tue, May 20
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KAYAK's insights & trends for Santiago de los Caballeros to O'Hare Intl flights

Get data-powered insights and trends into flights from Santiago de los Caballeros to O'Hare Intl 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 Santiago de los Caballeros to Chicago?

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

For Santiago de los Caballeros to Chicago, Saturday is the cheapest day to fly on average and Wednesday is the most expensive. Flying from Chicago back to Santiago de los Caballeros, the best deals are generally found on Tuesday, with Saturday being the most expensive.

Good to know

Low seasonJune
High seasonMay
Cheapest flight$213
Best time to beat the crowds with an average 25% drop in price.
Most popular time to fly and prices are also 5% lower on average.
Flight from Santiago de los Caballeros to Chicago

When to book flights from Santiago de los Caballeros to O'Hare Intl

Are your dates flexible? Find out the best times to travel from Santiago de los Caballeros to O'Hare Intl 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 Santiago de los Caballeros to Chicago flights

  • What is the cheapest flight from Santiago de los Caballeros to Chicago O'Hare Intl Airport?

    In the last 3 days, the lowest price for a flight from Santiago de los Caballeros to Chicago O'Hare Intl Airport was $213 for a one-way ticket and $443 for a round-trip.

  • Do I need a passport to fly between Santiago de los Caballeros and Chicago?

    Yes, you'll most likely have to show a valid passport before boarding the plane in Santiago de los Caballeros and on arrival in Chicago.

  • Which aircraft models fly most regularly from Santiago de los Caballeros to Chicago?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Santiago de los Caballeros to Chicago?

    SkyTeam, oneworld, and Star Alliance are the airline alliances operating flights between Santiago de los Caballeros and Chicago, with SkyTeam being the most commonly used for this route.

  • How does KAYAK find such low prices on flights from Santiago de los Caballeros to Chicago?

    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 Santiago de los Caballeros to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Santiago de los Caballeros to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Santiago de los Caballeros 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 Santiago de los Caballeros to Chicago?

    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 Chicago with an airline and back to Santiago de los Caballeros with another airline. Booking your flights between Santiago de los Caballeros and ORD can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Santiago de los Caballeros to Chicago?

    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 Chicago from Santiago de los Caballeros up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Top airline flying from Santiago de los Caballeros to O'Hare Intl

 
See real verified KAYAK customer reviews for airlines flying from Santiago de los Caballeros to Chicago. 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 Santiago de los Caballeros to O'Hare Intl? 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.
7.2
American AirlinesOverall score based on 10000 reviews
7.5Boarding
7.2Comfort
6.5Food
6.9Entertainment
8.0Crew
Airline reviews

To start, I’d like to say that every American Airline personnel I interacted with on the ground, especially flight crew, was very friendly and did their best to help me out. Despite this, however, my experience with the airline was an entire mess. The 7:19 PM flight was heavily delayed due to weather, and pushed to 10:30 AM the next morning. Because of this, I had to spend the night inside of the airport. At some point later in the night, I got an email saying that the flight had been canceled. I called the support number, and the representative on the other line told me that the flight was still on and that I didn’t need to rebook. The next morning, no one came to the gate to open the door for the crew until almost 11 AM. By this time the flight crew had been waiting for over an hour, and they had called management to get someone to open the door for them multiple times. Around 11:30, the gate screen had changed to a different flight. I ended up buying a last minute ticket with Southwest airline just to get to Chicago, because the next flight with American wasn’t until 7:19 pm that day. Now, earlier that morning my suitcase had been sent ahead of me to ORD. I went to baggage claim to ask them if I could have my suitcase forwarded to where I was staying. The representative at SDF baggage claim said they could and put the claim in for me. As I was going back through TSA, I got an email that the airline had found my suitcase, but the next step was to send it BACK to SDF. I called the airline support number again, and I made it clear that my suitcase needed to stay in Chicago and to not come back to SDF. The representative told me that they would hold my suitcase at ORD and that it wasn’t going to be forwarded anywhere. Once I got there, I found that they had loaded my suitcase onto a plane to send it back to SDF. Thankfully, I had gotten to the baggage claim counter in time for them to put in a request to bring my suitcase back up. My refund with the airline is processing already, but because of this entire experience and miscommunication at every turn of the way, I will not book with American Airlines in the future.

2.0 MediocreAnonymous, Apr 2025SDF - ORD
Read more American Airlines reviews

To start, I’d like to say that every American Airline personnel I interacted with on the ground, especially flight crew, was very friendly and did their best to help me out. Despite this, however, my experience with the airline was an entire mess. The 7:19 PM flight was heavily delayed due to weather, and pushed to 10:30 AM the next morning. Because of this, I had to spend the night inside of the airport. At some point later in the night, I got an email saying that the flight had been canceled. I called the support number, and the representative on the other line told me that the flight was still on and that I didn’t need to rebook. The next morning, no one came to the gate to open the door for the crew until almost 11 AM. By this time the flight crew had been waiting for over an hour, and they had called management to get someone to open the door for them multiple times. Around 11:30, the gate screen had changed to a different flight. I ended up buying a last minute ticket with Southwest airline just to get to Chicago, because the next flight with American wasn’t until 7:19 pm that day. Now, earlier that morning my suitcase had been sent ahead of me to ORD. I went to baggage claim to ask them if I could have my suitcase forwarded to where I was staying. The representative at SDF baggage claim said they could and put the claim in for me. As I was going back through TSA, I got an email that the airline had found my suitcase, but the next step was to send it BACK to SDF. I called the airline support number again, and I made it clear that my suitcase needed to stay in Chicago and to not come back to SDF. The representative told me that they would hold my suitcase at ORD and that it wasn’t going to be forwarded anywhere. Once I got there, I found that they had loaded my suitcase onto a plane to send it back to SDF. Thankfully, I had gotten to the baggage claim counter in time for them to put in a request to bring my suitcase back up. My refund with the airline is processing already, but because of this entire experience and miscommunication at every turn of the way, I will not book with American Airlines in the future.

The plane was late and then sat on the runway for almost 45 minutes before taking off.

Crew professional. Easy bag drop off. On time. Good entertainment.

Everything was great. Boarding, early departure, early arrival, and deplaning were smooth. Smooth flight.

Per usual, flight status, staff courtesy and professionalism were excellent

The only thing is if Wi-Fi is available after you land and taxi to the gate. It takes forever to get to the gate, and having the Wi-Fi continue would be great to bide the time at least 5 minutes before you arrive at the entrance. That is my only comment; otherwise, everything was good.

Had to wait on pilot and crew to depart and had to wait to arrive at the gate because they only had 2 crews working. Delays, delays....Planes just keep getting smaller and tighter and they nickle and dime for everything. When will an airline actually wake up and make flying more enjoyable?

Seating was horrible. Small seats. Access to flight information and extras very iser unfriendly. Kept losing internet after paying for it. Staff in madison was as unprofessional and unhelpful.

Delayed due to no crew. On a major holiday travel day.

Other than being delayed 5.5 hours and having to get a hotel because I missed my connecting flight, it was an okay flight. No in-flight Wi-Fi or entertainment.

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