CHI - STI

$196 Find Cheap Flights from Chicago to Santiago de los Caballeros - Compare and Save

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Everything you should know

Cheapest round-trip
$739
Typical prices: $461-$834
American Airlines
Sat 12/1Thu 12/13
ORD - STI • 2 stops
Cheapest one-way
$196
Typical prices: $231-$482
American Airlines
Fri 2/9
ORD - STI • 2 stops
Nonstop flights
Not available
There are currently no direct flights between Chicago and Santiago de los Caballeros. You'll need to take a connecting flight to reach the destination.
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Top routes
MDW - STI
Cheapest • 17% average savings
ORD - STI
Most popular
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When to travel
March
Cheapest • 27% price drop
November
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Boston Logan Intl (BOS)
Cheapest • Avg $425 (round-trip)
Fort Lauderdale (FLL)
Shortest trip • 8h 24m (one-way)
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We hope you love your trip to Santiago de los Caballeros!

Cheap Flights from Chicago to Santiago de los Caballeros (CHI-STI)

 

Cheap flights from Chicago to Santiago de los Caballeros with top airlines, updated regularly. Compare round-trip, one-way, direct and last-minute deals.

Tue, Dec 1 - Sun, Dec 13
American Airlines Logo
9:06 pm - 4:01 pmORD  Chicago O'Hare Intl-STI Santiago de los Caballeros
16h 55m2 stops Charlotte Douglas Miami
American Airlines Logo
2:14 pm - 10:32 pmSTI  Santiago de los Caballeros-ORD Chicago O'Hare Intl
10h 18m2 stops Miami Charlotte Douglas
$739American Airlines
Sat, Feb 13 - Sat, Feb 20
American Airlines Logo
9:45 pm - 3:40 pmORD  Chicago O'Hare Intl-STI Santiago de los Caballeros
15h 55m1 stop Philadelphia
American Airlines Logo
7:00 am - 6:29 pmSTI  Santiago de los Caballeros-ORD Chicago O'Hare Intl
13h 29m2 stops Miami Washington, D.C. Reagan-National
$746American Airlines
Mon, Nov 23 - Fri, Nov 27
American Airlines Logo
9:06 pm - 1:32 pmORD  Chicago O'Hare Intl-STI Santiago de los Caballeros
14h 26m2 stops Charlotte Douglas Miami
American Airlines Logo
5:08 pm - 7:32 amSTI  Santiago de los Caballeros-ORD Chicago O'Hare Intl
16h 24m2 stops Miami Washington, D.C. Reagan-National
$749American Airlines
Wed, Jan 27 - Sun, Feb 28
Delta Logo
6:00 am - 6:40 pmORD  Chicago O'Hare Intl-STI Santiago de los Caballeros
10h 40m1 stop New York John F Kennedy Intl
Delta Logo
2:30 pm - 9:33 pmSTI  Santiago de los Caballeros-ORD Chicago O'Hare Intl
9h 03m1 stop New York John F Kennedy Intl
$785Delta
Sun, Jan 31 - Sun, Feb 28
Delta Logo
1:30 pm - 11:50 pmORD  Chicago O'Hare Intl-STI Santiago de los Caballeros
8h 20m1 stop New York John F Kennedy Intl
Delta Logo
2:30 pm - 9:33 pmSTI  Santiago de los Caballeros-ORD Chicago O'Hare Intl
9h 03m1 stop New York John F Kennedy Intl
$785Delta
Mon, Feb 1 - Sun, Feb 28
Delta Logo
1:30 pm - 11:50 pmORD  Chicago O'Hare Intl-STI Santiago de los Caballeros
8h 20m1 stop New York John F Kennedy Intl
Delta Logo
2:30 pm - 9:33 pmSTI  Santiago de los Caballeros-ORD Chicago O'Hare Intl
9h 03m1 stop New York John F Kennedy Intl
$785Delta
Sat, Feb 13 - Sun, Feb 21
American Airlines Logo
9:05 am - 11:16 pmORD  Chicago O'Hare Intl-STI Santiago de los Caballeros
12h 11m2 stops Charlotte Douglas Miami
American Airlines Logo
4:45 pm - 11:30 pmSTI  Santiago de los Caballeros-ORD Chicago O'Hare Intl
8h 45m1 stop Philadelphia
$814American Airlines
Tue, Dec 29 - Thu, Jan 7
JetBlue Logo
2:32 pm - 12:59 amORD  Chicago O'Hare Intl-STI Santiago de los Caballeros
8h 27m1 stop Fort Lauderdale
JetBlue Logo
4:42 pm - 11:42 pmSTI  Santiago de los Caballeros-ORD Chicago O'Hare Intl
9h 00m1 stop Fort Lauderdale
$1,072JetBlue
Tue, Dec 29 - Tue, Jan 5
JetBlue Logo
2:32 pm - 12:59 amORD  Chicago O'Hare Intl-STI Santiago de los Caballeros
8h 27m1 stop Fort Lauderdale
JetBlue Logo
4:42 pm - 11:42 pmSTI  Santiago de los Caballeros-ORD Chicago O'Hare Intl
9h 00m1 stop Fort Lauderdale
$1,167JetBlue
Tue, Dec 29 - Sun, Jan 3
JetBlue Logo
2:32 pm - 12:59 amORD  Chicago O'Hare Intl-STI Santiago de los Caballeros
8h 27m1 stop Fort Lauderdale
JetBlue Logo
4:15 pm - 11:33 pmSTI  Santiago de los Caballeros-ORD Chicago O'Hare Intl
9h 18m1 stop Fort Lauderdale
$1,432JetBlue

Price, demand and travel trends for Chicago to Santiago de los Caballeros flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

How much is a round-trip flight from Chicago to Santiago de los Caballeros?

Round-trip flights from Chicago to Santiago de los Caballeros typically range from $461 to $834. The lowest price found in the past 5 days was $739, on American Airlines.

What is the cheapest Chicago to Santiago de los Caballeros flight route?

Chicago Midway Airport (MDW) to Santiago de los Caballeros (STI) is the cheapest Chicago to Santiago de los Caballeros route, averaging $427 round-trip. Other Chicago to Santiago de los Caballeros routes average $598, based on KAYAK data over the past 12 months.

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

Based on deals KAYAK users found in the last 12 months, Wednesday is the cheapest day of the week to fly from Chicago to Santiago de los Caballeros. It’s 18% cheaper than the average day, while Saturday is the most expensive, with prices 29% higher.

What’s the cheapest month to fly from Chicago to Santiago de los Caballeros?

•March is the cheapest month to fly from Chicago to Santiago de los Caballeros at $439 round-trip.
•December ($1,132) and June ($665) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 157% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

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Key details for Chicago to Santiago de los Caballeros flights

Low season

August

Cheapest flight

$196
Beat the crowds with an average 56% drop in travelers.
The most popular month to fly with an average 57% increase in travelers.
One-way flight from Chicago O'Hare Intl 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

Your Chicago to Santiago de los Caballeros flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • What cabin classes can I book on flights from Chicago to Santiago de los Caballeros?

    Two cabin classes are available on flights from Chicago to Santiago de los Caballeros:

    • Economy Class
    • First Class

  • How long is a flight from Chicago to Santiago de los Caballeros?

    A nonstop flight from Chicago to Santiago de los Caballeros takes 00m, covering 1,844 miles.

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

    Yes, a valid passport is required for this international route. Many destinations require at least six months of validity beyond your travel dates. Check your passport expiry well before booking.

  • How much should I expect to pay for a Chicago to Santiago de los Caballeros flight?

    Round-trip flights from Chicago to Santiago de los Caballeros range from $461 to $834, with an average of $598 over the past 12 months. Anything below $461 counts as a good deal.

  • Have flight prices from Chicago to Santiago de los Caballeros changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $739 to $3,256. That means the highest observed fare was about 4x higher than the lowest one.

  • How are flight prices from Chicago to Santiago de los Caballeros looking right now?

    One-way fares from Chicago to Santiago de los Caballeros are currently lower than usual. Average one-way flight prices are about $210, which is 27% below the typical average for this route.

  • What car rental options are available at Santiago de los Caballeros Airport (STI)?

    Santiago de los Caballeros Airport (STI) hosts 5 major car rental companies, with daily rates starting from around $9 for economy cars. Top options include:

    • Zezgo
    • America Car Rental
    • Alamo
    • Infinity Car Rental
    • Europcar

  • Which airports can I use when flying from Chicago to Santiago de los Caballeros?

    Flights from Chicago to Santiago de los Caballeros may depart from several airports in Chicago area, including Chicago Midway (MDW), Chicago O'Hare Intl (ORD) and Chicago Greater Rockford (RFD). Flights usually arrive at Santiago de los Caballeros (STI).

  • Which airports do connecting flights from Chicago to Santiago de los Caballeros pass through?

    One-stop flights from Chicago to Santiago de los Caballeros most commonly connect through:

    • Miami (MIA) - 61% of one-stop connections
    • Fort Lauderdale (FLL) - 21% of one-stop connections
    • Newark (EWR) - 8% of one-stop connections
    • New York John F Kennedy Intl (JFK) - 6% of one-stop connections

  • Can I save money by using flexible dates for flights from Chicago to Santiago de los Caballeros?

    Yes. Flexible dates can save you up to 37% on flights from Chicago to Santiago de los Caballeros. Wednesday is the cheapest departure day at $493 round-trip on average, while Saturday is the most expensive at $777, a difference of $284.

    KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • How much time can I save by choosing a different layover airport from Chicago to Santiago de los Caballeros?

    Flying via Fort Lauderdale (FLL) gives the shortest average 1-stop total travel time at 8h 24m, compared with 9h 23m via Miami (MIA) and 9h 26m via Philadelphia (PHL).

  • What is the time difference between Chicago and Santiago de los Caballeros?

    Santiago de los Caballeros is 1 hour ahead of Chicago (Atlantic Time vs Central Time). Plan for the time shift when scheduling connections or first-day activities.

Your guide to booking Chicago to Santiago de los Caballeros flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates are flexible, aim for a Wednesday departure and avoid flying on Saturday. On this route, Wednesday flights average $493, about $284 less than Saturday fares (37% savings) based on the last 12 months.
  • If you can choose when to travel, plan your Chicago to Santiago de los Caballeros trip for March. Fares historically average $439 round-trip in that month - typically $693 less than the most expensive month, which is December (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Santiago de los Caballeros Airport.

    • Hodelpa Garden Court

More options for your flight from Chicago to Santiago de los Caballeros

Complete your trip to Santiago de los Caballeros with a hotel stay or car rental

Car rentals in Santiago de los Caballeros
Hotels in Santiago de los Caballeros