Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Chicago to Santiago de los Caballeros from $185

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Santiago de los Caballeros departing on 4/22. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo
Big names and deals
Big names and deals
Search 100s of travel sites to compare prices.
Filter for what you want
Filter for what you want
Free Wi-Fi? Stopover? Instantly customize your results.
Trusted and free
Trusted and free
We’re completely free to use - no hidden charges or fees.
Price Alerts
Price Alerts
Not ready to book? to track prices.

Find the cheapest flights from Chicago to Santiago de los Caballeros

Cheap round-trip flights

KAYAK's recommended round-trip deals from the most popular airlines that fly from Chicago to Santiago de los Caballeros.
1:50 pm - 12:27 amORD-STI
9h 37m1 stop
6:11 am - 5:29 pmSTI-ORD
12h 18m1 stop
$393Delta
Find Deal
Thu, Apr 24 - Wed, May 7
1:50 pm - 12:27 amORD-STI
9h 37m1 stop
6:10 am - 4:22 pmSTI-ORD
11h 12m2 stops
$397Delta
Find Deal
Sat, Apr 26 - Sat, May 3
7:10 am - 3:12 pmORD-STI
7h 02m1 stop
4:23 pm - 11:44 pmSTI-ORD
8h 21m1 stop
$416United Airlines
Find Deal
Sun, May 11 - Thu, May 15
5:36 am - 2:46 pmORD-STI
8h 10m1 stop
3:51 pm - 12:20 amSTI-ORD
9h 29m1 stop
$422Spirit Airlines
Find Deal
Thu, Apr 24 - Tue, Apr 29
1:24 pm - 1:54 amORD-STI
11h 30m1 stop
10:55 pm - 12:13 pmSTI-ORD
14h 18m1 stop
$423JetBlue
Find Deal
Tue, Apr 29 - Fri, May 2
5:36 am - 2:46 pmORD-STI
8h 10m1 stop
3:51 pm - 9:24 amSTI-ORD
18h 33m1 stop
$451Spirit Airlines
Find Deal
Tue, Apr 29 - Thu, May 1
1:26 pm - 1:48 amORD-STI
11h 22m1 stop
3:45 am - 6:36 pmSTI-ORD
15h 51m1 stop
$472JetBlue
Find Deal
Thu, Apr 24 - Mon, May 5
7:16 pm - 12:29 pmORD-STI
16h 13m1 stop
7:05 am - 9:15 pmSTI-ORD
15h 10m1 stop
$474American Airlines
Find Deal
Wed, Jun 4 - Wed, Jun 11
7:05 am - 9:05 pmORD-STI
13h 00m2 stops
7:05 am - 6:35 pmSTI-ORD
12h 30m2 stops
$559American Airlines
Find Deal
Thu, Jun 19 - Fri, Jul 4
7:10 am - 3:12 pmORD-STI
7h 02m1 stop
4:23 pm - 11:44 pmSTI-ORD
8h 21m1 stop
$685United Airlines
Find Deal
Mon, Apr 28 - Fri, May 2

Delta flights from Chicago to Santiago de los Caballeros

Our best Delta deals on Chicago to Santiago de los Caballeros flight tickets
Delta
Apr 24
ORD1:50 pmChicago O'Hare Intl
9h 37m
1 stop
STI12:27 amSantiago de los Caballeros
May 7
STI6:11 amSantiago de los Caballeros
12h 18m
1 stop
ORD5:29 pmChicago O'Hare Intl
Delta
Apr 26
ORD1:50 pmChicago O'Hare Intl
9h 37m
1 stop
STI12:27 amSantiago de los Caballeros
May 3
STI6:10 amSantiago de los Caballeros
11h 12m
2 stops
ORD4:22 pmChicago O'Hare Intl
Delta
Apr 27
ORD7:10 amChicago O'Hare Intl
10h 31m
1 stop
STI6:41 pmSantiago de los Caballeros
May 7
STI6:11 amSantiago de los Caballeros
12h 18m
1 stop
ORD5:29 pmChicago O'Hare Intl

United Airlines flights from Chicago to Santiago de los Caballeros

Our best United Airlines deals on Chicago to Santiago de los Caballeros flight tickets
United Airlines
May 11
ORD7:10 amChicago O'Hare Intl
7h 02m
1 stop
STI3:12 pmSantiago de los Caballeros
May 15
STI4:23 pmSantiago de los Caballeros
8h 21m
1 stop
ORD11:44 pmChicago O'Hare Intl
United Airlines
Apr 28
ORD7:10 amChicago O'Hare Intl
7h 02m
1 stop
STI3:12 pmSantiago de los Caballeros
May 2
STI4:23 pmSantiago de los Caballeros
8h 21m
1 stop
ORD11:44 pmChicago O'Hare Intl
United Airlines
Apr 10
ORD6:00 amChicago O'Hare Intl
8h 12m
1 stop
STI3:12 pmSantiago de los Caballeros
Dec 8
STI4:00 pmSantiago de los Caballeros
9h 42m
1 stop
ORD11:42 pmChicago O'Hare Intl

See travel insights to Santiago de los Caballeros from

How to get the cheapest flight ticket from Chicago to Santiago de los Caballeros

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Santiago de los Caballeros?

The cheapest month to fly to Santiago de los Caballeros from Chicago is in April. Flight prices, which tend to average around $207, are often lower during this time because this is during the off-season. If you aren’t able to travel to Santiago de los Caballeros during the month of April, then flying in September is also cheap. Prices for this month can be found on momondo for an average of $373.

What is the cheapest day to depart on your flight to Santiago de los Caballeros?

The cheapest day to depart from Chicago to Santiago de los Caballeros is on a Tuesday when prices can be found for as low as $425. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Chicago to Santiago de los Caballeros for around $683.

What is the cheapest time of day to depart on your flight to Santiago de los Caballeros?

Our data shows that the cheapest Chicago to Santiago de los Caballeros flights are usually those with departure times in the afternoon. Our users have found flights to Santiago de los Caballeros in the afternoon for as low as $393. In the morning is when there is more demand to fly to Santiago de los Caballeros, so prices are often more expensive at around $564 per ticket.

When to book flights from Chicago to Santiago de los Caballeros

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago to Santiago de los Caballeros according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago to Santiago de los Caballeros (CHI to STI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Santiago de los Caballeros

Best Price Found

$185

Fastest flight time

7h 02m

Direct flights

None

Airports in Santiago de los Caballeros

1 airport
The best one-way flight to Santiago de los Caballeros from Chicago in the past 72 hours is $185. The best round-trip flight deal from Chicago to Santiago de los Caballeros found on momondo in the last 72 hours is $393.
The fastest flight from Chicago to Santiago de los Caballeros takes 7h 02m
There are no direct flights from Chicago to Santiago de los Caballeros. Popular non-direct routes for this connection are Chicago Midway Airport - Santiago de los Caballeros Airport and Chicago O'Hare Intl Airport - Santiago de los Caballeros Airport.
There is 1 airport near Santiago de los Caballeros: Santiago de los Caballeros (STI)

  • How far is Chicago to Santiago de los Caballeros by plane?

    The distance between Chicago and Santiago de los Caballeros is about 1838.3 mi. 7h 02m is a normal flight duration for this route.

  • When did momondo last update prices for flights from Chicago to Santiago de los Caballeros Airport?

    Prices for flights from Chicago to Santiago de los Caballeros Airport were last updated today.

  • How many operators does momondo search for flights from Chicago to Santiago de los Caballeros Airport?

  • How old do you have to be to fly from Chicago to Santiago de los Caballeros Airport?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago to Santiago de los Caballeros Airport.

  • What documentation or ID do you need to fly to Santiago de los Caballeros Airport?

    The travel and health documents required for your trip to Santiago de los Caballeros Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Santiago de los Caballeros Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular airline from Chicago to Santiago de los Caballeros?


Best airlines flying from Chicago to Santiago de los Caballeros

Compare and see reviews for airlines that fly from Chicago to Santiago de los Caballeros with momondo
Airline
Rating
Free Cancellation
Price
United AirlinesPriceFrom $226Free CancellationRating
7.4
8,603 reviews
Search United Airlines flights
Spirit AirlinesPriceFrom $228Free CancellationRating
6.3
7,882 reviews
Search Spirit Airlines flights
JetBluePriceFrom $343Free CancellationRating
7.3
2,923 reviews
Search JetBlue flights
DeltaPriceFrom $345Free CancellationRating
8.0
7,895 reviews
Search Delta flights
American AirlinesPriceFrom $381Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Santiago de los Caballeros?

It is quick and easy to find Chicago to Santiago de los Caballeros flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Santiago de los Caballeros that suits you.

Can I find flights from Chicago to Santiago de los Caballeros with flexible booking policies on momondo?

Flights from Chicago to Santiago de los Caballeros with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Chicago to Santiago de los Caballeros?

momondo provides multiple filters to help you find the best flight to Santiago de los Caballeros from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Chicago to Santiago de los Caballeros right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Chicago to Santiago de los Caballeros flights. All you need is a valid email address and we will do the rest; it is that quick and easy.


An easier way to manage your Santiago de los Caballeros trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
From?
To?
Tue 4/1
Tue 4/8

Find better results for your trip to the Dominican Republic