Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Chicago to Santiago de los Caballeros from $196

1 adult
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Chicago to Santiago de los Caballeros

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
6:00 am - 4:08 pmORD  Chicago O'Hare Intl-STI Santiago de los Caballeros
8h 08m1 stop Miami
American Airlines Logo
5:08 pm - 8:00 amSTI  Santiago de los Caballeros-ORD Chicago O'Hare Intl
16h 52m1 stop Miami
$426American Airlines
Tue, Nov 10 - Tue, Nov 17
American Airlines Logo
6:00 am - 4:08 pmORD  Chicago O'Hare Intl-STI Santiago de los Caballeros
8h 08m1 stop Miami
American Airlines Logo
5:08 pm - 7:42 amSTI  Santiago de los Caballeros-ORD Chicago O'Hare Intl
16h 34m1 stop Miami
$426American Airlines
Tue, Nov 10 - Wed, Dec 9
American Airlines Logo
6:59 am - 4:08 pmORD  Chicago O'Hare Intl-STI Santiago de los Caballeros
7h 09m1 stop Miami
American Airlines Logo
5:03 pm - 11:30 pmSTI  Santiago de los Caballeros-ORD Chicago O'Hare Intl
8h 27m1 stop Philadelphia
$426American Airlines
Tue, Nov 3 - Tue, Nov 10
Copa Airlines Logo
2:13 pm - 2:54 pmORD  Chicago O'Hare Intl-STI Santiago de los Caballeros
22h 41m1 stop Panama City Tocumen Intl
Copa Airlines Logo
4:01 pm - 12:11 amSTI  Santiago de los Caballeros-ORD Chicago O'Hare Intl
10h 10m1 stop Panama City Tocumen Intl
$428Copa Airlines
Fri, Nov 6 - Mon, Nov 9
Delta Logo
6:10 am - 5:33 pmORD  Chicago O'Hare Intl-STI Santiago de los Caballeros
10h 23m1 stop New York John F Kennedy Intl
Delta Logo
9:25 pm - 9:27 amSTI  Santiago de los Caballeros-ORD Chicago O'Hare Intl
14h 02m1 stop New York John F Kennedy Intl
$430Delta
Wed, Oct 28 - Tue, Nov 10
Delta Logo
5:27 am - 6:33 pmORD  Chicago O'Hare Intl-STI Santiago de los Caballeros
11h 06m2 stops Atlanta Hartsfield-Jackson New York John F Kennedy Intl
Delta Logo
7:00 am - 4:18 pmSTI  Santiago de los Caballeros-ORD Chicago O'Hare Intl
11h 18m2 stops New York John F Kennedy Intl Detroit Metropolitan Wayne County
$435Delta
Tue, Nov 3 - Tue, Nov 10
JetBlue Logo
2:59 pm - 12:57 amORD  Chicago O'Hare Intl-STI Santiago de los Caballeros
7h 58m1 stop Fort Lauderdale
JetBlue Logo
6:01 am - 1:30 pmSTI  Santiago de los Caballeros-ORD Chicago O'Hare Intl
9h 29m1 stop Fort Lauderdale
$440JetBlue
Tue, Dec 1 - Tue, Dec 8
JetBlue Logo
7:00 am - 3:33 pmORD  Chicago O'Hare Intl-STI Santiago de los Caballeros
6h 33m1 stop Fort Lauderdale
JetBlue Logo
4:33 pm - 11:55 pmSTI  Santiago de los Caballeros-ORD Chicago O'Hare Intl
9h 22m1 stop Fort Lauderdale
$462JetBlue
Mon, Nov 2 - Mon, Nov 9
United Airlines Logo
12:59 pm - 11:51 pmORD  Chicago O'Hare Intl-STI Santiago de los Caballeros
8h 52m1 stop Newark
United Airlines Logo
4:00 pm - 12:01 amSTI  Santiago de los Caballeros-ORD Chicago O'Hare Intl
10h 01m1 stop Newark
$495United Airlines
Mon, Nov 23 - Fri, Nov 27
United Airlines Logo
5:00 am - 1:53 pmORD  Chicago O'Hare Intl-STI Santiago de los Caballeros
7h 53m1 stop Newark
United Airlines Logo
4:00 pm - 12:01 amSTI  Santiago de los Caballeros-ORD Chicago O'Hare Intl
10h 01m1 stop Newark
$504United Airlines
Thu, Oct 29 - Mon, Nov 2

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.
Search flight deals

JetBlue flights from Chicago to Santiago de los Caballeros

Our best JetBlue deals on Chicago to Santiago de los Caballeros flight tickets
JetBlue
Nov 2
ORD7:00 amChicago O'Hare Intl
6h 33m
1 stop
STI3:33 pmSantiago de los Caballeros
Nov 9
STI4:33 pmSantiago de los Caballeros
9h 22m
1 stop
ORD11:55 pmChicago O'Hare Intl
$462
JetBlue
Dec 3
ORD2:59 pmChicago O'Hare Intl
7h 58m
1 stop
STI12:57 amSantiago de los Caballeros
Dec 7
STI6:01 amSantiago de los Caballeros
9h 29m
1 stop
ORD1:30 pmChicago O'Hare Intl
$473
JetBlue
Nov 1
ORD7:00 amChicago O'Hare Intl
6h 13m
1 stop
STI3:13 pmSantiago de los Caballeros
Nov 8
STI4:33 pmSantiago de los Caballeros
9h 22m
1 stop
ORD11:55 pmChicago O'Hare Intl
$476

American Airlines flights from Chicago to Santiago de los Caballeros

Our best American Airlines deals on Chicago to Santiago de los Caballeros flight tickets
American Airlines
Nov 10
ORD6:00 amChicago O'Hare Intl
8h 08m
1 stop
STI4:08 pmSantiago de los Caballeros
Dec 9
STI5:08 pmSantiago de los Caballeros
16h 34m
1 stop
ORD7:42 amChicago O'Hare Intl
$426
American Airlines
Nov 10
ORD9:06 pmChicago O'Hare Intl
17h 02m
2 stops
STI4:08 pmSantiago de los Caballeros
Dec 9
STI5:08 pmSantiago de los Caballeros
16h 19m
2 stops
ORD7:27 amChicago O'Hare Intl
$431
American Airlines
Nov 4
ORD7:50 pmChicago O'Hare Intl
15h 36m
1 stop
STI1:26 pmSantiago de los Caballeros
Nov 11
STI5:08 pmSantiago de los Caballeros
17h 52m
2 stops
ORD9:00 amChicago O'Hare Intl
$436

momondo Fare Finder

 
Use the filters below to find and compare flights from Chicago to Santiago de los Caballeros that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoSantiago de los Caballeros

ORD Chicago O'Hare Intl - STI Santiago de los Caballeros

ORDSTI

Chicago O'Hare Intl

Tue 11/10

6:00 am-4:08 pm

1 stop8h 08m

Santiago de los Caballeros

Tue 11/17

5:08 pm-8:00 am

1 stop16h 52m

$426

ChicagoSantiago de los Caballeros

ORD Chicago O'Hare Intl - STI Santiago de los Caballeros

ORDSTI

Chicago O'Hare Intl

Tue 11/10

6:00 am-4:08 pm

1 stop8h 08m

Santiago de los Caballeros

Wed 12/9

5:08 pm-7:42 am

1 stop16h 34m

$426
Quickest round-trip

ChicagoSantiago de los Caballeros

ORD Chicago O'Hare Intl - STI Santiago de los Caballeros

ORDSTI

Chicago O'Hare Intl

Tue 11/3

6:59 am-4:08 pm

1 stop7h 09m

Santiago de los Caballeros

Tue 11/10

5:03 pm-11:30 pm

1 stop8h 27m

$426

ChicagoSantiago de los Caballeros

ORD Chicago O'Hare Intl - STI Santiago de los Caballeros

ORDSTI

Chicago O'Hare Intl

Fri 11/6

2:13 pm-2:54 pm

1 stop22h 41m

Santiago de los Caballeros

Mon 11/9

4:01 pm-12:11 am

1 stop10h 10m

$428

ChicagoSantiago de los Caballeros

ORD Chicago O'Hare Intl - STI Santiago de los Caballeros

ORDSTI

Chicago O'Hare Intl

Wed 10/28

6:10 am-5:33 pm

1 stop10h 23m

Santiago de los Caballeros

Tue 11/10

9:25 pm-9:27 am

1 stop14h 02m

$430

ChicagoSantiago de los Caballeros

ORD Chicago O'Hare Intl - STI Santiago de los Caballeros

ORDSTI

Chicago O'Hare Intl

Tue 11/3

5:27 am-6:33 pm

2 stops11h 06m

Santiago de los Caballeros

Tue 11/10

7:00 am-4:18 pm

2 stops11h 18m

$435

ChicagoSantiago de los Caballeros

ORD Chicago O'Hare Intl - STI Santiago de los Caballeros

ORDSTI

Chicago O'Hare Intl

Tue 12/1

2:59 pm-12:57 am

1 stop7h 58m

Santiago de los Caballeros

Tue 12/8

6:01 am-1:30 pm

1 stop9h 29m

$440

ChicagoSantiago de los Caballeros

ORD Chicago O'Hare Intl - STI Santiago de los Caballeros

ORDSTI

Chicago O'Hare Intl

Mon 11/2

7:00 am-3:33 pm

1 stop6h 33m

Santiago de los Caballeros

Mon 11/9

4:33 pm-11:55 pm

1 stop9h 22m

$462

ChicagoSantiago de los Caballeros

ORD Chicago O'Hare Intl - STI Santiago de los Caballeros

ORDSTI

Chicago O'Hare Intl

Mon 11/23

12:59 pm-11:51 pm

1 stop8h 52m

Santiago de los Caballeros

Fri 11/27

4:00 pm-12:01 am

1 stop10h 01m

$495

ChicagoSantiago de los Caballeros

ORD Chicago O'Hare Intl - STI Santiago de los Caballeros

ORDSTI

Chicago O'Hare Intl

Thu 10/29

5:00 am-1:53 pm

1 stop7h 53m

Santiago de los Caballeros

Mon 11/2

4:00 pm-12:01 am

1 stop10h 01m

$504

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 typical price of a round-trip flight between Chicago and Santiago de los Caballeros?

Prices are currently low for flights on this route.

Typical prices usually range from $566 to $621.
The lowest price recently found on this route was $426.

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 February. Flight prices, which tend to average around $392, 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 February, then flying in March is also cheap. Prices for this month can be found on momondo for an average of $439.

Can stopping save me money on Chicago to Santiago de los Caballeros flights?

You could potentially save up to 19% on your flight if you consider stops on a Chicago to Santiago de los Caballeros flight.

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

$196

Fastest flight time

6h 23m

Direct flights

None
The best one-way flight to Santiago de los Caballeros from Chicago in the past 72 hours is $196. The best round-trip flight deal from Chicago to Santiago de los Caballeros found on momondo in the last 72 hours is $426.
The fastest flight from Chicago to Santiago de los Caballeros takes 6h 23m
There are no direct flights from Chicago to Santiago de los Caballeros. There are no popular flight routes from Chicago to Santiago de los Caballeros.
Search flight deals

Frequently asked questions about flying from Chicago to Santiago de los Caballeros

  • 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. 6h 23m 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
DeltaPriceFrom $239Free CancellationRating
7.8
8,597 reviews
Search Delta flights
JetBluePriceFrom $255Free CancellationRating
7.1
3,036 reviews
Search JetBlue flights
American AirlinesPriceFrom $407Free CancellationRating
7.0
12,082 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.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Thu 10/22
Thu 10/29
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the Dominican Republic