Latest deals
Insights
When to book
FAQs
Price Alerts

Cheap flights from Santiago de los Caballeros to Chicago from $237

1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Santiago de los Caballeros to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
United Airlines Logo
6:00 am - 10:53 amSTI  Santiago de los Caballeros-ORD Chicago O'Hare Intl
29h 53m1 stop Newark
United Airlines Logo
12:09 pm - 10:52 pmORD  Chicago O'Hare Intl-STI Santiago de los Caballeros
9h 43m1 stop Newark
$495United Airlines
Fri, Oct 16 - Wed, Oct 21
United Airlines Logo
6:00 am - 10:53 amSTI  Santiago de los Caballeros-ORD Chicago O'Hare Intl
29h 53m1 stop Newark
United Airlines Logo
12:09 pm - 10:52 pmORD  Chicago O'Hare Intl-STI Santiago de los Caballeros
9h 43m1 stop Newark
$497United Airlines
Fri, Oct 16 - Wed, Oct 21
Multiple Airlines Logo
11:43 am - 10:39 pmSTI  Santiago de los Caballeros-ORD Chicago O'Hare Intl
11h 56m1 stop Philadelphia
Multiple Airlines Logo
7:00 am - 2:47 pmORD  Chicago O'Hare Intl-STI Santiago de los Caballeros
6h 47m1 stop Fort Lauderdale
$500Multiple Airlines
Sat, Oct 17 - Wed, Oct 21
Multiple Airlines Logo
11:43 am - 10:39 pmSTI  Santiago de los Caballeros-ORD Chicago O'Hare Intl
11h 56m1 stop Philadelphia
Multiple Airlines Logo
7:00 am - 2:47 pmORD  Chicago O'Hare Intl-STI Santiago de los Caballeros
6h 47m1 stop Fort Lauderdale
$505Multiple Airlines
Sat, Oct 17 - Wed, Oct 21
United Airlines Logo
6:00 am - 11:21 pmSTI  Santiago de los Caballeros-ORD Chicago O'Hare Intl
18h 21m1 stop Newark
United Airlines Logo
5:00 am - 10:51 pmORD  Chicago O'Hare Intl-STI Santiago de los Caballeros
16h 51m1 stop Newark
$510United Airlines
Thu, Oct 22 - Mon, Oct 26
Multiple Airlines Logo
3:57 pm - 11:30 pmSTI  Santiago de los Caballeros-ORD Chicago O'Hare Intl
8h 33m1 stop Fort Lauderdale
Multiple Airlines Logo
4:41 pm - 10:28 amORD  Chicago O'Hare Intl-STI Santiago de los Caballeros
16h 47m1 stop Philadelphia
$514Multiple Airlines
Tue, Oct 20 - Fri, Oct 23
United Airlines Logo
6:00 am - 7:42 amSTI  Santiago de los Caballeros-ORD Chicago O'Hare Intl
26h 42m1 stop Newark
United Airlines Logo
9:48 pm - 1:53 pmORD  Chicago O'Hare Intl-STI Santiago de los Caballeros
15h 05m1 stop Newark
$527United Airlines
Thu, Oct 22 - Mon, Oct 26
United Airlines Logo
6:00 am - 11:21 pmSTI  Santiago de los Caballeros-ORD Chicago O'Hare Intl
18h 21m1 stop Newark
United Airlines Logo
5:00 am - 10:51 pmORD  Chicago O'Hare Intl-STI Santiago de los Caballeros
16h 51m1 stop Newark
$533United Airlines
Thu, Oct 22 - Mon, Oct 26
American Airlines Logo
3:12 pm - 7:27 amSTI  Santiago de los Caballeros-ORD Chicago O'Hare Intl
17h 15m2 stops Miami Washington, D.C. Reagan-National
American Airlines Logo
9:00 pm - 1:18 pmORD  Chicago O'Hare Intl-STI Santiago de los Caballeros
15h 18m1 stop Philadelphia
$539American Airlines
Fri, Oct 16 - Wed, Oct 21
American Airlines Logo
3:12 pm - 7:27 amSTI  Santiago de los Caballeros-ORD Chicago O'Hare Intl
17h 15m2 stops Miami Washington, D.C. Reagan-National
American Airlines Logo
5:00 am - 2:12 pmORD  Chicago O'Hare Intl-STI Santiago de los Caballeros
8h 12m2 stops Charlotte Douglas Miami
$539American Airlines
Fri, Oct 16 - Wed, Oct 21

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

United Airlines flights from Santiago de los Caballeros to Chicago O'Hare Intl Airport

Our best United Airlines deals on Santiago de los Caballeros to Chicago O'Hare Intl Airport flight tickets
United Airlines
Oct 16
STI6:00 amSantiago de los Caballeros
29h 53m
1 stop
ORD10:53 amChicago O'Hare Intl
Oct 21
ORD12:09 pmChicago O'Hare Intl
9h 43m
1 stop
STI10:52 pmSantiago de los Caballeros
$495
United Airlines
Oct 16
STI6:00 amSantiago de los Caballeros
29h 53m
1 stop
ORD10:53 amChicago O'Hare Intl
Oct 21
ORD12:09 pmChicago O'Hare Intl
9h 43m
1 stop
STI10:52 pmSantiago de los Caballeros
$497
United Airlines
Oct 22
STI6:00 amSantiago de los Caballeros
18h 21m
1 stop
ORD11:21 pmChicago O'Hare Intl
Oct 26
ORD5:00 amChicago O'Hare Intl
16h 51m
1 stop
STI10:51 pmSantiago de los Caballeros
$510

JetBlue flights from Santiago de los Caballeros to Chicago O'Hare Intl Airport

Our best JetBlue deals on Santiago de los Caballeros to Chicago O'Hare Intl Airport flight tickets
JetBlue
Oct 20
STI6:05 amSantiago de los Caballeros
14h 09m
1 stop
ORD7:14 pmChicago O'Hare Intl
Oct 24
ORD7:00 amChicago O'Hare Intl
6h 47m
1 stop
STI2:47 pmSantiago de los Caballeros
$572
JetBlue
Oct 8
STI7:05 pmSantiago de los Caballeros
15h 19m
1 stop
ORD9:24 amChicago O'Hare Intl
Oct 11
ORD6:10 amChicago O'Hare Intl
10h 23m
1 stop
STI5:33 pmSantiago de los Caballeros
$690
JetBlue
Sep 26
STI3:30 pmSantiago de los Caballeros
8h 38m
1 stop
ORD11:08 pmChicago O'Hare Intl
Sep 30
ORD6:00 amChicago O'Hare Intl
6h 27m
1 stop
STI1:27 pmSantiago de los Caballeros
$787

momondo Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Santiago de los CaballerosChicago

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

STIORD

Santiago de los Caballeros

Fri 10/16

6:00 am-10:53 am

1 stop29h 53m

Chicago O'Hare Intl

Wed 10/21

12:09 pm-10:52 pm

1 stop9h 43m

$495

Santiago de los CaballerosChicago

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

STIORD

Santiago de los Caballeros

Fri 10/16

6:00 am-10:53 am

1 stop29h 53m

Chicago O'Hare Intl

Wed 10/21

12:09 pm-10:52 pm

1 stop9h 43m

$497
Quickest round-trip

Santiago de los CaballerosChicago

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

STIORD

Santiago de los Caballeros

Sat 10/17

11:43 am-10:39 pm

1 stop11h 56m

Chicago O'Hare Intl

Wed 10/21

7:00 am-2:47 pm

1 stop6h 47m

$500

Santiago de los CaballerosChicago

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

STIORD

Santiago de los Caballeros

Sat 10/17

11:43 am-10:39 pm

1 stop11h 56m

Chicago O'Hare Intl

Wed 10/21

7:00 am-2:47 pm

1 stop6h 47m

$505

Santiago de los CaballerosChicago

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

STIORD

Santiago de los Caballeros

Thu 10/22

6:00 am-11:21 pm

1 stop18h 21m

Chicago O'Hare Intl

Mon 10/26

5:00 am-10:51 pm

1 stop16h 51m

$510

Santiago de los CaballerosChicago

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

STIORD

Santiago de los Caballeros

Tue 10/20

3:57 pm-11:30 pm

1 stop8h 33m

Chicago O'Hare Intl

Fri 10/23

4:41 pm-10:28 am

1 stop16h 47m

$514

Santiago de los CaballerosChicago

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

STIORD

Santiago de los Caballeros

Thu 10/22

6:00 am-7:42 am

1 stop26h 42m

Chicago O'Hare Intl

Mon 10/26

9:48 pm-1:53 pm

1 stop15h 05m

$527

Santiago de los CaballerosChicago

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

STIORD

Santiago de los Caballeros

Thu 10/22

6:00 am-11:21 pm

1 stop18h 21m

Chicago O'Hare Intl

Mon 10/26

5:00 am-10:51 pm

1 stop16h 51m

$533

Santiago de los CaballerosChicago

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

STIORD

Santiago de los Caballeros

Fri 10/16

3:12 pm-7:27 am

2 stops17h 15m

Chicago O'Hare Intl

Wed 10/21

9:00 pm-1:18 pm

1 stop15h 18m

$539

Santiago de los CaballerosChicago

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

STIORD

Santiago de los Caballeros

Fri 10/16

3:12 pm-7:27 am

2 stops17h 15m

Chicago O'Hare Intl

Wed 10/21

5:00 am-2:12 pm

2 stops8h 12m

$539

Flights are sorted by cheapest round-trip flights first.

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

See travel insights to Chicago from

How to get the cheapest flight ticket from Santiago de los Caballeros to Chicago O'Hare Intl Airport

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 Chicago O'Hare Intl Airport?

The month of March is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Santiago de los Caballeros averaging around $224.

How have Santiago de los Caballeros to Chicago O'Hare Intl Airport flight prices changed over time?

As of September 2026, prices for Santiago de los Caballeros to Chicago O'Hare Intl Airport flights are approximately 10% cheaper when compared to flights at the same time last year.

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

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

Cheap Santiago de los Caballeros to Chicago O'Hare Intl Airport (STI to ORD) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Santiago de los Caballeros to Chicago O'Hare Intl Airport

Best Price Found

$237

Fastest flight time

26h 42m

Direct flights

None
The best one-way flight to Chicago O'Hare Intl Airport from Santiago de los Caballeros in the past 72 hours is $237. The best round-trip flight deal from Santiago de los Caballeros to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $495.
The fastest flight from Santiago de los Caballeros to Chicago O'Hare Intl Airport takes 26h 42m
There are no direct flights from Santiago de los Caballeros to Chicago O'Hare Intl Airport. There are no popular flight routes from Santiago de los Caballeros to Chicago O'Hare Intl Airport.
Search flight deals

Frequently asked questions about flying from Santiago de los Caballeros to Chicago O'Hare Intl Airport

  • How far is Santiago de los Caballeros to Chicago O'Hare Intl by plane?

    The distance between Santiago de los Caballeros and Chicago O'Hare Intl is about 1852.8 mi. A reasonable flight in good conditions will take 26h 42m.

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

    Prices for flights from Santiago de los Caballeros Airport to Chicago O'Hare Intl Airport are refreshed on a daily basis.

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

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Santiago de los Caballeros Airport to Chicago O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The required travel and health documents for your Chicago O'Hare Intl Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago O'Hare Intl Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lake Geneva
Schaumburg
Merrillville
Rockford
South Haven
Rosemont
Gurnee
Oak Brook
Orland Park
Joliet
Naperville
New Buffalo
Kenosha
Hammond
Aurora
Racine
Elgin
Janesville
Evanston
Skokie

Why use momondo?

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

Finding the right flight to Chicago from Santiago de los Caballeros is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

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

Yes. All flights to Chicago from Santiago de los Caballeros on momondo can be compared and filtered by various policies on offer, including flexible booking.

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

Once you have performed a search for Santiago de los Caballeros to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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

Yes momondo offers price alerts on flights to Chicago from Santiago de los Caballeros. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

An easier way to manage your Chicago O'Hare Intl Airport 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 10/15
Thu 10/22
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago