Latest deals
Insights
When to book
FAQs
Price Alerts

Cheap flights from Santiago de los Caballeros to Chicago from $155

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Santiago de los Caballeros to Chicago departing on 1/14. 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

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

Find the cheapest flights from Santiago de los Caballeros to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Spirit Airlines Logo
3:43 am - 11:14 am
STI
-
ORD
9h 31m1 stop
Spirit Airlines Logo
5:15 am - 3:33 pm
ORD
-
STI
8h 18m1 stop
$307Spirit Airlines
Fri, Dec 26 - Sun, Jan 11
Multiple Airlines Logo
6:14 pm - 7:36 pm
STI
-
ORD
27h 22m2 stops
Multiple Airlines Logo
5:15 am - 3:33 pm
ORD
-
STI
8h 18m1 stop
$363Multiple Airlines
Wed, Jan 28 - Wed, Feb 4
Spirit Airlines Logo
3:43 am - 6:39 pm
STI
-
ORD
16h 56m1 stop
Spirit Airlines Logo
8:43 pm - 3:33 pm
ORD
-
STI
16h 50m1 stop
$392Spirit Airlines
Fri, Dec 26 - Sun, Jan 11
Delta Logo
6:38 am - 4:55 pm
STI
-
ORD
12h 17m2 stops
Delta Logo
6:50 am - 8:34 pm
ORD
-
STI
11h 44m2 stops
$394Delta
Wed, Jan 21 - Wed, Feb 4
Spirit Airlines Logo
3:43 am - 6:39 pm
STI
-
ORD
16h 56m1 stop
Spirit Airlines Logo
5:53 pm - 3:33 pm
ORD
-
STI
19h 40m2 stops
$412Spirit Airlines
Fri, Dec 26 - Sun, Jan 11
Multiple Airlines Logo
3:43 am - 12:30 am
STI
-
ORD
22h 47m1 stop
Multiple Airlines Logo
5:57 pm - 3:33 pm
ORD
-
STI
19h 36m2 stops
$415Multiple Airlines
Fri, Dec 26 - Tue, Jan 13
Spirit Airlines Logo
3:43 am - 6:39 pm
STI
-
ORD
16h 56m1 stop
Spirit Airlines Logo
5:53 pm - 3:33 pm
ORD
-
STI
19h 40m3 stops
$420Spirit Airlines
Fri, Dec 26 - Sun, Jan 11
Spirit Airlines Logo
3:43 am - 12:30 am
STI
-
ORD
22h 47m1 stop
Spirit Airlines Logo
4:38 pm - 3:33 pm
ORD
-
STI
20h 55m2 stops
$434Spirit Airlines
Fri, Dec 26 - Sun, Jan 11
Spirit Airlines Logo
3:43 am - 4:00 pm
STI
-
ORD
14h 17m2 stops
Spirit Airlines Logo
4:38 pm - 3:33 pm
ORD
-
STI
20h 55m3 stops
$474Spirit Airlines
Fri, Dec 26 - Sun, Jan 11
Delta Logo
6:00 am - 5:10 pm
STI
-
ORD
12h 10m1 stop
Delta Logo
6:00 am - 12:14 am
ORD
-
STI
17h 14m2 stops
$486Delta
Wed, Apr 8 - Mon, Apr 13

American Airlines flights from Santiago de los Caballeros to Chicago

Our best American Airlines deals on Santiago de los Caballeros to Chicago flight tickets
American Airlines
Mar 17
STI7:00 amSantiago de los Caballeros
13h 45m
2 stops
ORD7:45 pmChicago O'Hare Intl
Mar 25
ORD8:23 amChicago O'Hare Intl
11h 06m
2 stops
STI8:29 pmSantiago de los Caballeros
$446
Find similar
American Airlines
Mar 17
STI7:00 amSantiago de los Caballeros
12h 30m
1 stop
ORD6:30 pmChicago O'Hare Intl
Mar 25
ORD8:41 amChicago O'Hare Intl
10h 48m
1 stop
STI8:29 pmSantiago de los Caballeros
$491
Find similar
American Airlines
Dec 30
STI6:00 amSantiago de los Caballeros
8h 00m
1 stop
ORD12:00 pmChicago O'Hare Intl
Jan 4
ORD7:35 pmChicago O'Hare Intl
16h 49m
1 stop
STI2:24 pmSantiago de los Caballeros
$500
Find similar

Delta flights from Santiago de los Caballeros to Chicago

Our best Delta deals on Santiago de los Caballeros to Chicago flight tickets
Delta
Jan 21
STI6:38 amSantiago de los Caballeros
8h 36m
1 stop
ORD1:14 pmChicago O'Hare Intl
Feb 4
ORD7:00 amChicago O'Hare Intl
11h 34m
1 stop
STI8:34 pmSantiago de los Caballeros
$394
Find similar
Delta
Mar 17
STI7:41 pmSantiago de los Caballeros
15h 19m
1 stop
ORD10:00 amChicago O'Hare Intl
Mar 25
ORD1:37 pmChicago O'Hare Intl
8h 50m
1 stop
STI11:27 pmSantiago de los Caballeros
$415
Find similar
Delta
Apr 8
STI6:00 amSantiago de los Caballeros
12h 10m
1 stop
ORD5:10 pmChicago O'Hare Intl
Apr 13
ORD6:00 amChicago O'Hare Intl
17h 14m
2 stops
STI12:14 amSantiago de los Caballeros
$486
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Santiago de los Caballeros to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated December 15, 2025.
Use the filters below to find and compare flights from Santiago de los Caballeros to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Santiago de los CaballerosChicago

STI - ORD

STIORD

Santiago de los Caballeros

Fri 12/26

3:43 am-11:14 am

1 stop9h 31m

Chicago O'Hare Intl

Sun 1/11

5:15 am-3:33 pm

1 stop8h 18m

$307

Santiago de los CaballerosChicago

STI - ORD

STIORD

Santiago de los Caballeros

Wed 1/28

6:14 pm-7:36 pm

2 stops27h 22m

Chicago O'Hare Intl

Wed 2/4

5:15 am-3:33 pm

1 stop8h 18m

$363

Santiago de los CaballerosChicago

STI - ORD

STIORD

Santiago de los Caballeros

Fri 12/26

3:43 am-6:39 pm

1 stop16h 56m

Chicago O'Hare Intl

Sun 1/11

8:43 pm-3:33 pm

1 stop16h 50m

$392

Santiago de los CaballerosChicago

STI - ORD

STIORD

Santiago de los Caballeros

Wed 1/21

6:38 am-4:55 pm

2 stops12h 17m

Chicago O'Hare Intl

Wed 2/4

6:50 am-8:34 pm

2 stops11h 44m

$394

Santiago de los CaballerosChicago

STI - ORD

STIORD

Santiago de los Caballeros

Fri 12/26

3:43 am-6:39 pm

1 stop16h 56m

Chicago O'Hare Intl

Sun 1/11

5:53 pm-3:33 pm

2 stops19h 40m

$412

Santiago de los CaballerosChicago

STI - ORD

STIORD

Santiago de los Caballeros

Fri 12/26

3:43 am-12:30 am

1 stop22h 47m

Chicago O'Hare Intl

Tue 1/13

5:57 pm-3:33 pm

2 stops19h 36m

$415

Santiago de los CaballerosChicago

STI - ORD

STIORD

Santiago de los Caballeros

Fri 12/26

3:43 am-6:39 pm

1 stop16h 56m

Chicago O'Hare Intl

Sun 1/11

5:53 pm-3:33 pm

3 stops19h 40m

$420

Santiago de los CaballerosChicago

STI - ORD

STIORD

Santiago de los Caballeros

Fri 12/26

3:43 am-12:30 am

1 stop22h 47m

Chicago O'Hare Intl

Sun 1/11

4:38 pm-3:33 pm

2 stops20h 55m

$434

Santiago de los CaballerosChicago

STI - ORD

STIORD

Santiago de los Caballeros

Fri 12/26

3:43 am-4:00 pm

2 stops14h 17m

Chicago O'Hare Intl

Sun 1/11

4:38 pm-3:33 pm

3 stops20h 55m

$474

Santiago de los CaballerosChicago

STI - ORD

STIORD

Santiago de los Caballeros

Wed 4/8

6:00 am-5:10 pm

1 stop12h 10m

Chicago O'Hare Intl

Mon 4/13

6:00 am-12:14 am

2 stops17h 14m

$486

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

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 day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Thursday when prices can be found for as low as $370. This is often the case because there is less demand to fly during this day of the week. When flying out on a Wednesday, the most expensive travel day of the week, you can expect to see flight prices from Santiago de los Caballeros to Chicago for around $637.

When to book flights from Santiago de los Caballeros to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Santiago de los Caballeros to Chicago 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 (STI to CHI) flight deals and tips

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

Fastest flight time

12h 10m

Direct flights

None
The fastest flight from Santiago de los Caballeros to Chicago takes 12h 10m
There are no direct flights from Santiago de los Caballeros to Chicago. There are no popular flight routes from Santiago de los Caballeros to Chicago.
Search flight deals

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

    The distance between Santiago de los Caballeros and Chicago is about 1838.3 mi. Flights usually cover this in 12h 10m, depending on flying conditions and air traffic around both airports.

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

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

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

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, 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.

  • What documentation or ID do you need to fly to Chicago?

    The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Valparaiso
Schererville
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

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

It is quick and easy to find Santiago de los Caballeros to Chicago 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 Chicago that suits you.

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 all potential Santiago de los Caballeros to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

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

Price alerts on flights to Chicago from Santiago de los Caballeros are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

An easier way to manage your Chicago 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
Wed 1/14
Wed 1/21
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport