Latest deals
Insights
When to book
FAQs
Price Alerts

Cheap flights from Santiago de los Caballeros to Chicago from $177

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 1/29. 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 - 11:08 amSTI-ORD
9h 25m1 stop
Spirit Airlines Logo
3:26 pm - 2:42 amORD-STI
9h 16m1 stop
$337Spirit Airlines
Find Deal
Wed, Dec 10 - Sun, Dec 14
Multiple Airlines Logo
3:43 am - 1:57 pmSTI-ORD
12h 14m1 stop
Multiple Airlines Logo
8:45 am - 2:42 amORD-STI
15h 57m2 stops
$385Multiple Airlines
Find Deal
Wed, Dec 10 - Sun, Dec 14
Spirit Airlines Logo
6:18 pm - 11:42 pmSTI-ORD
7h 24m1 stop
Spirit Airlines Logo
8:41 am - 5:06 pmORD-STI
6h 25m1 stop
$389Spirit Airlines
Find Deal
Fri, Feb 20 - Fri, Feb 27
Spirit Airlines Logo
1:17 pm - 11:13 pmSTI-ORD
11h 56m1 stop
Spirit Airlines Logo
3:26 pm - 2:42 amORD-STI
9h 16m1 stop
$394Spirit Airlines
Find Deal
Tue, Nov 25 - Fri, Dec 5
American Airlines Logo
4:35 pm - 12:37 amSTI-ORD
10h 02m1 stop
American Airlines Logo
7:00 am - 10:56 pmORD-STI
13h 56m1 stop
$410American Airlines
Find Deal
Thu, Nov 20 - Sun, Nov 30
Delta Logo
6:00 am - 9:35 pmSTI-ORD
16h 35m1 stop
Delta Logo
11:19 am - 12:14 amORD-STI
11h 55m2 stops
$415Delta
Find Deal
Wed, Apr 8 - Mon, Apr 13
American Airlines Logo
8:00 am - 7:40 pmSTI-ORD
13h 40m2 stops
American Airlines Logo
5:26 pm - 1:32 pmORD-STI
18h 06m1 stop
$427American Airlines
Find Deal
Wed, Feb 18 - Sat, Feb 21
JetBlue Logo
4:35 am - 11:10 pmSTI-ORD
20h 35m1 stop
JetBlue Logo
6:04 am - 8:39 pmORD-STI
12h 35m1 stop
$477JetBlue
Find Deal
Tue, Feb 17 - Sat, Feb 21
Delta Logo
6:00 am - 9:14 pmSTI-ORD
16h 14m2 stops
Delta Logo
10:35 am - 12:14 amORD-STI
12h 39m2 stops
$539Delta
Find Deal
Wed, Apr 8 - Mon, Apr 13
JetBlue Logo
4:35 am - 11:10 pmSTI-ORD
20h 35m1 stop
JetBlue Logo
7:00 am - 8:39 pmORD-STI
11h 39m1 stop
$541JetBlue
Find Deal
Thu, Feb 19 - Fri, Feb 27

Delta flights from Santiago de los Caballeros to Chicago

Our best Delta deals on Santiago de los Caballeros to Chicago flight tickets
Delta
Apr 8
STI6:00 amSantiago de los Caballeros
16h 35m
1 stop
ORD9:35 pmChicago O'Hare Intl
Apr 13
ORD11:19 amChicago O'Hare Intl
11h 55m
2 stops
STI12:14 amSantiago de los Caballeros
$415
Find similar
Delta
Apr 8
STI6:00 amSantiago de los Caballeros
16h 14m
2 stops
ORD9:14 pmChicago O'Hare Intl
Apr 13
ORD10:35 amChicago O'Hare Intl
12h 39m
2 stops
STI12:14 amSantiago de los Caballeros
$539
Find similar

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
Nov 20
STI4:35 pmSantiago de los Caballeros
10h 02m
1 stop
ORD12:37 amChicago O'Hare Intl
Nov 30
ORD7:00 amChicago O'Hare Intl
13h 56m
1 stop
STI10:56 pmSantiago de los Caballeros
$410
Find similar
American Airlines
Feb 18
STI8:00 amSantiago de los Caballeros
13h 40m
2 stops
ORD7:40 pmChicago O'Hare Intl
Feb 21
ORD5:26 pmChicago O'Hare Intl
18h 06m
1 stop
STI1:32 pmSantiago de los Caballeros
$427
Find similar
American Airlines
Jan 16
STI6:00 amSantiago de los Caballeros
8h 11m
1 stop
ORD12:11 pmChicago O'Hare Intl
Jan 23
ORD6:05 amChicago O'Hare Intl
13h 41m
2 stops
STI9:46 pmSantiago de los Caballeros
$514
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 October 30, 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

Wed 12/10

3:43 am-11:08 am

1 stop9h 25m

Chicago O'Hare Intl

Sun 12/14

3:26 pm-2:42 am

1 stop9h 16m

$337

Santiago de los CaballerosChicago

STI - ORD

STIORD

Santiago de los Caballeros

Wed 12/10

3:43 am-1:57 pm

1 stop12h 14m

Chicago O'Hare Intl

Sun 12/14

8:45 am-2:42 am

2 stops15h 57m

$385

Santiago de los CaballerosChicago

STI - ORD

STIORD

Santiago de los Caballeros

Fri 2/20

6:18 pm-11:42 pm

1 stop7h 24m

Chicago O'Hare Intl

Fri 2/27

8:41 am-5:06 pm

1 stop6h 25m

$389

Santiago de los CaballerosChicago

STI - ORD

STIORD

Santiago de los Caballeros

Tue 11/25

1:17 pm-11:13 pm

1 stop11h 56m

Chicago O'Hare Intl

Fri 12/5

3:26 pm-2:42 am

1 stop9h 16m

$394

Santiago de los CaballerosChicago

STI - ORD

STIORD

Santiago de los Caballeros

Thu 11/20

4:35 pm-12:37 am

1 stop10h 02m

Chicago O'Hare Intl

Sun 11/30

7:00 am-10:56 pm

1 stop13h 56m

$410

Santiago de los CaballerosChicago

STI - ORD

STIORD

Santiago de los Caballeros

Wed 4/8

6:00 am-9:35 pm

1 stop16h 35m

Chicago O'Hare Intl

Mon 4/13

11:19 am-12:14 am

2 stops11h 55m

$415

Santiago de los CaballerosChicago

STI - ORD

STIORD

Santiago de los Caballeros

Wed 2/18

8:00 am-7:40 pm

2 stops13h 40m

Chicago O'Hare Intl

Sat 2/21

5:26 pm-1:32 pm

1 stop18h 06m

$427

Santiago de los CaballerosChicago

STI - ORD

STIORD

Santiago de los Caballeros

Tue 2/17

4:35 am-11:10 pm

1 stop20h 35m

Chicago O'Hare Intl

Sat 2/21

6:04 am-8:39 pm

1 stop12h 35m

$477

Santiago de los CaballerosChicago

STI - ORD

STIORD

Santiago de los Caballeros

Wed 4/8

6:00 am-9:14 pm

2 stops16h 14m

Chicago O'Hare Intl

Mon 4/13

10:35 am-12:14 am

2 stops12h 39m

$539

Santiago de los CaballerosChicago

STI - ORD

STIORD

Santiago de los Caballeros

Thu 2/19

4:35 am-11:10 pm

1 stop20h 35m

Chicago O'Hare Intl

Fri 2/27

7:00 am-8:39 pm

1 stop11h 39m

$541

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

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

Direct flights

None
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 7h 24m, 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
Schererville
Valparaiso
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
Sat 11/29
Sat 12/6
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