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Cheap flights from Santiago de los Caballeros to Chicago from $164

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 9/13. 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

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Find the cheapest flights from Santiago de los Caballeros to Chicago

Cheap round-trip flights

Spirit Airlines Logo
10:20 am - 11:59 pmSTI-ORD
14h 39m1 stop
Spirit Airlines Logo
6:44 pm - 11:05 amORD-STI
15h 21m1 stop
$296Spirit Airlines
Find Deal
Tue, Sep 2 - Mon, Sep 15
Spirit Airlines Logo
12:10 pm - 10:48 pmSTI-ORD
11h 38m1 stop
Spirit Airlines Logo
7:11 pm - 11:05 amORD-STI
14h 54m1 stop
$300Spirit Airlines
Find Deal
Wed, Oct 1 - Wed, Oct 15
Spirit Airlines Logo
12:10 pm - 10:48 pmSTI-ORD
11h 38m1 stop
Spirit Airlines Logo
6:44 pm - 11:05 amORD-STI
15h 21m1 stop
$322Spirit Airlines
Find Deal
Mon, Sep 15 - Tue, Sep 30
Delta Logo
6:00 am - 9:24 pmSTI-ORD
16h 24m2 stops
Delta Logo
5:20 am - 6:38 pmORD-STI
12h 18m2 stops
$391Delta
Find Deal
Fri, Oct 24 - Wed, Oct 29
American Airlines Logo
7:00 am - 5:11 pmSTI-ORD
11h 11m2 stops
American Airlines Logo
7:03 pm - 12:27 pmORD-STI
16h 24m2 stops
$423American Airlines
Find Deal
Thu, Aug 28 - Thu, Sep 4
American Airlines Logo
1:29 pm - 7:47 amSTI-ORD
19h 18m2 stops
American Airlines Logo
5:00 am - 12:27 pmORD-STI
6h 27m1 stop
$434American Airlines
Find Deal
Mon, Sep 15 - Tue, Sep 30
JetBlue Logo
3:20 am - 12:10 pmSTI-ORD
9h 50m1 stop
JetBlue Logo
11:30 am - 3:04 amORD-STI
14h 34m1 stop
$561JetBlue
Find Deal
Thu, Oct 23 - Wed, Oct 29
United Airlines Logo
4:00 pm - 11:34 pmSTI-ORD
9h 34m1 stop
United Airlines Logo
11:59 pm - 11:46 amORD-STI
9h 47m1 stop
$563United Airlines
Find Deal
Wed, Nov 26 - Sun, Nov 30
JetBlue Logo
3:08 am - 3:32 pmSTI-ORD
13h 24m1 stop
JetBlue Logo
6:45 am - 6:04 pmORD-STI
10h 19m1 stop
$748JetBlue
Find Deal
Mon, Sep 1 - Mon, Sep 15
United Airlines Logo
6:00 am - 1:08 pmSTI-ORD
8h 08m1 stop
United Airlines Logo
4:50 pm - 1:46 amORD-STI
7h 56m1 stop
$1,175United Airlines
Find Deal
Wed, Oct 8 - Wed, Oct 15

United Airlines flights from Santiago de los Caballeros to Chicago

Our best United Airlines deals on Santiago de los Caballeros to Chicago flight tickets
United Airlines
Nov 26
STI4:00 pmSantiago de los Caballeros
9h 34m
1 stop
ORD11:34 pmChicago O'Hare Intl
Nov 30
ORD11:59 pmChicago O'Hare Intl
9h 47m
1 stop
STI11:46 amSantiago de los Caballeros
$563
Find similar
United Airlines
Oct 8
STI6:00 amSantiago de los Caballeros
8h 08m
1 stop
ORD1:08 pmChicago O'Hare Intl
Oct 15
ORD4:50 pmChicago O'Hare Intl
7h 56m
1 stop
STI1:46 amSantiago de los Caballeros
$1,175
Find similar
United Airlines
Oct 8
STI6:00 amSantiago de los Caballeros
9h 55m
1 stop
ORD2:55 pmChicago O'Hare Intl
Oct 15
ORD4:50 pmChicago O'Hare Intl
7h 56m
1 stop
STI1:46 amSantiago de los Caballeros
$1,196
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
Aug 28
STI7:00 amSantiago de los Caballeros
11h 11m
2 stops
ORD5:11 pmChicago O'Hare Intl
Sep 4
ORD7:03 pmChicago O'Hare Intl
16h 24m
2 stops
STI12:27 pmSantiago de los Caballeros
$423
Find similar
American Airlines
Sep 15
STI1:29 pmSantiago de los Caballeros
19h 18m
2 stops
ORD7:47 amChicago O'Hare Intl
Sep 30
ORD5:00 amChicago O'Hare Intl
6h 27m
1 stop
STI12:27 pmSantiago de los Caballeros
$434
Find similar
American Airlines
Sep 15
STI1:29 pmSantiago de los Caballeros
19h 18m
2 stops
ORD7:47 amChicago O'Hare Intl
Sep 30
ORD5:00 amChicago O'Hare Intl
6h 27m
1 stop
STI12:27 pmSantiago de los Caballeros
$436
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 July 31, 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

Tue 9/2

10:20 am-11:59 pm

1 stop14h 39m

Chicago O'Hare Intl

Mon 9/15

6:44 pm-11:05 am

1 stop15h 21m

$296

Santiago de los CaballerosChicago

STI - ORD

STIORD

Santiago de los Caballeros

Wed 10/1

12:10 pm-10:48 pm

1 stop11h 38m

Chicago O'Hare Intl

Wed 10/15

7:11 pm-11:05 am

1 stop14h 54m

$300

Santiago de los CaballerosChicago

STI - ORD

STIORD

Santiago de los Caballeros

Mon 9/15

12:10 pm-10:48 pm

1 stop11h 38m

Chicago O'Hare Intl

Tue 9/30

6:44 pm-11:05 am

1 stop15h 21m

$322

Santiago de los CaballerosChicago

STI - ORD

STIORD

Santiago de los Caballeros

Fri 10/24

6:00 am-9:24 pm

2 stops16h 24m

Chicago O'Hare Intl

Wed 10/29

5:20 am-6:38 pm

2 stops12h 18m

$391

Santiago de los CaballerosChicago

STI - ORD

STIORD

Santiago de los Caballeros

Thu 8/28

7:00 am-5:11 pm

2 stops11h 11m

Chicago O'Hare Intl

Thu 9/4

7:03 pm-12:27 pm

2 stops16h 24m

$423

Santiago de los CaballerosChicago

STI - ORD

STIORD

Santiago de los Caballeros

Mon 9/15

1:29 pm-7:47 am

2 stops19h 18m

Chicago O'Hare Intl

Tue 9/30

5:00 am-12:27 pm

1 stop6h 27m

$434

Santiago de los CaballerosChicago

STI - ORD

STIORD

Santiago de los Caballeros

Thu 10/23

3:20 am-12:10 pm

1 stop9h 50m

Chicago O'Hare Intl

Wed 10/29

11:30 am-3:04 am

1 stop14h 34m

$561

Santiago de los CaballerosChicago

STI - ORD

STIORD

Santiago de los Caballeros

Wed 11/26

4:00 pm-11:34 pm

1 stop9h 34m

Chicago O'Hare Intl

Sun 11/30

11:59 pm-11:46 am

1 stop9h 47m

$563

Santiago de los CaballerosChicago

STI - ORD

STIORD

Santiago de los Caballeros

Mon 9/1

3:08 am-3:32 pm

1 stop13h 24m

Chicago O'Hare Intl

Mon 9/15

6:45 am-6:04 pm

1 stop10h 19m

$748

Santiago de los CaballerosChicago

STI - ORD

STIORD

Santiago de los Caballeros

Wed 10/8

6:00 am-1:08 pm

1 stop8h 08m

Chicago O'Hare Intl

Wed 10/15

4:50 pm-1:46 am

1 stop7h 56m

$1,175

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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

Best Price Found

$164

Fastest flight time

8h 08m

Direct flights

None

Airports in Chicago

1 airport
The best one-way flight to Chicago from Santiago de los Caballeros in the past 72 hours is $164. The best round-trip flight deal from Santiago de los Caballeros to Chicago found on momondo in the last 72 hours is $296.
The fastest flight from Santiago de los Caballeros to Chicago takes 8h 08m
There are no direct flights from Santiago de los Caballeros to Chicago. Popular non-direct route for this connection is Santiago de los Caballeros Airport - Chicago O'Hare Intl Airport.
There is 1 airport near Chicago: Chicago O'Hare Intl (ORD)
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  • 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 8h 08m, 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 many operators does momondo search for flights from Santiago de los Caballeros Airport to Chicago?

  • 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.

Best airlines flying from Santiago de los Caballeros to Chicago

Compare and see reviews for airlines that fly from Santiago de los Caballeros to Chicago with momondo
Airline
Rating
Free Cancellation
Price
United AirlinesPriceFrom $502Free CancellationRating
7.4
8,900 reviews
Search United Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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Porter
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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.

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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