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

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 5/23. 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

Enter your travel dates to find the best prices.
Multiple Airlines Logo
3:52 pm - 11:59 pm
STI
-
ORD
9h 07m
1 stop
Multiple Airlines Logo
8:00 pm - 9:54 am
ORD
-
STI
12h 54m
1 stop
$458Multiple Airlines
Fri, Jun 19 - Sat, Jun 20
Spirit Airlines Logo
3:17 pm - 11:15 pm
STI
-
ORD
8h 58m
1 stop
Spirit Airlines Logo
5:05 am - 2:12 pm
ORD
-
STI
8h 07m
1 stop
$472Spirit Airlines
Sat, May 30 - Sat, Jun 6
Multiple Airlines Logo
4:20 pm - 11:59 pm
STI
-
ORD
8h 39m
1 stop
Multiple Airlines Logo
8:00 pm - 9:54 am
ORD
-
STI
12h 54m
1 stop
$478Multiple Airlines
Fri, Jun 19 - Sat, Jun 20
Spirit Airlines Logo
3:52 pm - 11:59 pm
STI
-
ORD
9h 07m
1 stop
Spirit Airlines Logo
5:10 am - 3:15 pm
ORD
-
STI
9h 05m
1 stop
$505Spirit Airlines
Sat, Jul 4 - Mon, Jul 27
Delta Logo
8:59 pm - 12:20 pm
STI
-
ORD
16h 21m
1 stop
Delta Logo
10:00 am - 1:55 am
ORD
-
STI
14h 55m
1 stop
$524Delta
Fri, Jul 3 - Tue, Jul 28
Delta Logo
6:00 am - 5:11 pm
STI
-
ORD
12h 11m
1 stop
Delta Logo
10:00 am - 1:55 am
ORD
-
STI
14h 55m
1 stop
$529Delta
Wed, Jul 1 - Tue, Jul 28
American Airlines Logo
3:44 pm - 11:30 pm
STI
-
ORD
8h 46m
1 stop
American Airlines Logo
10:00 am - 9:28 pm
ORD
-
STI
10h 28m
1 stop
$530American Airlines
Thu, Jul 2 - Wed, Jul 29
Multiple Airlines Logo
5:01 am - 10:06 am
STI
-
ORD
30h 05m
1 stop
Multiple Airlines Logo
8:00 pm - 9:54 am
ORD
-
STI
12h 54m
1 stop
$531Multiple Airlines
Mon, Jun 15 - Sat, Jun 20
American Airlines Logo
3:44 pm - 11:30 pm
STI
-
ORD
8h 46m
1 stop
American Airlines Logo
8:30 am - 9:28 pm
ORD
-
STI
11h 58m
2 stops
$535American Airlines
Thu, Jul 2 - Wed, Jul 29
Multiple Airlines Logo
6:30 pm - 8:45 am
STI
-
ORD
15h 15m
1 stop
Multiple Airlines Logo
8:00 pm - 9:54 am
ORD
-
STI
12h 54m
1 stop
$537Multiple Airlines
Fri, Jun 12 - Sat, Jun 20

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

Our best Spirit Airlines deals on Santiago de los Caballeros to Chicago O'Hare Intl Airport flight tickets
Spirit Airlines
May 30
STI3:17 pmSantiago de los Caballeros
8h 58m
1 stop
ORD11:15 pmChicago O'Hare Intl
Jun 6
ORD5:05 amChicago O'Hare Intl
8h 07m
1 stop
STI2:12 pmSantiago de los Caballeros
$472
Spirit Airlines
Jul 4
STI3:52 pmSantiago de los Caballeros
9h 07m
1 stop
ORD11:59 pmChicago O'Hare Intl
Jul 27
ORD5:10 amChicago O'Hare Intl
9h 05m
1 stop
STI3:15 pmSantiago de los Caballeros
$505
Spirit Airlines
Jul 4
STI3:52 pmSantiago de los Caballeros
18h 30m
1 stop
ORD9:22 amChicago O'Hare Intl
Jul 27
ORD5:10 amChicago O'Hare Intl
9h 05m
1 stop
STI3:15 pmSantiago de los Caballeros
$573

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

Our best American Airlines deals on Santiago de los Caballeros to Chicago O'Hare Intl Airport flight tickets
American Airlines
Jul 2
STI3:44 pmSantiago de los Caballeros
8h 46m
1 stop
ORD11:30 pmChicago O'Hare Intl
Jul 29
ORD10:00 amChicago O'Hare Intl
10h 28m
1 stop
STI9:28 pmSantiago de los Caballeros
$530
American Airlines
Jul 2
STI3:44 pmSantiago de los Caballeros
8h 46m
1 stop
ORD11:30 pmChicago O'Hare Intl
Jul 29
ORD8:30 amChicago O'Hare Intl
11h 58m
2 stops
STI9:28 pmSantiago de los Caballeros
$535
American Airlines
May 30
STI7:03 amSantiago de los Caballeros
11h 24m
2 stops
ORD5:27 pmChicago O'Hare Intl
Jun 6
ORD8:29 amChicago O'Hare Intl
11h 43m
2 stops
STI9:12 pmSantiago de los Caballeros
$580

momondo Fare Finder

 
Customize your flight search to find flights from Santiago de los Caballeros to Chicago O'Hare Intl Airport 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 May 3, 2026.
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 - ORD

STIORD

Santiago de los Caballeros

Fri 6/19

3:52 pm-11:59 pm

1 stop9h 07m

Chicago O'Hare Intl

Sat 6/20

8:00 pm-9:54 am

1 stop12h 54m

$458
Quickest round-trip

Santiago de los CaballerosChicago

STI - ORD

STIORD

Santiago de los Caballeros

Sat 5/30

3:17 pm-11:15 pm

1 stop8h 58m

Chicago O'Hare Intl

Sat 6/6

5:05 am-2:12 pm

1 stop8h 07m

$472

Santiago de los CaballerosChicago

STI - ORD

STIORD

Santiago de los Caballeros

Fri 6/19

4:20 pm-11:59 pm

1 stop8h 39m

Chicago O'Hare Intl

Sat 6/20

8:00 pm-9:54 am

1 stop12h 54m

$478

Santiago de los CaballerosChicago

STI - ORD

STIORD

Santiago de los Caballeros

Sat 7/4

3:52 pm-11:59 pm

1 stop9h 07m

Chicago O'Hare Intl

Mon 7/27

5:10 am-3:15 pm

1 stop9h 05m

$505

Santiago de los CaballerosChicago

STI - ORD

STIORD

Santiago de los Caballeros

Fri 7/3

8:59 pm-12:20 pm

1 stop16h 21m

Chicago O'Hare Intl

Tue 7/28

10:00 am-1:55 am

1 stop14h 55m

$524

Santiago de los CaballerosChicago

STI - ORD

STIORD

Santiago de los Caballeros

Wed 7/1

6:00 am-5:11 pm

1 stop12h 11m

Chicago O'Hare Intl

Tue 7/28

10:00 am-1:55 am

1 stop14h 55m

$529

Santiago de los CaballerosChicago

STI - ORD

STIORD

Santiago de los Caballeros

Thu 7/2

3:44 pm-11:30 pm

1 stop8h 46m

Chicago O'Hare Intl

Wed 7/29

10:00 am-9:28 pm

1 stop10h 28m

$530

Santiago de los CaballerosChicago

STI - ORD

STIORD

Santiago de los Caballeros

Mon 6/15

5:01 am-10:06 am

1 stop30h 05m

Chicago O'Hare Intl

Sat 6/20

8:00 pm-9:54 am

1 stop12h 54m

$531

Santiago de los CaballerosChicago

STI - ORD

STIORD

Santiago de los Caballeros

Thu 7/2

3:44 pm-11:30 pm

1 stop8h 46m

Chicago O'Hare Intl

Wed 7/29

8:30 am-9:28 pm

2 stops11h 58m

$535

Santiago de los CaballerosChicago

STI - ORD

STIORD

Santiago de los Caballeros

Fri 6/12

6:30 pm-8:45 am

1 stop15h 15m

Chicago O'Hare Intl

Sat 6/20

8:00 pm-9:54 am

1 stop12h 54m

$537

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 typical price of a round-trip flight between Santiago de los Caballeros and Chicago O'Hare Intl Airport?

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 May 2026, prices for Santiago de los Caballeros to Chicago O'Hare Intl Airport flights are approximately 10% more expensive 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

Fastest flight time

8h 00m

Direct flights

None
The fastest flight from Santiago de los Caballeros to Chicago O'Hare Intl Airport takes 8h 00m
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 8h 00m.

  • 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
South Haven
Rockford
Merrillville
Gurnee
Rosemont
Naperville
New Buffalo
Orland Park
Oak Brook
Kenosha
Joliet
Aurora
Janesville
Racine
Hammond
Tinley Park
Elgin
Evanston

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.

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