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Cheap flights from Santiago de los Caballeros to Chicago from $288

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 9/16. 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
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.
JetBlue Logo
3:30 pm - 11:08 pm
STI
-
ORD
8h 38m
1 stop
JetBlue Logo
6:00 am - 1:27 pm
ORD
-
STI
6h 27m
1 stop
$467JetBlue
Thu, Sep 17 - Mon, Sep 21
JetBlue Logo
4:54 pm - 11:44 pm
STI
-
ORD
7h 50m
1 stop
JetBlue Logo
6:00 am - 1:27 pm
ORD
-
STI
6h 27m
1 stop
$484JetBlue
Sun, Sep 6 - Sun, Sep 13
JetBlue Logo
8:13 am - 11:44 pm
STI
-
ORD
16h 31m
1 stop
JetBlue Logo
10:59 am - 8:28 pm
ORD
-
STI
8h 29m
1 stop
$596JetBlue
Wed, Sep 2 - Mon, Sep 14
JetBlue Logo
6:01 am - 1:20 pm
STI
-
ORD
9h 19m
1 stop
JetBlue Logo
2:15 pm - 1:51 am
ORD
-
STI
9h 36m
1 stop
$621JetBlue
Thu, Nov 12 - Sat, Nov 14
American Airlines Logo
3:16 pm - 9:28 am
STI
-
ORD
19h 12m
1 stop
American Airlines Logo
2:38 pm - 4:08 pm
ORD
-
STI
23h 30m
1 stop
$623American Airlines
Wed, Oct 28 - Mon, Nov 2
American Airlines Logo
3:16 pm - 7:27 am
STI
-
ORD
17h 11m
2 stops
American Airlines Logo
9:06 pm - 4:08 pm
ORD
-
STI
17h 02m
2 stops
$628American Airlines
Wed, Oct 28 - Mon, Nov 2
American Airlines Logo
3:16 pm - 7:27 am
STI
-
ORD
17h 11m
2 stops
American Airlines Logo
3:21 pm - 4:03 pm
ORD
-
STI
22h 42m
1 stop
$628American Airlines
Wed, Oct 28 - Mon, Nov 2
United Airlines Logo
6:00 am - 9:13 am
STI
-
ORD
28h 13m
1 stop
United Airlines Logo
9:35 pm - 10:52 pm
ORD
-
STI
24h 17m
1 stop
$632United Airlines
Mon, Sep 14 - Mon, Sep 21
JetBlue Logo
3:30 pm - 11:08 pm
STI
-
ORD
8h 38m
1 stop
JetBlue Logo
6:00 am - 1:27 pm
ORD
-
STI
6h 27m
1 stop
$649JetBlue
Thu, Sep 17 - Mon, Sep 21
JetBlue Logo
3:49 pm - 11:08 pm
STI
-
ORD
8h 19m
1 stop
JetBlue Logo
6:00 am - 1:27 pm
ORD
-
STI
6h 27m
1 stop
$653JetBlue
Wed, Sep 9 - Wed, Sep 16

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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
Sep 17
STI3:30 pmSantiago de los Caballeros
8h 38m
1 stop
ORD11:08 pmChicago O'Hare Intl
Sep 21
ORD6:00 amChicago O'Hare Intl
6h 27m
1 stop
STI1:27 pmSantiago de los Caballeros
$467
JetBlue
Sep 6
STI4:54 pmSantiago de los Caballeros
7h 50m
1 stop
ORD11:44 pmChicago O'Hare Intl
Sep 13
ORD6:00 amChicago O'Hare Intl
6h 27m
1 stop
STI1:27 pmSantiago de los Caballeros
$484
JetBlue
Sep 2
STI8:13 amSantiago de los Caballeros
16h 31m
1 stop
ORD11:44 pmChicago O'Hare Intl
Sep 14
ORD10:59 amChicago O'Hare Intl
8h 29m
1 stop
STI8:28 pmSantiago de los Caballeros
$596

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
Oct 28
STI3:16 pmSantiago de los Caballeros
19h 12m
1 stop
ORD9:28 amChicago O'Hare Intl
Nov 2
ORD2:38 pmChicago O'Hare Intl
23h 30m
1 stop
STI4:08 pmSantiago de los Caballeros
$623
American Airlines
Oct 28
STI3:16 pmSantiago de los Caballeros
17h 11m
2 stops
ORD7:27 amChicago O'Hare Intl
Nov 2
ORD3:21 pmChicago O'Hare Intl
22h 42m
1 stop
STI4:03 pmSantiago de los Caballeros
$628
American Airlines
Oct 28
STI3:16 pmSantiago de los Caballeros
17h 11m
2 stops
ORD7:27 amChicago O'Hare Intl
Nov 1
ORD9:06 pmChicago O'Hare Intl
14h 19m
2 stops
STI1:25 pmSantiago de los Caballeros
$683

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 August 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

Thu 9/17

3:30 pm-11:08 pm

1 stop8h 38m

Chicago O'Hare Intl

Mon 9/21

6:00 am-1:27 pm

1 stop6h 27m

$467
Quickest round-trip

Santiago de los CaballerosChicago

STI - ORD

STIORD

Santiago de los Caballeros

Sun 9/6

4:54 pm-11:44 pm

1 stop7h 50m

Chicago O'Hare Intl

Sun 9/13

6:00 am-1:27 pm

1 stop6h 27m

$484

Santiago de los CaballerosChicago

STI - ORD

STIORD

Santiago de los Caballeros

Wed 9/2

8:13 am-11:44 pm

1 stop16h 31m

Chicago O'Hare Intl

Mon 9/14

10:59 am-8:28 pm

1 stop8h 29m

$596

Santiago de los CaballerosChicago

STI - ORD

STIORD

Santiago de los Caballeros

Thu 11/12

6:01 am-1:20 pm

1 stop9h 19m

Chicago O'Hare Intl

Sat 11/14

2:15 pm-1:51 am

1 stop9h 36m

$621

Santiago de los CaballerosChicago

STI - ORD

STIORD

Santiago de los Caballeros

Wed 10/28

3:16 pm-9:28 am

1 stop19h 12m

Chicago O'Hare Intl

Mon 11/2

2:38 pm-4:08 pm

1 stop23h 30m

$623

Santiago de los CaballerosChicago

STI - ORD

STIORD

Santiago de los Caballeros

Wed 10/28

3:16 pm-7:27 am

2 stops17h 11m

Chicago O'Hare Intl

Mon 11/2

9:06 pm-4:08 pm

2 stops17h 02m

$628

Santiago de los CaballerosChicago

STI - ORD

STIORD

Santiago de los Caballeros

Wed 10/28

3:16 pm-7:27 am

2 stops17h 11m

Chicago O'Hare Intl

Mon 11/2

3:21 pm-4:03 pm

1 stop22h 42m

$628

Santiago de los CaballerosChicago

STI - ORD

STIORD

Santiago de los Caballeros

Mon 9/14

6:00 am-9:13 am

1 stop28h 13m

Chicago O'Hare Intl

Mon 9/21

9:35 pm-10:52 pm

1 stop24h 17m

$632

Santiago de los CaballerosChicago

STI - ORD

STIORD

Santiago de los Caballeros

Thu 9/17

3:30 pm-11:08 pm

1 stop8h 38m

Chicago O'Hare Intl

Mon 9/21

6:00 am-1:27 pm

1 stop6h 27m

$649

Santiago de los CaballerosChicago

STI - ORD

STIORD

Santiago de los Caballeros

Wed 9/9

3:49 pm-11:08 pm

1 stop8h 19m

Chicago O'Hare Intl

Wed 9/16

6:00 am-1:27 pm

1 stop6h 27m

$653

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 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 August 2026, prices for Santiago de los Caballeros to Chicago O'Hare Intl Airport flights are approximately 30% 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

Fastest flight time

7h 50m

Direct flights

None
The fastest flight from Santiago de los Caballeros to Chicago O'Hare Intl Airport takes 7h 50m
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 7h 50m.

  • 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
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Gurnee
Rosemont
Orland Park
Oak Brook
Naperville
Joliet
New Buffalo
Kenosha
Hammond
Aurora
Racine
Janesville
Elgin
Evanston
South Holland

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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