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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

Our best JetBlue deals on Santiago de los Caballeros to Chicago 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

Our best American Airlines deals on Santiago de los Caballeros to Chicago 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 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 2, 2026.
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

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

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?

The month of April is, on average, the cheapest month to fly to Chicago from Santiago de los Caballeros, with most prices found around $0. If you’re not able to fly to Chicago in April, then March is your next best option. Flight prices from Santiago de los Caballeros to Chicago during March average around $224.

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

7h 50m

Direct flights

None
The fastest flight from Santiago de los Caballeros to Chicago takes 7h 50m
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

Frequently asked questions about flying from Santiago de los Caballeros to Chicago

  • 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 50m, 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
Portage
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Schererville
Munster
Chesterton
Monticello
Crown Point
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.

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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