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Cheap flights from Santiago de los Caballeros to Chicago from $240

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 7/14. 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.
United Airlines Logo
6:00 am - 11:21 pm
STI
-
ORD
18h 21m
1 stop
United Airlines Logo
6:00 am - 10:52 pm
ORD
-
STI
15h 52m
1 stop
$467United Airlines
Thu, Sep 24 - Mon, Sep 28
United Airlines Logo
6:00 am - 9:32 pm
STI
-
ORD
16h 32m
1 stop
United Airlines Logo
5:00 am - 10:52 pm
ORD
-
STI
16h 52m
1 stop
$479United Airlines
Thu, Oct 15 - Mon, Oct 19
JetBlue Logo
5:01 am - 1:39 pm
STI
-
ORD
9h 38m
1 stop
JetBlue Logo
2:35 pm - 11:51 pm
ORD
-
STI
8h 16m
1 stop
$526JetBlue
Tue, Jul 28 - Tue, Aug 4
JetBlue Logo
5:01 am - 1:39 pm
STI
-
ORD
9h 38m
1 stop
JetBlue Logo
2:35 pm - 11:51 pm
ORD
-
STI
8h 16m
1 stop
$545JetBlue
Mon, Jul 13 - Mon, Jul 20
JetBlue Logo
4:54 pm - 11:44 pm
STI
-
ORD
7h 50m
1 stop
JetBlue Logo
2:35 pm - 11:51 pm
ORD
-
STI
8h 16m
1 stop
$556JetBlue
Fri, Jul 17 - Thu, Jul 23
United Airlines Logo
4:23 pm - 11:21 pm
STI
-
ORD
7h 58m
1 stop
United Airlines Logo
5:00 am - 3:12 pm
ORD
-
STI
9h 12m
1 stop
$572United Airlines
Thu, Oct 8 - Tue, Oct 13
JetBlue Logo
1:55 am - 4:16 pm
STI
-
ORD
15h 21m
1 stop
JetBlue Logo
2:35 pm - 11:51 pm
ORD
-
STI
8h 16m
1 stop
$584JetBlue
Fri, Jul 3 - Mon, Jul 27
American Airlines Logo
1:40 pm - 8:53 am
STI
-
ORD
20h 13m
1 stop
American Airlines Logo
8:35 pm - 12:10 pm
ORD
-
STI
14h 35m
2 stops
$588American Airlines
Fri, Oct 9 - Tue, Oct 13
American Airlines Logo
9:00 am - 12:26 am
STI
-
ORD
16h 26m
1 stop
American Airlines Logo
8:00 am - 9:29 pm
ORD
-
STI
12h 29m
2 stops
$593American Airlines
Tue, Jul 28 - Tue, Aug 4
JetBlue Logo
6:30 pm - 8:45 am
STI
-
ORD
15h 15m
1 stop
JetBlue Logo
2:35 pm - 11:51 pm
ORD
-
STI
8h 16m
1 stop
$595JetBlue
Sat, Jul 4 - Mon, Jul 27

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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
Jul 28
STI5:01 amSantiago de los Caballeros
9h 38m
1 stop
ORD1:39 pmChicago O'Hare Intl
Aug 4
ORD2:35 pmChicago O'Hare Intl
8h 16m
1 stop
STI11:51 pmSantiago de los Caballeros
$526
JetBlue
Jul 17
STI4:54 pmSantiago de los Caballeros
7h 50m
1 stop
ORD11:44 pmChicago O'Hare Intl
Jul 23
ORD2:35 pmChicago O'Hare Intl
8h 16m
1 stop
STI11:51 pmSantiago de los Caballeros
$556
JetBlue
Jul 3
STI1:55 amSantiago de los Caballeros
15h 21m
1 stop
ORD4:16 pmChicago O'Hare Intl
Jul 27
ORD2:35 pmChicago O'Hare Intl
8h 16m
1 stop
STI11:51 pmSantiago de los Caballeros
$584

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 22
STI3:35 pmSantiago de los Caballeros
8h 55m
1 stop
ORD11:30 pmChicago O'Hare Intl
Sep 5
ORD7:11 pmChicago O'Hare Intl
16h 11m
1 stop
STI12:22 pmSantiago de los Caballeros
$538
American Airlines
Aug 22
STI7:00 amSantiago de los Caballeros
17h 30m
1 stop
ORD11:30 pmChicago O'Hare Intl
Sep 5
ORD8:00 amChicago O'Hare Intl
12h 07m
2 stops
STI9:07 pmSantiago de los Caballeros
$542
American Airlines
Oct 9
STI1:40 pmSantiago de los Caballeros
20h 13m
1 stop
ORD8:53 amChicago O'Hare Intl
Oct 13
ORD8:35 pmChicago O'Hare Intl
14h 35m
2 stops
STI12:10 pmSantiago de los Caballeros
$588

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 June 18, 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 9/24

6:00 am-11:21 pm

1 stop18h 21m

Chicago O'Hare Intl

Mon 9/28

6:00 am-10:52 pm

1 stop15h 52m

$467

Santiago de los CaballerosChicago

STI - ORD

STIORD

Santiago de los Caballeros

Thu 10/15

6:00 am-9:32 pm

1 stop16h 32m

Chicago O'Hare Intl

Mon 10/19

5:00 am-10:52 pm

1 stop16h 52m

$479

Santiago de los CaballerosChicago

STI - ORD

STIORD

Santiago de los Caballeros

Tue 7/28

5:01 am-1:39 pm

1 stop9h 38m

Chicago O'Hare Intl

Tue 8/4

2:35 pm-11:51 pm

1 stop8h 16m

$526

Santiago de los CaballerosChicago

STI - ORD

STIORD

Santiago de los Caballeros

Mon 7/13

5:01 am-1:39 pm

1 stop9h 38m

Chicago O'Hare Intl

Mon 7/20

2:35 pm-11:51 pm

1 stop8h 16m

$545
Quickest round-trip

Santiago de los CaballerosChicago

STI - ORD

STIORD

Santiago de los Caballeros

Fri 7/17

4:54 pm-11:44 pm

1 stop7h 50m

Chicago O'Hare Intl

Thu 7/23

2:35 pm-11:51 pm

1 stop8h 16m

$556

Santiago de los CaballerosChicago

STI - ORD

STIORD

Santiago de los Caballeros

Thu 10/8

4:23 pm-11:21 pm

1 stop7h 58m

Chicago O'Hare Intl

Tue 10/13

5:00 am-3:12 pm

1 stop9h 12m

$572

Santiago de los CaballerosChicago

STI - ORD

STIORD

Santiago de los Caballeros

Fri 7/3

1:55 am-4:16 pm

1 stop15h 21m

Chicago O'Hare Intl

Mon 7/27

2:35 pm-11:51 pm

1 stop8h 16m

$584

Santiago de los CaballerosChicago

STI - ORD

STIORD

Santiago de los Caballeros

Fri 10/9

1:40 pm-8:53 am

1 stop20h 13m

Chicago O'Hare Intl

Tue 10/13

8:35 pm-12:10 pm

2 stops14h 35m

$588

Santiago de los CaballerosChicago

STI - ORD

STIORD

Santiago de los Caballeros

Tue 7/28

9:00 am-12:26 am

1 stop16h 26m

Chicago O'Hare Intl

Tue 8/4

8:00 am-9:29 pm

2 stops12h 29m

$593

Santiago de los CaballerosChicago

STI - ORD

STIORD

Santiago de los Caballeros

Sat 7/4

6:30 pm-8:45 am

1 stop15h 15m

Chicago O'Hare Intl

Mon 7/27

2:35 pm-11:51 pm

1 stop8h 16m

$595

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
Benton Harbor
Portage
Saint Joseph
Lansing
Valparaiso
Schererville
Munster
Crown Point
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.

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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