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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

Our best Spirit Airlines deals on Santiago de los Caballeros to Chicago 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

Our best American Airlines deals on Santiago de los Caballeros to Chicago 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 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 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

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 May is your next best option. Flight prices from Santiago de los Caballeros to Chicago during May 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

8h 00m

Direct flights

None
The fastest flight from Santiago de los Caballeros to Chicago takes 8h 00m
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 8h 00m, 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
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
Crown Point
Monticello
Chesterton
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