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

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 - 10:53 amSTI  Santiago de los Caballeros-ORD Chicago O'Hare Intl
29h 53m1 stop Newark
United Airlines Logo
12:09 pm - 10:52 pmORD  Chicago O'Hare Intl-STI Santiago de los Caballeros
9h 43m1 stop Newark
$495United Airlines
Fri, Oct 16 - Wed, Oct 21
United Airlines Logo
6:00 am - 10:53 amSTI  Santiago de los Caballeros-ORD Chicago O'Hare Intl
29h 53m1 stop Newark
United Airlines Logo
12:09 pm - 10:52 pmORD  Chicago O'Hare Intl-STI Santiago de los Caballeros
9h 43m1 stop Newark
$497United Airlines
Fri, Oct 16 - Wed, Oct 21
Multiple Airlines Logo
11:43 am - 10:39 pmSTI  Santiago de los Caballeros-ORD Chicago O'Hare Intl
11h 56m1 stop Philadelphia
Multiple Airlines Logo
7:00 am - 2:47 pmORD  Chicago O'Hare Intl-STI Santiago de los Caballeros
6h 47m1 stop Fort Lauderdale
$500Multiple Airlines
Sat, Oct 17 - Wed, Oct 21
Multiple Airlines Logo
11:43 am - 10:39 pmSTI  Santiago de los Caballeros-ORD Chicago O'Hare Intl
11h 56m1 stop Philadelphia
Multiple Airlines Logo
7:00 am - 2:47 pmORD  Chicago O'Hare Intl-STI Santiago de los Caballeros
6h 47m1 stop Fort Lauderdale
$505Multiple Airlines
Sat, Oct 17 - Wed, Oct 21
United Airlines Logo
6:00 am - 11:21 pmSTI  Santiago de los Caballeros-ORD Chicago O'Hare Intl
18h 21m1 stop Newark
United Airlines Logo
5:00 am - 10:51 pmORD  Chicago O'Hare Intl-STI Santiago de los Caballeros
16h 51m1 stop Newark
$510United Airlines
Thu, Oct 22 - Mon, Oct 26
United Airlines Logo
4:23 pm - 9:32 pmSTI  Santiago de los Caballeros-ORD Chicago O'Hare Intl
30h 09m1 stop Newark
United Airlines Logo
3:43 pm - 1:53 pmORD  Chicago O'Hare Intl-STI Santiago de los Caballeros
21h 10m1 stop Newark
$527United Airlines
Thu, Oct 22 - Mon, Oct 26
United Airlines Logo
6:00 am - 7:42 amSTI  Santiago de los Caballeros-ORD Chicago O'Hare Intl
26h 42m1 stop Newark
United Airlines Logo
9:48 pm - 1:53 pmORD  Chicago O'Hare Intl-STI Santiago de los Caballeros
15h 05m1 stop Newark
$527United Airlines
Thu, Oct 22 - Mon, Oct 26
JetBlue Logo
3:44 pm - 11:57 pmSTI  Santiago de los Caballeros-ORD Chicago O'Hare Intl
9h 13m1 stop Fort Lauderdale
JetBlue Logo
7:00 am - 3:23 pmORD  Chicago O'Hare Intl-STI Santiago de los Caballeros
6h 23m1 stop Fort Lauderdale
$530JetBlue
Fri, Oct 30 - Fri, Nov 6
American Airlines Logo
3:12 pm - 7:27 amSTI  Santiago de los Caballeros-ORD Chicago O'Hare Intl
17h 15m2 stops Miami Washington, D.C. Reagan-National
American Airlines Logo
9:00 pm - 1:18 pmORD  Chicago O'Hare Intl-STI Santiago de los Caballeros
15h 18m1 stop Philadelphia
$539American Airlines
Fri, Oct 16 - Wed, Oct 21
American Airlines Logo
3:12 pm - 7:27 amSTI  Santiago de los Caballeros-ORD Chicago O'Hare Intl
17h 15m2 stops Miami Washington, D.C. Reagan-National
American Airlines Logo
5:00 am - 2:12 pmORD  Chicago O'Hare Intl-STI Santiago de los Caballeros
8h 12m2 stops Charlotte Douglas Miami
$539American Airlines
Fri, Oct 16 - Wed, Oct 21

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United Airlines flights from Santiago de los Caballeros to Chicago

Our best United Airlines deals on Santiago de los Caballeros to Chicago flight tickets
United Airlines
Oct 16
STI6:00 amSantiago de los Caballeros
29h 53m
1 stop
ORD10:53 amChicago O'Hare Intl
Oct 21
ORD12:09 pmChicago O'Hare Intl
9h 43m
1 stop
STI10:52 pmSantiago de los Caballeros
$495
United Airlines
Oct 16
STI6:00 amSantiago de los Caballeros
29h 53m
1 stop
ORD10:53 amChicago O'Hare Intl
Oct 21
ORD12:09 pmChicago O'Hare Intl
9h 43m
1 stop
STI10:52 pmSantiago de los Caballeros
$497
United Airlines
Oct 22
STI6:00 amSantiago de los Caballeros
18h 21m
1 stop
ORD11:21 pmChicago O'Hare Intl
Oct 26
ORD5:00 amChicago O'Hare Intl
16h 51m
1 stop
STI10:51 pmSantiago de los Caballeros
$510

JetBlue flights from Santiago de los Caballeros to Chicago

Our best JetBlue deals on Santiago de los Caballeros to Chicago flight tickets
JetBlue
Oct 30
STI3:44 pmSantiago de los Caballeros
9h 13m
1 stop
ORD11:57 pmChicago O'Hare Intl
Nov 6
ORD7:00 amChicago O'Hare Intl
6h 23m
1 stop
STI3:23 pmSantiago de los Caballeros
$530
JetBlue
Oct 18
STI3:57 pmSantiago de los Caballeros
8h 33m
1 stop
ORD11:30 pmChicago O'Hare Intl
Oct 26
ORD7:00 amChicago O'Hare Intl
6h 34m
1 stop
STI2:34 pmSantiago de los Caballeros
$544
JetBlue
Sep 26
STI3:30 pmSantiago de los Caballeros
8h 38m
1 stop
ORD11:08 pmChicago O'Hare Intl
Sep 30
ORD6:00 amChicago O'Hare Intl
6h 27m
1 stop
STI1:27 pmSantiago de los Caballeros
$787

momondo Fare Finder

 
Use the filters below to find and compare flights from Santiago de los Caballeros to Chicago that are best for you.

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Route

Depart

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Price

Cheapest round-trip

Santiago de los CaballerosChicago

STI Santiago de los Caballeros - ORD Chicago O'Hare Intl

STIORD

Santiago de los Caballeros

Fri 10/16

6:00 am-10:53 am

1 stop29h 53m

Chicago O'Hare Intl

Wed 10/21

12:09 pm-10:52 pm

1 stop9h 43m

$495

Santiago de los CaballerosChicago

STI Santiago de los Caballeros - ORD Chicago O'Hare Intl

STIORD

Santiago de los Caballeros

Fri 10/16

6:00 am-10:53 am

1 stop29h 53m

Chicago O'Hare Intl

Wed 10/21

12:09 pm-10:52 pm

1 stop9h 43m

$497

Santiago de los CaballerosChicago

STI Santiago de los Caballeros - ORD Chicago O'Hare Intl

STIORD

Santiago de los Caballeros

Sat 10/17

11:43 am-10:39 pm

1 stop11h 56m

Chicago O'Hare Intl

Wed 10/21

7:00 am-2:47 pm

1 stop6h 47m

$500

Santiago de los CaballerosChicago

STI Santiago de los Caballeros - ORD Chicago O'Hare Intl

STIORD

Santiago de los Caballeros

Sat 10/17

11:43 am-10:39 pm

1 stop11h 56m

Chicago O'Hare Intl

Wed 10/21

7:00 am-2:47 pm

1 stop6h 47m

$505

Santiago de los CaballerosChicago

STI Santiago de los Caballeros - ORD Chicago O'Hare Intl

STIORD

Santiago de los Caballeros

Thu 10/22

6:00 am-11:21 pm

1 stop18h 21m

Chicago O'Hare Intl

Mon 10/26

5:00 am-10:51 pm

1 stop16h 51m

$510

Santiago de los CaballerosChicago

STI Santiago de los Caballeros - ORD Chicago O'Hare Intl

STIORD

Santiago de los Caballeros

Thu 10/22

4:23 pm-9:32 pm

1 stop30h 09m

Chicago O'Hare Intl

Mon 10/26

3:43 pm-1:53 pm

1 stop21h 10m

$527

Santiago de los CaballerosChicago

STI Santiago de los Caballeros - ORD Chicago O'Hare Intl

STIORD

Santiago de los Caballeros

Thu 10/22

6:00 am-7:42 am

1 stop26h 42m

Chicago O'Hare Intl

Mon 10/26

9:48 pm-1:53 pm

1 stop15h 05m

$527
Quickest round-trip

Santiago de los CaballerosChicago

STI Santiago de los Caballeros - ORD Chicago O'Hare Intl

STIORD

Santiago de los Caballeros

Fri 10/30

3:44 pm-11:57 pm

1 stop9h 13m

Chicago O'Hare Intl

Fri 11/6

7:00 am-3:23 pm

1 stop6h 23m

$530

Santiago de los CaballerosChicago

STI Santiago de los Caballeros - ORD Chicago O'Hare Intl

STIORD

Santiago de los Caballeros

Fri 10/16

3:12 pm-7:27 am

2 stops17h 15m

Chicago O'Hare Intl

Wed 10/21

9:00 pm-1:18 pm

1 stop15h 18m

$539

Santiago de los CaballerosChicago

STI Santiago de los Caballeros - ORD Chicago O'Hare Intl

STIORD

Santiago de los Caballeros

Fri 10/16

3:12 pm-7:27 am

2 stops17h 15m

Chicago O'Hare Intl

Wed 10/21

5:00 am-2:12 pm

2 stops8h 12m

$539

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

Best Price Found

$237

Fastest flight time

8h 33m

Direct flights

None
The best one-way flight to Chicago from Santiago de los Caballeros in the past 72 hours is $237. The best round-trip flight deal from Santiago de los Caballeros to Chicago found on momondo in the last 72 hours is $495.
The fastest flight from Santiago de los Caballeros to Chicago takes 8h 33m
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 33m, 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
Porter
Crown Point
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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Fly into one of these airports located in Chicago

Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport