Latest deals
Insights
FAQs
Reviews
Price Alerts

Cheap flights from Illinois to Santiago de los Caballeros from $226

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Illinois to Santiago de los Caballeros departing on 8/31. 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

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Illinois to Santiago de los Caballeros

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
8:55 pm - 2:15 pm
ORD
-
STI
16h 20m
2 stops
American Airlines Logo
3:15 pm - 7:58 am
STI
-
ORD
17h 43m
2 stops
$393American Airlines
Mon, Sep 21 - Thu, Sep 24
American Airlines Logo
4:35 pm - 2:15 pm
ORD
-
STI
20h 40m
1 stop
American Airlines Logo
3:15 pm - 7:58 am
STI
-
ORD
17h 43m
2 stops
$402American Airlines
Mon, Sep 21 - Thu, Sep 24
American Airlines Logo
9:15 pm - 2:15 pm
ORD
-
STI
16h 00m
2 stops
American Airlines Logo
3:15 pm - 7:42 am
STI
-
ORD
17h 27m
2 stops
$403American Airlines
Mon, Sep 21 - Thu, Sep 24
American Airlines Logo
7:00 pm - 2:15 pm
ORD
-
STI
18h 15m
1 stop
American Airlines Logo
3:15 pm - 7:48 am
STI
-
ORD
17h 33m
1 stop
$408American Airlines
Mon, Sep 21 - Thu, Sep 24
American Airlines Logo
9:01 pm - 2:15 pm
ORD
-
STI
16h 14m
2 stops
American Airlines Logo
3:15 pm - 12:33 am
STI
-
ORD
10h 18m
1 stop
$413American Airlines
Thu, Sep 17 - Wed, Sep 30
American Airlines Logo
7:00 pm - 2:15 pm
ORD
-
STI
18h 15m
1 stop
American Airlines Logo
3:15 pm - 7:48 am
STI
-
ORD
17h 33m
1 stop
$418American Airlines
Thu, Sep 17 - Wed, Sep 30
Delta Logo
5:15 pm - 12:03 pm
MDW
-
STI
17h 48m
2 stops
Delta Logo
7:16 pm - 10:38 am
STI
-
MDW
16h 22m
2 stops
$506Delta
Sun, Oct 18 - Fri, Oct 23
Frontier Logo
6:34 pm - 9:59 am
STL
-
STI
38h 25m
2 stops
Frontier Logo
11:14 am - 11:59 pm
STI
-
STL
37h 45m
2 stops
$524Frontier
Tue, Aug 4 - Tue, Aug 11
Delta Logo
4:25 pm - 12:03 pm
MDW
-
STI
18h 38m
2 stops
Delta Logo
7:16 pm - 6:05 pm
STI
-
MDW
23h 49m
2 stops
$535Delta
Sat, Oct 17 - Mon, Oct 26
United Airlines Logo
7:04 pm - 10:49 am
STL
-
STI
14h 45m
2 stops
United Airlines Logo
6:00 am - 12:40 pm
STI
-
STL
8h 40m
1 stop
$665United Airlines
Fri, Oct 30 - Sun, Nov 15

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Delta flights from Illinois to Santiago de los Caballeros

Our best Delta deals on Illinois to Santiago de los Caballeros flight tickets
Delta
Oct 18
MDW5:15 pmChicago Midway
17h 48m
2 stops
STI12:03 pmSantiago de los Caballeros
Oct 23
STI7:16 pmSantiago de los Caballeros
16h 22m
2 stops
MDW10:38 amChicago Midway
$506
Delta
Oct 16
ORD6:10 amChicago O'Hare Intl
10h 36m
1 stop
STI5:46 pmSantiago de los Caballeros
Oct 31
STI1:29 pmSantiago de los Caballeros
9h 04m
1 stop
ORD9:33 pmChicago O'Hare Intl
$530
Delta
Oct 17
MDW4:25 pmChicago Midway
18h 38m
2 stops
STI12:03 pmSantiago de los Caballeros
Oct 26
STI7:16 pmSantiago de los Caballeros
23h 49m
2 stops
MDW6:05 pmChicago Midway
$535

United Airlines flights from Illinois to Santiago de los Caballeros

Our best United Airlines deals on Illinois to Santiago de los Caballeros flight tickets
United Airlines
Oct 30
STL7:04 pmLambert-St Louis
14h 45m
2 stops
STI10:49 amSantiago de los Caballeros
Nov 15
STI6:00 amSantiago de los Caballeros
8h 40m
1 stop
STL12:40 pmLambert-St Louis
$665
United Airlines
Aug 2
STL6:01 amLambert-St Louis
8h 11m
1 stop
STI3:12 pmSantiago de los Caballeros
Aug 10
STI2:07 pmSantiago de los Caballeros
10h 37m
1 stop
STL11:44 pmLambert-St Louis
$745
United Airlines
Sep 29
STL9:30 amLambert-St Louis
12h 22m
1 stop
STI10:52 pmSantiago de los Caballeros
Oct 1
STI6:00 amSantiago de los Caballeros
16h 09m
1 stop
STL9:09 pmLambert-St Louis
$774

momondo Fare Finder

 
Customize your flight search to find flights from Illinois to Santiago de los Caballeros 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 July 18, 2026.
Use the filters below to find and compare flights from Illinois to Santiago de los Caballeros that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Mon 9/21

8:55 pm-2:15 pm

2 stops16h 20m

Santiago de los Caballeros

Thu 9/24

3:15 pm-7:58 am

2 stops17h 43m

$393

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Mon 9/21

4:35 pm-2:15 pm

1 stop20h 40m

Santiago de los Caballeros

Thu 9/24

3:15 pm-7:58 am

2 stops17h 43m

$402

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Mon 9/21

9:15 pm-2:15 pm

2 stops16h 00m

Santiago de los Caballeros

Thu 9/24

3:15 pm-7:42 am

2 stops17h 27m

$403

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Mon 9/21

7:00 pm-2:15 pm

1 stop18h 15m

Santiago de los Caballeros

Thu 9/24

3:15 pm-7:48 am

1 stop17h 33m

$408

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Thu 9/17

9:01 pm-2:15 pm

2 stops16h 14m

Santiago de los Caballeros

Wed 9/30

3:15 pm-12:33 am

1 stop10h 18m

$413

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Thu 9/17

7:00 pm-2:15 pm

1 stop18h 15m

Santiago de los Caballeros

Wed 9/30

3:15 pm-7:48 am

1 stop17h 33m

$418

ChicagoSantiago de los Caballeros

MDW - STI

MDWSTI

Chicago Midway

Sun 10/18

5:15 pm-12:03 pm

2 stops17h 48m

Santiago de los Caballeros

Fri 10/23

7:16 pm-10:38 am

2 stops16h 22m

$506

St. LouisSantiago de los Caballeros

STL - STI

STLSTI

Lambert-St Louis

Tue 8/4

6:34 pm-9:59 am

2 stops38h 25m

Santiago de los Caballeros

Tue 8/11

11:14 am-11:59 pm

2 stops37h 45m

$524

ChicagoSantiago de los Caballeros

MDW - STI

MDWSTI

Chicago Midway

Sat 10/17

4:25 pm-12:03 pm

2 stops18h 38m

Santiago de los Caballeros

Mon 10/26

7:16 pm-6:05 pm

2 stops23h 49m

$535
Quickest round-trip

St. LouisSantiago de los Caballeros

STL - STI

STLSTI

Lambert-St Louis

Fri 10/30

7:04 pm-10:49 am

2 stops14h 45m

Santiago de los Caballeros

Sun 11/15

6:00 am-12:40 pm

1 stop8h 40m

$665

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

See travel insights to Santiago de los Caballeros from

How to get the cheapest flight ticket from Illinois to Santiago de los Caballeros

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 Santiago de los Caballeros?

The cheapest month to fly to Santiago de los Caballeros from Illinois is in February. Flight prices, which tend to average around $392, are often lower during this time because this is during the off-season. If you aren’t able to travel to Santiago de los Caballeros during the month of February, then flying in March is also cheap. Prices for this month can be found on momondo for an average of $439.

Can stopping save me money on Illinois to Santiago de los Caballeros flights?

You could potentially save up to 18% on your flight if you consider stops on a Illinois to Santiago de los Caballeros flight.

Cheap Illinois to Santiago de los Caballeros flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Illinois to Santiago de los Caballeros

Fastest flight time

6h 27m

Direct flights

None
The fastest flight from Illinois to Santiago de los Caballeros takes 6h 27m
There are no direct flights from Illinois to Santiago de los Caballeros. There are no popular flight routes from Illinois to Santiago de los Caballeros.
Search flight deals

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

  • When did momondo last update prices for flights from Illinois to Santiago de los Caballeros Airport?

    Prices for flights from Illinois to Santiago de los Caballeros Airport refresh daily.

  • How many operators does momondo search for flights from Illinois to Santiago de los Caballeros Airport?

  • How old do you have to be to fly from Illinois to Santiago de los Caballeros 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 Illinois to Santiago de los Caballeros Airport.

  • What documentation or ID do you need to fly to Santiago de los Caballeros Airport?

    The required travel and health documents for your Santiago de los Caballeros 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 Santiago de los Caballeros Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

Best airlines flying from Illinois to Santiago de los Caballeros

Compare and see reviews for airlines that fly from Illinois to Santiago de los Caballeros with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $239Free CancellationRating
7.8
8,476 reviews
Search Delta flights
JetBluePriceFrom $255Free CancellationRating
7.1
3,012 reviews
Search JetBlue flights
American AirlinesPriceFrom $407Free CancellationRating
7.1
11,825 reviews
Search American Airlines flights

Why use momondo?

Why should I use momondo to find a flight deal from Illinois to Santiago de los Caballeros?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Santiago de los Caballeros from Illinois.

Can I find flights from Illinois to Santiago de los Caballeros with flexible booking policies on momondo?

Flights from Illinois to Santiago de los Caballeros with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Illinois to Santiago de los Caballeros?

momondo provides multiple filters to help you find the best flight to Santiago de los Caballeros from Illinois. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Illinois to Santiago de los Caballeros right now. Can momondo alert me if prices change?

Price alerts on flights to Santiago de los Caballeros from Illinois 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.

An easier way to manage your Santiago de los Caballeros trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Mon 8/17
Mon 8/24
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the Dominican Republic