Cheap flights from Chicago (CHI) to Santiago de los Caballeros (STI)

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The best prices from Chicago to Santiago de los Caballeros are usually found in August or February, booked 13 days in advance, depart on a Saturday or Friday and return on a Thursday

Home Caribbean Dominican Republic Santiago de los Caballeros Cheap flights from Chicago to Santiago de los Caballeros

How to find the cheapest flight from
Chicago (CHI) to Santiago de los Caballeros (STI)

All the information you need to plan the best CHI to STI flight in 2022: compare Chicago to Santiago de los Caballeros flight prices with the expected peak season, weather and rainfall in Santiago de los Caballeros.
CHI - STI
Price
$247 - $721
STI
Temperature
73.4 - 80.6 °F
STI
Rainfall
3 - 11.6 inches

Popular in

December

High demand for flights, 40% potential price rise

Cheapest in

August

Best time to find cheap flights, 43% potential price drop

Average price

$382

Average for round-trip flights in May 2022

Round-trip from

$247

From Chicago (CHI) to Santiago de los Caballeros

Flight route prices based on searches on Cheapflights within the last 3 days, monthly prices based on aggregated historical data.
What is the cheapest month to fly from Chicago to Santiago de los Caballeros?

August can be a great time to fly to Santiago de los Caballeros from Chicago with a flight ticket averaging about $431. Cheapflights users have found deals in the month of August for as cheap as $191. The most expensive prices can be found in the month of December.

When is the cheapest time to fly from Chicago to Santiago de los Caballeros (CHI - STI)?

One of the essential ways to save on airfare from Chicago to Santiago de los Caballeros is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the evening could potentially save you up to 57% on airfare.

How far in advance should I book a flight from Chicago to Santiago de los Caballeros?

Find a great deal and save up to 19% by booking at least 14 days prior to your desired departure date, rather than waiting until the week of travel. According to our data, there are a number of flights available from Chicago to Santiago de los Caballeros within the next two weeks, with the cheapest ticket starting at $393.

What is the cheapest day to fly round-trip from Chicago to Santiago de los Caballeros?

Wednesday flights are generally found to be more expensive for flights from Chicago to Santiago de los Caballeros. This shouldn’t discourage you from searching, as you can still find great deals by being flexible with your options. Use our search form to find deals on tickets to Santiago de los Caballeros.

Cheap flights from Chicago to Santiago de los Caballeros in May, June 2022

The best prices found for CHI to STI flights for May, June
23 May - 5 Jun
$377pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
STI
Santiago de los Caballeros
STI
Santiago de los Caballeros
Spirit Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
23 May - 5 Jun
$383pp
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
STI
Santiago de los Caballeros
STI
Santiago de los Caballeros
American Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
23 May - 5 Jun
$399pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
STI
Santiago de los Caballeros
STI
Santiago de los Caballeros
Spirit Airlines
     
3 STOPS
ORD
Chicago O'Hare Intl

Chicago to Santiago de los Caballeros 2022 flight deals

Cheap flights to Santiago de los Caballeros from Chicago found for this year
23 May - 5 Jun
$377pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
STI
Santiago de los Caballeros
STI
Santiago de los Caballeros
Spirit Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
23 May - 5 Jun
$383pp
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
STI
Santiago de los Caballeros
STI
Santiago de los Caballeros
American Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
23 May - 5 Jun
$399pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
STI
Santiago de los Caballeros
STI
Santiago de los Caballeros
Spirit Airlines
     
3 STOPS
ORD
Chicago O'Hare Intl

Last minute flights from Chicago to Santiago de los Caballeros

Late deals on round-trip flights to Santiago de los Caballeros from Chicago, departing today and this week
18 May - 24 May
$416pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
STI
Santiago de los Caballeros
STI
Santiago de los Caballeros
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
18 May - 24 May
$453pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
STI
Santiago de los Caballeros
STI
Santiago de los Caballeros
Spirit Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
18 May - 25 May
$463pp
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
STI
Santiago de los Caballeros
STI
Santiago de los Caballeros
Delta
 
1 STOP
ORD
Chicago O'Hare Intl

One-way flights to Santiago from Chicago

The cheapest one-way flights from Chicago to Santiago de los Caballeros
9:14 am - 9:35 pm
JetBlue
1 Stop
11h 21m
ORD - STI
JetBlue
$303
9:19 am - 8:24 am
American Airlines
2 Stops
22h 05m
ORD - STI
American Airlines
$327
4:22 pm - 9:49 pm
Multiple Airlines
2 Stops
28h 27m
MDW - STI
Multiple Airlines
$350
Kiwi.com

Related info for your journey

Useful info, stats and facts about <span class="emphasized">Chicago</span> to <span class="emphasized">Santiago de los Caballeros</span> flights.

Flight FAQs

From Chicago to Santiago de los Caballeros

What airport do you fly into for flights to Santiago de los Caballeros from Chicago?

For a flight from Chicago to Santiago de los Caballeros, you will be flying into Santiago. Santiago de los Caballeros (STI) is just 6.8 mi from the center of the city. Santiago is the only Santiago de los Caballeros airport and it handles 0 inbound flights from Chicago per day. 6 airlines have flights to Santiago de los Caballeros from Chicago on a regular basis.

Which airlines flying from Chicago to Santiago de los Caballeros have flexible cancellations due to COVID-19?

Spirit Airlines, American Airlines, and Copa Airlines are some of the carriers that may have flexible cancellation policies. You can use our site to filter for other airlines that may also have this kind of flexibility.

Can I find flights from Chicago to Santiago de los Caballeros for under $400 on Cheapflights?

Yes, there are multiple flights from Chicago to Santiago de los Caballeros for under $400. The cheapest flight booked recently is on Spirit Airlines for just $377, but on average you can expect to pay $435.

Are there last-minute flights available from Chicago to Santiago de los Caballeros for under $500?

There are currently 16+ open flights from Chicago to Santiago de los Caballeros within the next 7 days for less than $500.

What are the cheapest airlines flying from Chicago to Santiago de los Caballeros round-trip?

Currently priced at $377, Spirit Airlines will fly you from Chicago to Santiago de los Caballeros and back. In addition to Spirit Airlines, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from American Airlines and JetBlue - these airlines can fly you to your destination from $412 and $431, respectively. Users have found that Spirit Airlines is 12% cheaper than the other options available to this destination.

What are the cheapest airlines to fly from Chicago to Santiago de los Caballeros one-way?

For one-way options, check prices for Spirit Airlines. According to our data, you can fly for as low as $158. Users have also found prices from $195 and $303 on American Airlines and JetBlue, respectively.

What are the most popular airlines that fly from Chicago to Santiago de los Caballeros?

Before booking your flight from Chicago to Santiago de los Caballeros check out the most popular airlines for this route: American Airlines, JetBlue or Copa Airlines.

What are the cheapest flights from Chicago to Santiago de los Caballeros?

On average you can expect to pay $366 for a flight from Chicago to Santiago de los Caballeros. The cheapest flight overall is $157 while the most popular route, (Chicago O'Hare Intl - Santiago de los Caballeros) is currently priced at $383.

Related searches

Flights to Santiago de los Caballeros (STI) from Chicago
Flights to Chicago Flights to Santiago de los Caballeros Flights from Chicago

Other flights from Chicago

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Other flights to Santiago de los Caballeros

Newark to Santiago de los Caballeros John F. Kennedy Intl to Santiago de los Caballeros New York to Santiago de los Caballeros Boston to Santiago de los Caballeros Miami to Santiago de los Caballeros

Rent a Car

Car Rentals in Santiago de los Caballeros Car Rentals at Santiago de los Caballeros

COVID Restrictions

View COVID Travel Restrictions for Santiago de los Caballeros, Dominican Republic

Do I need a COVID test to fly to Santiago de los Caballeros from Chicago?

Information is based on travel restrictions from Chicago to Santiago de los Caballeros

Most visitors from Chicago can enter Santiago de los Caballeros without restrictions.

COVID-19 testing requirements
Visitors from Chicago are not required to present a negative COVID-19 PCR test or antigen result upon entering Santiago de los Caballeros.

Quarantine requirements
Visitors from Chicago are not required to quarantine after entering Santiago de los Caballeros.

Documents
E-Ticket form - All foreign and Dominican passengers entering or leaving Dominican Republic on commercial flights must complete the free electronic entry and exit form, which combines the Traveler’s Health Affidavit, Customs Declaration and International Embarkation/Disembarkation forms. The form is available in English, Spanish, French, Italian, German, Portuguese and Russian.


Do I need a test to fly back to Chicago from Santiago de los Caballeros?

Returning to Chicago from Santiago de los Caballeros

COVID-19 testing requirements
Visitors from Santiago de los Caballeros must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 1 day for RT-PCR (NAAT) and 1 day for Antigen (quick-test) before departing to Chicago.

Quarantine requirements
Visitors from Santiago de los Caballeros are not required to quarantine after entering Chicago.

Hide COVID Travel Restrictions for Santiago de los Caballeros, Dominican Republic

Alternative routes for Chicago to Santiago de los Caballeros

See prices for flight routes from nearby airports that may be better suited for you.
Greater Peoria to Punta Cana from $595 pp
Moline Quad-City to Punta Cana from $904 pp

Destination information for Santiago de los Caballeros

Things to know before you go - useful duration and weather info for your trip from Chicago to Santiago de los Caballeros.
Today's exchange rate
$1 = RD$ 54.66
Average temperature for May in Santiago de los Caballeros
89.6 °F
Avg rainfall for May in Santiago de los Caballeros
5.1 ″

Airports servicing Chicago

O'Hare Intl (ORD)
Midway (MDW)
Rockford (RFD)

Airports servicing Santiago de los Caballeros

Santiago de los Caballeros (STI)

Top 6 airlines flying from Chicago to Santiago de los Caballeros

The chart below displays the airlines Cheapflights users traveling from Chicago to Santiago de los Caballeros choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
Airline Cheapest Average Flexibility On-time COVID-19 safety
Copa Airlines 		$215 $432 No cancel fee 70%
Spirit Airlines 		$246 $397 No cancel fee 65%
American Airlines 		$285 $606 No cancel fee 71%
JetBlue 		$357 $633 No cancel fee 62%
United Airlines 		$421 $685 No cancel fee 69%
Delta 		$527 $606 No cancel fee N/A

Popular flight searches

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