Find Cheap Flights from Chicago to Santiago de los Caballeros (CHI - STI)

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Good to Know

Average Price:
$549
(avg. price over the last 2 weeks)
Good Deal:
$450
or less (round trip)

When to Book Flights from Chicago to Santiago de los Caballeros

Flight prices as travel date approaches
-1 day
-2 days

Top tips for Finding a Cheap Flight

Looking for a cheap flight? 25% of our users found flights on this route for $449 or less.
The cheapest flight from Chicago to Santiago de los Caballeros was found 80 days before departure, on average.
Book at least 1 week before departure in order to get a below-average price.
Morning departure is around 8% more expensive than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

FAQs for Booking Chicago to Santiago de los Caballeros Flights

How long does a flight from Chicago to Santiago de los Caballeros take?
An average nonstop flight takes 6h 17m, covering a distance of 1838 miles.
Which airlines provide the cheapest flights from Chicago to Santiago de los Caballeros?
In the past 3 days, the cheapest round-trip tickets were found on Spirit Airlines ($342), Multiple Airlines ($354) and JetBlue ($390).
Do I need a passport to fly between Chicago and Santiago de los Caballeros?
Yes.
What’s the cheapest day of the week to fly Chicago to Santiago de los Caballeros?
For Chicago to Santiago de los Caballeros, Tuesday is the cheapest day to fly on average and Friday is the most expensive. Flying from Santiago de los Caballeros back to Chicago, the best deals are generally found on Tuesday, with Wednesday being the most expensive.

Book cheap flights from Chicago to Santiago de los Caballeros (round-trip)

Airports
Origin
Chicago
$342
only
$342
$421
only
$421
Destination
Santiago de los Caballeros
$342
only
$342
Tue, Jan 23
ORD
STI
6h 17m
Tue, Jan 30
STI
ORD
9h 19m
Trip: 8 days
5.5OkayShow reviews
Overall 5.5 Okay
Based on 51957 reviews
Overall
5.7
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
LAS
SEA
Excellent 10.0

The employees were extremely courteous and professional. I really enjoyed my trip.

SJU
FLL
Okay 5.0

Price and boarding

Delay (like always), cheap seating and no entertainment. Also, food selection is garbage.

ORD
TPA
Good 6.0

Food and entertainment NA

DFW
PHX
Mediocre 2.0

I got from point A to point B without dying and on time.

Staff was rude on the ground. Crew was rude in the air. Lap babies everywhere with the plane seated six across. It was smelly, overcrowded and chaotic. Lesson learned.

MBJ
FLL
Excellent 8.0

It was ok just had a long delay to get off the plane at Fort Lauderdale

Wed, Jan 31
ORD
STI
7h 18m
Tue, Feb 6
STI
ORD
9h 19m
Trip: 7 days
Overall 0.0 Poor
Based on 0 reviews
Wed, Jan 31
ORD
STI
7h 18m
Tue, Feb 13
STI
ORD
10h 23m
Trip: 14 days
8.1ExcellentShow reviews
Overall 8.1 Excellent
Based on 7618 reviews
Overall
8.2
Boarding
8.2
Comfort
8.3
Crew
8.6
Entertainment
8.0
Food
7.8
FLL
CUN
Excellent 10.0

More leg room

EWR
FLL
Mediocre 2.6

Heavy delay without accommodated hotel and food

BOS
MSY
Excellent 10.0

Being on time is the most important thing for me! Thank you for landing earlier.

DCA
BDL
Mediocre 2.0

flight delayed 2 hours - ugh.

ABQ
JFK
Poor 0.0

We cancelled the flight. I did not like the refund that we ended up getting. You did not get get much of a refund. We were very disappointed on the amount. We had to cancel because there was a serious family emergency, so we had no other choice but to cancel. I know you probably did what your policy says, but .....

Wed, Feb 7
ORD
STI
10h 23m
Tue, Feb 13
STI
ORD
8h 52m
Trip: 7 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15112 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
BHM
ATL
Excellent 8.0

Short flight.

SLC
LAX
Excellent 9.3

Nicest crew

SFO
LAX
Good 7.6

Everyone was really nice and responsive.

Seats are a little older. Not as comfortable as other flights. But not bad.

MSP
YEG
Good 7.6

Upon arriving in Minneapolis-St. Paul, it was a struggle to determine whether or not my bags had made it, whether or not I needed to collect them from baggage claim due to the cancellations/delays, and if I was even going to be able to transfer my ticket. Flight arrived late in the evening when most flights were basically complete for the day. Luckily, I happened upon a red-eye arrival, and spoke to an agent at that gate (Taj). Taj was without a doubt, THE BEST GATE AGENT I HAVE ENCOUNTERED IN MY 40+ YEARS OF TRAVELLING!! I explained my situation to him, and he immediately asked to see my travel info. He proceeded to get me on a flight much earlier than originally anticipated, upgraded me to Premium fare status, and did his best to re-route my luggage (which he informed me was still sitting in ATLANTA 18 hours after having left there...) - how does someone get on a flight, and their check-in get noted, but their luggage does not get put on said flight?? Things that make you go hmmmmm.... All that aside...I will be planning a trip to Minneapolis-St. Paul specifically to take a gift of appreciation to Taj! Well done on this end Delta - Taj is an excellent example of intelligent customer service.

Last minute notifications of delays/cancellations. Luggage was not placed on my original departing flight from Atlanta 18 HOURS EARLIER...not cool Delta. As a result, I did not receive my luggage for another 2 1/2 days .

SJC
LAX
Good 7.6

Travel got delayed by an hour but we were satisfied by the crew and food

The delay of the flight. Not sure on the reason

Tue, Jan 23
ORD
STI
6h 17m
Tue, Jan 30
STI
ORD
9h 19m
Trip: 8 days
5.5OkayShow reviews
Overall 5.5 Okay
Based on 51957 reviews
Overall
5.7
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
SAN
IAH
Excellent 9.0

Clean plane. Easy boarding. Great value.

Everything was good.

LAS
OAK
Mediocre 2.0

Nothing

After a two-and-a-half-hour delay the flight was cancelled due to mechanical problem. The crew didn't seem very prepared to deal with the problem. When I called for a refund it took forever to process. I will never booked another flight with Spirit again

DFW
PHX
Mediocre 2.0

I got from point A to point B without dying and on time.

Staff was rude on the ground. Crew was rude in the air. Lap babies everywhere with the plane seated six across. It was smelly, overcrowded and chaotic. Lesson learned.

BWI
BOS
Mediocre 2.0

God Spirit sucks

OAK
LAS
Good 6.3

no delay

Attitude of the female flight attendant. She gave me a cold look when she demanded me to move to center seat.

Fri, Feb 2
ORD
STI
6h 50m
Tue, Feb 6
STI
ORD
9h 19m
Trip: 5 days
Overall 0.0 Poor
Based on 0 reviews
Sat, Jan 20
ORD
STI
6h 17m
Tue, Jan 30
STI
ORD
9h 19m
Trip: 11 days
5.5OkayShow reviews
Overall 5.5 Okay
Based on 51957 reviews
Overall
5.7
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
MBJ
FLL
Excellent 8.0

It was ok just had a long delay to get off the plane at Fort Lauderdale

SJU
FLL
Okay 5.0

Price and boarding

Delay (like always), cheap seating and no entertainment. Also, food selection is garbage.

ORD
TPA
Good 6.0

Food and entertainment NA

SAN
IAH
Excellent 9.0

Clean plane. Easy boarding. Great value.

Everything was good.

LAS
OAK
Mediocre 2.0

Nothing

After a two-and-a-half-hour delay the flight was cancelled due to mechanical problem. The crew didn't seem very prepared to deal with the problem. When I called for a refund it took forever to process. I will never booked another flight with Spirit again

Fri, Feb 9
ORD
STI
8h 21m
Tue, Feb 13
STI
ORD
8h 52m
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15112 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
PHX
ATL
Okay 4.3

Full flight and tiny seats surrounded by 2 300lb guys and they wouldn't let me switch my seat.

OMA
MSP
Okay 4.4

Gate agent was fantastic! Her positive demeanor made for the delays and cancellations to not seem as much of an issue. She was extremely pleasant when explaining what was happening to flights, connections, etc. She was helpful when checking boarding passes to ensure that travellers were ok for their flight.

Again, last minute notification of delayed or cancelled flights made things somewhat worrisome. The late notification led to me missing my nest connection in Minneapolis, and having to sleep in the airport until the following morning in order to transfer my ticket to another flight leaving in the morning/afternoon/evening...very nerve-wracking to say the least.

SJC
LAX
Good 7.6

Travel got delayed by an hour but we were satisfied by the crew and food

The delay of the flight. Not sure on the reason

BHM
ATL
Excellent 8.0

Short flight.

SFO
LAX
Good 7.6

Everyone was really nice and responsive.

Seats are a little older. Not as comfortable as other flights. But not bad.

Sat, Jan 20
ORD
STI
6h 17m
Tue, Jan 30
STI
ORD
9h 19m
Trip: 11 days
5.5OkayShow reviews
Overall 5.5 Okay
Based on 51957 reviews
Overall
5.7
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
FLL
CLE
Good 6.5

Staff was very helpful and pleasant. flights we on time.

nickel and dimed for everything from reserved seats to baggage fees, seat spacing is very tight

OAK
LAS
Good 6.3

no delay

Attitude of the female flight attendant. She gave me a cold look when she demanded me to move to center seat.

SJU
FLL
Okay 5.0

Price and boarding

Delay (like always), cheap seating and no entertainment. Also, food selection is garbage.

ORD
TPA
Good 6.0

Food and entertainment NA

BWI
BOS
Mediocre 2.0

God Spirit sucks

Tue, Feb 13
ORD
STI
6h 17m
Tue, Feb 27
STI
ORD
11h 44m
Trip: 15 days
Overall 0.0 Poor
Based on 0 reviews
Mon, Jan 29
ORD
STI
7h 18m
Tue, Feb 6
STI
ORD
8h 53m
Trip: 9 days
8.1ExcellentShow reviews
Overall 8.1 Excellent
Based on 7618 reviews
Overall
8.2
Boarding
8.2
Comfort
8.3
Crew
8.6
Entertainment
8.0
Food
7.8
ABQ
JFK
Poor 0.0

We cancelled the flight. I did not like the refund that we ended up getting. You did not get get much of a refund. We were very disappointed on the amount. We had to cancel because there was a serious family emergency, so we had no other choice but to cancel. I know you probably did what your policy says, but .....

BOS
MSY
Excellent 10.0

Being on time is the most important thing for me! Thank you for landing earlier.

PAP
FLL
Excellent 10.0

Everything

Nah

DCA
BDL
Mediocre 2.0

flight delayed 2 hours - ugh.

EWR
FLL
Mediocre 2.6

Heavy delay without accommodated hotel and food

Tue, Feb 13
ORD
STI
8h 21m
Tue, Feb 20
STI
ORD
14h 57m
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15112 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
MSP
YVR
Mediocre 2.0

I was rerouted.

No one would reissue me a ticket for the next flight. Delta and West Jet kept saying the other company should do this, and in the end no one did and I had to purchase another ticket.

MCO
BOS
Good 7.0

One crew member, young dark haired woman, was particularly accommodating. Male attendant was firm and funny.

Typical cramped plane, too many planes going out of same gate are simultaneously

SJC
LAX
Good 7.6

Travel got delayed by an hour but we were satisfied by the crew and food

The delay of the flight. Not sure on the reason

SLC
LAX
Excellent 9.3

Nicest crew

LAX
ATL
Okay 4.0

Friendly crew.

Minimal leg room; seat didn’t decline, delayed by 40 minutes.

Tue, Jan 23
ORD
STI
6h 17m
Fri, Feb 2
STI
ORD
9h 19m
Trip: 11 days
5.5OkayShow reviews
Overall 5.5 Okay
Based on 51957 reviews
Overall
5.7
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
SJU
FLL
Okay 5.0

Price and boarding

Delay (like always), cheap seating and no entertainment. Also, food selection is garbage.

DFW
PHX
Mediocre 2.0

I got from point A to point B without dying and on time.

Staff was rude on the ground. Crew was rude in the air. Lap babies everywhere with the plane seated six across. It was smelly, overcrowded and chaotic. Lesson learned.

MBJ
FLL
Excellent 8.0

It was ok just had a long delay to get off the plane at Fort Lauderdale

FLL
CLE
Good 6.5

Staff was very helpful and pleasant. flights we on time.

nickel and dimed for everything from reserved seats to baggage fees, seat spacing is very tight

BWI
BOS
Mediocre 2.0

God Spirit sucks

Fri, Feb 23
ORD
STI
9h 49m
Fri, Mar 2
STI
ORD
9h 21m
Trip: 8 days
Overall 0.0 Poor
Based on 0 reviews
Sat, Feb 17
MDW
STI
6h 58m
Sat, Mar 3
STI
MDW
8h 30m
Trip: 15 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15112 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
BHM
ATL
Excellent 8.0

Short flight.

MSP
YVR
Mediocre 2.0

I was rerouted.

No one would reissue me a ticket for the next flight. Delta and West Jet kept saying the other company should do this, and in the end no one did and I had to purchase another ticket.

SJC
LAX
Good 7.6

Travel got delayed by an hour but we were satisfied by the crew and food

The delay of the flight. Not sure on the reason

MCO
BOS
Good 7.0

One crew member, young dark haired woman, was particularly accommodating. Male attendant was firm and funny.

Typical cramped plane, too many planes going out of same gate are simultaneously

MSP
YEG
Good 7.6

Upon arriving in Minneapolis-St. Paul, it was a struggle to determine whether or not my bags had made it, whether or not I needed to collect them from baggage claim due to the cancellations/delays, and if I was even going to be able to transfer my ticket. Flight arrived late in the evening when most flights were basically complete for the day. Luckily, I happened upon a red-eye arrival, and spoke to an agent at that gate (Taj). Taj was without a doubt, THE BEST GATE AGENT I HAVE ENCOUNTERED IN MY 40+ YEARS OF TRAVELLING!! I explained my situation to him, and he immediately asked to see my travel info. He proceeded to get me on a flight much earlier than originally anticipated, upgraded me to Premium fare status, and did his best to re-route my luggage (which he informed me was still sitting in ATLANTA 18 hours after having left there...) - how does someone get on a flight, and their check-in get noted, but their luggage does not get put on said flight?? Things that make you go hmmmmm.... All that aside...I will be planning a trip to Minneapolis-St. Paul specifically to take a gift of appreciation to Taj! Well done on this end Delta - Taj is an excellent example of intelligent customer service.

Last minute notifications of delays/cancellations. Luggage was not placed on my original departing flight from Atlanta 18 HOURS EARLIER...not cool Delta. As a result, I did not receive my luggage for another 2 1/2 days .

Fri, Jun 1
ORD
STI
10h 59m
Thu, Jun 7
STI
ORD
13h 38m
Trip: 7 days
8.1ExcellentShow reviews
Overall 8.1 Excellent
Based on 7618 reviews
Overall
8.2
Boarding
8.2
Comfort
8.3
Crew
8.6
Entertainment
8.0
Food
7.8
PAP
FLL
Excellent 10.0

Everything

Nah

ABQ
JFK
Poor 0.0

We cancelled the flight. I did not like the refund that we ended up getting. You did not get get much of a refund. We were very disappointed on the amount. We had to cancel because there was a serious family emergency, so we had no other choice but to cancel. I know you probably did what your policy says, but .....

LAX
BOS
Excellent 10.0

Incredible seat on Mint. Comfortable, fully reclining. Great service and truly delicious food.

EWR
FLL
Mediocre 2.6

Heavy delay without accommodated hotel and food

LGA
BOS
Excellent 9.6

Comfort

Tue, Jan 23
ORD
STI
6h 17m
Fri, Feb 2
STI
ORD
9h 19m
Trip: 11 days
5.5OkayShow reviews
Overall 5.5 Okay
Based on 51957 reviews
Overall
5.7
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
EWR
FLL
Okay 4.0

Efficient boarding and un boarding. No problem with luggage storage space. Nice and helpful staff.

The flight was 3 hours late. During boarding, staff annunciated that the flight was overbooked, which is extremely stressful for passengers who have to compete to onboard at first. The seats were not reclinable, my back hurts and I couldn't sleep. There were no food or entertainment proposed in the flight, however this last drawback was fair given the price.

SAN
IAH
Excellent 9.0

Clean plane. Easy boarding. Great value.

Everything was good.

OAK
LAS
Good 6.3

no delay

Attitude of the female flight attendant. She gave me a cold look when she demanded me to move to center seat.

DFW
PHX
Mediocre 2.0

I got from point A to point B without dying and on time.

Staff was rude on the ground. Crew was rude in the air. Lap babies everywhere with the plane seated six across. It was smelly, overcrowded and chaotic. Lesson learned.

FLL
LGA
Mediocre 2.0

Flight crew were very polite

My flight was supposed to leave FLL at 8:30pm and arrive in LGA AT 11:30pm, however, I received an email in the afternoon indicating that even though my flight was still leaving at 8:30pm, we would be arriving in LGA at 2am. This gave me the impression that something was wrong. I called the airline and they confirmed that my flight was leaving on time at 8:30pm and would be arriving in LGA at 11:30pm. On my way to the airport I received an email indicating that the flight was delayed and would be leaving at 9:09pm and arriving at 12:25am. As soon as I passed security, I went to the customer service desk and they indicated that the plane was running late from San Juan but that I should hurry to the gate because we could be departing earlier than indicated, so I did. Once at the gate, we were told that the crew was not available and we would not be taking off until 10:15, this gem got pushed out to 11:24. At this point we asked for some sort of compensation and the staff at the gate told us that We would get any kind of compensation because the flight was delayed due to weather conditions. This was not consistent with previous explanations. At the end of the day we arrived in LGA at 2:15am as indicated by the first email that we received in the afternoon. It seems like the staff was lying to us left and right. Very disappointed with the service today.

Sat, Feb 3
ORD
STI
6h 17m
Tue, Feb 20
STI
ORD
37h 18m
Trip: 18 days
Overall 0.0 Poor
Based on 0 reviews
Thu, Mar 1
ORD
STI
14h 55m
Tue, Mar 6
STI
ORD
14h 27m
Trip: 6 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15112 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
SFO
LAX
Good 7.6

Everyone was really nice and responsive.

Seats are a little older. Not as comfortable as other flights. But not bad.

PHX
ATL
Okay 4.3

Full flight and tiny seats surrounded by 2 300lb guys and they wouldn't let me switch my seat.

SLC
LAX
Excellent 9.3

Nicest crew

BHM
ATL
Excellent 8.0

Short flight.

MSP
YVR
Mediocre 2.0

I was rerouted.

No one would reissue me a ticket for the next flight. Delta and West Jet kept saying the other company should do this, and in the end no one did and I had to purchase another ticket.

Sat, Jun 2
ORD
STI
7h 01m
Thu, Jun 7
STI
ORD
13h 38m
Trip: 6 days
8.1ExcellentShow reviews
Overall 8.1 Excellent
Based on 7618 reviews
Overall
8.2
Boarding
8.2
Comfort
8.3
Crew
8.6
Entertainment
8.0
Food
7.8
LAX
BOS
Excellent 10.0

Incredible seat on Mint. Comfortable, fully reclining. Great service and truly delicious food.

AUS
JFK
Okay 5.6

how much training is provided to flight attendants for listening skills?

uncomfortable seat

PAP
FLL
Excellent 10.0

Everything

Nah

LGA
BOS
Excellent 9.6

Comfort

EWR
FLL
Mediocre 2.6

Heavy delay without accommodated hotel and food

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Chicago to Santiago de los Caballeros Flight Information

Flights Arrive in Santiago de los Caballeros
Flights Depart from Chicago
Flight Price $342
Distance 1838 miles
Airlines Spirit Airlines, JetBlue, Delta