CHI - SDQ

$132 Find Cheap Flights from Chicago to Santo Domingo

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Santo Domingo departing on 4/20. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Santo Domingo

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Santo Domingo, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Santo Domingo, as well as popular online travel agencies
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Everything you should know

Cheapest round-trip
$344
Typical prices: $613-$413
Spirit Airlines
Mon 4/27Fri 5/1
ORD - SDQ • 1 stop
Cheapest one-way
$145
Typical prices: $211-$237
Spirit Airlines
Mon 4/20
ORD - SDQ • 1 stop
Top airlines
Cheapest • from $344 (round-trip)
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between Chicago and Santo Domingo. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $438 (round-trip)
Shortest trip • 6h 24m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 24% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Santo Domingo!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Chicago to Santo Domingo (CHI-SDQ)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Santo Domingo that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Santo Domingo

Mon, Apr 27 - Fri, May 1
Spirit Airlines Logo
5:05 am - 1:29 pm
ORD
-
SDQ
7h 24m
1 stop
Spirit Airlines Logo
2:35 pm - 12:24 am
SDQ
-
ORD
10h 49m
1 stop
$344Spirit Airlines
Tue, Apr 28 - Fri, May 15
Multiple Airlines Logo
5:05 am - 1:29 pm
ORD
-
SDQ
7h 24m
1 stop
Multiple Airlines Logo
10:19 am - 11:56 pm
SDQ
-
ORD
14h 37m
1 stop
$352Multiple Airlines
Sat, May 16 - Wed, May 20
Multiple Airlines Logo
12:59 pm - 7:18 pm
ORD
-
SDQ
29h 19m
1 stop
Multiple Airlines Logo
12:41 pm - 10:46 pm
SDQ
-
ORD
11h 05m
1 stop
$358Multiple Airlines
Sat, May 2 - Wed, May 13
Multiple Airlines Logo
5:05 am - 1:29 pm
ORD
-
SDQ
7h 24m
1 stop
Multiple Airlines Logo
12:41 pm - 4:54 pm
SDQ
-
ORD
29h 13m
2 stops
$363Multiple Airlines
Tue, Apr 28 - Sat, May 2
Multiple Airlines Logo
5:05 am - 1:29 pm
ORD
-
SDQ
7h 24m
1 stop
Multiple Airlines Logo
3:35 pm - 11:59 pm
SDQ
-
ORD
9h 24m
1 stop
$367Multiple Airlines
Mon, Apr 27 - Fri, May 1
Spirit Airlines Logo
5:05 am - 1:29 pm
ORD
-
SDQ
7h 24m
1 stop
Spirit Airlines Logo
2:35 pm - 9:05 am
SDQ
-
ORD
19h 30m
2 stops
$372Spirit Airlines
Sun, Apr 26 - Sat, May 2
Spirit Airlines Logo
5:05 am - 1:29 pm
ORD
-
SDQ
7h 24m
1 stop
Spirit Airlines Logo
2:35 pm - 12:24 am
SDQ
-
ORD
10h 49m
1 stop
$378Spirit Airlines
Sun, Sep 6 - Tue, Sep 15
Delta Logo
6:00 am - 1:12 pm
MDW
-
SDQ
6h 12m
1 stop
Delta Logo
2:56 pm - 9:46 pm
SDQ
-
MDW
7h 50m
1 stop
$502Delta
Sat, May 2 - Sat, May 9
Delta Logo
11:18 am - 12:17 am
MDW
-
SDQ
11h 59m
2 stops
Delta Logo
6:05 am - 6:33 pm
SDQ
-
MDW
13h 28m
2 stops
$507Delta
Thu, Aug 6 - Tue, Aug 11
Delta Logo
6:05 am - 1:17 pm
MDW
-
SDQ
6h 12m
1 stop
Delta Logo
2:37 pm - 9:46 pm
SDQ
-
MDW
8h 09m
1 stop
$526Delta
Booking Insights

KAYAK's insights & trends for Chicago to Santo Domingo flights

Get data-powered insights and trends into flights from Chicago to Santo Domingo to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Chicago to Santo Domingo?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago to Santo Domingo departing in April.

What is the cheapest month to fly from Chicago to Santo Domingo?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Santo Domingo, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago to Santo Domingo is February, where tickets cost $382 (return) on average. On the other hand, the most expensive months are December and July, where the average cost of round-trip tickets is $686 and $608 respectively.

How far in advance should I book a flight from Chicago to Santo Domingo?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago to Santo Domingo, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago to Santo Domingo, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 19 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$145
Best time to beat the crowds with an average 7% drop in price.
Most popular time to fly with an average 19% increase in price.
Flight from Chicago O'Hare Airport to Santo Domingo

When to book flights from Chicago to Santo Domingo

Are your dates flexible? Find out the best times to travel from Chicago to Santo Domingo based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Chicago to Santo Domingo

  • What is the cheapest flight from Chicago to Santo Domingo?

    In the last 3 days, the lowest price for a flight from Chicago to Santo Domingo was $132 for a one-way ticket and $344 for a round-trip.

  • Do I need a passport to fly between Chicago and Santo Domingo?

    Yes, you’ll need a passport to travel to Santo Domingo from Chicago.

  • Which airports will I be using when flying from Chicago to Santo Domingo?

    Chicago is served by 2 major airports and there is only 1 main airport in Santo Domingo. You will leave Chicago from one of these airports: Chicago Midway or Chicago O'Hare Intl. You will be arriving at Santo Domingo Las Americas.

  • Which aircraft models fly most regularly from Chicago to Santo Domingo?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Chicago to Santo Domingo?

    SkyTeam, Star Alliance, and oneworld are the airline alliances operating flights between Chicago and Santo Domingo, with SkyTeam being the most commonly used for this route.

  • Which is the best airline for flights from Chicago to Santo Domingo, Delta or American Airlines?

    The two airlines most popular with KAYAK users for flights from Chicago to Santo Domingo are Delta and American Airlines. With an average price for the route of $570 and an overall rating of 7.9, Delta is the most popular choice. American Airlines is also a great choice for the route, with an average price of $519 and an overall rating of 7.1.

  • How does KAYAK find such low prices on flights from Chicago to Santo Domingo?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Santo Domingo.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Santo Domingo?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Santo Domingo from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Santo Domingo?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Santo Domingo with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Santo Domingo?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Santo Domingo from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 3 airlines serving from Chicago to Santo Domingo

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Santo Domingo. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Chicago to Santo Domingo? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.9
DeltaOverall score based on 8407 reviews
7.8Entertainment
8.1Boarding
7.2Food
7.9Comfort
8.5Crew
Airline reviews

No entertainment. Plane was so small had to pink tag a carry on ive used for 20 years easily on board. The fact the flight got in at midnight, had to wait for crew in fort wayne to allow the plane to approach the gate, THEN had to wait for bag on jet bridge made experience irritating at best.

4.0 OkayRay, Apr 2026
ATL - FWA
Read more Delta reviews

No entertainment. Plane was so small had to pink tag a carry on ive used for 20 years easily on board. The fact the flight got in at midnight, had to wait for crew in fort wayne to allow the plane to approach the gate, THEN had to wait for bag on jet bridge made experience irritating at best.

Crew was great. Near on time departure and early arrival. Snacks are always meh. Not a fan of the "pay for everything including miles " proposal unless base flight rate going to be 100 bucks.

Would have been better if there was a nonstop flight from Tampa to Norfolk or Tampa to New Port News.

Overall Good! The weather delayed our takeoff from Atlanta and our arrival in Miami! If Mother Nature can mess up a flight she will do it every time!

The flight was smooth, the crew was great but the plane was quite old

Everything was great until I lost my water bottle and they can’t seem to locate it. I know I left it on the plane though.

WiFi didn’t work most of the time. The usb chargers would work only occasionally for 5 mins and wouldn’t charge after that. Had to keep trying repeatedly at each of the seats in the row.

The crew bent over backwards to thank us for flying and make us comfortable. The food service was quick and efficient. The Captain communicated and said goodbye and thank you as we departed. They really stood out!

Okay considering we had weather delays which the Pilot notified us of immediately!

Generally on time departures and arrivals, clean planes, sky miles membership provides great benefits (complimentary upgrades, etc).

Delays experienced in boarding/take off due to incoming plane delayed. However, the boarding time/depart time in the app was significantly delayed in providing these updates. Usually not updated until an hour after we should have already boarded. Poorly managed.

Moved to earlier flight which unexpectedly had maintenance issues initially indicated as quick fix to ultimately plane changes. Moved back to original flight, also delayed. In all cases customer updates and communication very unclear, no updates on drivers for delays.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

The gate got changed several times and the flight was delayed over an hour. Awful experience

American continues to decline in their customer service and its beyond disappointing.

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

As previously stated the delay I experienced flying from Wichita to Chicago caused a host of issues. When I finally was able to be booked on the last remaining American flight from Chicago to Cincinnati, the gate changed four times with the last change occurring very near the scheduled boarding time. While I didn't have a problem moving from gate to gate, I did notice and make note of others that had mobility issues and had to move each time for the gate change.

Maintenance took a very long time and then we were in a holding pattern. While a one-off maintenance issue is standard, there were delays on both of my flights for this trip based on maintenance issues with the planes, which delayed both flights over 45 minutes. Thankfully, I didn't have any connections but it wasn't an experience that would make me pick AA if I have other options.

No Snacks or Entertainment. The flight was short, snacks should still be given.

Attention to detail. Luggage was lost in flight, after I confirmed it was connecting. Never made it to the destination airport.

They cancelled our flight. 2 hours before we were supposed to take off and offered us nothing! We got our money back and that was it. No other flight to get to our cruise no working with another airline or with us to get there. Terrible customer service, no apology.

We get stuck in the plane when landed during 45min and no communication from the crew People were listening to their phone and music out loud and nobody told them anything I definitely want stop booking spirit flight it is a disaster

Good: It was cheap and they got us to our destination safely. Not so Good: Gates experience with many, many nauseatingly (almost) threatening announcements about bags size and how much they were going to charge us if our bag was too big, even to the point of having a gate agent roaming around through the passengers eyeballing bags size and making people go check their bags in the sizers.

Terrible. The flight was randomly delayed in Chicago causing us to miss our connection and they offered us a flight the next day at 6 am and it would have taken till 345 to get to Pensacola. They didn’t cover any fees. Our bags also supposedly were on the flight to Pensacola and we tried to get them yesterday after driving 6 hours and nobody was available. Worst company ever and will never use them again. Had to pay for a rental. Spirit is claiming in climate weather for the delay but there wasn’t any weather issuesz it’s a bunch of bullshit and I am not happy

Checking in at desk in Chicago was horrible. Person was not friendly never smiled and said my flight was not paid for so I had to give another credit card. Then it ended up that I was charged twice. Then after arriving at my destination had to wait on the phone a long time to speak to a person to fix the double charge! Thank goodness the flight was perfect.

Flight was delayed for 12 h. They should stop overlooking flights.

Horrible we lost a day at the destination. Flight was canceled at 2am left us scrambling for another airline to get us to destination

All of our flights were canceled, though every other airline was flying out and in

it was terrible. flight was cancelled hours before the flight without a given reason and no other booking available .

Everything you need to know for your flight from Chicago to Santo Domingo

Information on your arrival and departure airports