CHI - SDQ

$157 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 9/9. 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
$346
Typical prices: $453-$330
JetBlue
Wed 10/28Wed 11/4
ORD - SDQ • 1 stop
Cheapest one-way
$157
Typical prices: $199-$234
JetBlue
Wed 9/9
ORD - SDQ • 1 stop
Top airlines
Cheapest • from $346 (round-trip)
Best reviews • 7.8 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 $401 (round-trip)
Shortest trip • 6h 29m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 61% 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

Wed, Oct 28 - Wed, Nov 4
JetBlue Logo
2:35 pm - 11:59 pm
ORD
-
SDQ
8h 24m
1 stop
JetBlue Logo
2:28 pm - 11:44 pm
SDQ
-
ORD
11h 16m
1 stop
$346JetBlue
Tue, Jul 28 - Thu, Jul 30
JetBlue Logo
2:35 pm - 11:59 pm
ORD
-
SDQ
8h 24m
1 stop
JetBlue Logo
5:01 am - 1:39 pm
SDQ
-
ORD
9h 38m
1 stop
$347JetBlue
Mon, Aug 10 - Wed, Aug 12
JetBlue Logo
2:35 pm - 11:59 pm
ORD
-
SDQ
8h 24m
1 stop
JetBlue Logo
5:01 am - 1:39 pm
SDQ
-
ORD
9h 38m
1 stop
$353JetBlue
Sat, Sep 26 - Tue, Oct 6
JetBlue Logo
7:00 am - 3:16 pm
ORD
-
SDQ
7h 16m
1 stop
JetBlue Logo
5:01 am - 1:39 pm
SDQ
-
ORD
9h 38m
1 stop
$355JetBlue
Mon, Sep 14 - Sat, Sep 19
JetBlue Logo
2:35 pm - 11:59 pm
ORD
-
SDQ
8h 24m
1 stop
JetBlue Logo
1:32 pm - 11:44 pm
SDQ
-
ORD
11h 12m
1 stop
$363JetBlue
Tue, Sep 29 - Wed, Sep 30
JetBlue Logo
2:35 pm - 11:59 pm
ORD
-
SDQ
8h 24m
1 stop
JetBlue Logo
5:01 am - 1:39 pm
SDQ
-
ORD
9h 38m
1 stop
$368JetBlue
Sun, Aug 30 - Tue, Sep 8
JetBlue Logo
2:35 pm - 11:59 pm
ORD
-
SDQ
8h 24m
1 stop
JetBlue Logo
4:44 pm - 11:44 pm
SDQ
-
ORD
8h 00m
1 stop
$373JetBlue
Tue, Jul 28 - Thu, Aug 6
JetBlue Logo
2:35 pm - 11:59 pm
ORD
-
SDQ
8h 24m
1 stop
JetBlue Logo
5:01 am - 1:39 pm
SDQ
-
ORD
9h 38m
1 stop
$375JetBlue
Thu, Aug 13 - Mon, Aug 24
Delta Logo
6:05 am - 1:28 pm
MDW
-
SDQ
6h 23m
1 stop
Delta Logo
2:53 pm - 10:36 pm
SDQ
-
MDW
8h 43m
1 stop
$502Delta
Tue, Oct 13 - Thu, Oct 15
Delta Logo
6:00 am - 6:24 pm
MDW
-
SDQ
11h 24m
2 stops
Delta Logo
2:56 pm - 12:33 pm
SDQ
-
MDW
22h 37m
2 stops
$507Delta
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 October.

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 January, where tickets cost $84 (return) on average. On the other hand, the most expensive months are May and June, where the average cost of round-trip tickets is $352 and $314 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 seasonApril
Cheapest flight$157
Best time to beat the crowds but there is an average 1% increase in price.
Most popular time to fly with an average 15% 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 5 days, the lowest price for a flight from Chicago to Santo Domingo was $157 for a one-way ticket and $346 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?

    Star Alliance, SkyTeam, and oneworld are the airline alliances operating flights between Chicago and Santo Domingo, with Star Alliance 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 $555 and an overall rating of 7.8, Delta is the most popular choice. American Airlines is also a great choice for the route, with an average price of $503 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 airlines flying 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.
7.8
DeltaOverall score based on 8395 reviews
7.2Food
8.5Crew
7.8Comfort
7.8Entertainment
8.1Boarding
Airline reviews

Connection flights should be spaced out farther because too close I missed my connection.

8.0 ExcellentAnonymous, Jun 2026
PHL - ATL
Read more Delta reviews

Connection flights should be spaced out farther because too close I missed my connection.

Definitely a southern flavor. Cordiality was evident even though no drinks or snacks were served.

On time! There were plenty of airport employees who were able to keep us moving in the right direction. The crew on the plane were professional.

Left /arrived on time. Decent seat space. Like the wifi/plugs and entertainment. Windows and tray table were kinda gross. Attendants didn't start snack service til 40mins before landing. Two rows before us, captain came on to say there's turbulence and recalled staff to seats. So, no drink/snack. Later, attendants didn't stop to see if we had trash nor even look our way. Felt invisible! Almost all pilot announcements were not only unintelligible, but so quiet. We had no idea what she said.

Average seat comfort, a drink and chips were provided, early boarding because we checked a carryon at the gate was nice. Ticket pricing shenanigans, including fees to pick a seat, check a bag, and get food onboard - evidence the industry is reinvigorating last century’s strategies- destroys the experience before one ever arrives at the airport. It’s difficult to recognize any value or sustain loyalty in the end-to-end process making air travel more drudgery than pleasure.

Gate agent was unhelpful for handicapped boarding. Flight attendant seemed untrained.

No service flight that took 5 hrs and a stop at an unscheduled airport. Crew and pilots did their jobs

Clean planes and not take my comfort class seat away.

The crew were efficient. The pilots seemed professional. It was a bit chilly in our seats. The sheet provided weren’t very helpful.

Weather caused a long delay, but the efficiency and updates from the pilot were helpful. We were able to make our connection fortunately.

My pillow had a shoe print on it, when I asked if I can have another pillow, I was told “I’m sorry but it is one pillow per guest, do YOU want to turn it inside out” to which I responded , no thanks I will go without. This is generally not ok, but For the price tag I paid flying business this is absolutely unacceptable. Hopefully American Airlines can update their accommodations to bedding that is not tossed on the ground and stepped on, or at least have a couple of extra pillows in hand, incase someone had decided to step on the pillows for what ever reason

American Airlines II: Delay Boogaloo. Multiple gate changes, delays, boarded and then MORE delays. I hate to say this won’t matter, but posting stuff about major corporations in 2026 is a post-modern “scream into the void.” Was multiple hours late coming home, so there you go.

Our flight was cancelled while we are on our way to the airport. So, no notice. We were rescheduled to another airline with a 2 hour later takeoff and so arrived at our destination on time. We pre-paid American Airlines $190 to upgrade our seats. No refund. So no use for AA or Kayak.

Terrible, horrible, disappointing- without telling us they changed planes and moved and separated our seats to opposite sides - said they changed seats putting us together - got to airport to find no, they did not - we sat opposing sides of plane - food overly salty to inedible, never saw stewardess but once - it was terrible

The airplane was an old model, the overhead didn’t have enough room for people’s items and made boarding and boarding disappointing and stressful. Crew allowed passengers to bring more than the permitted baggage sizes.

Original flight was on time, then late, then changed gates...4 times. Once our newest plane came in, it was fine.

I almost missed my flight and they helped me out enormously

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.

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

Information on your arrival and departure airports