CHI - SDQ

$154 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 8/9. 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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$332
Typical prices: $405-$554
Multiple Airlines
Fri 8/28Sat 9/5
ORD - SDQ • 1 stop
Cheapest one-way
$154
Typical prices: $205-$239
Multiple Airlines
Sun 8/9
ORD - SDQ • 1 stop
Top airlines
Cheapest • from $359 (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 $387 (round-trip)
Shortest trip • 6h 20m (one-way)
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 3 weeks in advance save around 25% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 63% 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

Fri, Aug 28 - Sat, Sep 5
Multiple Airlines Logo
12:29 am - 7:18 pm
ORD
-
SDQ
17h 49m
1 stop
Multiple Airlines Logo
3:30 pm - 10:26 pm
SDQ
-
ORD
7h 56m
1 stop
$332Multiple Airlines
Sat, Aug 29 - Fri, Sep 4
Multiple Airlines Logo
12:12 pm - 9:40 pm
ORD
-
SDQ
8h 28m
1 stop
Multiple Airlines Logo
1:40 am - 11:12 am
SDQ
-
ORD
10h 32m
1 stop
$335Multiple Airlines
Sun, Nov 1 - Fri, Nov 6
Multiple Airlines Logo
3:20 am - 4:45 pm
ORD
-
SDQ
11h 25m
1 stop
Multiple Airlines Logo
1:40 am - 8:57 am
SDQ
-
ORD
9h 17m
1 stop
$345Multiple Airlines
Sun, Nov 1 - Thu, Nov 12
JetBlue Logo
2:35 pm - 12:59 am
ORD
-
SDQ
8h 24m
1 stop
JetBlue Logo
2:28 pm - 11:44 pm
SDQ
-
ORD
11h 16m
1 stop
$359JetBlue
Wed, Aug 12 - Sat, Aug 29
JetBlue Logo
2:35 pm - 11:59 pm
ORD
-
SDQ
8h 24m
1 stop
JetBlue Logo
1:34 pm - 11:44 pm
SDQ
-
ORD
11h 10m
1 stop
$363JetBlue
Mon, Sep 14 - Mon, Sep 21
JetBlue Logo
6:00 am - 2:49 pm
ORD
-
SDQ
7h 49m
1 stop
JetBlue Logo
3:59 pm - 11:31 pm
SDQ
-
ORD
8h 32m
1 stop
$367JetBlue
Wed, Aug 5 - Wed, Aug 19
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
$388Delta
Wed, Nov 11 - Wed, Nov 18
Delta Logo
6:00 am - 2:40 pm
MDW
-
SDQ
6h 40m
1 stop
Delta Logo
6:45 am - 6:37 pm
SDQ
-
MDW
13h 52m
2 stops
$393Delta
Tue, Sep 8 - Tue, Sep 15
Delta Logo
6:05 am - 1:27 pm
MDW
-
SDQ
6h 22m
1 stop
Delta Logo
2:56 pm - 10:25 pm
SDQ
-
MDW
8h 29m
1 stop
$424Delta
Thu, Nov 26 - Thu, Dec 3
Delta Logo
9:55 am - 1:35 am
MDW
-
SDQ
13h 40m
2 stops
Delta Logo
6:45 am - 6:37 pm
SDQ
-
MDW
13h 52m
2 stops
$429Delta
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 August.

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 June and May, where the average cost of round-trip tickets is $410 and $352 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 3 weeks before departure, which saves you about 25% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 19 weeks before departure.

Good to know

Low seasonMay
Cheapest flight$154
Best time to beat the crowds but there is an average 3% increase in price.
Most popular time to fly with an average 13% 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 $154 for a one-way ticket and $332 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 $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 $507 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.
7.8
DeltaOverall score based on 8413 reviews
8.5Crew
7.8Entertainment
7.8Comfort
7.2Food
8.1Boarding
Airline reviews

Horrible. Faucet in sink not working, wifi not working. Didn’t bring food or snacks

2.0 MediocreMargaret, Jun 2026
MSY - LGA
Read more Delta reviews

Horrible. Faucet in sink not working, wifi not working. Didn’t bring food or snacks

Flight was delayed before take off and at landing. Baggage took 20 minutes. Flight crew would not serve full soft drink and had to ask multiple times before receiving water.

From checking to boarding, it was a seamless experience. The service agents were so helpful. The flight crew was so pleasant.

Gate agent showed up 20 minutes before boarding and was not at all friendly. Had to take this flight due to the one on the day before being cancelled and any later options were already full with long standby lists. Despite having paid for Delta Comfort seats, Delta did not allow me (or anyone) to choose their seat. The agent assigned them for everyone just prior to boarding. Self seat selection was allowed on the original flight. Flight staff was great - very friendly.

Flight attendants were great. Cheerful, upbeat and friendly. Jet, in particular, was fantastic.

I have Precheck. Flew HPN to DEN and return this past weekend. Delta didn't attach my Precheck number to this trip. So it was waiting in general line especially in Denver. Unavailable.

Original flight was delayed, then cancelled and the gate staff did not expedite rebooking. Also, no instructions were given that a ticket number was needed before being called to facilitate rebooking. This could have been much more organized.

Be on time? When not on time a circling for over an hour offer more than 1 bag of chips to the passengers? It was a 7 hour flight by the time we got done.

Five hour delays every hour, I wish it were all at once

Flight delayed four separate times. I’m now one hour hours late to landing.

Delayed by 5 hours and I had to wit in the airport for more than 6+ hours.

I’ve got 31F seat and window seat . My 2 co passengers was AA crew members and they were very rude attitude and when I was going to use bathroom their gestures was very different and awkward and the guy beside me completely occupied the hand rest and I was really uncomfortable

It was so much better than expected, Ohare is not such a pleasant experience but American Airlines with the new, clean aeroplane and free Wi-Fi was outstanding and the crew so pleasant and helpful.

It wa sort of on time; the cab was left with some trash

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 tried to book a flight with Jet Blue. Your third party company hijacked my attempt with a website that looked like I was booking with Jet Blue. I realized it when I paid. I tried to cancel and was told by a man in India that there were no refunds. $735 stolen, Thanks Kayak!

It was inexplicably canceled and we are stuck in LA, haven't gotten home and it has been an inconvenience having lost work (on unpaid leave for my husband).

I like everything. Blythe at DCA is the absolute best!

JetBlue worker, Blythe, was so amazing at the DCA counter. If it wasn’t for her, I’m not sure we would’ve made it through. Please thank her!

They lost my luggage and refuse to help. Terrible airline. I've never experienced worse customer service in my life. Pretty much just told me too bad that I lost all my luggage, not caring that I am stuck in Europe for 2 weeks with absolutely nothing.

You should have had Wifi to make it much enjoyable.

The flight out was delayed from 3:40pm to 5pm and again to 8pm. We boarded after 5pm, had to disembark because they could not get the Engine started, then we switched gates and got a new plane and did not board until after 8pm.

The flight was delayed after already taxiing from the gate due to a malfunction. After 3 hours we were told the flight was canceled. The next flight available was Sunday. My daughter and I stayed overnight in the airport due to this issue. I was given a $12 meal voucher. Unacceptable

Whole experience was poor. Delayed 2 hours. Lied about the delays. Was all jet blues fault and tried to blame on air traffic control. Sent out other let trips and wouldn't allow people to switch aircraft.

My bag was not loaded on my flight. it was not communicated to me until i was waiting for my bag at my destination. there was no confirmation of when my bag was arriving and no way to track it.

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

Information on your arrival and departure airports