CHI - SDQ

$130 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 4/29. 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
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Everything you should know

Cheapest round-trip
$301
Overall average: $586
Multiple Airlines
Mon 3/9Tue 3/17
ORD - SDQ • 1 stop
Cheapest one-way
$130
Multiple Airlines
Wed 4/29
MDW - SDQ • 1 stop
Top airlines
Spirit Airlines
Cheapest • from $320 (round-trip)
Delta
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
Bogotá (BOG)
Cheapest • Avg $446 (round-trip)
Atlanta (ATL)
Shortest trip • 6h 21m (one-way)
Insights
Insights
Insights
Insights
When to book
4 weeks
in advance
Our data shows that travelers who book at least 4 weeks in advance save around 17% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
August
Cheapest • 15% price drop
March
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, Mar 9 - Tue, Mar 17
Multiple Airlines Logo
6:45 am - 4:55 pm
ORD
-
SDQ
9h 10m
1 stop
Multiple Airlines Logo
3:25 pm - 11:40 pm
SDQ
-
ORD
9h 15m
1 stop
$301Multiple Airlines
Mon, Apr 20 - Wed, Apr 29
Multiple Airlines Logo
1:27 pm - 2:39 pm
ORD
-
SDQ
24h 12m
1 stop
Multiple Airlines Logo
3:44 pm - 9:17 pm
SDQ
-
ORD
30h 33m
1 stop
$303Multiple Airlines
Mon, Apr 13 - Mon, Apr 20
Multiple Airlines Logo
4:30 am - 4:55 pm
ORD
-
SDQ
11h 25m
1 stop
Multiple Airlines Logo
3:44 pm - 9:17 pm
SDQ
-
ORD
30h 33m
1 stop
$304Multiple Airlines
Sat, Apr 25 - Mon, Apr 27
Multiple Airlines Logo
1:27 pm - 2:39 pm
ORD
-
SDQ
24h 12m
1 stop
Multiple Airlines Logo
3:44 pm - 11:22 am
SDQ
-
ORD
20h 38m
1 stop
$306Multiple Airlines
Sat, Apr 18 - Sat, Apr 25
Multiple Airlines Logo
5:09 pm - 5:29 am
ORD
-
SDQ
11h 20m
1 stop
Multiple Airlines Logo
3:35 pm - 11:59 pm
SDQ
-
ORD
9h 24m
1 stop
$313Multiple Airlines
Fri, Apr 24 - Mon, Apr 27
Multiple Airlines Logo
1:43 pm - 11:17 am
ORD
-
SDQ
20h 34m
1 stop
Multiple Airlines Logo
3:44 pm - 9:17 pm
SDQ
-
ORD
30h 33m
1 stop
$314Multiple Airlines
Tue, Apr 28 - Sun, May 3
Multiple Airlines Logo
1:27 pm - 2:39 pm
ORD
-
SDQ
24h 12m
1 stop
Multiple Airlines Logo
3:44 pm - 11:57 pm
SDQ
-
ORD
9h 13m
1 stop
$317Multiple Airlines
Fri, May 1 - Sun, May 3
Multiple Airlines Logo
6:45 am - 3:45 pm
ORD
-
SDQ
8h 00m
1 stop
Multiple Airlines Logo
1:55 pm - 10:10 pm
SDQ
-
ORD
9h 15m
1 stop
$318Multiple Airlines
Mon, Apr 20 - Fri, May 15
Spirit Airlines Logo
5:05 am - 2:39 pm
ORD
-
SDQ
8h 34m
1 stop
Spirit Airlines Logo
3:44 pm - 12:14 am
SDQ
-
ORD
9h 30m
1 stop
$320Spirit Airlines
Fri, Apr 10 - Fri, Apr 17
Multiple Airlines Logo
4:51 pm - 1:56 pm
ORD
-
SDQ
20h 05m
1 stop
Multiple Airlines Logo
3:44 pm - 10:54 pm
SDQ
-
ORD
8h 10m
1 stop
$322Multiple Airlines
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.

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 August, where tickets cost $416 (return) on average. On the other hand, the most expensive months are December and March, where the average cost of round-trip tickets is $682 and $578 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 4 weeks before departure, which saves you about 17% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 19 weeks before departure.

Good to know

Low seasonAugust
Cheapest flight$130
Best time to beat the crowds with an average 16% drop in price.
Most popular time to fly with an average 17% increase in price.
Flight from Chicago Midway 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 $130 for a one-way ticket and $301 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 Copa Airlines?

    The two airlines most popular with KAYAK users for flights from Chicago to Santo Domingo are Delta and Copa Airlines. With an average price for the route of $552 and an overall rating of 7.9, Delta is the most popular choice. Copa Airlines is also a great choice for the route, with an average price of $476 and an overall rating of 7.5.

  • 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 4 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 8242 reviews
7.8Entertainment
8.1Boarding
8.5Crew
7.2Food
7.9Comfort
Airline reviews

Everything was good except wifi and a leaking drink chiller. The floor was all wet and my bag was soaked. Did not notice until debarking. Have not heard back from Delta. Even though this was leg one of an international flight in first class, they denied access to their Sky Club - very disappointing!

6.0 GoodAnonymous, Feb 2026
RDU - SEA
Read more Delta reviews

Everything was good except wifi and a leaking drink chiller. The floor was all wet and my bag was soaked. Did not notice until debarking. Have not heard back from Delta. Even though this was leg one of an international flight in first class, they denied access to their Sky Club - very disappointing!

The staff was fine. The plane was extremely tight, and I paid for the wifi and it did not work at all. I was actually going to ask for a refund.

two hour delay and the Delta representative on the PA system was unable to understand

An awesome flight crew. FC seat cushion just doesn’t cut it for a 3+ hour flight.

2+hrs delay without any reason provided and a cramped flight

We waited an hour on the runway to get a gate in Orlando

Flight was delayed by 3-hours and their fix was… complimentary pretzels.

Flight was delayed due to crew being not on time

Flight crew issues delayed my flight by 2 1/2 hours. Causing me to miss my connection.

The staff on board and gate was nice - a welcome change from the usual. We also arrived early, which was a great benefit, given that it takes 30 minutes plus to get bags at SRQ.

There should be a warning regarding the quality of the aircraft on the website as we reserve the tickets. There was no TV or any type of screen onboard. The wifi they offer is good for nothing. Traveling 9 hours straight with kids and no type of entetainment was horrible. I wish I had been informed prior so I could buy a ticket with another airline. The food was a joke too. A very tiny portion per passenger. They also charged $100 per checked bag. With United I used to pay $60. So, fair to say that I wont be flying Copa anymore. Their aircraft was super old, outdated, no entertainment, with nearly no onboard food.

The flight was good overall. Everything went smoothly, although the landing was a bit rough. Still, it was a pleasant experience

Very strict carry on rules meant most of the plane had to gate check their luggage. As is often the case had things that were broken because of this, but I appreciated not being charged to gate check. Otherwise good flight and great crew once on the plane

Some of the Air hostesses are not that friendly. Need improvement

Simply as follows:- First, there was no vegetarian option for the meal Second, only 2 washrooms for the entire economy class.

I liked the meatloaf the chicken was awful but the plane was on time and got there and the staff was nice.

Boarding was quick & efficient; they gave boarding groups due priority; staff & air crew were very cordial and helpful, pleasant flight.

Very happy with my flight. I would definitely recommend it.

Did upgrade, travel in business it was great (more room I could sleep)

Tell people to remain in their seats during the meal/beverage distribution. Enforce boarding by group numbers. No one was checking. Tell people to turn their electronics speakers off. Bigger cups for drinks.

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.

See prior comment about how Kayak mishandled my reservation and delayed my arrival by 6 hours.

Boarding delayed 20 minutes for no reason, no wifi, in flight entertainment, or snacks / waters?

Delayed an hour due to operational issues. Minimal apologies or care for the significant inconvenience caused. Landed at nearly 1am and they still couldn’t find ground staff to get us off the plane promptly.

The aircraft had several problems - from excess fuel to non operational ac. Two hours of delay in Chicago could have been avoided with proper planning and aircraft maintenance.

Crew in Columbia was not prepared for landing. It was a bit of a disaster and getting bags took forever.

We were upgraded to First Class and it was a great flight

I cannot effectively rate the food and drink as I had not. Otherwise, the trip was fine. The seats were nice, the crew was fine. They could smile once in a while. They all look like they were mad.

4 hour delay, 2 hours in the airport and then 2 hours on the tarmac. With a flight full of kids it would have been better to leave us in the airport for the delay, it was crying kids chaos on the flight. Miserable. And no apology or airline credit for the significant delay.

Flight was on time with no issues. Price is very competitive. Flight schedule works well for me

They charged late fees for selecting seats (no $0 options). They also changed my gate within the last half hour and are refusing to reimburse my costs to drive across the country with two small children in a rental car.

I was waiting in line for the restroom onboard, the flight attendant told me to step back two rows and stay on the carpet. She was rude and I expected a tik tok experience with me getting thrown off the plane. She was rude and frankly there was no where else to stand.

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 .

Spirit Airlines has a reputation for being a terrible, cheap airline, this is why. I took a gamble on them, having never flown with them before, and the flight got cancelled. First they delayed the flight about 4 times before finally canceling it because a flight attendant didn’t show up to work that day. That’s so stupid. When I asked a ticketing agent she said that’s “company policy”. A company policy that inconveniences hundreds of passengers because a single flight attendant didn’t show is ridiculous and inefficient. I will never, ever try flying Spirit Airlines again.

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

Information on your arrival and departure airports