SDQ - CHI

$141 Find Cheap Flights from Santo Domingo to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Santo Domingo to Chicago departing on 4/23. 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 Chicago

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

Cheapest round-trip
$264
Overall average: $335
Multiple Airlines
Thu 4/16Fri 4/17
SDQ - ORD • 1 stop
Cheapest one-way
$141
Typical prices: $258-$288
Multiple Airlines
Thu 4/23
SDQ - ORD • 1 stop
Top airlines
Spirit Airlines
Cheapest • from $313 (round-trip)
American Airlines
Best reviews • 7.1 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between Santo Domingo and Chicago. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Fort Lauderdale (FLL)
Cheapest • Avg $296 (round-trip)
Atlanta (ATL)
Shortest trip • 7h 07m (one-way)
Insights
Insights
Insights
Insights
When to travel
February
Cheapest • 19% price drop
September
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
Flight Deals
Booking Insights
Flight Deals

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

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Santo Domingo to Chicago 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 Santo Domingo to Chicago

Thu, Apr 16 - Fri, Apr 17
Multiple Airlines Logo
3:30 pm - 11:40 pm
SDQ
-
ORD
9h 10m
1 stop
Multiple Airlines Logo
6:45 am - 3:45 pm
ORD
-
SDQ
8h 00m
1 stop
$264Multiple Airlines
Tue, Apr 21 - Tue, May 5
Multiple Airlines Logo
3:44 pm - 9:17 pm
SDQ
-
ORD
30h 33m
1 stop
Multiple Airlines Logo
1:27 pm - 2:39 pm
ORD
-
SDQ
24h 12m
1 stop
$287Multiple Airlines
Mon, Mar 23 - Tue, Mar 31
Multiple Airlines Logo
2:52 am - 10:36 am
SDQ
-
ORD
8h 44m
1 stop
Multiple Airlines Logo
4:51 pm - 4:29 pm
ORD
-
SDQ
22h 38m
1 stop
$295Multiple Airlines
Wed, Apr 22 - Tue, May 5
Multiple Airlines Logo
3:44 pm - 12:14 am
SDQ
-
ORD
9h 30m
1 stop
Multiple Airlines Logo
1:27 pm - 2:39 pm
ORD
-
SDQ
24h 12m
1 stop
$296Multiple Airlines
Fri, Apr 17 - Wed, Apr 22
Multiple Airlines Logo
3:44 pm - 10:54 pm
SDQ
-
ORD
8h 10m
1 stop
Multiple Airlines Logo
1:27 pm - 2:39 pm
ORD
-
SDQ
24h 12m
1 stop
$301Multiple Airlines
Wed, Apr 8 - Sun, Apr 12
Multiple Airlines Logo
3:01 pm - 9:50 am
SDQ
-
ORD
19h 49m
1 stop
Multiple Airlines Logo
4:51 pm - 1:56 pm
ORD
-
SDQ
20h 05m
1 stop
$303Multiple Airlines
Fri, Apr 24 - Thu, May 7
Multiple Airlines Logo
3:44 pm - 9:17 pm
SDQ
-
ORD
30h 33m
1 stop
Multiple Airlines Logo
3:52 pm - 4:29 pm
ORD
-
SDQ
23h 37m
1 stop
$308Multiple Airlines
Thu, Apr 16 - Mon, Apr 20
Spirit Airlines Logo
3:44 pm - 12:14 am
SDQ
-
ORD
9h 30m
1 stop
Spirit Airlines Logo
5:05 am - 2:39 pm
ORD
-
SDQ
8h 34m
1 stop
$313Spirit Airlines
Wed, Apr 8 - Sun, Apr 12
Frontier Logo
4:08 pm - 8:07 pm
SDQ
-
MDW
28h 59m
1 stop
Frontier Logo
5:05 am - 10:07 am
MDW
-
SDQ
28h 02m
1 stop
$391Frontier
Mon, Apr 6 - Fri, Apr 10
Frontier Logo
4:08 pm - 8:07 pm
SDQ
-
MDW
28h 59m
1 stop
Frontier Logo
6:00 am - 2:53 pm
MDW
-
SDQ
7h 53m
1 stop
$426Frontier
Booking Insights

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

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

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Santo Domingo to Chicago, 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 Santo Domingo to Chicago is February, where tickets cost $403 (return) on average. On the other hand, the most expensive months are March and June, where the average cost of round-trip tickets is $679 and $517 respectively.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Santo Domingo to Chicago, 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 Santo Domingo to Chicago, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 23 weeks before departure.

Find deals

Good to know

Low seasonJanuary
Cheapest flight$141
Best time to beat the crowds but there is an average 1% increase in price.
Most popular time to fly and prices are also 10% lower on average.
Flight from Santo Domingo to Chicago O'Hare Airport

When to book flights from Santo Domingo to Chicago

Are your dates flexible? Find out the best times to travel from Santo Domingo to Chicago 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 Santo Domingo to Chicago

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

    In the last 3 days, the lowest price for a flight from Santo Domingo to Chicago was $141 for a one-way ticket and $264 for a round-trip.

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

    A passport is required to fly from Santo Domingo to Chicago.

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

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

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

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

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

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

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

    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 Santo Domingo to Chicago.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Santo Domingo 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 Santo Domingo to Chicago?

    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 Chicago with an airline and back to Santo Domingo with another airline.

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

    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 Chicago from Santo Domingo up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from Santo Domingo to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Santo Domingo to Chicago. 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 Santo Domingo to Chicago? 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.
7.1
American AirlinesOverall score based on 11345 reviews
7.5Boarding
6.9Entertainment
8.0Crew
7.2Comfort
6.4Food
Airline reviews

The gate agent had a really bad attitude and refused to help me get on the standby list. She just handed me a card and said I needed to call a number. I asked her to help with the AA app on my phone and she just shrugged and said she didnt know. After a few phone calls, I eventually just went to a different gate agent on the other side of the terminal and got the help I needed.

2.0 MediocreMarius, Feb 2026
LGA - ORD
Read more American Airlines reviews

The gate agent had a really bad attitude and refused to help me get on the standby list. She just handed me a card and said I needed to call a number. I asked her to help with the AA app on my phone and she just shrugged and said she didnt know. After a few phone calls, I eventually just went to a different gate agent on the other side of the terminal and got the help I needed.

Overall, my last three trips on American Airlines have all been either delayed or "rescheduled" due to mechanical issues. At least on delay caused me to miss two possible connecting flights each later than the first. My last option for my last connection required the assistance of the onsite service desk (O'Hare Airport). The wait time for the service desk was such that it jeopardized getting booked on the last connecting flight available for the night. Suffice it to say, my latest experiences with American Airlines have caused me extensive loss of productive business and personal time and can therefore be classified as significantly less than satisfactory.

Waiting for gate in RDU for more than 20mins is crazy.

American Airlines was great and worked very hard to change my ticket so I could get an earlier, direct flight back to Dallas. However, I was informed that Kayak made mistakes with my itinerary and classified my ticket as desiring to be on the earlier flight instead of taking the necessary step of calling AA to get me on the standby list. This ended up keeping me from being added to the standby list and delayed me getting home by 6 hours. I am happy to discuss this further with Kayak so they can correct their procedures so this won't happen again.

Waited for oxygen tanks for 30 minutes after boarding was complete.

We flew in first class. The crew did not offer drinks before the flight took off, but they treated us well during the flight. The food was excellent. There was actually too much food served, but it was nice to have all the options.

Flight from CHI to PVD was delayed by over 20 hours.

Update to handle the delay was very bad, crews no smiles or welcome or thanks. Don’t care attitude

Pilot navigated severe weather/snow storm with skill. Described his intentions clearly

Little warm on the plane and delayed for an hour

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

Information on your arrival and departure airports

Santo Domingo (SDQ)