SDQ - CHI

$218 Find Cheap Flights from Santo Domingo to Chicago - Compare and Save

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 8/28. 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

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Everything you should know

Cheapest round-trip
$388
Typical prices: $448-$527
Multiple Airlines
Thu 10/29Sun 11/1
SDQ - ORD • 1 stop
Cheapest one-way
$218
Typical prices: $237-$333
Multiple Airlines
Fri 8/28
SDQ - ORD • 1 stop
Top airlines
Delta
Cheapest • from $425 (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 $386 (round-trip)
Atlanta (ATL)
Shortest trip • 7h 07m (one-way)
Insights
Insights
Insights
Insights
When to travel
August
Cheapest • 39% price drop
September
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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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, Oct 29 - Sun, Nov 1
Multiple Airlines Logo
1:45 pm - 11:40 pm
SDQ
-
ORD
10h 55m
1 stop
Multiple Airlines Logo
3:20 am - 4:45 pm
ORD
-
SDQ
11h 25m
1 stop
$388Multiple Airlines
Mon, Aug 17 - Sun, Aug 23
Multiple Airlines Logo
12:41 pm - 12:50 pm
SDQ
-
ORD
49h 09m
2 stops
Multiple Airlines Logo
12:44 am - 4:29 pm
ORD
-
SDQ
14h 45m
1 stop
$403Multiple Airlines
Mon, Aug 31 - Sun, Sep 6
Multiple Airlines Logo
12:41 pm - 12:50 pm
SDQ
-
ORD
49h 09m
2 stops
Multiple Airlines Logo
12:44 am - 4:29 pm
ORD
-
SDQ
14h 45m
1 stop
$417Multiple Airlines
Mon, Aug 31 - Sun, Sep 6
Multiple Airlines Logo
12:41 pm - 12:50 pm
SDQ
-
ORD
49h 09m
2 stops
Multiple Airlines Logo
12:44 am - 4:29 pm
ORD
-
SDQ
14h 45m
1 stop
$418Multiple Airlines
Wed, Aug 26 - Sat, Aug 29
Delta Logo
2:53 pm - 11:57 pm
SDQ
-
ORD
10h 04m
1 stop
Delta Logo
5:30 am - 1:28 pm
ORD
-
SDQ
6h 58m
1 stop
$425Delta
Tue, Aug 25 - Sat, Sep 5
Delta Logo
2:53 pm - 10:36 pm
SDQ
-
MDW
8h 43m
1 stop
Delta Logo
6:05 am - 1:28 pm
MDW
-
SDQ
6h 23m
1 stop
$425Delta
Tue, Oct 27 - Wed, Nov 4
JetBlue Logo
4:28 pm - 11:44 pm
SDQ
-
ORD
8h 16m
1 stop
JetBlue Logo
2:35 pm - 12:59 am
ORD
-
SDQ
8h 24m
1 stop
$426JetBlue
Tue, Sep 22 - Fri, Sep 25
Delta Logo
2:53 pm - 10:37 am
SDQ
-
ORD
20h 44m
2 stops
Delta Logo
5:30 am - 1:27 pm
ORD
-
SDQ
6h 57m
1 stop
$435Delta
Thu, Aug 27 - Tue, Sep 1
JetBlue Logo
5:01 am - 1:39 pm
SDQ
-
ORD
9h 38m
1 stop
JetBlue Logo
7:00 am - 3:23 pm
ORD
-
SDQ
7h 23m
1 stop
$441JetBlue
Thu, Nov 5 - Mon, Nov 9
American Airlines Logo
4:59 pm - 12:38 am
SDQ
-
ORD
9h 39m
1 stop
American Airlines Logo
7:10 pm - 12:12 pm
ORD
-
SDQ
15h 02m
1 stop
$444American Airlines
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.

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

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

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 August, where tickets cost $139 (return) on average. On the other hand, the most expensive months are March and October, where the average cost of round-trip tickets is $405 and $290 respectively.

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Good to know

Low seasonJanuary
Cheapest flight$218
Best time to beat the crowds with an average 16% drop in price.
Most popular time to fly and prices are also 14% 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 5 days, the lowest price for a flight from Santo Domingo to Chicago was $218 for a one-way ticket and $388 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?

    oneworld is the only airline alliance operating flights between Santo Domingo and Chicago.

  • 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 11812 reviews
7.5Boarding
7.9Crew
7.2Comfort
6.4Food
6.8Entertainment
Airline reviews

I will never but. through kayak again. and American Airlines. I will never fly again on. They're both thieves.

2.0 MediocreDino, Jul 2026
OMA - ORD
Read more American Airlines reviews

I will never but. through kayak again. and American Airlines. I will never fly again on. They're both thieves.

Nothing, I wont be flying American Airlines again and will not be recommending anyone to fly American Airlines. It was the worst experience flying I've ever had.

My luggage was not sent with us. Not sure if this is Envoy Air responsibility but that was a very BAD experience

The planes can use an actual cleaning. The armrest and seats do not appear to be cleaned on this one and most other planes.

Flight was delayed…once landed at ORD, no gates were available so made us wait for 56 minutes after we landed to let us out of the aircraft!

Very efficient boarding and quick flight. Attendants don’t come by often so would often have a lot of trash at seat.

The flight de-boarded after being informed of a 3 hour delay. The gate agent said we could go to lounge. The flight ended up boarding 20 minutes later and I missed it.

They should have MSNBC available on board. A 4- hour flight should provide more than a cookie.

Even though there was space, they made me check out my luggage. It was very annoying. That’s the reason I bring a carry on so that I don’t have to check out my luggage!!!!

Pilots were very conscious about giving us a smooth flight

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

Information on your arrival and departure airports

Santo Domingo (SDQ)