SDQ - CHI

$146 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 4/24. 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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 24% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$377
Typical prices: $759-$493
Multiple Airlines
Mon 6/15Tue 6/23
SDQ - ORD • 1 stop
Cheapest one-way
$146
Typical prices: $270-$423
Spirit Airlines
Fri 4/24
SDQ - ORD • 1 stop
Top airlines
Cheapest • from $400 (round-trip)
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
Cheapest • Avg $330 (round-trip)
Shortest trip • 7h 07m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 36% 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 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

Mon, Jun 15 - Tue, Jun 23
Multiple Airlines Logo
12:41 pm - 3:11 pm
SDQ
-
ORD
27h 30m
1 stop
Multiple Airlines Logo
1:50 pm - 5:29 am
ORD
-
SDQ
14h 39m
1 stop
$377Multiple Airlines
Thu, May 7 - Sun, May 10
Multiple Airlines Logo
4:01 pm - 11:38 pm
SDQ
-
ORD
8h 37m
1 stop
Multiple Airlines Logo
9:20 am - 11:05 am
ORD
-
SDQ
24h 45m
2 stops
$379Multiple Airlines
Thu, May 7 - Sun, May 10
Multiple Airlines Logo
4:01 pm - 11:38 pm
SDQ
-
ORD
8h 37m
1 stop
Multiple Airlines Logo
5:49 pm - 4:29 pm
ORD
-
SDQ
21h 40m
1 stop
$384Multiple Airlines
Thu, Jun 11 - Tue, Jun 23
Multiple Airlines Logo
5:02 pm - 11:56 pm
SDQ
-
ORD
7h 54m
1 stop
Multiple Airlines Logo
1:50 pm - 5:29 am
ORD
-
SDQ
14h 39m
1 stop
$385Multiple Airlines
Thu, May 7 - Sun, May 10
Multiple Airlines Logo
4:01 pm - 11:38 pm
SDQ
-
ORD
8h 37m
1 stop
Multiple Airlines Logo
7:30 am - 4:29 pm
ORD
-
SDQ
31h 59m
2 stops
$387Multiple Airlines
Fri, May 8 - Fri, May 15
Multiple Airlines Logo
10:19 am - 11:56 pm
SDQ
-
ORD
14h 37m
1 stop
Multiple Airlines Logo
5:30 pm - 7:18 pm
ORD
-
SDQ
24h 48m
2 stops
$392Multiple Airlines
Sat, May 2 - Wed, May 6
Delta Logo
2:37 pm - 10:28 pm
SDQ
-
MDW
8h 51m
1 stop
Delta Logo
6:00 am - 1:12 pm
MDW
-
SDQ
6h 12m
1 stop
$561Delta
Mon, May 11 - Wed, Sep 9
Delta Logo
2:49 pm - 9:09 pm
SDQ
-
MDW
7h 20m
1 stop
Delta Logo
6:00 am - 1:12 pm
MDW
-
SDQ
6h 12m
1 stop
$585Delta
Tue, May 12 - Fri, May 15
Delta Logo
2:49 pm - 8:43 am
SDQ
-
MDW
18h 54m
2 stops
Delta Logo
6:36 pm - 1:23 pm
MDW
-
SDQ
17h 47m
2 stops
$591Delta
Tue, Jun 30 - Tue, Jul 14
Frontier Logo
12:21 pm - 10:11 pm
SDQ
-
MDW
34h 50m
2 stops
Frontier Logo
12:27 pm - 11:06 am
MDW
-
SDQ
45h 39m
2 stops
$633Frontier
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 June.

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 $309 (return) on average. On the other hand, the most expensive months are March and June, where the average cost of round-trip tickets is $665 and $517 respectively.

Good to know

Low seasonJanuary
Cheapest flight$146
Best time to beat the crowds with an average 8% drop in price.
Most popular time to fly with an average 3% increase in price.
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 $146 for a one-way ticket and $377 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 11569 reviews
6.9Entertainment
6.4Food
7.9Crew
7.5Boarding
7.2Comfort
Airline reviews

The new planes (American Eagle) are beautiful and especially comfortable. The flight attendants are consistently professional and courteous. And, while it may seem inconsequential, the new liquid tube of coffee creamer—in contrast to the powdered coffee creamer—makes all the difference in a cup of coffee.

10.0 ExcellentDeborah Jacqueline Diana, Apr 2026
MIA - ORD
Read more American Airlines reviews

The new planes (American Eagle) are beautiful and especially comfortable. The flight attendants are consistently professional and courteous. And, while it may seem inconsequential, the new liquid tube of coffee creamer—in contrast to the powdered coffee creamer—makes all the difference in a cup of coffee.

I'm not sure American is capable of on-time arrivals and departures. When you land at ORD, you almost always get held on the tarmac because your gate is still occupied. I may have missed my connection, but that ended up up being significantly delayed as well. Once again, I finally got home well after midnight.

Didn't make it back on American Airlines due to a maintenance issue. The communication and updates were terrible. I ended up returning on Aero Mexico which had a much nicer aircraft with a large entertainment screen with movies and shows AND they had a nice inflight meal. That was a treat after being delayed 26 hours! I think some additional flight miles, or something should be offered for that long of a delay ---it was not pleasant at all---very physical and emotional experience.

Crew at the gate was very crabby and not at all polite. The plane was very hot the entire flight. And the seat cushion was very worn out.

The staff are very, very professional. It's what flying should feel like.

Flight was delayed half hour before boarding, but when I checked flight aware the plane that would Pick us up had a delay of more than an hour. AA should let us know in advance to avoid waiting several hours in the airport

Delays with no explanation. It could have been handled better.

Jill was the flight attendant in first class she was fabulous!! Best flight attendant I have had in years.!! And I fly every other week. Other can learn from her!!

As a first class customer, there was no power the entire flight which limited my ability to work. I find this unacceptable. The first 11 rows on the left side of the plan were out. I was only offered the option to charge my phone which was not the issue because my laptop was out of power. I asked if there was anything that can be done for me, and the answer was, "no". I was not offered any type of compensation for this AA problem which caused me unnecessary stress due to inability to address business issues on an already challenging travel day. Flight attendants tried to reset the power once but that was the extent of their support. Very disappointing for the lack of expected services on a flight. Please contact me with customer focused response to this complaint.

There was no inflight service. Once we landed we were delayed to find a gate for an hour and a half which was 1/2 the total time in the air.

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

Information on your arrival and departure airports