Cheap Flights from Chicago to Santo Domingo

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Find the cheapest month or even day of the year to fly to Santo Domingo

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Flight deals from Chicago to Santo Domingo

Looking for a cheap last-minute deal or the best return flight from Chicago to Santo Domingo? Find the lowest prices on one-way and return tickets right here.

Find the cheapest month to fly from Chicago to Santo Domingo

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago to Santo Domingo flights are currently cheapest in November.

Alternative Chicago to Santo Domingo routes

Looking for the cheapest, fastest or easiest route from Chicago to Santo Domingo? You could fly into the following airports instead.

Chicago to Santo Domingo: Flight information

The things to know before you go.
Cheapest flight foundج.م.‏ 6,102
Cheapest month to flyNovember

Finding cheap flights from Chicago to Santo Domingo: Frequently asked questions

There are 3 airports in Santo Domingo: La Isabela International, Santo Domingo Las Americas and Samana.
The best price we found for a return flight from Chicago to Santo Domingo is ج.م.‏ 13,298. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
Currently, there are no airlines that fly direct from Chicago to Santo Domingo. But we found flights with one or more stops from ج.م.‏ 13,298.
As of September 2025, there are no flights flying from Chicago to Santo Domingo.
The cheapest month to fly from Chicago to Santo Domingo is usually November.
If you're flying from Chicago, the cheapest airport near Santo Domingo is Santo Domingo Las Americas – which is 23.4 km away from the centre of Santo Domingo. We've found flights into this airport from ج.م.‏ 13,298.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Santo Domingo on Wednesday, 12 November 2025.
No airlines currently offer direct flights between Chicago and Santo Domingo. Most routes have one or more stops.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Santo Domingo but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Santo Domingo is around 40 days in advance, so don’t leave your flight to the last minute.
In September, the average temperature is usually around 28°C. August is typically the warmest month in Santo Domingo, when it usually averages around 31°C. You can expect the least rain in March. The coldest month is January, with temperatures averaging 21°C. The rainiest month is September.
The cheapest airline that flies to Santo Domingo is Spirit Airlines .

Travelling from Chicago to Santo Domingo: what you need to know

  • There are a couple of main airports to choose from in Chicago. Check out your options leaving from O'Hare International Airport (ORD) or Chicago Midway International Airport (MDW) when reserving your flight from Chicago to Santo Domingo.

  • Las Americas International Airport (SDQ) and Dr. Joaquin Balaguer International Airport (JBQ) are Santo Domingo's primary gateways.

  • Santo Domingo is one hour ahead of Chicago and observes the UTC-4 timezone.

  • To ensure you make your Chicago to Santo Domingo flight, leave plenty of time for things like baggage drop and finding your gate. Arriving two hours before international departures and an hour before domestic flights is a good rule of thumb.

  • You'll likely experience bigger queues in popular months such as August. Arriving up to four hours in advance for an international flight and two hours for domestic departures is a good idea.

How to find the cheapest flights from Chicago to Santo Domingo

  • Booking early is often the key to locking in a cheap Chicago to Santo Domingo flight. Prices tend to rise as demand increases, so the nearer you get to departure, the more you'll likely spend on your ticket.

  • If you can be flexible with your travel dates, use the 'Whole month' tool. It'll give you the lowest price in each month when looking for your plane ticket from Chicago to Santo Domingo.

  • Getting a cheap flight from Chicago to Santo Domingo couldn't be easier with Price Alerts. All you need to do is create one of these automatic alerts and we'll get in touch as soon as a better deal is available.

  • Select your preferred arrival and departure times, airlines and number of stops with the filters. Alternatively, sort your Chicago to Santo Domingo flight results by 'Cheapest,' 'Best' or 'Fastest.'

Flying from Chicago

O'Hare International Airport (ORD)

  • A stopover is the perfect opportunity to break up your journey — and possibly even visit a new city. When browsing Chicago to Santo Domingo flights departing from O'Hare International Airport, deselect the 'Direct flights only' box to see where you can stop along the way. Here are some options to consider:

    • Hartsfield-Jackson Atlanta International Airport (ATL)

    • Philadelphia International Airport (PHL)

    • Fort Lauderdale-Hollywood International Airport (FLL)

  • Located around 26 kilometres from central Chicago, ORD can be reached in about 35 minutes by car (depending on traffic). The journey by public transport is roughly 55 minutes.

  • Planning to catch an early flight from Chicago to Santo Domingo? Avoid the hassle of rushing to the terminal (and catch some extra z's) by choosing one of these stays close to O'Hare International Airport:

  • 74.85% of flights that leave from O'Hare International Airport touch down at their destination on time.

  • ORD is located at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • Visit family or friends or just take a moment to stretch your legs with a stopover. If you'd like to break up your Chicago to Santo Domingo flight, browse these options when leaving from Chicago Midway International Airport:

    • Hartsfield-Jackson Atlanta International Airport (ATL)

    • Orlando International Airport (MCO)

    • Fort Lauderdale-Hollywood International Airport (FLL)

  • With public transport, you can travel from central Chicago to MDW in around 45 minutes. The terminal is roughly 14 kilometres away. Driving will take you about 20 minutes.

  • Kick off your holiday early with an extra night away from home. Before your flight from Chicago to Santo Domingo, unwind in one of these hotels close to Chicago Midway International Airport:

  • Chicago Midway International Airport has an on-time performance rate of 78%. This figure gives an insight into how frequently flights that depart from this airport arrive at their destination on schedule.

  • You'll find MDW at 5700 South Cicero.

Arriving in Santo Domingo

Las Americas International Airport (SDQ)

Dr. Joaquin Balaguer International Airport (JBQ)

  • Central Santo Domingo is around 13 kilometres from Dr. Joaquin Balaguer International Airport (JBQ). After your flight from Chicago to Santo Domingo has touched down and you've made your way to arrivals, expect a drive of around 25 minutes.

  • You'll find a few comfortable places to lay your head within an easy drive of JBQ. Ease into relaxation mode at Moderno Apartamento Para tu Estancia after your Chicago to Santo Domingo flight.

  • Grab a Dr. Joaquin Balaguer International Airport rental car and see and do more with your own set of wheels. FlexWays is just moments from baggage claim, ensuring a fast and easy pick-up.

  • Pick the vehicle you actually want, not just what's left, by reserving your ride from JBQ before your arrival. You'll also avoid paying more than you need to, especially during busy airport times.

Best time to go to Santo Domingo

  • May is the quietest month for flights from Chicago to Santo Domingo, while January is the busiest. Find the best time to visit Santo Domingo based on whether you like a lively atmosphere or a more laid-back vibe.

  • The warmest month in Santo Domingo is September, with temperatures ranging between 23ºC and 33ºC. Lock in your Chicago to Santo Domingo ticket then if this is the type of weather you enjoy.

  • Search for cheap flights from Chicago to Santo Domingo in February if you want to travel in cooler conditions. Temperatures are at their lowest then, ranging between 19ºC and 29ºC on average.

More about Santo Domingo

  • Start your Santo Domingo trip off on the right foot by choosing the ideal place to stay. Once you've booked your flight from Chicago to Santo Domingo, browse our selection of accommodation options including:

  • Alcazar de Colon and National Palace are a couple of leading attractions to put on your Santo Domingo itinerary. Keep the sightseeing going at Basilica Cathedral of Santa Maria la Menor.

Explore more of Dominican Republic

  • You've visited Santo Domingo, now it's time to explore more of Dominican Republic. Journey about 13 kilometres east to Santo Domingo Este to tick off its top sights. From Museo Las Tres Aves to billeteros Park and Abuela Mota Final Resting Place, you'll have a packed itinerary ahead.

  • If you're eager to discover another major destination in Dominican Republic, head for San Pedro de Macorís, roughly 64 kilometres east of Santo Domingo. El Parquecito, Patrimonio arquitectónico de la ciudad de San Pedro de Macoris and Museo Cultural San Pedro are highlights.

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.