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Cheap Flights from Santo Domingo to Chicago

Compare Santo Domingo to Chicago flight deals

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Flight deals from Santo Domingo to Chicago

Looking for a cheap last-minute deal or the best round-trip flight from Santo Domingo to Chicago? If you want to travel next month, round-trip fares start from AED 1,318. Find the lowest prices on one-way and round-trip tickets right here.
Chicago.AED 1,300 per passenger.Departing Fri, Apr 24, returning Sun, May 3.Round-trip flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departing from Santo Domingo Las Americas on Fri, Apr 24, arriving in Chicago O'Hare International.Inbound indirect flight with Spirit Airlines, departing from Chicago O'Hare International on Sun, May 3, arriving in Santo Domingo Las Americas.Price includes taxes and charges.From AED 1,300, select.
Chicago.AED 1,316 per passenger.Departing Fri, May 1, returning Sun, May 3.Round-trip flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departing from Santo Domingo Las Americas on Fri, May 1, arriving in Chicago O'Hare International.Inbound indirect flight with Spirit Airlines, departing from Chicago O'Hare International on Sun, May 3, arriving in Santo Domingo Las Americas.Price includes taxes and charges.From AED 1,316, select.
Chicago.AED 1,318 per passenger.Departing Fri, Apr 24, returning Mon, Apr 27.Round-trip flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departing from Santo Domingo Las Americas on Fri, Apr 24, arriving in Chicago O'Hare International.Inbound indirect flight with Spirit Airlines, departing from Chicago O'Hare International on Mon, Apr 27, arriving in Santo Domingo Las Americas.Price includes taxes and charges.From AED 1,318, select.
Chicago.AED 1,356 per passenger.Departing Tue, Mar 24, returning Wed, Apr 1.Round-trip flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departing from Santo Domingo Las Americas on Tue, Mar 24, arriving in Chicago O'Hare International.Inbound indirect flight with Spirit Airlines, departing from Chicago O'Hare International on Wed, Apr 1, arriving in Santo Domingo Las Americas.Price includes taxes and charges.From AED 1,356, select.
Chicago.AED 1,419 per passenger.Departing Sat, Sep 5, returning Sat, Sep 12.Round-trip flight with Arajet.Outbound indirect flight with Arajet, departing from Santo Domingo Las Americas on Sat, Sep 5, arriving in Chicago O'Hare International.Inbound indirect flight with Arajet, departing from Chicago O'Hare International on Sat, Sep 12, arriving in Santo Domingo Las Americas.Price includes taxes and charges.From AED 1,419, select.
Chicago.AED 1,522 per passenger.Departing Sat, Jul 4, returning Sat, Jul 11.Round-trip flight with Arajet.Outbound indirect flight with Arajet, departing from Santo Domingo Las Americas on Sat, Jul 4, arriving in Chicago O'Hare International.Inbound indirect flight with Arajet, departing from Chicago O'Hare International on Sat, Jul 11, arriving in Santo Domingo Las Americas.Price includes taxes and charges.From AED 1,522, select.
Chicago.AED 1,554 per passenger.Departing Tue, Mar 24, returning Tue, Mar 31.Round-trip flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departing from Santo Domingo Las Americas on Tue, Mar 24, arriving in Chicago O'Hare International.Inbound indirect flight with Spirit Airlines, departing from Chicago O'Hare International on Tue, Mar 31, arriving in Santo Domingo Las Americas.Price includes taxes and charges.From AED 1,554, select.
Chicago.AED 1,609 per passenger.Departing Sun, May 17, returning Sun, Jun 7.Round-trip flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departing from Santo Domingo Las Americas on Sun, May 17, arriving in Chicago O'Hare International.Inbound indirect flight with Spirit Airlines, departing from Chicago O'Hare International on Sun, Jun 7, arriving in Santo Domingo Las Americas.Price includes taxes and charges.From AED 1,609, select.
Chicago.AED 1,755 per passenger.Departing Tue, Apr 14, returning Thu, Sep 3.Round-trip flight with Spirit Airlines and jetBlue.Outbound indirect flight with Spirit Airlines, departing from Santo Domingo Las Americas on Tue, Apr 14, arriving in Chicago O'Hare International.Inbound indirect flight with jetBlue, departing from Chicago O'Hare International on Thu, Sep 3, arriving in Santo Domingo Las Americas.Price includes taxes and charges.From AED 1,755, select.
Chicago.AED 1,810 per passenger.Departing Sat, Jun 6, returning Sat, Jun 13.Round-trip flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departing from Santo Domingo Las Americas on Sat, Jun 6, arriving in Chicago O'Hare International.Inbound indirect flight with Spirit Airlines, departing from Chicago O'Hare International on Sat, Jun 13, arriving in Santo Domingo Las Americas.Price includes taxes and charges.From AED 1,810, select.
Chicago.AED 1,814 per passenger.Departing Wed, Aug 26, returning Sun, Aug 30.Round-trip flight with Arajet and Spirit Airlines.Outbound indirect flight with Arajet, departing from Santo Domingo Las Americas on Wed, Aug 26, arriving in Chicago O'Hare International.Inbound indirect flight with Spirit Airlines, departing from Chicago O'Hare International on Sun, Aug 30, arriving in Santo Domingo Las Americas.Price includes taxes and charges.From AED 1,814, select.
Chicago.AED 1,852 per passenger.Departing Sun, May 31, returning Wed, Aug 5.Round-trip flight with Arajet and Frontier Airlines.Outbound indirect flight with Arajet, departing from Santo Domingo Las Americas on Sun, May 31, arriving in Chicago O'Hare International.Inbound indirect flight with Frontier Airlines, departing from Chicago O'Hare International on Wed, Aug 5, arriving in Santo Domingo Las Americas.Price includes taxes and charges.From AED 1,852, select.
Chicago.AED 1,863 per passenger.Departing Mon, May 11, returning Wed, Sep 9.Round-trip flight with Copa.Outbound indirect flight with Copa, departing from Santo Domingo Las Americas on Mon, May 11, arriving in Chicago O'Hare International.Inbound indirect flight with Copa, departing from Chicago O'Hare International on Wed, Sep 9, arriving in Santo Domingo Las Americas.Price includes taxes and charges.From AED 1,863, select.
Chicago.AED 2,007 per passenger.Departing Mon, Aug 31, returning Thu, Sep 3.Round-trip flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departing from Santo Domingo Las Americas on Mon, Aug 31, arriving in Chicago O'Hare International.Inbound indirect flight with Spirit Airlines, departing from Chicago O'Hare International on Thu, Sep 3, arriving in Santo Domingo Las Americas.Price includes taxes and charges.From AED 2,007, select.
Chicago.AED 2,027 per passenger.Departing Thu, Oct 29, returning Sun, Nov 1.Round-trip flight with United.Outbound indirect flight with United, departing from Santo Domingo Las Americas on Thu, Oct 29, arriving in Chicago O'Hare International.Inbound indirect flight with United, departing from Chicago O'Hare International on Sun, Nov 1, arriving in Santo Domingo Las Americas.Price includes taxes and charges.From AED 2,027, select.
Chicago.AED 2,058 per passenger.Departing Sat, Dec 26, returning Sat, Jan 2.Round-trip flight with Delta.Outbound indirect flight with Delta, departing from Santo Domingo Las Americas on Sat, Dec 26, arriving in Chicago O'Hare International.Inbound indirect flight with Delta, departing from Chicago Midway on Sat, Jan 2, arriving in Santo Domingo Las Americas.Price includes taxes and charges.From AED 2,058, select.

Find the cheapest month to fly from Santo Domingo to Chicago

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Santo Domingo to Chicago flights are currently cheapest in May.
Mar
from AED 1,554
Apr
from AED 1,318
May
from AED 1,316
Jun
from AED 1,810
Jul
from AED 1,522
Aug
from AED 1,814
Sep
from AED 1,419
Oct
from AED 2,249
Nov
Find prices
Dec
from AED 2,816
Jan
Find prices
Feb
Find prices

Alternative Santo Domingo to Chicago routes

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

Chicago Midway

14km from central Chicago
Closest
from AED 1,726
Search flights

Chicago O'Hare International

25km from central Chicago
Cheapest
from AED 1,300
Search flights

Chicago Dupage County

51km from central Chicago
Search flights

Chicago Rockford

126km from central Chicago
from AED 2,034
Search flights

Santo Domingo to Chicago: Flight information

The things to know before you go.
Cheapest flight foundAED 1,300
Cheapest month to flyApril

Check out these Chicago hotels

Ready to plan your stay? Other travelers rate these Chicago hotels for cleanliness, service, and location.
House 5863- Chicago's Premier Bed and Breakfast
12.62 km from city center
‎AED 896
Per night
The St. Regis Chicago
1.45 km from city center
‎AED 2,389
Per night
The Sono Chicago
3.50 km from city center
‎AED 955
Per night
House 5863- Chicago's Premier Bed and Breakfast
12.62 km from city center
‎AED 896
Per night
The St. Regis Chicago
1.45 km from city center
‎AED 2,389
Per night
The Sono Chicago
3.50 km from city center
‎AED 955
Per night
Explore top-rated hotels

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

There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.
The best price we found for a round-trip flight from Santo Domingo to Chicago is AED 1,300. 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 Santo Domingo to Chicago. But we found flights with one or more stops from AED 1,300.
There are no flights flying from Santo Domingo to Chicago, as of March 2026.
The cheapest month to fly from Santo Domingo to Chicago is usually April.
If you're flying from Santo Domingo, the cheapest airport near Chicago is Chicago O'Hare International – which is 25.4 km away from the center of Chicago. We've found flights to this airport from AED 1,300.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Santo Domingo to Chicago on Friday, April 24, 2026.
No airlines currently offer direct flights between Santo Domingo and Chicago. 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 Chicago 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 Chicago is around 40 days in advance, so don’t leave your flight to the last minute.
In March, the average temperature is usually around 3°C. July is typically the warmest month in Chicago, when it usually averages around 26°C. You can expect the least rain in January. The coldest month is January, with temperatures averaging -8°C. The rainiest month is August.
The cheapest airline that flies to Chicago is Spirit Airlines.

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

  • There are two main airports you can fly out of in Santo Domingo. Check out your options leaving from Las Americas International Airport (SDQ) or Dr. Joaquin Balaguer International Airport (JBQ) when reserving your flight from Santo Domingo to Chicago.

  • When it comes to choosing where to land in Chicago, O'Hare International Airport (ORD) and Chicago Midway International Airport (MDW) are the primary gateways.

  • Chicago's timezone is UTC-5, making Chicago one hour behind Santo Domingo.

  • Give yourself plenty of time to catch your Santo Domingo to Chicago flight. As a general rule, turn up at least two hours before international departures and an hour ahead for domestic flights.

  • Traveling during a popular month such as August? Public holidays and other high seasons can lead to longer queues and delays at security. Be extra cautious and get there up to four hours ahead of international flights and two hours before a domestic departure.

How to find the cheapest flights from Santo Domingo to Chicago

  • Don't leave things to the last minute. You're more likely to get cheap Santo Domingo to Chicago flights if you book early. Airlines often have some excellent early bird rates.

  • If you're flexible with your travel plans, use the 'Whole month' tool. It'll show you the cheapest price in every month when looking for your plane ticket from Santo Domingo to Chicago.

  • There's no need to search every day to see if prices have dropped when you set up a Price Alert. We'll let you know as soon as there's a better deal on cheap flights from Santo Domingo to Chicago.

  • Find an affordable Santo Domingo to Chicago flight with the help of our filters. Choose your ideal times, number of stops and airlines, then sort the results by 'Cheapest' to see the best deals.

Flying from Santo Domingo

Las Americas International Airport (SDQ)

  • Stopovers are the ideal opportunity to take a break from traveling — and perhaps even explore a different city. When browsing Santo Domingo to Chicago flights departing from Las Americas International Airport, uncheck the 'Direct flights only' box to see where you can visit along the way. Here are some popular options to consider:

    • Hartsfield-Jackson Atlanta International Airport (ATL)

    • Miami International Airport (MIA)

    • Fort Lauderdale-Hollywood International Airport (FLL)

  • SDQ is around 27 kilometers from central Santo Domingo. If you're catching a cab, ride-sharing or driving from the center, it'll take you 30 minutes or so to arrive, depending on traffic conditions.

  • Want a leisurely start to your trip? Stay near Las Americas International Airport. Whether you're taking an early flight from Santo Domingo to Chicago or want to avoid feeling rushed, these hotels are ideal:

  • Of the departures from Las Americas International Airport, 72.45% land on schedule at their destination.

Arriving in Chicago

O'Hare International Airport (ORD)

  • The distance from O'Hare International Airport (ORD) to central Chicago is approximately 26 kilometers. It takes about 35 minutes to reach the center driving.

  • Getting to the center on public transport will take you around 55 minutes.

  • If you're arriving on a late flight from Santo Domingo to Chicago, few things beat the convenience of staying close to the terminal. Pick up your bags from the carousel and then be showered and snoozing not long after at one of these hotels near ORD:

  • Begin your adventure by picking up an O'Hare International Airport rental car. Grab a set of wheels from Routes Car Rentals, Dollar or Budget and explore beyond Chicago's main sights.

  • To get the lowest price, book your vehicle from O'Hare International Airport about four weeks ahead of your Santo Domingo to Chicago flight.

  • You'll find ORD at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • Chicago Midway International Airport (MDW) is roughly 14 kilometers from the center of Chicago. Following your flight from Santo Domingo to Chicago, it'll take you approximately 20 minutes to get to the heart of the city in a ride-share or cab.

  • Traveling by public transport will take about 45 minutes.

  • You'll find some great places ready to welcome you near MDW. Unwind after your Santo Domingo to Chicago flight at one of these well-located options:

  • The quickest way to get to where you're going is with a Chicago Midway International Airport rental car. Grab your wheels from Dollar, Hertz or Budget and make a speedy getaway.

  • Avoid paying extra. Securing your ride four weeks ahead of your arrival at MDW can help you lock in a better rate.

  • The address for Chicago Midway International Airport is 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • Step off your flight from Santo Domingo to Chicago and go directly to your hotel or jump right into exploring. The center of Chicago is around 129 kilometers from Chicago Rockford International Airport (RFD) and usually takes 1 hour 25 minutes to reach driving.

  • If you're using public transport, expect a journey of around 4 hours 15 minutes.

  • Whether you'd like an economy for a solo getaway or a spacious SUV to move the whole family, you'll find the right Chicago Rockford International Airport rental car for your needs. Browse the types of wheels available from names such as Budget, Alamo and National.

  • If you prefer a particular model or make, booking early increases your chances of finding what you want. Reserve your ride from RFD at least a few weeks ahead of your flight from Santo Domingo to Chicago.

  • The street address for Chicago Rockford International Airport is 2 Airport Cir.

Best time to go to Chicago

  • January is the quietest month for flights from Santo Domingo to Chicago, while August is the most popular. Choose the ideal time to visit Chicago based on whether you like a laid-back vibe or a more bustling atmosphere.

  • Book a Santo Domingo to Chicago ticket departing in July if you're eager to visit the city during its warmest month. You can expect temperatures in Chicago to range from 15ºC (59ºF) to 29ºC (84ºF).

  • January has average temperatures of between -12ºC (10ºF) and 3ºC (37ºF). Search for cheap flights from Santo Domingo to Chicago around that time if you want to travel when it's cooler.

More about Chicago

Explore more of United States

  • You've visited Chicago, now it's time to discover more of United States. Journey about 451 kilometers south-east to Columbus to check off its leading sights. From Franklin Park Conservatory and Botanical Gardens to Ohio Statehouse and German Village, there's plenty to keep you busy.

  • If you want to check out another side of United States, consider Indianapolis, roughly 257 kilometers south-east of Chicago. The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo are among the biggest draws.

More travel options

Plan the rest of your trip from Santo Domingo to Chicago

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