$146+ Cheap flights from the Dominican Republic to Chicago (CHI)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 7/12. Fares are subject to change and may not be available on all flights or dates of travel.
Find cheap flights from Dominican Republic to Chicago with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Dominican Republic to Chicago
Keep the following information in mind while searching for Dominican Republic to Chicago flight deals. Data was last updated June 12, 2025.
Round-trip from | $284 (American Airlines) |
|---|---|
One-way from | $146 (Southwest) |
Popular in | June |
Cheapest in | May |
Average price | $619 |
Good round-trip deal | $371 or less |
Good one-way deal | $193 or less |
Find flight deals from Dominican Republic to Chicago
Cheapest flights from Dominican Republic to ChicagoExplore the most affordable flight options available from Dominican Republic to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 12, 2025.
Explore the most affordable flight options available from Dominican Republic to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 12, 2025.
This American Airlines deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This United Airlines deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This SmartFares deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This CheapOair deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Cheapflightsfares deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Copa Airlines deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Delta deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Frontier deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Frontier deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Cheapflightsfares deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Booking.com deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Booking.com deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Cheapflights Fare Finder
Customize your flight search to find flights from Dominican Republic to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 12, 2025.
Use the filters below to find and compare flights from the Dominican Republic to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Price
Punta CanaChicago
PUJ - ORD
PUJORD
Punta Cana
Wed 7/9
3:31 pm-7:36 pm
Nonstop5h 05m
Chicago O'Hare Intl
Wed 8/13
8:34 pm-11:05 am
1 stop13h 31m
Punta CanaChicago
PUJ - ORD
PUJORD
Punta Cana
Tue 8/5
4:35 pm-4:46 pm
1 stop25h 11m
Chicago O'Hare Intl
Tue 8/26
12:50 pm-12:40 pm
1 stop22h 50m
Punta CanaChicago
PUJ - ORD
PUJORD
Punta Cana
Tue 8/19
3:29 pm-9:55 am
1 stop19h 26m
Chicago O'Hare Intl
Wed 8/27
5:05 am-2:34 pm
1 stop8h 29m
Punta CanaChicago
PUJ - ORD
PUJORD
Punta Cana
Tue 8/19
3:35 pm-11:59 pm
1 stop9h 24m
Chicago O'Hare Intl
Thu 8/28
5:10 am-2:23 pm
1 stop8h 13m
Santo DomingoChicago
SDQ - ORD
SDQORD
Santo Domingo Las Americas
Sun 9/7
7:30 am-2:15 pm
1 stop7h 45m
Chicago O'Hare Intl
Tue 9/16
1:03 pm-2:10 am
1 stop12h 07m
Punta CanaChicago
PUJ - ORD
PUJORD
Punta Cana
Sat 8/2
2:41 pm-12:22 am
1 stop10h 41m
Chicago O'Hare Intl
Wed 8/6
3:07 pm-11:05 am
1 stop18h 58m
Punta CanaChicago
PUJ - ORD
PUJORD
Punta Cana
Sun 8/17
1:05 pm-11:56 pm
1 stop11h 51m
Chicago O'Hare Intl
Sun 9/7
7:05 am-2:34 pm
1 stop6h 29m
Santo DomingoChicago
SDQ - ORD
SDQORD
Santo Domingo Las Americas
Thu 10/9
3:11 pm-12:10 am
1 stop9h 59m
Chicago O'Hare Intl
Sun 10/19
5:10 am-1:51 pm
1 stop7h 41m
Santo DomingoChicago
SDQ - MDW
SDQMDW
Santo Domingo Las Americas
Thu 10/9
3:11 pm-11:25 pm
1 stop9h 14m
Chicago Midway
Sun 10/19
6:15 am-1:51 pm
1 stop6h 36m
Santiago de los CaballerosChicago
STI - ORD
STIORD
Santiago de los Caballeros
Wed 7/2
11:29 am-11:45 pm
1 stop13h 16m
Chicago O'Hare Intl
Thu 7/10
5:40 pm-9:50 am
1 stop15h 10m
Best time to book a flight from Dominican Republic to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Dominican Republic with our price prediction graph.
Cheapflights Insights
Everything you need to know about your flight from the Dominican Republic to Chicago
What is the cheapest month to book a flight from Dominican Republic to Chicago?
Currently, August is the cheapest month in which you can book a flight from Dominican Republic to Chicago (average of $245). Flying from Dominican Republic to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from DO to CHI?
Find hourly flight availability from Dominican Republic to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 12, 2025.
It’s optimal to fly from Dominican Republic to Chicago in the morning. By choosing this option you can save up to 21% on the cost of your flight, compared to a flight in the afternoon.
What is the cheapest day to fly from Dominican Republic to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Dominican Republic to Chicago. Price data was last updated on December 16, 2024.
Travelers seeking maximum savings on their Dominican Republic to Chicago flight should consider departing on Friday afternoons when fares are most often at their lowest. Tuesday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Weekly flight availability from Dominican Republic to Chicago
Explore weekly flight availability from Dominican Republic to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated June 12, 2025.
The most flights from DO0 to CHI are scheduled on a Wednesday (4 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (2 on average).
Rainfall in Chicago by month
Plan your trip to Chicago by taking into account the average rainfall totals by month.
In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.
Temperature in Chicago by month
Plan your trip to Chicago by taking into account the average temperature totals by month.
If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated June 12, 2025.
See what other customers who have flown with Southwest, Delta and Copa Airlines from Dominican Republic to Chicago have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Overall
Food
Boarding
Comfort
Entertainment
Crew
Reviews
John,May 2025
PVD - BNA
Overall
Food
Boarding
Comfort
Entertainment
Crew
Reviews
John,May 2025
PVD - BNA
Overall
Food
Boarding
Comfort
Entertainment
Crew
Reviews
John,May 2025
PVD - BNA
Overall
Food
Boarding
Comfort
Entertainment
Crew
Reviews
John,May 2025
PVD - BNA
Overall
Food
Boarding
Comfort
Entertainment
Crew
Reviews
John,May 2025
PVD - BNA
Overall
Food
Boarding
Comfort
Entertainment
Crew
Reviews
John,May 2025
PVD - BNA
Related info for your journey
Find useful and relevant information for your journey from Dominican Republic to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near the Dominican Republic?
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Alternative routes for Dominican Republic to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Top 4 airlines flying from Dominican Republic to Chicago
Discover the top 4 airlines that operate flights from Dominican Republic to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 12, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$224 | Average$387 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$312 | Average$474 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$324 | Average$507 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$402 | Average$607 | FlexibilityNo cancel fee | On-time71% |