Cheap flights from the Dominican Republic to Chicago from $188
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from the Dominican Republic to Chicago departing on 11/7. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Fly from
Fly to
Route
Depart
Return
Punta CanaChicago
PUJ Punta Cana - ORD Chicago O'Hare Intl
PUJORD
Punta Cana
Sat 11/21
7:00 am-10:10 am
Nonstop5h 10m
Chicago O'Hare Intl
Sat 11/28
11:10 am-5:55 pm
Nonstop4h 45m
Punta CanaChicago
PUJ Punta Cana - ORD Chicago O'Hare Intl
PUJORD
Punta Cana
Sat 11/21
7:00 am-10:10 am
Nonstop5h 10m
Chicago O'Hare Intl
Sat 11/28
11:10 am-5:55 pm
Nonstop4h 45m
Punta CanaChicago
PUJ Punta Cana - ORD Chicago O'Hare Intl
PUJORD
Punta Cana
Sat 12/26
7:00 am-10:10 am
Nonstop5h 10m
Chicago O'Hare Intl
Sat 1/2
11:10 am-5:55 pm
Nonstop4h 45m
Santo DomingoChicago
SDQ Santo Domingo Las Americas - ORD Chicago O'Hare Intl
SDQORD
Santo Domingo Las Americas
Fri 11/20
1:40 am-10:10 am
1 stop10h 30m
Chicago O'Hare Intl
Sat 11/28
11:10 am-9:40 pm
1 stop8h 30m
Punta CanaChicago
PUJ Punta Cana - ORD Chicago O'Hare Intl
PUJORD
Punta Cana
Thu 10/29
1:55 pm-6:10 pm
Nonstop5h 15m
Chicago O'Hare Intl
Sun 11/1
8:50 am-5:28 pm
1 stop6h 38m
Punta CanaChicago
PUJ Punta Cana - ORD Chicago O'Hare Intl
PUJORD
Punta Cana
Thu 11/5
2:55 pm-6:10 pm
Nonstop5h 15m
Chicago O'Hare Intl
Mon 11/9
5:59 am-5:28 pm
1 stop9h 29m
Punta CanaChicago
PUJ Punta Cana - ORD Chicago O'Hare Intl
PUJORD
Punta Cana
Fri 12/25
5:34 pm-9:08 pm
Nonstop5h 34m
Chicago O'Hare Intl
Fri 1/1
9:52 am-4:29 pm
Nonstop4h 37m
Punta CanaChicago
PUJ Punta Cana - ORD Chicago O'Hare Intl
PUJORD
Punta Cana
Sat 11/21
4:08 pm-7:47 pm
Nonstop5h 39m
Chicago O'Hare Intl
Sat 11/28
6:00 am-3:48 pm
1 stop7h 48m
Santo DomingoChicago
SDQ Santo Domingo Las Americas - ORD Chicago O'Hare Intl
SDQORD
Santo Domingo Las Americas
Mon 11/9
2:32 pm-11:36 pm
1 stop11h 04m
Chicago O'Hare Intl
Mon 11/16
7:00 am-4:18 pm
1 stop7h 18m
Santo DomingoChicago
SDQ Santo Domingo Las Americas - ORD Chicago O'Hare Intl
SDQORD
Santo Domingo Las Americas
Tue 11/10
6:01 am-1:42 pm
1 stop9h 41m
Chicago O'Hare Intl
Tue 11/17
7:00 am-4:18 pm
1 stop7h 18m
See travel insights to Chicago from
How to get the cheapest flight ticket from Dominican Republic to Chicago
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the cheapest month to fly to Chicago?
The month of February is, on average, the cheapest month to fly to Chicago from Dominican Republic, with most prices found around $375. If you’re not able to fly to Chicago in February, then September is your next best option. Flight prices from Dominican Republic to Chicago during September average around $450.
What is the cheapest day to depart on your flight to Chicago?
The cheapest day to depart on your flight to Chicago is on a Sunday when prices can be found for as low as $386. This is often the case because there is less demand to fly during this day of the week. When flying out on a Friday, the most expensive travel day of the week, you can expect to see flight prices from Dominican Republic to Chicago for around $589.
What is the cheapest time of day to depart on your flight to Chicago?
Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Dominican Republic to Chicago during this time can be as low as $236. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $509.
What is the cheapest Dominican Republic to Chicago flight route?
Fly from Punta Cana to Chicago O'Hare Intl for the best Dominican Republic - Chicago flight prices
What cabin class options are available on Dominican Republic to Chicago flights?
There are 3 cabin classes available to choose from on Dominican Republic to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
Can stopping save me money on Dominican Republic to Chicago flights?
You could potentially save up to 7% on your flight if you consider stops on a Dominican Republic to Chicago flight.
What is the cheapest airline that flies from Dominican Republic to Chicago?
Arajet, Frontier, and Southwest are the most popular carriers operating from Dominican Republic to Chicago
What airlines fly to Chicago?
American Airlines, Arajet and JetBlue are the top three most popular airlines that fly to Chicago from Dominican Republic according to our data. American Airlines is the first choice among our users, with 54% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 3 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.
How many flights depart from Dominican Republic to Chicago on average per day?
As of October 2026, 1 flights take off from Dominican Republic and land in Chicago each day. The most common flight departure time for this route is 1:00PM, with 66% of daily flights taking off in the afternoon.
How many flights depart from Dominican Republic to Chicago on average per week?
As of October 2026, 7 flights take off from Dominican Republic and land in Chicago each week. The most common flight departure day for this route is Mon, with 14% of weekly flights taking off on this day.
Cheap Dominican Republic to Chicago flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Dominican Republic to Chicago
Frequently asked questions about flying from the Dominican Republic to Chicago
When did momondo last update prices for flights from Dominican Republic to Chicago?
Prices for flights from Dominican Republic to Chicago are updated daily.
How many operators does momondo search for flights from Dominican Republic to Chicago?
There are 3 operators available for flights from Dominican Republic to Chicago as of October 2026.
How old do you have to be to fly from Dominican Republic to Chicago?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Dominican Republic to Chicago.
What documentation or ID do you need to fly to Chicago?
The travel and health documents required for your trip to Chicago can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from Dominican Republic to Chicago?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Dominican Republic to Chicago is Boeing 737 MAX 8 (37.55% of total bookings). The next most popular plane models are Boeing 737 (17.14%), Boeing 737 MAX 9 (14.69%), and Airbus A321-100/200 (8.98%).
Best airlines flying from Dominican Republic to Chicago
Compare and see reviews for airlines that fly from Dominican Republic to Chicago with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $266 | Free Cancellation | Rating 6.2 55 reviews | |||
| PriceFrom $283 | Free Cancellation | Rating 7.0 12,129 reviews | |||
| PriceFrom $375 | Free Cancellation | Rating 7.1 3,044 reviews |
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsWhy use momondo?
Why should I use momondo to find a flight deal from Dominican Republic to Chicago?
Finding the right flight to Chicago from Dominican Republic is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.
Can I find flights from Dominican Republic to Chicago with flexible booking policies on momondo?
momondo does allow users to show only those flights to Chicago from Dominican Republic which offer a flexible booking policy as well as other useful filters and features.
How can momondo help me find flights from Dominican Republic to Chicago?
momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Dominican Republic to Chicago.
I’m not ready to book a flight from Dominican Republic to Chicago right now. Can momondo alert me if prices change?
Yes momondo offers price alerts on flights to Chicago from Dominican Republic. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.