Cheap flights from Chicago Midway Airport to the Dominican Republic from $121
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to the Dominican Republic departing on 7/12. 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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Southwest flights from Chicago Midway Airport to Dominican Republic
Our best Southwest deals on Chicago Midway Airport to Dominican Republic flight tickets
Delta flights from Chicago Midway Airport to Dominican Republic
Our best Delta deals on Chicago Midway Airport to Dominican Republic flight tickets
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How to get the cheapest flight ticket from Chicago Midway Airport to Dominican Republic
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 Dominican Republic?
In general, August is the cheapest month to fly from Chicago Midway Airport to Dominican Republic. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $340. If you are unable to visit Dominican Republic during the month of August, then departing from Chicago Midway Airport during the month October is also very affordable. Most momondo users find prices during this month for around $471.
What is the cheapest day to depart on your flight to Dominican Republic?
The cheapest day to depart on your flight to Dominican Republic is on a Saturday when prices can be found for as low as $620. This is often the case because there is less demand to fly during this day of the week. Flights from Chicago Midway Airport to Dominican Republic on a Friday will generally be more expensive and average around $839. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.
What is the cheapest time of day to depart on your flight to Dominican Republic?
Flying to Dominican Republic from Chicago Midway Airport in the evening is the least expensive time of day to depart. momondo users have found prices as low as $281 when looking at flights departing in the evening. Flights in the morning are often more expensive with an average ticket price of $705.
What is the cheapest Chicago Midway to Dominican Republic flight route?
Fly from Chicago Midway to Punta Cana for the best Chicago Midway - Dominican Republic flight prices
What cabin class options are available on Chicago Midway to Dominican Republic flights?
There are 1 cabin classes available to choose from on Chicago Midway to Dominican Republic 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 Chicago Midway Airport to Dominican Republic flights?
No. A direct flight is the cheapest option for a flight between Chicago Midway Airport to Dominican Republic.
What is the cheapest airline that flies from Chicago Midway to Dominican Republic?
Southwest, Frontier, and Delta are the most popular carriers operating from Chicago Midway to Dominican Republic
What airlines fly to Dominican Republic?
Southwest, Frontier and Delta are the top three most popular airlines that fly to Dominican Republic from Chicago Midway Airport according to our data. Southwest is the first choice among our users, with 73% of people opting to fly with this airline when traveling to Dominican Republic. Keep in mind that there are 3 different airlines that fly to Dominican Republic on a routine basis, so you have a few additional options to choose from.
How many flights depart from Chicago Midway Airport to Dominican Republic on average per week?
As of June 2025, 5 flights take off from Chicago Midway Airport and land in Dominican Republic each week. The most common flight departure day for this route is Mon, with 20% of weekly flights taking off on this day.
Cheap Chicago Midway Airport to Dominican Republic flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Dominican Republic
Best Price Found | $121 |
|---|---|
Fastest flight time | 4h 30m |
Direct flights | Every day |
Airports in Dominican Republic | 3 airports |
When did momondo last update prices for flights from Chicago Midway Airport to Dominican Republic?
Prices for flights from Chicago Midway Airport to Dominican Republic are updated daily.
How many operators does momondo search for flights from Chicago Midway Airport to Dominican Republic?
As of June 2025, there are 3 operators available to choose from for flights from Chicago Midway Airport to Dominican Republic.
How old do you have to be to fly from Chicago Midway Airport to Dominican Republic?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago Midway Airport to Dominican Republic.
What documentation or ID do you need to fly to Dominican Republic?
The travel and health documents you'll need for your trip to Dominican Republic may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Dominican Republic. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Chicago Midway Airport to Dominican Republic?
Based on momondo bookings for flights between Chicago Midway Airport and Dominican Republic, the leading plane model is Boeing 737-700 Passenger/BBJ1 (winglets), making up 40.14% of the total bookings. Other popular models include Airbus A320neo with 23.90%, Boeing 737 MAX 8 with 14.15%, and Airbus A321-100/200 with 9.05%.
Best airlines flying from Chicago Midway Airport to Dominican Republic
Compare and see reviews for airlines that fly from Chicago Midway Airport to Dominican Republic with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $370 | Free Cancellation | Rating 5.9 3,295 reviews | |||
| PriceFrom $375 | Free Cancellation | Rating 8.0 7,946 reviews | |||
| PriceFrom $495 | Free Cancellation | Rating 8.0 4,287 reviews |
Why use momondo?
Why should I use momondo to find a flight deal from Chicago to Dominican Republic?
momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Chicago to Dominican Republic. momondo saves you time and could save you money on your trip.
Can I find flights from Chicago to Dominican Republic with flexible booking policies on momondo?
Yes. momondo enables you to select and highlight flights to Dominican Republic from Chicago with this policy.
How can momondo help me find flights from Chicago to Dominican Republic?
momondo provides multiple filters to help you find the best flight to Dominican Republic from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.
I’m not ready to book a flight from Chicago to Dominican Republic right now. Can momondo alert me if prices change?
If you are simply researching potential flights to Dominican Republic, momondo offers a useful price alert feature which will track prices for flights to Dominican Republic from Chicago and alert you when they change.