Cheap flights from Chicago Midway Airport to Punta Cana from $168
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 Punta Cana departing on 1/1. 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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Not ready to book? to track prices.Southwest flights from Chicago Midway Airport to Punta Cana
Our best Southwest deals on Chicago Midway Airport to Punta Cana flight tickets
Delta flights from Chicago Midway Airport to Punta Cana
Our best Delta deals on Chicago Midway Airport to Punta Cana flight tickets
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Use the filters below to find and compare flights from Chicago Midway Airport to Punta Cana that are best for you.
Fly from
Fly to
Route
Depart
Return
ChicagoPunta Cana
MDW Chicago Midway - PUJ Punta Cana
MDWPUJ
Chicago Midway
Sat 11/28
8:40 am-3:15 pm
Nonstop4h 35m
Punta Cana
Sat 12/5
2:05 pm-7:40 pm
1 stop7h 35m
ChicagoPunta Cana
MDW Chicago Midway - PUJ Punta Cana
MDWPUJ
Chicago Midway
Sat 11/28
5:25 am-4:00 pm
1 stop8h 35m
Punta Cana
Sat 12/5
2:05 pm-7:40 pm
1 stop7h 35m
ChicagoPunta Cana
MDW Chicago Midway - PUJ Punta Cana
MDWPUJ
Chicago Midway
Sun 11/15
5:05 am-3:10 pm
1 stop8h 05m
Punta Cana
Thu 11/19
3:35 pm-9:30 pm
1 stop7h 55m
ChicagoPunta Cana
MDW Chicago Midway - PUJ Punta Cana
MDWPUJ
Chicago Midway
Sun 11/15
5:05 am-3:10 pm
1 stop8h 05m
Punta Cana
Fri 11/20
4:50 pm-11:00 pm
1 stop8h 10m
ChicagoPunta Cana
MDW Chicago Midway - PUJ Punta Cana
MDWPUJ
Chicago Midway
Fri 1/22
5:59 pm-12:30 pm
1 stop16h 31m
Punta Cana
Mon 1/25
4:20 pm-8:49 am
1 stop18h 29m
ChicagoPunta Cana
MDW Chicago Midway - PUJ Punta Cana
MDWPUJ
Chicago Midway
Mon 11/16
5:13 pm-12:28 pm
1 stop17h 15m
Punta Cana
Wed 11/18
1:53 pm-10:54 pm
1 stop11h 01m
ChicagoPunta Cana
MDW Chicago Midway - PUJ Punta Cana
MDWPUJ
Chicago Midway
Fri 1/22
6:00 am-4:42 pm
1 stop8h 42m
Punta Cana
Thu 1/28
4:55 pm-10:10 pm
1 stop7h 15m
ChicagoPunta Cana
MDW Chicago Midway - PUJ Punta Cana
MDWPUJ
Chicago Midway
Mon 11/23
9:09 am-3:18 pm
1 stop28h 09m
Punta Cana
Thu 11/26
4:28 pm-8:12 am
1 stop17h 44m
ChicagoPunta Cana
MDW Chicago Midway - PUJ Punta Cana
MDWPUJ
Chicago Midway
Mon 11/23
1:16 pm-3:18 pm
1 stop24h 02m
Punta Cana
Tue 11/24
7:30 pm-12:21 pm
2 stops18h 51m
ChicagoPunta Cana
MDW Chicago Midway - PUJ Punta Cana
MDWPUJ
Chicago Midway
Sat 11/21
2:40 pm-3:18 pm
1 stop22h 38m
Punta Cana
Thu 11/26
4:28 pm-8:12 am
1 stop17h 44m
See travel insights to Punta Cana from
How to get the cheapest flight ticket from Chicago Midway Airport to Punta Cana
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 Punta Cana?
If you’re not able to fly to Punta Cana in December, then November is your next best option. Flight prices from Chicago Midway Airport to Punta Cana during November average around $0.
What is the cheapest day to depart on your flight to Punta Cana?
The cheapest day to depart from Chicago Midway Airport to Punta Cana is on a Monday when prices can be found for as low as $532. Be sure to avoid booking your departure on a Thursday as prices are generally higher than usual. According to our data, the average ticket price to Punta Cana on Thursday is $658.
What is the cheapest time of day to depart on your flight to Punta Cana?
In the evening is the cheapest time of day to fly from Chicago Midway Airport to Punta Cana when you can find flight prices for as low as $459. Flying to Punta Cana in the evening is an ideal time because this is during off-peak travel hours. In the morning is when there is more demand to fly to Punta Cana, so prices are often more expensive at around $587 per ticket.
What is the cheapest Chicago Midway to Punta Cana flight route?
Fly from Chicago Midway to Punta Cana for the best Chicago Midway - Punta Cana flight prices
What cabin class options are available on Chicago Midway Airport to Punta Cana flights?
There is only 1 cabin class available to choose from on Chicago Midway Airport to Punta Cana 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 Punta Cana flights?
You could potentially save up to 23% on your flight if you consider stops on a Chicago Midway Airport to Punta Cana flight.
How often are flights from Chicago to Punta Cana delayed?
Historically, on average around 39% of flights between Chicago and Punta Cana have experienced a delay on any given week. The average delay length over the past 12 months has been 90 minutes.
What is the most punctual flight time for Chicago to Punta Cana flights?
Generally, flights departing in the morning tend to experience fewer delays. Flights in the morning have, in the past, seen delays more frequently in comparison.
What day of the week experiences the fewest flight delays on this route?
Friday is statistically the day of the week which experiences the fewest number of delays on this flight route. Wednesday has historically seen more delays on average compared to the rest of the week.
Which airline has the best punctuality record on Chicago to Punta Cana flights?
According to our data, Southwest have had the least number of delays on this route over the last 12 months; with about 39% of their flights experiencing any sort of delay.
When to book flights from Chicago Midway Airport to Punta Cana
Cheap Chicago Midway Airport to Punta Cana (MDW to PUJ) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Punta Cana
Frequently asked questions about flying from Chicago Midway Airport to Punta Cana
How far is Chicago Midway to Punta Cana by plane?
The straight-line distance from Chicago Midway to Punta Cana is 1957.5 mi. A reasonable flight in good conditions will take 4h 25m.
When did momondo last update prices for flights from Chicago Midway Airport to Punta Cana Airport?
Prices for flights from Chicago Midway Airport to Punta Cana Airport are refreshed on a daily basis.
How many operators does momondo search for flights from Chicago Midway Airport to Punta Cana Airport?
As of October 2026, there are 2 operators available to choose from for flights from Chicago Midway Airport to Punta Cana Airport.
How old do you have to be to fly from Chicago Midway Airport to Punta Cana Airport?
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 Punta Cana Airport.
What documentation or ID do you need to fly to Punta Cana Airport?
The necessary travel and health documents for your Punta Cana Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Chicago Midway Airport to Punta Cana?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Chicago Midway Airport to Punta Cana is Boeing 737 (24.14% of total bookings). The next most popular plane models are Boeing 737 MAX 8 (20.69%), Boeing 737 MAX 9 (10.34%), and Airbus A321neo (10.34%).
What is the most popular airline from Chicago Midway Airport to Punta Cana?
momondo data reveals that the most frequently booked airline on the route from Chicago Midway Airport to Punta Cana is Southwest, representing 81% of all bookings. The subsequent popular airline is Frontier at 19%.
Best airlines flying from Chicago Midway Airport to Punta Cana
Compare and see reviews for airlines that fly from Chicago Midway Airport to Punta Cana with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $478 | Free Cancellation | Rating 5.6 2,551 reviews | |||
| PriceFrom $511 | Free Cancellation | Rating 7.9 4,220 reviews |
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Why should I use momondo to find a flight deal from Chicago to Punta Cana?
To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Punta Cana from Chicago.
Can I find flights from Chicago to Punta Cana with flexible booking policies on momondo?
All flight searches from Chicago to Punta Cana on momondo can be filtered to show those which offer flexible booking policies.
How can momondo help me find flights from Chicago to Punta Cana?
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 Chicago to Punta Cana.
I’m not ready to book a flight from Chicago to Punta Cana right now. Can momondo alert me if prices change?
If you are simply researching potential flights to Punta Cana, momondo offers a useful price alert feature which will track prices for flights to Punta Cana from Chicago and alert you when they change.