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MDW - PUJ

$123 Find cheap flights from Chicago Midway Airport to Punta Cana

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Punta Cana departing on 5/26. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Wed 6/5
Wed 6/12

Search hundreds of travel sites at once for deals on flights to Punta Cana

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Punta Cana, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Punta Cana, as well as popular online travel agencies
In the last 7 days travelers have searched 42,830,901 times on KAYAK, and here is why:

Save 22% or moreCompare multiple travel sites with one search.

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Cheap flight deals from Midway to Punta Cana (MDW-PUJ)

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to Punta Cana that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
7:23 pm - 9:42 amMDW-PUJ
13h 19m1 stop
6:16 pm - 6:27 pmPUJ-MDW
25h 11m1 stop
$212Frontier
Find Deal
Mon, May 20 - Tue, May 21
8:51 pm - 3:37 pmMDW-PUJ
17h 46m1 stop
6:10 pm - 7:31 amPUJ-MDW
14h 21m1 stop
$223Frontier
Find Deal
Thu, Jun 6 - Tue, Jun 11
8:13 pm - 10:02 amMDW-PUJ
12h 49m1 stop
11:17 am - 7:18 pmPUJ-MDW
9h 01m1 stop
$224Frontier
Find Deal
Wed, Aug 21 - Mon, Aug 26
7:23 pm - 4:56 pmMDW-PUJ
20h 33m1 stop
10:42 am - 6:27 pmPUJ-MDW
8h 45m1 stop
$227Frontier
Find Deal
Wed, May 29 - Mon, Jun 3
2:28 pm - 11:06 amMDW-PUJ
19h 38m1 stop
6:16 pm - 6:27 pmPUJ-MDW
25h 11m1 stop
$234Frontier
Find Deal
Thu, May 16 - Thu, May 23
7:23 pm - 9:42 amMDW-PUJ
13h 19m1 stop
2:59 pm - 6:54 amPUJ-MDW
16h 55m2 stops
Mon, May 20 - Tue, May 21
6:00 am - 3:03 pmMDW-PUJ
8h 03m1 stop
4:23 pm - 9:12 amPUJ-MDW
17h 49m1 stop
$440Delta
Find Deal
Sun, Sep 1 - Thu, Sep 5
6:00 am - 3:03 pmMDW-PUJ
8h 03m1 stop
4:23 pm - 8:45 amPUJ-MDW
17h 22m2 stops
$490Delta
Find Deal
Sun, Sep 15 - Sat, Sep 21
5:50 pm - 12:36 pmMDW-PUJ
17h 46m2 stops
4:23 pm - 9:17 amPUJ-MDW
17h 54m1 stop
$495Delta
Find Deal
Sat, Oct 5 - Sat, Oct 12
6:00 am - 3:03 pmMDW-PUJ
8h 03m1 stop
4:23 pm - 9:17 amPUJ-MDW
17h 54m1 stop
$540Delta
Find Deal
Sun, Sep 15 - Sat, Sep 21

Flights from Midway to Punta Cana - Travel Insights & Trends

Get data-powered insights and trends into flights from Midway to Punta Cana to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest month to fly from Chicago Midway Airport to Punta Cana?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Chicago Midway Airport to Punta Cana, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.
The cheapest month for flights from Chicago Midway Airport to Punta Cana is April, where tickets cost $456 on average. On the other hand, the most expensive months are March and June, where the average cost of tickets is $704 and $611 respectively.

How far in advance should I book a flight from Chicago Midway Airport to Punta Cana?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Chicago Midway Airport to Punta Cana, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price on the flight from Chicago Midway Airport to Punta Cana, you should book around 1 day before departure. For the absolute cheapest price, our data suggests you should book 15 days before departure.

Which airlines provide the cheapest flights from Chicago Midway Airport to Punta Cana?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
The best deals for a one-way ticket found by KAYAK users over the last 3 days were on Frontier ($123) and Delta ($206). The cheapest round-trip tickets were found on Frontier ($212) and Delta ($440).

How many flights are there between Chicago Midway Airport and Punta Cana per day?

Each day, there are between 1 and 2 nonstop flights that take off from Chicago Midway Airport and land in Punta Cana, with an average flight time of 4h 30m. The most common departure time is 9:00 am and most flights take off in the morning. Each week, there are 10 flights. The most frequent day of departure is Wednesday, when 20% of all weekly flights depart. The fewest flights depart on a Tuesday.

What’s the earliest departure time from Chicago Midway Airport to Punta Cana?

Early birds can take the earliest flight from Chicago Midway Airport at 8:20 am and will be landing in Punta Cana at 1:55 pm.

What’s the latest departure time from Chicago Midway Airport to Punta Cana?

If you prefer to fly at night, the latest flight from Chicago Midway Airport to Punta Cana jets off at 9:55 am and lands at 3:25 pm.

Good to know

Low season

April

High season

February

Cheapest flight

$123
Best time to beat the crowds with an average 19% drop in price.
Most popular time to fly with an average 31% increase in price.
Flight from Chicago Midway Airport to Punta Cana

When to book flights from Midway to Punta Cana

Are your dates flexible? Find out the best times to travel from Midway to Punta Cana based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago Midway Airport to Punta Cana flights

  • What is the cheapest flight from Chicago Midway Airport to Punta Cana?

    In the last 3 days, the lowest price for a flight from Chicago Midway Airport to Punta Cana was $123 for a one-way ticket and $212 for a round-trip.

  • Do I need a passport to fly between Chicago Midway Airport and Punta Cana?

    A passport is required to fly from Chicago Midway Airport to Punta Cana.

  • Which aircraft models fly most regularly from Chicago Midway Airport to Punta Cana?

    We unfortunately don’t have that data for this specific route.

  • On which days can I fly direct from Chicago Midway Airport to Punta Cana?

    There are nonstop flights from Chicago Midway Airport to Punta Cana on a daily basis.

  • Which is the best airline for flights from Chicago to Punta Cana, Delta or Frontier?

    The two airlines most popular with KAYAK users for flights from Chicago to Punta Cana are Delta and Frontier. With an average price for the route of $845 and an overall rating of 8.0, Delta is the most popular choice. Frontier is also a great choice for the route, with an average price of $465 and an overall rating of 6.2.

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to Punta Cana?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago Midway Airport to Punta Cana.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport to Punta Cana?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Punta Cana from Chicago Midway Airport is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago Midway Airport to Punta Cana?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Punta Cana with an airline and back to Chicago Midway Airport with another airline. Booking your flights between Chicago Midway Airport and PUJ can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway Airport to Punta Cana?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Punta Cana from Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Prefer to fly non-stop from Chicago Midway Airport to Punta Cana?

Find which airlines fly direct from Midway to Punta Cana, which days they fly and book direct flights.

Nonstop departures

Chicago Midway to Punta Cana

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Nonstop returns

Punta Cana to Chicago Midway

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights
See more direct flights

Top 3 airlines serving from Midway to Punta Cana

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Punta Cana. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Midway to Punta Cana? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
Alaska AirlinesOverall score based on 9134 reviews
8.2Boarding
7.9Comfort
8.6Crew
7.3Food
7.3Entertainment
Airline reviews

Ground crew was great in Austin, flight crew left a lot to be desired. Not particularly friendly, helpful or nice.

6.0 GoodAnonymous, May 2024AUS - SFO
Read more about Alaska Airlines reviews

Ground crew was great in Austin, flight crew left a lot to be desired. Not particularly friendly, helpful or nice.

Everything was fine -- on time, clear, clean. I don't want to pay extra for in-flight wi-fi

First time flying with Alaska and the staff were All professional from checkin to departure! I do plan to book more flights with Alaska. Thanks

The flight was delayed because the pilots had not arrived on their previous flight yet. The flight was 100% full so it was pretty crowded. I miss having the screens on the back of the seats. It would be great if the Alaska planes had the clip so you can put your phone or tablet on the back of the seat in front of you to not strain your neck. Everything else was very smooth.

Boarded the plain and had to wait 1 hour for crew Captain to arrive from another flight

It was fine since it ensure we went to our destination in time.

Overall good flight, smooth and on time and comfortable. Disappointing that food is not served and you can't purchase the snack packs on the plane.

The space for legs in coach is better than other Airlines you can even cross your legs!!

There was a row with three women who were very loud - talking and laughing. In an open, outdoor setting that's fine. On an airplane, no. The flight attendants told the women they were the fun row. It took the woman sitting in the row ahead of the loud women to tell them they were too loud, but everyone in the general vicinity was irritated. I didn't think it would be possible to be so rowdy for so long. Then when we landed we weren't let off at a gate. We had to be bussed in and the bus contended with airline traffic. After dealing with the loud passengers, this was not what I was expecting. An incredibly disappointing experience with an airline that I have always regarded as one of the better ones.

I bought the cheapest ticket. No meal, no checked luggage so I didn't expect much and was surprised by how good the flight and service was. Alaska is now my favorite airline.

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

Very frustrated with boarding gate crew. She announced the plane was small and they would be limiting us to one item to carry on. Not a problem for me as I understand the tiny planes have limited space!! Not the case here! It was a rather large plane and had plenty of room for bags! So because I don’t want to be one of “those people” who ignores the request to check a carry on I did so asking if I would be able to pick it up at the bottom of the ramp on arrival in Knoxville to which she responded “yes”! Then I watched as every other passenger held onto their 2 items and boarded!! Then when we arrived in Knoxville our 2 carry ons had been put with all the other luggage and we had to go to baggage pick up and wait for all the big checked bags to come off the carousel! So she lied!! Frustrating. Next time I won’t be so nice!

It was a good experience except when boarding a female flight attendant did not go out of her way to assist my teenage daughters in finding space for their carry-ons after their compartments were full.

On time departure, smooth trip, flight attendant told through passengers the gate we would arrive at and the gate our outbound flight was departing from. Early arrival

Checking in at the airport the agent only booked the first keg of my trip and had my checked luggage going to the airport with a layover! Never was issued a boarding pass for the second leg or received sticker fir my checked bag. All was well in the end! Delta agents helped to resolve the situation!!!

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

Big plane, long flight, absolutely no leg room and basically non existent air! I am 5”4’ and always travel Main Cabin, I was miserable on this plane and could barely move when we arrived in Cabo due to the cramped leg area!

From Atlanta to Cabo I would have hoped on a plane that size I would have been able to breathe and wiggle my feet a little! The leg room in that plane is non existent and I am only 5”4’. And the air vent either wasn’t working very well or just could not blow air from the ceiling to the seat area as I was suffocating through the entire flight! And please don’t say I would have been more comfortable in first class because I cannot afford those rates and have always travelled Main Cabin without issues !

The pilots were good. Disappointing when planes don't have electrical ports

Not good 😐 Over priced baggage fees Small hard seats No wifi or entertainment options 😕

Didn't like anything!! Horrible flight. Small seating area and hard seats. Butt was sore after 2 hour flight to Seattle No entertainment or free refreshments No wifi or USB charging receptacles to charge phone entoute like other airliners Luggage rates were 3 times as much as competitors. Difficult to navigate online luggue process to pre pay before flight Overall bad experience WILL NEVER RIDE OR RECOMMEND FRONTIER TO FRIENDS OR FAMILY MEMBERS!!! THIS IS A SHAME!! MOST MESERIBLE FLIGHT OF MY LIFE!! AND I THOUGHT SPIRIT WAS 👎 YOU GOT THEM BEAD HANDS DOWN!!

Flight was a little late taking off. Seats are too upright, no ports to charge devices, no wifi, no entertainment

Six hour delay. Poor customer service. No voucher. Bad communication. Missed important appointments.

Our flight was delayed an hour, then when we got to board our flight finally, we were waiting in our seats for take off for 45 minutes before it was communicated that there was a maintenance issue therefore we waited on the plane for over an hour while that was resolved. We did not get to Phoenix until almost 3 hours after we were originally supposed to. This was the first and last time I will be flying Frontier.

Flight was canceled with little warning. Flight was rebooked through Ontario, California and connecting flight was delayed by over three hours. Frontier is living up to their Greyhound of the skies reputation for sure.

I purchased a carry on bag online…was supposed to cost $72 but after a whole slew of bs charges, the total was over $175.00. Because of these hidden charges, I will not even consider flying Frontier ever again. It’s just not worth the hassle. I’m scratching this company off my list forever.

Flight was OK. Seats were good no cell phone charges on the plane no TVs or entertainment.

There were 3 leg for the trip and each leg was delayed by 90 minutes or more. The boarding process takes forever with people waiting on the jetway even though most folks do not have carry-on. The whole process is poorly managed.

Flight cancelled and was told by a rude gate agent that they don’t accommodate on other airlines. Had to wait 5 hours for a connecting flight that had a 7 hour layover. Would not allow bags to be checked early so we couldn’t go through security .Had to rent a car for the afternoon to store bags and get a meal. Also incurred a hotel fee. No apology or reason given for the cancellation- just rudeness.

Book cheap flights from Chicago to Punta Cana

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Chicago to Punta Cana found on KAYAK in the last 72 hours.
5/26Sun
1 stopFrontier
13h 04mMDW-PUJ
$123
7/14Sun
1 stopFrontier
12h 49mMDW-PUJ
$134
6/4Tue
1 stopFrontier
23h 38mMDW-PUJ
$142
6/4Tue
2 stopsFrontier
23h 02mMDW-PUJ
$144
8/4Sun
1 stopFrontier
12h 49mMDW-PUJ
$152
8/31Sat
2 stopsDelta
16h 45mMDW-PUJ
$206
9/22Sun
2 stopsDelta
17h 37mMDW-PUJ
$256
5/26Sun
3 stops
26h 11mMDW-PUJ
$465
7/14Sun
2 stopsDelta
16h 59mMDW-PUJ
$493
6/16Sun
2 stopsDelta
17h 01mMDW-PUJ
$641

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Last minute flights from Midway to Punta Cana

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Chicago to Punta Cana that are departing in the next 10 days.
5/11Sat
multi-stopFrontier
26h 22mMDW-PUJ
5/13Mon
multi-stopFrontier
25h 46mPUJ-MDW
$324
5/9Thu
multi-stopFrontier
12h 43mMDW-PUJ
5/13Mon
multi-stopFrontier
25h 46mPUJ-MDW
$334
5/7Tue
multi-stopFrontier
13h 08mMDW-PUJ
5/8Wed
multi-stopFrontier
25h 20mPUJ-MDW
$335
5/10Fri
multi-stopFrontier
22h 51mMDW-PUJ
5/13Mon
multi-stopFrontier
25h 46mPUJ-MDW
$342
5/7Tue
multi-stopDelta
8h 00mMDW-PUJ
5/8Wed
multi-stopDelta
16h 30mPUJ-MDW
$435
5/7Tue
multi-stopDelta
6h 25mMDW-PUJ
5/8Wed
multi-stopDelta
19h 16mPUJ-MDW
$440
5/7Tue
multi-stopDelta
16h 54mMDW-PUJ
5/11Sat
multi-stopDelta
19h 16mPUJ-MDW
$465
5/11Sat
multi-stopDelta
16h 54mMDW-PUJ
5/18Sat
multi-stopDelta
16h 56mPUJ-MDW
$557
5/7Tue
multi-stopLATAM Airlines
21h 19mMDW-PUJ
5/8Wed
multi-stopLATAM Airlines
19h 22mPUJ-MDW
$3,356
5/7Tue
multi-stopLATAM Airlines
21h 19mMDW-PUJ
5/8Wed
multi-stopLATAM Airlines
19h 22mPUJ-MDW
$3,758

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Chicago Midway Airport - Punta Cana Flights

Departure:

Chicago Midway Airport (MDW)United States

Destination:

Punta Cana (PUJ)Dominican Republic

Return flight deals:

Punta Cana - Chicago Midway Airport

Cabin classes: