Skyscanner home

Cheap Flights from Punta Cana (PUJ) to Chicago Midway (MDW)

Compare Punta Cana to Chicago Midway flight deals

Find the cheapest month or even day of the year to fly to Chicago Midway

Book the best Chicago Midway fare with no extra fees

Flight deals from Punta Cana to Chicago Midway

Looking for a cheap last-minute deal or the best return flight from Punta Cana Airport to Chicago Midway Airport? If you want to travel next month, return fares start from £297. Find the lowest prices on one-way and return tickets right here.
Chicago.£134 per passenger.Departing Sat, 2 May.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Punta Cana on Sat, 2 May, arriving in Chicago Midway.Price includes taxes and charges.From £134, select.
Chicago.£142 per passenger.Departing Thu, 23 Apr.One-way flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departs from Punta Cana on Thu, 23 Apr, arriving in Chicago Midway.Price includes taxes and charges.From £142, select.
Chicago.£169 per passenger.Departing Tue, 1 Sep.One-way flight with Arajet.Outbound indirect flight with Arajet, departs from Punta Cana on Tue, 1 Sep, arriving in Chicago Midway.Price includes taxes and charges.From £169, select.
Chicago.£200 per passenger.Departing Fri, 10 Jul.One-way flight with Arajet.Outbound indirect flight with Arajet, departs from Punta Cana on Fri, 10 Jul, arriving in Chicago Midway.Price includes taxes and charges.From £200, select.
Chicago.£203 per passenger.Departing Thu, 11 Jun.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Punta Cana on Thu, 11 Jun, arriving in Chicago Midway.Price includes taxes and charges.From £203, select.
Chicago.£212 per passenger.Departing Thu, 13 Aug.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Punta Cana on Thu, 13 Aug, arriving in Chicago Midway.Price includes taxes and charges.From £212, select.
Chicago.£216 per passenger.Departing Sat, 2 May.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Punta Cana on Sat, 2 May, arriving in Chicago Midway.Price includes taxes and charges.From £216, select.
Chicago.£244 per passenger.Departing Thu, 1 Oct.One-way flight with Breeze Airways.Outbound indirect flight with Breeze Airways, departs from Punta Cana on Thu, 1 Oct, arriving in Chicago Midway.Price includes taxes and charges.From £244, select.
Chicago.£250 per passenger.Departing Thu, 9 Jul.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Punta Cana on Thu, 9 Jul, arriving in Chicago Midway.Price includes taxes and charges.From £250, select.
Chicago.£259 per passenger.Departing Thu, 17 Dec.One-way flight with Delta.Outbound indirect flight with Delta, departs from Punta Cana on Thu, 17 Dec, arriving in Chicago Midway.Price includes taxes and charges.From £259, select.
Chicago.£301 per passenger.Departing Thu, 4 Jun.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Punta Cana on Thu, 4 Jun, arriving in Chicago Midway.Price includes taxes and charges.From £301, select.
Chicago.£339 per passenger.Departing Wed, 20 Jan.One-way flight with Delta.Outbound indirect flight with Delta, departs from Punta Cana on Wed, 20 Jan, arriving in Chicago Midway.Price includes taxes and charges.From £339, select.
Chicago.£810 per passenger.Departing Mon, 3 Aug.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Punta Cana on Mon, 3 Aug, arriving in Chicago Midway.Price includes taxes and charges.From £810, select.

Find the cheapest month to fly from Punta Cana to Chicago Midway

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Punta Cana to Chicago Midway flights are currently cheapest in May.
Apr
from £142
May
from £134
Jun
from £203
Jul
from £200
Aug
from £212
Sep
from £169
Oct
from £244
Nov
Find prices
Dec
from £259
Jan
from £339
Feb
Find prices
Mar
Find prices

Direct flights from Punta Cana to Chicago Midway

Punta Cana to Chicago Midway: Alternative routes

Compare routes from Punta Cana to Chicago below. You may find an airport to fly into that's cheaper, faster, or easier than Chicago Midway.

Chicago Midway

9 miles from central Chicago
Closest
from £134
Search flights

Chicago O'Hare International

16 miles from central Chicago
Cheapest
from £99
Search flights

Chicago Dupage County

32 miles from central Chicago
Search flights

Chicago Rockford

78 miles from central Chicago
from £156
Search flights

Punta Cana to Chicago: Flight information

The things to know before you go.
Cheapest flight found£134
Cheapest month to flyMay
Average flight time4 hrs, 49 mins
Most popular airlineSouthwest Airlines
Average flights per week5

Finding cheap flights from Punta Cana to Chicago Midway: Frequently asked questions

The best price we found for a return flight from Punta Cana to Chicago Midway is £297. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
4 hours and 49 minutes is the average flight time from Punta Cana to Chicago Midway.
Southwest Airlines flies direct from Punta Cana to Chicago Midway.
As of April 2026, there are 5 flights per week flying from Punta Cana to Chicago Midway.
Yes – the average flight time is 4 hours and 49 minutes.
Currently, Frontier Airlines and Southwest Airlines offer the cheapest flight tickets to Chicago Midway.

How to find cheap flights to Chicago (MDW) from Punta Cana (PUJ) in 2026

Looking for cheap tickets from Punta Cana to Chicago Midway? Return tickets start from £297 and one-way flights to Chicago Midway from Punta Cana start from £134


Here are a few tips on how to secure the best flight price and make your journey as smooth as possible.

  • Simply hit 'search'. From British Airways to international carriers like Emirates, we compare all major airlines along with the most popular online travel agents to find the cheapest plane tickets from Punta Cana to Chicago Midway. And with us there are no hidden fees - what you see is what you pay.
  • Compare flight deals to Chicago from Punta Cana from over 1,000 providers. Then choose the cheapest or fastest plane tickets. Flight tickets to Chicago start from £134 one-way.
  • Flex your dates to find the best PUJ-MDW ticket prices. If you are flexible when it comes to your travel dates, use Skyscanner's 'Whole month' tool to find the cheapest month, and even day to fly to Chicago Midway from Punta Cana.
  • Set up a Price Alert. You can easily track the fare of your cheap Punta Cana-Chicago Midway flights by creating an alert. Whenever prices go down or up, you'll get an email or push notification to help make sure you get the best possible flight deal.
  • Flexible on when you travel? The cheapest month to fly from Punta Cana to Chicago Midway is May.
  • Fly without stops. Only interested in direct flights between Punta Cana and Chicago Midway? Make sure to tick 'Direct flights only' when performing a search. If there are direct flights available on the route, these will appear in the results.
  • Find the cheapest Business class flights from Punta Cana and Chicago Midway. We scour the internet for the best Business, Premium Economy and First Class flight fares to Chicago, too. Check the difference in price as you search – you might just chance upon a last-minute low fare. Note that not all cabin classes are available for every destination or airline.
  • Include nearby airports in your search. Widen your search for Punta Cana to Chicago Midway flight deals by selecting the "add nearby airports" option. This will allow you to see flight prices for all the nearest airports at your departure point and your destination and could help you save next time you travel.
  • Search for cheap flights regardless of where you are. To get the best flight booking experience when out and about, download the app and search for plane tickets between Punta Cana and Chicago Midway whenever you want.

Combine your flight to Chicago Midway from Punta Cana with hotels and car hire

Once you've secured your cheap flight ticket from Punta Cana to Chicago Midway, discover the best prices and exclusive rates for hotels in Chicago or nearby. You can also compare hundreds of car hire companies in one go so that you get the best car hire price for your trip.


Plan the rest of your trip from Punta Cana to Chicago

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.