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Cheap Flights from Punta Cana to Chicago Midway

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 to Chicago Midway? Find the lowest prices on one-way and return tickets right here.
Chicago.ر.ق.‏ 576 per passenger.Departing Sat, 16 May.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Punta Cana on Sat, 16 May, arriving in Chicago Midway.Price includes taxes and charges.From ر.ق.‏ 576, select.
Chicago.ر.ق.‏ 677 per passenger.Departing Sat, 7 Mar.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Punta Cana on Sat, 7 Mar, arriving in Chicago Midway.Price includes taxes and charges.From ر.ق.‏ 677, select.
Chicago.ر.ق.‏ 722 per passenger.Departing Sat, 18 Apr.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Punta Cana on Sat, 18 Apr, arriving in Chicago Midway.Price includes taxes and charges.From ر.ق.‏ 722, select.
Chicago.ر.ق.‏ 794 per passenger.Departing Sat, 14 Mar.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Punta Cana on Sat, 14 Mar, arriving in Chicago Midway.Price includes taxes and charges.From ر.ق.‏ 794, select.
Chicago.ر.ق.‏ 883 per passenger.Departing Sat, 18 Apr.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Punta Cana on Sat, 18 Apr, arriving in Chicago Midway.Price includes taxes and charges.From ر.ق.‏ 883, select.
Chicago.ر.ق.‏ 893 per passenger.Departing Tue, 2 Jun.One-way flight with Arajet.Outbound indirect flight with Arajet, departs from Punta Cana on Tue, 2 Jun, arriving in Chicago Midway.Price includes taxes and charges.From ر.ق.‏ 893, select.
Chicago.ر.ق.‏ 994 per passenger.Departing Sat, 28 Feb.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Punta Cana on Sat, 28 Feb, arriving in Chicago Midway.Price includes taxes and charges.From ر.ق.‏ 994, select.
Chicago.ر.ق.‏ 1,041 per passenger.Departing Tue, 28 Jul.One-way flight with Arajet.Outbound indirect flight with Arajet, departs from Punta Cana on Tue, 28 Jul, arriving in Chicago Midway.Price includes taxes and charges.From ر.ق.‏ 1,041, 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.
Feb
from ر.ق.‏ 992
Mar
from ر.ق.‏ 676
Apr
from ر.ق.‏ 721
May
from ر.ق.‏ 576
Jun
from ر.ق.‏ 892
Jul
from ر.ق.‏ 1,039
Aug
from ر.ق.‏ 1,321
Sep
Find prices
Oct
Find prices
Nov
from ر.ق.‏ 1,198
Dec
from ر.ق.‏ 1,172
Jan
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

14km from central Chicago
Closest
from ر.ق.‏ 576
Search flights

Chicago O'Hare International

25km from central Chicago
Cheapest
from ر.ق.‏ 437
Search flights

Chicago Dupage County

51km from central Chicago
Search flights

Chicago Rockford

126km from central Chicago
from ر.ق.‏ 746
Search flights

Punta Cana to Chicago: Flight information

The things to know before you go.
Cheapest flight foundر.ق.‏ 576
Cheapest month to flyMay
Average flight time5 hrs
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 ر.ق.‏ 1,465. 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.
5 hours is the average flight time from Punta Cana to Chicago Midway.
Southwest Airlines flies direct from Punta Cana to Chicago Midway.
As of February 2026, there are 5 flights per week flying from Punta Cana to Chicago Midway.
The cheapest month to fly from Punta Cana to Chicago Midway is usually April.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Punta Cana Airport to Chicago Midway Airport on Tuesday, 7 April 2026.
Yes – the average flight time is 5 hours.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago Midway but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.
Currently, Frontier Airlines and Southwest Airlines offer the cheapest flight tickets to Chicago Midway.

How to find cheap flights to Chicago Midway from Punta Cana

Looking for cheap tickets from Punta Cana to Chicago Midway? 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 Midway from Punta Cana from over 1,000 providers. Then choose the cheapest or fastest plane tickets.
  • Flex your dates to find the best Punta Cana-Chicago Midway 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.
  • 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 Midway, 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.

    • 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 Midway 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.