$148 Find Cheap Flights from Dominican Republic to Chicago Midway Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Midway departing on 12/31. 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
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago Midway Airport

 
These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago, as well as popular online travel agencies
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Flight Deals

Cheap Flights from the Dominican Republic to Midway

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from the Dominican Republic to Midway 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 for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from the Dominican Republic to Midway

Wed, Dec 24 - Wed, Dec 31
Multiple Airlines Logo
6:08 pm - 5:38 pmPUJ-MDW
25h 30m2 stops
Multiple Airlines Logo
6:12 am - 10:27 amMDW-PUJ
26h 15m1 stop
$306Multiple Airlines
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Wed, Dec 31 - Wed, Jan 7
Multiple Airlines Logo
4:19 pm - 10:12 pmPUJ-MDW
7h 53m1 stop
Multiple Airlines Logo
3:52 pm - 4:31 pmMDW-PUJ
22h 39m1 stop
$309Multiple Airlines
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Thu, Dec 4 - Thu, Dec 11
Multiple Airlines Logo
9:38 am - 9:53 pmPUJ-MDW
14h 15m1 stop
Multiple Airlines Logo
2:16 pm - 7:54 pmMDW-PUJ
27h 38m1 stop
$317Multiple Airlines
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Wed, Dec 31 - Wed, Jan 7
Multiple Airlines Logo
4:19 pm - 10:12 pmPUJ-MDW
7h 53m1 stop
Multiple Airlines Logo
6:00 am - 12:16 pmMDW-PUJ
28h 16m2 stops
$321Multiple Airlines
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Fri, Dec 5 - Fri, Dec 12
Delta Logo
3:50 pm - 11:47 pmPUJ-MDW
9h 57m1 stop
Delta Logo
6:00 am - 3:39 pmMDW-PUJ
7h 39m1 stop
$344Delta
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Sat, Dec 20 - Sat, Jan 3
Frontier Logo
11:16 am - 9:04 pmSDQ-MDW
11h 48m1 stop
Frontier Logo
2:16 pm - 11:30 amMDW-SDQ
19h 14m1 stop
$362Frontier
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Thu, Feb 19 - Sun, Feb 22
Delta Logo
5:11 pm - 8:54 amPUJ-MDW
17h 43m1 stop
Delta Logo
6:45 pm - 2:30 pmMDW-PUJ
17h 45m1 stop
$368Delta
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Wed, Dec 24 - Wed, Dec 31
Frontier Logo
4:19 pm - 5:38 pmPUJ-MDW
27h 19m1 stop
Frontier Logo
8:15 am - 10:27 amMDW-PUJ
24h 12m1 stop
$370Frontier
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Sat, Nov 22 - Sat, Nov 29
Southwest Logo
3:20 pm - 6:20 pmPUJ-MDW
5h 00mnonstop
Southwest Logo
8:30 am - 2:50 pmMDW-PUJ
4h 20mnonstop
$379Southwest
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Sat, Nov 22 - Sat, Nov 29
Southwest Logo
3:20 pm - 6:20 pmPUJ-MDW
5h 00mnonstop
Southwest Logo
5:25 am - 3:30 pmMDW-PUJ
8h 05m1 stop
$384Southwest
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Everything you should know

Cheapest round-trip
$306
Multiple Airlines
Wed 12/24Wed 12/31
PUJ - MDW • 2 stops
Cheapest non-stop
$379
Southwest
Sat 11/22Sat 11/29
PUJ - MDW • Non-stop
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Midway!
Booking Insights

KAYAK's insights & trends for flights to Midway

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

How long is the flight to Chicago Midway Airport?

The duration of your flight to Chicago depends on your departure and arrival airports. Obviously any flights that include a layover will also be longer. The most popular routes to Chicago on KAYAK are from Punta Cana, which takes 5h 10m, Santiago de los Caballeros, which takes 7h 24m, and Santo Domingo, which takes 9h 48m.

How many direct flights to Chicago Midway Airport are there each day?

There are around 311 direct flights from within Dominican Republic to Chicago Midway Airport every day. Most flights depart in the morning, with 6:00 am the most common departure time and 48% of flights departing in the morning.

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Good to know

Cheapest flight$148
Flight from Punta Cana to Chicago Midway Airport

FAQs - booking Chicago Midway Airport flights

  • How far is Chicago Midway Airport from central Chicago?

    Chicago Midway Airport is 9 miles from the center of Chicago.

  • How many cities have direct flights to Chicago Midway Airport?

    From the Dominican Republic, there are direct flights to Chicago Midway Airport from 1 city. This city is Punta Cana and there are 1 direct flights each week.

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

    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 to Chicago Midway Airport.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to 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 to Chicago Midway Airport?

    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 Chicago Midway Airport with an airline and back with another airline.

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

    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 Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • How many direct flights to Chicago Midway Airport are there each week?

    Each week there are around 2,176 direct flights from within Dominican Republic to Chicago Midway Airport. The most common day for departures is Monday, with 16% of flights taking off on this day.

Top tips for finding cheap flights to Chicago Midway Airport

  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago Midway Airport flight deals.

Traveling to a place near Midway?

Book flights to Midway if you plan to visit one of these locations
Merrillville
Saint Joseph
Hammond
Portage
Lansing
Valparaiso
Chesterton
Schererville
Munster
Porter
Monticello
Saint John
Griffith

Everything you need to know for your flight to Midway

Information on the airport you'll fly into in Chicago

Chicago Midway Airport (MDW)

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