$162 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 2/20. 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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Everything you should know

Cheapest round-trip
$321
Multiple Airlines
Mon 1/26Mon 2/2
PUJ - MDW • 2 stops
Cheapest non-stop
$466
Southwest
Sat 1/31Sat 2/7
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!
Flight Deals
Booking Insights
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

Mon, Jan 26 - Mon, Feb 2
Multiple Airlines Logo
5:47 pm - 12:05 pm
PUJ
-
MDW
20h 18m2 stops
Multiple Airlines Logo
1:00 pm - 6:00 pm
MDW
-
PUJ
27h 00m1 stop
$321Multiple Airlines
Sun, Feb 22 - Sun, Mar 1
Multiple Airlines Logo
11:35 am - 1:04 pm
PUJ
-
MDW
27h 29m2 stops
Multiple Airlines Logo
6:30 am - 6:38 pm
MDW
-
PUJ
10h 08m1 stop
$324Multiple Airlines
Fri, Jan 16 - Fri, Jan 23
Multiple Airlines Logo
1:01 pm - 6:54 pm
PUJ
-
MDW
7h 53m1 stop
Multiple Airlines Logo
5:01 pm - 3:01 pm
MDW
-
PUJ
20h 00m1 stop
$326Multiple Airlines
Sun, Feb 22 - Sun, Mar 1
Multiple Airlines Logo
11:35 am - 2:29 pm
PUJ
-
MDW
28h 54m2 stops
Multiple Airlines Logo
6:15 am - 6:38 pm
MDW
-
PUJ
10h 23m1 stop
$330Multiple Airlines
Sat, Jan 17 - Sat, Jan 24
Multiple Airlines Logo
4:32 pm - 8:03 am
PUJ
-
MDW
17h 31m1 stop
Multiple Airlines Logo
9:38 am - 4:36 pm
MDW
-
PUJ
52h 58m2 stops
$337Multiple Airlines
Tue, Dec 23 - Wed, Jan 7
Frontier Logo
12:35 pm - 9:58 pm
SDQ
-
MDW
11h 23m1 stop
Frontier Logo
5:10 pm - 9:41 am
MDW
-
SDQ
14h 31m2 stops
$339Frontier
Sat, Jan 31 - Sat, Feb 7
Multiple Airlines Logo
4:11 pm - 11:45 am
PUJ
-
MDW
21h 34m1 stop
Multiple Airlines Logo
9:38 am - 4:36 pm
MDW
-
PUJ
28h 58m2 stops
$339Multiple Airlines
Mon, Feb 2 - Mon, Feb 9
Multiple Airlines Logo
5:47 pm - 12:05 pm
PUJ
-
MDW
20h 18m2 stops
Multiple Airlines Logo
1:00 pm - 6:00 pm
MDW
-
PUJ
27h 00m1 stop
$341Multiple Airlines
Fri, Jan 16 - Fri, Jan 23
Multiple Airlines Logo
1:01 pm - 6:54 pm
PUJ
-
MDW
7h 53m1 stop
Multiple Airlines Logo
1:00 pm - 4:36 pm
MDW
-
PUJ
25h 36m2 stops
$343Multiple Airlines
Tue, Dec 23 - Thu, Jan 8
Frontier Logo
12:35 pm - 9:58 pm
SDQ
-
MDW
11h 23m1 stop
Frontier Logo
12:41 pm - 11:55 am
MDW
-
SDQ
21h 14m2 stops
$344Frontier
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, Santo Domingo, which takes 9h 41m, and Santiago de los Caballeros, which takes 14h 43m.

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

There are around 375 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 50% of flights departing in the morning.

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

Each week there are around 2,620 direct flights from within Dominican Republic to Chicago Midway Airport. The most common day for departures is Monday, with 18% of flights taking off on this day.

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Good to know

Cheapest flight$162
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.

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)