$149 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 3/11. 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
Travelers love KAYAK
41.299.237 searches in the past 7 days on KAYAK

Save 23% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$384
Multiple Airlines
Sat 3/14Mon 3/23
SDQ - MDW • 1 stop
Cheapest non-stop
$1,351
Southwest
Thu 4/2Sun 4/5
PUJ - MDW • Non-stop
Start a new search
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

Sat, Mar 14 - Mon, Mar 23
Multiple Airlines Logo
10:56 am - 9:45 pm
SDQ
-
MDW
11h 49m
1 stop
Multiple Airlines Logo
9:51 pm - 1:25 pm
MDW
-
SDQ
14h 34m
2 stops
$384Multiple Airlines
Sat, Feb 7 - Mon, Feb 9
Multiple Airlines Logo
3:35 pm - 11:45 am
SDQ
-
MDW
22h 10m
2 stops
Multiple Airlines Logo
7:00 pm - 12:26 pm
MDW
-
SDQ
15h 26m
1 stop
$388Multiple Airlines
Sat, Mar 14 - Mon, Mar 23
Multiple Airlines Logo
10:56 am - 9:45 pm
SDQ
-
MDW
11h 49m
1 stop
Multiple Airlines Logo
6:00 am - 4:29 pm
MDW
-
SDQ
9h 29m
1 stop
$410Multiple Airlines
Mon, Mar 9 - Sat, Mar 21
Multiple Airlines Logo
7:10 pm - 1:02 pm
SDQ
-
MDW
18h 52m
1 stop
Multiple Airlines Logo
6:55 am - 1:38 am
MDW
-
SDQ
17h 43m
2 stops
$419Multiple Airlines
Sat, Mar 28 - Wed, Apr 29
Multiple Airlines Logo
2:30 pm - 10:19 pm
SDQ
-
MDW
32h 49m
2 stops
Multiple Airlines Logo
7:30 am - 5:29 am
MDW
-
SDQ
20h 59m
1 stop
$474Multiple Airlines
Wed, Feb 25 - Wed, Mar 4
Delta Logo
7:30 am - 5:45 pm
SDQ
-
MDW
12h 15m
2 stops
Delta Logo
10:49 am - 12:32 am
MDW
-
SDQ
11h 43m
2 stops
$477Delta
Thu, Feb 5 - Sun, Feb 8
Delta Logo
7:31 am - 5:29 pm
SDQ
-
MDW
11h 58m
2 stops
Delta Logo
6:00 am - 2:21 pm
MDW
-
SDQ
6h 21m
1 stop
$489Delta
Tue, Mar 10 - Tue, Mar 17
Frontier Logo
3:32 pm - 6:13 pm
PUJ
-
MDW
27h 41m
2 stops
Frontier Logo
6:00 am - 2:17 pm
MDW
-
PUJ
7h 17m
1 stop
$539Frontier
Thu, May 7 - Sat, May 30
Southwest Logo
1:40 pm - 10:20 pm
PUJ
-
MDW
9h 40m
1 stop
Southwest Logo
7:45 am - 2:50 pm
MDW
-
PUJ
6h 05m
1 stop
$752Southwest
Thu, May 7 - Sat, May 30
Southwest Logo
2:05 pm - 7:10 am
PUJ
-
MDW
18h 05m
2 stops
Southwest Logo
7:45 am - 2:50 pm
MDW
-
PUJ
6h 05m
1 stop
$780Southwest
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 08m, Santo Domingo, which takes 7h 31m, and Santiago de los Caballeros, which takes 8h 34m.

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

There are around 250 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 1,750 direct flights from within Dominican Republic to Chicago Midway Airport. The most common day for departures is Sunday, with 17% of flights taking off on this day.

How many long-haul flights are there to Chicago Midway Airport each week?

There are not any long-haul (6-12 hour flight duration) or short-haul (up to 3 hour flight duration) flights to Chicago Midway Airport. Instead, there are 1 medium-haul flights (3-6 hour flight duration), with the most arriving from Punta Cana.

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.

Find deals

Good to know

Cheapest flight$149
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 much is a flight to Chicago?

    On average, a flight to Chicago costs $492. The cheapest price found on KAYAK in the last 2 weeks cost $266 and departed from Punta Cana Airport.

  • 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

  • Looking for cheap airfare to Chicago Midway Airport? 25% of our users found round-trip tickets to Chicago Midway Airport for the following prices or less: From Punta Cana $464
  • 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
Griffith
Saint John

Everything you need to know for your flight to Midway

Information on the airport you'll fly into in Chicago

Chicago Midway Airport (MDW)