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$127 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 5/18. 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
0 bags
Fri 5/31
Fri 6/7

Search 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
In the last 7 days travelers have searched 43,740,974 times on KAYAK, and here is why:

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Flights to Midway - Travel Insights & Trends

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.

What is the cheapest day to fly to Chicago?

The average price of all flights to Chicago Midway Airport clicked on KAYAK for each day over the last 12 months.
Based on KAYAK data, the cheapest day to fly to Chicago is Saturday where tickets can be as cheap as $322. On the other hand, the most expensive day to fly is Saturday, where prices are $322 on average.

Which airline offers the most flights to Chicago Midway Airport?

Of the 5 airlines that fly to Chicago Midway Airport, Southwest offers the most flights, with around 1,443 per week, followed by Frontier with 138 flights per week.

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 4h 59m, Santo Domingo, which takes 8h 19m, and Santiago de los Caballeros, which takes 9h 16m.

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

There are around 242 direct flights from within Dominican Republic to Chicago Midway Airport every day. Most flights depart in the morning, with 12:00 pm the most common departure time and 47% of flights departing in the morning.

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

Each week there are around 1,688 direct flights from within Dominican Republic to Chicago Midway Airport. The most common day for departures is Friday, with 16% 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 5 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 5 direct flights each week.

Good to know

Cheapest flight

$127
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 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.

See more FAQs

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.

Prefer to fly non-stop to Chicago Midway?

Find which airlines fly direct to Midway, which days they fly and book direct flights.

Nonstop departures

Dominican Republic to Chicago Midway

Monday

Aeromexico, Air France, Allegiant Air, +11 more

Aeromexico, Air France, +12 more

Tuesday

Aeromexico, Air France, Delta, +9 more

Aeromexico, Air France, +10 more

Wednesday

Aeromexico, Air France, Delta, +9 more

Aeromexico, Air France, +10 more

Thursday

Aeromexico, Air France, Allegiant Air, +10 more

Aeromexico, Air France, +11 more

Friday

Aeromexico, Air France, Allegiant Air, +11 more

Aeromexico, Air France, +12 more

Saturday

Aeromexico, Air France, Delta, +9 more

Aeromexico, Air France, +10 more

Sunday

Aeromexico, Air France, Allegiant Air, +10 more

Aeromexico, Air France, +11 more

See more direct flights

Nonstop returns

Chicago Midway to Dominican Republic

Monday

Aeromexico, Air France, Allegiant Air, +11 more

Aeromexico, Air France, +12 more

Tuesday

Aeromexico, Air France, Delta, +9 more

Aeromexico, Air France, +10 more

Wednesday

Aeromexico, Air France, Delta, +9 more

Aeromexico, Air France, +10 more

Thursday

Aeromexico, Air France, Allegiant Air, +10 more

Aeromexico, Air France, +11 more

Friday

Aeromexico, Air France, Allegiant Air, +11 more

Aeromexico, Air France, +12 more

Saturday

Aeromexico, Air France, Delta, +9 more

Aeromexico, Air France, +10 more

Sunday

Aeromexico, Air France, Allegiant Air, +10 more

Aeromexico, Air France, +11 more

See more direct flights
See more direct flights

Book cheap flights from the Dominican Republic to Chicago

Recent round-trip flight deals

 
These are the cheapest round-trip flights to Chicago found on KAYAK in the last 72 hours.
6/9Sun
1 stopFrontier
21h 48mSDQ-MDW
6/15Sat
1 stopFrontier
23h 03mMDW-SDQ
$224
5/30Thu
1 stopFrontier
22h 28mSDQ-MDW
6/6Thu
1 stopFrontier
13h 41mMDW-SDQ
$233
6/6Thu
1 stopFrontier
21h 58mSDQ-MDW
6/9Sun
1 stopFrontier
13h 37mMDW-SDQ
$256
5/30Thu
2 stopsFrontier
20h 11mSDQ-MDW
6/6Thu
1 stopFrontier
13h 41mMDW-SDQ
$261
5/21Tue
1 stopFrontier
23h 18mSDQ-MDW
5/25Sat
1 stopFrontier
23h 15mMDW-SDQ
$262
5/29Wed
1 stop
15h 17mSDQ-MDW
6/5Wed
2 stops
24h 02mMDW-SDQ
$279
5/29Wed
1 stop
15h 17mSDQ-MDW
6/5Wed
1 stop
16h 52mMDW-SDQ
$293
5/11Sat
2 stopsDelta
19h 36mSDQ-MDW
5/18Sat
2 stopsDelta
14h 23mMDW-SDQ
$381
9/25Wed
2 stopsDelta
18h 49mSDQ-MDW
9/30Mon
2 stopsDelta
17h 28mMDW-SDQ
$422
10/22Tue
2 stopsLATAM Airlines
32h 47mPUJ-MDW
10/27Sun
2 stopsLATAM Airlines
22h 15mMDW-PUJ
$2,136

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Recent one-way flight deals

 
Only flying one-way? Below are some of the best deals for one-way flights to Chicago found on KAYAK in the last 72 hours.
5/18Sat
1 stopFrontier
14h 06mPUJ-MDW
$127
5/7Tue
1 stopFrontier
12h 37mSDQ-MDW
$129
5/16Thu
1 stopFrontier
14h 48mPUJ-MDW
$132
5/22Wed
1 stop
15h 17mSDQ-MDW
$136
5/17Fri
1 stopFrontier
28h 21mPUJ-MDW
$138
5/30Thu
1 stopFrontier
22h 28mSDQ-MDW
$143
5/7Tue
2 stops
18h 43mSDQ-MDW
$154
5/7Tue
2 stopsDelta
19h 36mSDQ-MDW
$202
5/18Sat
2 stopsDelta
19h 36mSDQ-MDW
$208
9/2Mon
2 stopsLATAM Airlines
32h 42mPUJ-MDW
$1,477

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Last minute flights to Midway

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights to Chicago that are departing in the next 10 days.
5/2Thu
multi-stopFrontier
13h 24mSDQ-MDW
5/7Tue
multi-stopFrontier
17h 43mMDW-SDQ
$394
5/3Fri
multi-stopDelta
7h 45mPUJ-MDW
5/6Mon
multi-stopDelta
7h 40mMDW-PUJ
$480
5/6Mon
multi-stopDelta
18h 05mSDQ-MDW
5/15Wed
multi-stopDelta
6h 05mMDW-SDQ
$483
5/3Fri
multi-stopDelta
10h 50mPUJ-MDW
5/6Mon
multi-stopDelta
7h 40mMDW-PUJ
$492
5/6Mon
multi-stopDelta
18h 05mSDQ-MDW
5/15Wed
multi-stopDelta
6h 05mMDW-SDQ
$537
5/2Thu
multi-stopDelta
18h 59mSDQ-MDW
5/7Tue
multi-stopDelta
17h 55mMDW-SDQ
$573
5/6Mon
multi-stopDelta
18h 25mSDQ-MDW
5/15Wed
multi-stopDelta
6h 05mMDW-SDQ
$649
5/6Mon
multi-stopDelta
18h 25mSDQ-MDW
5/15Wed
multi-stopDelta
6h 05mMDW-SDQ
$661
5/6Mon
multi-stopDelta
18h 49mSDQ-MDW
5/15Wed
multi-stopDelta
17h 55mMDW-SDQ
$855
5/6Mon
multi-stopDelta
18h 49mSDQ-MDW
5/15Wed
multi-stopDelta
17h 55mMDW-SDQ
$1,400

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Flights to Chicago Midway Airport

Destination:

Chicago Midway Airport (MDW)United States

Return flight deals:

Chicago Midway Airport - Dominican Republic

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