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Cheap flights from Chicago Midway Airport to the Dominican Republic from $133

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to the Dominican Republic departing on 11/10. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Chicago Midway Airport to the Dominican Republic

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
2:59 pm - 6:38 pmMDW-PUJ
25h 39m1 stop
Multiple Airlines Logo
9:38 am - 10:30 pmPUJ-MDW
14h 52m1 stop
$321Multiple Airlines
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Sat, Dec 6 - Sat, Dec 13
Multiple Airlines Logo
2:05 pm - 12:08 pmMDW-PUJ
20h 03m2 stops
Multiple Airlines Logo
9:38 am - 9:22 pmPUJ-MDW
13h 44m1 stop
$325Multiple Airlines
Find Deal
Sat, Nov 8 - Sat, Nov 15
Southwest Logo
8:15 am - 2:35 pmMDW-PUJ
4h 20mnonstop
Southwest Logo
3:00 pm - 5:55 pmPUJ-MDW
4h 55mnonstop
$331Southwest
Find Deal
Sat, Jan 24 - Sat, Jan 31
Multiple Airlines Logo
5:30 pm - 8:25 pmMDW-PUJ
24h 55m1 stop
Multiple Airlines Logo
9:38 am - 9:53 pmPUJ-MDW
14h 15m1 stop
$333Multiple Airlines
Find Deal
Thu, Nov 27 - Thu, Dec 4
Multiple Airlines Logo
2:16 pm - 7:54 pmMDW-PUJ
27h 38m1 stop
Multiple Airlines Logo
9:38 am - 9:53 pmPUJ-MDW
14h 15m1 stop
$336Multiple Airlines
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Thu, Dec 4 - Thu, Dec 11
Delta Logo
6:00 am - 4:46 pmMDW-PUJ
8h 46m1 stop
Delta Logo
6:11 pm - 11:47 pmPUJ-MDW
7h 36m1 stop
$338Delta
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Sun, Dec 7 - Thu, Dec 11
Delta Logo
5:13 pm - 1:12 pmMDW-PUJ
17h 59m2 stops
Delta Logo
5:19 pm - 11:47 pmPUJ-MDW
8h 28m1 stop
$342Delta
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Fri, Dec 5 - Sat, Dec 13
Southwest Logo
5:10 am - 2:00 pmMDW-PUJ
6h 50m1 stop
Southwest Logo
3:00 pm - 5:55 pmPUJ-MDW
4h 55mnonstop
$347Southwest
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Sat, Jan 24 - Sat, Jan 31
Frontier Logo
8:42 pm - 3:06 pmMDW-PUJ
16h 24m1 stop
Frontier Logo
3:24 pm - 1:01 pmPUJ-MDW
47h 37m2 stops
$380Frontier
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Fri, Dec 5 - Fri, Dec 12
Frontier Logo
2:49 pm - 9:42 amMDW-SDQ
16h 53m2 stops
Frontier Logo
2:53 pm - 9:58 pmSDQ-MDW
9h 05m1 stop
$585Frontier
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Wed, Dec 17 - Mon, Dec 22

Delta flights from Chicago Midway Airport to Dominican Republic

Our best Delta deals on Chicago Midway Airport to Dominican Republic flight tickets
Delta
Dec 7
MDW6:00 amChicago Midway
8h 46m
1 stop
PUJ4:46 pmPunta Cana
Dec 11
PUJ6:11 pmPunta Cana
7h 36m
1 stop
MDW11:47 pmChicago Midway
$338
Find similar
Delta
Dec 5
MDW5:13 pmChicago Midway
17h 59m
2 stops
PUJ1:12 pmPunta Cana
Dec 13
PUJ5:19 pmPunta Cana
8h 28m
1 stop
MDW11:47 pmChicago Midway
$342
Find similar
Delta
Nov 17
MDW6:00 amChicago Midway
6h 25m
1 stop
PUJ2:25 pmPunta Cana
Nov 24
PUJ5:03 pmPunta Cana
8h 37m
1 stop
MDW11:40 pmChicago Midway
$351
Find similar

Southwest flights from Chicago Midway Airport to Dominican Republic

Our best Southwest deals on Chicago Midway Airport to Dominican Republic flight tickets
Southwest
Jan 24
MDW8:15 amChicago Midway
4h 20m
PUJ2:35 pmPunta Cana
Jan 31
PUJ3:00 pmPunta Cana
4h 55m
MDW5:55 pmChicago Midway
$331
Find similar
Southwest
Jan 24
MDW5:10 amChicago Midway
6h 50m
1 stop
PUJ2:00 pmPunta Cana
Jan 31
PUJ3:00 pmPunta Cana
4h 55m
MDW5:55 pmChicago Midway
$347
Find similar
Southwest
Nov 15
MDW7:40 amChicago Midway
6h 25m
1 stop
PUJ4:05 pmPunta Cana
Nov 22
PUJ3:20 pmPunta Cana
5h 00m
MDW6:20 pmChicago Midway
$355
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Dominican Republic that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated October 22, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to the Dominican Republic that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sat 12/6

2:59 pm-6:38 pm

1 stop25h 39m

Punta Cana

Sat 12/13

9:38 am-10:30 pm

1 stop14h 52m

$321

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sat 11/8

2:05 pm-12:08 pm

2 stops20h 03m

Punta Cana

Sat 11/15

9:38 am-9:22 pm

1 stop13h 44m

$325

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sat 1/24

8:15 am-2:35 pm

Nonstop4h 20m

Punta Cana

Sat 1/31

3:00 pm-5:55 pm

Nonstop4h 55m

$331

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Thu 11/27

5:30 pm-8:25 pm

1 stop24h 55m

Punta Cana

Thu 12/4

9:38 am-9:53 pm

1 stop14h 15m

$333

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Thu 12/4

2:16 pm-7:54 pm

1 stop27h 38m

Punta Cana

Thu 12/11

9:38 am-9:53 pm

1 stop14h 15m

$336

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sun 12/7

6:00 am-4:46 pm

1 stop8h 46m

Punta Cana

Thu 12/11

6:11 pm-11:47 pm

1 stop7h 36m

$338

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Fri 12/5

5:13 pm-1:12 pm

2 stops17h 59m

Punta Cana

Sat 12/13

5:19 pm-11:47 pm

1 stop8h 28m

$342

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sat 1/24

5:10 am-2:00 pm

1 stop6h 50m

Punta Cana

Sat 1/31

3:00 pm-5:55 pm

Nonstop4h 55m

$347

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Fri 12/5

8:42 pm-3:06 pm

1 stop16h 24m

Punta Cana

Fri 12/12

3:24 pm-1:01 pm

2 stops47h 37m

$380

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Wed 12/17

2:49 pm-9:42 am

2 stops16h 53m

Santo Domingo Las Americas

Mon 12/22

2:53 pm-9:58 pm

1 stop9h 05m

$585

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to the Dominican Republic from

How to get the cheapest flight ticket from Chicago Midway Airport to Dominican Republic

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Dominican Republic?

In general, October is the cheapest month to fly from Chicago Midway Airport to Dominican Republic. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $482. If you are unable to visit Dominican Republic during the month of October, then departing from Chicago Midway Airport during the month February is also very affordable. Most momondo users find prices during this month for around $518.

What is the cheapest day to depart on your flight to Dominican Republic?

The cheapest day to depart on your flight to Dominican Republic is on a Saturday when prices can be found for as low as $620. This is often the case because there is less demand to fly during this day of the week. Flights from Chicago Midway Airport to Dominican Republic on a Friday will generally be more expensive and average around $839. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

What is the cheapest time of day to depart on your flight to Dominican Republic?

Flying to Dominican Republic from Chicago Midway Airport in the evening is the least expensive time of day to depart. momondo users have found prices as low as $281 when looking at flights departing in the evening. Flights in the morning are often more expensive with an average ticket price of $689.

What is the cheapest Chicago Midway to Dominican Republic flight route?

Fly from Chicago Midway to Punta Cana for the best Chicago Midway - Dominican Republic flight prices

What cabin class options are available on Chicago Midway to Dominican Republic flights?

There is only 1 cabin class available to choose from on Chicago Midway to Dominican Republic flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Chicago Midway Airport to Dominican Republic flights?

No. A direct flight is the cheapest option for a flight between Chicago Midway Airport to Dominican Republic.

Cheap Chicago Midway Airport to Dominican Republic flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Dominican Republic

Fastest flight time

4h 15m

Direct flights

Every day

Airports in Dominican Republic

1 airport
The fastest flight from Chicago Midway Airport to Dominican Republic takes 4h 15m
Direct flights go from Chicago Midway Airport to Dominican Republic every day.
There is 1 airport near Dominican Republic: Punta Cana (PUJ)
Search flight deals

  • When did momondo last update prices for flights from Chicago Midway Airport to Dominican Republic?

    Prices for flights from Chicago Midway Airport to Dominican Republic are updated daily.

  • How many operators does momondo search for flights from Chicago Midway Airport to Dominican Republic?

  • How old do you have to be to fly from Chicago Midway Airport to Dominican Republic?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago Midway Airport to Dominican Republic.

  • What documentation or ID do you need to fly to Dominican Republic?

    The travel and health documents you'll need for your trip to Dominican Republic may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Dominican Republic. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Chicago Midway Airport to Dominican Republic?

Best airlines flying from Chicago Midway Airport to Dominican Republic

Compare and see reviews for airlines that fly from Chicago Midway Airport to Dominican Republic with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $370Free CancellationRating
5.8
3,130 reviews
Search Frontier flights
DeltaPriceFrom $406Free CancellationRating
7.9
7,979 reviews
Search Delta flights
SouthwestPriceFrom $495Free CancellationRating
8.0
4,237 reviews
Search Southwest flights

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Dominican Republic?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Chicago to Dominican Republic. momondo saves you time and could save you money on your trip.

Can I find flights from Chicago to Dominican Republic with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Dominican Republic from Chicago with this policy.

How can momondo help me find flights from Chicago to Dominican Republic?

momondo provides multiple filters to help you find the best flight to Dominican Republic from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Chicago to Dominican Republic right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Dominican Republic, momondo offers a useful price alert feature which will track prices for flights to Dominican Republic from Chicago and alert you when they change.

An easier way to manage your Dominican Republic trip

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Fri 11/21
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