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Cheap flights from Chicago Midway Airport to the Dominican Republic from $160

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 10/6. 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

Southwest Logo
5:10 am - 2:05 pmMDW-PUJ
7h 55m1 stop
Southwest Logo
3:05 pm - 9:35 pmPUJ-MDW
7h 30m1 stop
$343Southwest
Find Deal
Mon, Sep 1 - Fri, Sep 5
Delta Logo
6:23 pm - 12:28 pmMDW-PUJ
17h 05m2 stops
Delta Logo
2:49 pm - 10:14 pmPUJ-MDW
8h 25m1 stop
$347Delta
Find Deal
Tue, Oct 14 - Thu, Oct 23
Frontier Logo
6:10 am - 2:07 pmMDW-PUJ
6h 57m1 stop
Frontier Logo
3:22 pm - 11:09 pmPUJ-MDW
8h 47m1 stop
$363Frontier
Find Deal
Sat, Oct 18 - Sat, Oct 25
Delta Logo
6:00 am - 1:15 pmMDW-PUJ
6h 15m1 stop
Delta Logo
2:45 pm - 9:10 pmPUJ-MDW
7h 25m1 stop
$368Delta
Find Deal
Tue, Sep 9 - Sat, Sep 13
Delta Logo
6:23 pm - 12:28 pmMDW-PUJ
17h 05m2 stops
Delta Logo
2:49 pm - 10:14 pmPUJ-MDW
8h 25m1 stop
$372Delta
Find Deal
Sat, Oct 18 - Thu, Oct 23
Frontier Logo
6:21 am - 4:34 pmMDW-PUJ
9h 13m1 stop
Frontier Logo
3:22 pm - 11:09 pmPUJ-MDW
8h 47m1 stop
$383Frontier
Find Deal
Sun, Oct 19 - Sat, Oct 25
Frontier Logo
6:00 am - 2:50 pmMDW-PUJ
6h 50m1 stop
Frontier Logo
3:22 pm - 11:05 pmPUJ-MDW
9h 43m1 stop
$385Frontier
Find Deal
Sat, Dec 6 - Sat, Dec 13
Frontier Logo
7:23 pm - 2:07 pmMDW-PUJ
17h 44m1 stop
Frontier Logo
3:22 pm - 11:09 pmPUJ-MDW
8h 47m1 stop
$386Frontier
Find Deal
Fri, Oct 17 - Sat, Oct 25
Delta Logo
10:35 am - 12:28 pmMDW-PUJ
24h 53m2 stops
Delta Logo
3:56 pm - 10:14 pmPUJ-MDW
7h 18m1 stop
$393Delta
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Wed, Oct 15 - Wed, Oct 22
Southwest Logo
5:25 am - 2:10 pmMDW-PUJ
7h 45m1 stop
Southwest Logo
3:10 pm - 8:20 amPUJ-MDW
18h 10m2 stops
$402Southwest
Find Deal
Wed, Oct 22 - Wed, Oct 29

Southwest flights from Chicago Midway Airport to Dominican Republic

Our best Southwest deals on Chicago Midway Airport to Dominican Republic flight tickets
Southwest
Sep 1
MDW5:10 amChicago Midway
7h 55m
1 stop
PUJ2:05 pmPunta Cana
Sep 5
PUJ3:05 pmPunta Cana
7h 30m
1 stop
MDW9:35 pmChicago Midway
$343
Find similar
Southwest
Oct 22
MDW5:25 amChicago Midway
7h 45m
1 stop
PUJ2:10 pmPunta Cana
Oct 29
PUJ3:10 pmPunta Cana
18h 10m
2 stops
MDW8:20 amChicago Midway
$402
Find similar
Southwest
Sep 5
MDW5:10 amChicago Midway
7h 55m
1 stop
PUJ2:05 pmPunta Cana
Sep 12
PUJ3:05 pmPunta Cana
7h 30m
1 stop
MDW9:35 pmChicago Midway
$414
Find similar

Frontier flights from Chicago Midway Airport to Dominican Republic

Our best Frontier deals on Chicago Midway Airport to Dominican Republic flight tickets
Frontier
Oct 18
MDW6:10 amChicago Midway
6h 57m
1 stop
PUJ2:07 pmPunta Cana
Oct 25
PUJ3:22 pmPunta Cana
8h 47m
1 stop
MDW11:09 pmChicago Midway
$363
Find similar
Frontier
Aug 16
MDW6:20 amChicago Midway
7h 14m
1 stop
PUJ2:34 pmPunta Cana
Aug 23
PUJ3:29 pmPunta Cana
8h 39m
1 stop
MDW11:08 pmChicago Midway
$365
Find similar
Frontier
Aug 15
MDW8:35 amChicago Midway
26h 34m
2 stops
PUJ12:09 pmPunta Cana
Aug 17
PUJ10:17 amPunta Cana
13h 07m
1 stop
MDW10:24 pmChicago Midway
$367
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 August 7, 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

Mon 9/1

5:10 am-2:05 pm

1 stop7h 55m

Punta Cana

Fri 9/5

3:05 pm-9:35 pm

1 stop7h 30m

$343

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Tue 10/14

6:23 pm-12:28 pm

2 stops17h 05m

Punta Cana

Thu 10/23

2:49 pm-10:14 pm

1 stop8h 25m

$347

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sat 10/18

6:10 am-2:07 pm

1 stop6h 57m

Punta Cana

Sat 10/25

3:22 pm-11:09 pm

1 stop8h 47m

$363

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Tue 9/9

6:00 am-1:15 pm

1 stop6h 15m

Punta Cana

Sat 9/13

2:45 pm-9:10 pm

1 stop7h 25m

$368

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sat 10/18

6:23 pm-12:28 pm

2 stops17h 05m

Punta Cana

Thu 10/23

2:49 pm-10:14 pm

1 stop8h 25m

$372

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sun 10/19

6:21 am-4:34 pm

1 stop9h 13m

Punta Cana

Sat 10/25

3:22 pm-11:09 pm

1 stop8h 47m

$383

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sat 12/6

6:00 am-2:50 pm

1 stop6h 50m

Punta Cana

Sat 12/13

3:22 pm-11:05 pm

1 stop9h 43m

$385

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Fri 10/17

7:23 pm-2:07 pm

1 stop17h 44m

Punta Cana

Sat 10/25

3:22 pm-11:09 pm

1 stop8h 47m

$386

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Wed 10/15

10:35 am-12:28 pm

2 stops24h 53m

Punta Cana

Wed 10/22

3:56 pm-10:14 pm

1 stop7h 18m

$393

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Wed 10/22

5:25 am-2:10 pm

1 stop7h 45m

Punta Cana

Wed 10/29

3:10 pm-8:20 am

2 stops18h 10m

$402

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, August 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 $340. If you are unable to visit Dominican Republic during the month of August, then departing from Chicago Midway Airport during the month October is also very affordable. Most momondo users find prices during this month for around $471.

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 $619. 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 $691.

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 are 1 cabin classes 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

Best Price Found

$160

Fastest flight time

6h 11m

Direct flights

Sun

Airports in Dominican Republic

3 airports
The best one-way flight to Dominican Republic from Chicago Midway Airport in the past 72 hours is $160. The best round-trip flight deal from Chicago Midway Airport to Dominican Republic found on momondo in the last 72 hours is $343.
The fastest flight from Chicago Midway Airport to Dominican Republic takes 6h 11m
Direct flights go from Chicago Midway Airport to Dominican Republic on Sunday. The only airline offering direct flights is Southwest.
There are 3 airports near Dominican Republic: Santo Domingo Las Americas (SDQ), Punta Cana (PUJ), Santiago de los Caballeros (STI)
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  • 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
3,231 reviews
Search Frontier flights
DeltaPriceFrom $375Free CancellationRating
8.0
7,985 reviews
Search Delta flights
SouthwestPriceFrom $495Free CancellationRating
8.0
4,244 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.

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Find better results for your trip to the Dominican Republic

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Popular flights according to clicks in the last 7 days on momondo
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