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Cheap flights from Chicago Midway Airport to the Dominican Republic from $112

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 1/31. 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

These are some of the best round-trip flight deals from Chicago Midway Airport to the Dominican Republic that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Chicago Midway Airport to the Dominican Republic.

Cheap last minute flights

Planning a quick getaway from Chicago Midway Airport to the Dominican Republic? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to the Dominican Republic, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Chicago Midway Airport to the Dominican Republic

Find recent round-trip train or bus tickets from Chicago Midway Airport to the Dominican Republic.

All round-trip flight deals from Chicago Midway Airport to the Dominican Republic

The cheapest plane tickets from Chicago Midway Airport to the Dominican Republic found on KAYAK recently.
7:10 pm - 1:08 pmMDW-SDQ
15h 58m2 stops
12:54 pm - 7:32 amSDQ-MDW
20h 38m2 stops
$270Frontier
Find Deal
Sat, Mar 1 - Mon, Mar 3
6:40 am - 11:10 amMDW-PUJ
26h 30m1 stop
12:20 pm - 11:29 pmPUJ-MDW
13h 09m1 stop
$294Frontier
Find Deal
Fri, Jan 31 - Sat, Feb 8
12:43 pm - 2:40 pmMDW-SDQ
23h 57m1 stop
2:36 pm - 7:07 amSDQ-MDW
42h 31m2 stops
$306Frontier
Find Deal
Sat, Mar 1 - Mon, Mar 3
6:00 am - 2:23 pmMDW-PUJ
6h 23m1 stop
4:50 pm - 10:20 pmPUJ-MDW
7h 30m1 stop
$355Delta
Find Deal
Tue, Feb 25 - Thu, Feb 27
6:00 am - 3:25 pmMDW-PUJ
7h 25m1 stop
3:48 pm - 10:20 pmPUJ-MDW
8h 32m1 stop
$365Delta
Find Deal
Mon, Feb 10 - Wed, Feb 19
12:43 pm - 12:42 pmMDW-PUJ
21h 59m1 stop
1:39 pm - 7:19 pmPUJ-MDW
7h 40m1 stop
Sun, Feb 23 - Fri, Feb 28
12:43 pm - 12:42 pmMDW-PUJ
21h 59m1 stop
12:00 pm - 10:04 pmPUJ-MDW
12h 04m1 stop
Sun, Feb 23 - Sat, Mar 1
6:00 am - 2:23 pmMDW-PUJ
6h 23m1 stop
4:50 pm - 10:20 pmPUJ-MDW
7h 30m1 stop
$498KLM
Find Deal
Tue, Feb 4 - Tue, Feb 4
5:35 am - 2:45 pmMDW-PUJ
7h 10m1 stop
3:55 pm - 8:10 pmPUJ-MDW
5h 15mnonstop
$515Southwest
Find Deal
Tue, Mar 4 - Sun, Mar 9
8:35 pm - 2:45 pmMDW-PUJ
16h 10m2 stops
3:45 pm - 12:15 amPUJ-MDW
10h 30m2 stops
$534Southwest
Find Deal
Sun, Feb 23 - Thu, Feb 27
6:40 am - 11:10 amMDW-PUJ
26h 30m1 stop
$112Frontier
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Fri, Jan 31
2:36 pm - 10:18 amMDW-PUJ
18h 42m1 stop
$114Frontier
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Tue, Apr 1
6:48 pm - 10:40 amMDW-PUJ
13h 52m1 stop
$124Frontier
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Fri, Feb 21
6:48 pm - 10:40 amMDW-PUJ
13h 52m1 stop
$127Frontier
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Fri, Feb 21
9:05 am - 2:30 pmMDW-PUJ
4h 25mnonstop
$161Southwest
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Tue, Mar 11
6:00 am - 2:23 pmMDW-PUJ
6h 23m1 stop
$162Delta
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Mon, Feb 24
12:43 pm - 12:42 pmMDW-PUJ
21h 59m1 stop
Sun, Mar 2
6:00 am - 3:25 pmMDW-PUJ
7h 25m1 stop
$166Delta
Find Deal
Tue, Feb 18
12:43 pm - 12:42 pmMDW-PUJ
21h 59m1 stop
Sun, Feb 16
9:05 am - 2:30 pmMDW-PUJ
4h 25mnonstop
$226Southwest
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Wed, Mar 12
5:35 am - 2:45 pmMDW-PUJ
7h 10m1 stop
3:45 pm - 9:45 pmPUJ-MDW
8h 00m1 stop
$585Southwest
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Sun, Jan 19 - Thu, Jan 23
6:59 pm - 2:59 pmMDW-PUJ
18h 00m1 stop
4:50 pm - 10:20 pmPUJ-MDW
7h 30m1 stop
$620Delta
Find Deal
Sat, Jan 18 - Wed, Jan 22
9:35 am - 4:00 pmMDW-PUJ
4h 25mnonstop
3:45 pm - 9:45 pmPUJ-MDW
8h 00m1 stop
$643Southwest
Find Deal
Sat, Jan 18 - Thu, Jan 23
6:35 am - 3:25 pmMDW-PUJ
6h 50m1 stop
3:45 pm - 9:45 pmPUJ-MDW
8h 00m1 stop
$650Southwest
Find Deal
Sat, Jan 18 - Thu, Jan 23
5:35 am - 2:45 pmMDW-PUJ
7h 10m1 stop
3:45 pm - 9:20 amPUJ-MDW
19h 35m2 stops
$674Southwest
Find Deal
Sun, Jan 19 - Thu, Jan 23
6:28 pm - 12:30 pmMDW-PUJ
16h 02m1 stop
4:50 pm - 10:20 pmPUJ-MDW
7h 30m1 stop
$743Delta
Find Deal
Fri, Jan 17 - Wed, Jan 22
6:59 pm - 3:54 pmMDW-PUJ
18h 55m3 stops
3:00 pm - 10:36 amPUJ-MDW
21h 36m2 stops
$1,014WestJet
Find Deal
Sat, Jan 18 - Fri, Jan 24
11:19 am - 12:04 pmMDW-PUJ
22h 45m2 stops
5:00 pm - 5:47 pmPUJ-MDW
26h 47m2 stops
$3,206WestJet
Find Deal
Sat, Jan 18 - Tue, Jan 21
5:07 pm - 3:00 pmMDW-PUJ
19h 53m2 stops
2:45 am - 10:20 pmPUJ-MDW
21h 35m2 stops
$3,249LATAM Airlines
Find Deal
Mon, Jan 20 - Tue, Jan 21
3:41 pm - 3:05 pmMDW-PUJ
21h 24m2 stops
2:45 am - 10:20 pmPUJ-MDW
21h 35m2 stops
$3,710LATAM Airlines
Find Deal
Sat, Jan 18 - Thu, Jan 23
9:05 am - 2:30 pmMDW-PUJ
4h 25mnonstop
3:30 pm - 7:45 pmPUJ-MDW
5h 15mnonstop
$562Southwest
Find Deal
Wed, Mar 26 - Wed, Apr 2
9:05 am - 2:30 pmMDW-PUJ
4h 25mnonstop
3:30 pm - 7:45 pmPUJ-MDW
5h 15mnonstop
$613Southwest
Find Deal
Thu, Apr 3 - Mon, Apr 7
9:35 am - 4:00 pmMDW-PUJ
4h 25mnonstop
4:25 pm - 7:30 pmPUJ-MDW
5h 05mnonstop
$673Southwest
Find Deal
Sat, Feb 22 - Sat, Mar 1
9:05 am - 2:30 pmMDW-PUJ
4h 25mnonstop
3:30 pm - 7:45 pmPUJ-MDW
5h 15mnonstop
$691Southwest
Find Deal
Wed, Mar 19 - Wed, Mar 26
8:25 am - 1:55 pmMDW-PUJ
4h 30mnonstop
2:50 pm - 6:55 pmPUJ-MDW
5h 05mnonstop
$693Southwest
Find Deal
Sat, Apr 26 - Sat, May 3
9:05 am - 3:30 pmMDW-PUJ
4h 25mnonstop
3:30 pm - 7:45 pmPUJ-MDW
5h 15mnonstop
$706Southwest
Find Deal
Thu, Mar 6 - Mon, Mar 10
8:25 am - 1:55 pmMDW-PUJ
4h 30mnonstop
2:50 pm - 6:55 pmPUJ-MDW
5h 05mnonstop
$716Southwest
Find Deal
Sat, May 10 - Sat, May 17
9:05 am - 3:30 pmMDW-PUJ
4h 25mnonstop
3:30 pm - 7:45 pmPUJ-MDW
5h 15mnonstop
$726Southwest
Find Deal
Thu, Mar 6 - Mon, Mar 10
9:05 am - 2:30 pmMDW-PUJ
4h 25mnonstop
3:30 pm - 7:45 pmPUJ-MDW
5h 15mnonstop
$729Southwest
Find Deal
Tue, Mar 11 - Fri, Mar 14
9:05 am - 2:30 pmMDW-PUJ
4h 25mnonstop
3:30 pm - 7:45 pmPUJ-MDW
5h 15mnonstop
$746Southwest
Find Deal
Thu, Mar 13 - Tue, Mar 18

Frontier flights from Chicago Midway Airport to Dominican Republic

Our best Frontier deals on Chicago Midway Airport to Dominican Republic flight tickets
Frontier
Mar 1
MDW7:10 pmChicago Midway
15h 58m
2 stops
SDQ1:08 pmSanto Domingo Las Americas
Mar 3
SDQ12:54 pmSanto Domingo Las Americas
20h 38m
2 stops
MDW7:32 amChicago Midway
Frontier
Jan 31
MDW6:40 amChicago Midway
26h 30m
1 stop
PUJ11:10 amPunta Cana
Feb 8
PUJ12:20 pmPunta Cana
13h 09m
1 stop
MDW11:29 pmChicago Midway
Frontier
Mar 1
MDW12:43 pmChicago Midway
23h 57m
1 stop
SDQ2:40 pmSanto Domingo Las Americas
Mar 3
SDQ2:36 pmSanto Domingo Las Americas
42h 31m
2 stops
MDW7:07 amChicago Midway

Southwest flights from Chicago Midway Airport to Dominican Republic

Our best Southwest deals on Chicago Midway Airport to Dominican Republic flight tickets
Southwest
Mar 4
MDW5:35 amChicago Midway
7h 10m
1 stop
PUJ2:45 pmPunta Cana
Mar 9
PUJ3:55 pmPunta Cana
5h 15m
MDW8:10 pmChicago Midway
Southwest
Feb 23
MDW8:35 pmChicago Midway
16h 10m
2 stops
PUJ2:45 pmPunta Cana
Feb 27
PUJ3:45 pmPunta Cana
10h 30m
2 stops
MDW12:15 amChicago Midway
Southwest
Apr 1
MDW9:05 amChicago Midway
4h 25m
PUJ2:30 pmPunta Cana
Apr 9
PUJ1:40 pmPunta Cana
9h 10m
1 stop
MDW9:50 pmChicago Midway

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 $484. If you are unable to visit Dominican Republic during the month of August, then departing from Chicago Midway Airport during the month February is also very affordable. Most momondo users find prices during this month for around $521.

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 Tuesday when prices can be found for as low as $525. 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 $950. 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 $855.

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.

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

$112

Fastest flight time

4h 25m

Direct flights

Every day

Airports in Dominican Republic

3 airports
The best one-way flight to Dominican Republic from Chicago Midway Airport in the past 72 hours is $112. The best round-trip flight deal from Chicago Midway Airport to Dominican Republic found on momondo in the last 72 hours is $270.
The fastest flight from Chicago Midway Airport to Dominican Republic takes 4h 25m
Direct flights go from Chicago Midway Airport to Dominican Republic every day.
There are 3 airports near Dominican Republic: Santo Domingo Las Americas (SDQ), Punta Cana (PUJ), Santiago de los Caballeros (STI)

  • 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 $224Free CancellationRating
6.0
3,435 reviews
Search Frontier flights
DeltaPriceFrom $375Free CancellationRating
8.0
8,511 reviews
Search Delta flights
SouthwestPriceFrom $671Free CancellationRating
8.1
4,659 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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