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Cheap flights from Midway (MDW) to the Dominican Republic from $99

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight 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.
MDW — PUJ
May 5 — May 121
From?
To?
Sun 5/5
Sun 5/12
1 adult, Economy
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How far in advance should I book a flight from Chicago Midway Airport to Dominican Republic?

To save up to 46% on this flight, we recommend booking at least 55 days prior to travel. The price may fluctuate and will likely increase closer to your departure date. Users on Cheapflights have found tickets from Chicago Midway Airport to Dominican Republic from $390 1-2 weeks out and tickets from $618 for flights departing within the next 72 hours.

What is the cheapest month to fly from Chicago Midway Airport to Dominican Republic?

Flights from Chicago Midway Airport to Dominican Republic lean towards being more expensive in November. Prices are generally better when you fly from Chicago Midway Airport to Dominican Republic in October, with the cheapest ticket starting at $260.

When is the cheapest time to fly from Chicago Midway Airport to Dominican Republic (MDW - DO)?

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago Midway Airport to Dominican Republic as you normally would.

Cheap Delta flights from Midway to Dominican Republic

Explore cheap flight options specifically provided by Delta for the route between Midway and Dominican Republic. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,948,547 searches. Data last updated April 30, 2024.
Check out some of the cheapest Delta flights we've come across from Chicago to Dominican Republic. It's recommended that users confirm their flight details before booking.
Tue 5/76:00 amMDW - SDQ
1 stop6h 05mDelta
Wed 5/82:30 pmSDQ - MDW
1 stop8h 31mDelta
Deal found 4/29$406
Sun 9/16:00 amMDW - PUJ
1 stop8h 03mDelta
Thu 9/54:23 pmPUJ - MDW
1 stop17h 49mDelta
Deal found 4/29$440
Sat 5/189:32 amMDW - SDQ
2 stops14h 23mDelta
Sun 5/262:30 pmSDQ - MDW
1 stop18h 25mDelta
Deal found 4/29$468
Sat 5/186:00 amMDW - SDQ
1 stop6h 05mDelta
Sun 5/262:30 pmSDQ - MDW
1 stop18h 25mDelta
Deal found 4/29$487
Wed 5/151:21 pmMDW - STI
2 stops10h 35mDelta
Sat 5/256:35 pmSTI - MDW
2 stops16h 36mDelta
Deal found 4/29$539
Thu 5/305:47 pmMDW - STI
2 stops17h 15mDelta
Fri 6/76:05 amSTI - MDW
2 stops11h 59mDelta
Deal found 4/29$665
Sat 5/189:32 amMDW - SDQ
2 stops14h 23mDelta
Sun 5/266:35 amSDQ - MDW
2 stops11h 20mDelta
Deal found 4/29$673
Thu 6/276:00 amMDW - SDQ
1 stop6h 25mDelta
Tue 7/92:56 pmSDQ - MDW
1 stop7h 45mDelta
Deal found 4/29$720
Fri 5/105:47 pmMDW - PUJ
2 stops16h 54mDelta
Tue 5/143:13 pmPUJ - MDW
2 stops17h 42mDelta
Deal found 4/29$767

Cheap Frontier flights from Midway to Dominican Republic

Explore cheap flight options specifically provided by Frontier for the route between Midway and Dominican Republic. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,948,547 searches. Data last updated April 30, 2024.
Take a gander at the lowest prices we've found on Frontier flights from Chicago to Dominican Republic. Deals are refreshing constantly so come back soon for more options.
Wed 5/297:49 amMDW - PUJ
1 stop6h 46mFrontier
Mon 6/312:01 pmPUJ - MDW
1 stop22h 20mFrontier
Deal found 4/29$209
Thu 5/302:28 pmMDW - PUJ
1 stop19h 38mFrontier
Mon 6/312:01 pmPUJ - MDW
1 stop22h 20mFrontier
Deal found 4/29$211
Wed 5/297:49 amMDW - PUJ
1 stop6h 46mFrontier
Mon 6/310:42 amPUJ - MDW
1 stop8h 45mFrontier
Deal found 4/29$218
Tue 5/78:16 pmMDW - PUJ
1 stop13h 08mFrontier
Sat 5/1110:52 amPUJ - MDW
1 stop13h 39mFrontier
Deal found 4/29$220
Wed 5/297:49 amMDW - PUJ
1 stop6h 46mFrontier
Mon 6/310:42 amPUJ - MDW
2 stops35h 49mFrontier
Deal found 4/29$228
Thu 5/302:28 pmMDW - PUJ
1 stop19h 38mFrontier
Mon 6/310:42 amPUJ - MDW
2 stops35h 49mFrontier
Deal found 4/29$230
Fri 5/103:44 pmMDW - PUJ
1 stop22h 51mFrontier
Tue 5/1411:17 amPUJ - MDW
1 stop8h 58mFrontier
Deal found 4/29$233
Sat 5/116:45 amMDW - PUJ
1 stop26h 22mFrontier
Sat 5/1810:07 amPUJ - MDW
1 stop11h 06mFrontier
Deal found 4/29$236
Sun 5/126:31 pmMDW - PUJ
1 stop20h 04mFrontier
Fri 5/174:52 pmPUJ - MDW
1 stop28h 21mFrontier
Deal found 4/29$242

Cheap Midway to Dominican Republic flights in April & May 2024

Find cheap flight options from Midway to Dominican Republic specifically for the months of April and May 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,948,547 searches. Prices were last updated on April 30, 2024.
These are some of the best deals we've found on flights to Dominican Republic in 2024 at this time. For more flight deals, be sure to check back very soon.
Wed 5/297:49 amMDW - PUJ
1 stop6h 46mFrontier
Mon 6/312:01 pmPUJ - MDW
1 stop22h 20mFrontier
Deal found 4/29$209
Thu 5/302:28 pmMDW - PUJ
1 stop19h 38mFrontier
Mon 6/312:01 pmPUJ - MDW
1 stop22h 20mFrontier
Deal found 4/29$211
Mon 5/66:55 amMDW - PUJ
1 stop26h 12mFrontier
Tue 5/1411:17 amPUJ - MDW
1 stop8h 58mFrontier
Deal found 4/29$212
Wed 5/297:49 amMDW - PUJ
1 stop6h 46mFrontier
Mon 6/310:42 amPUJ - MDW
1 stop8h 45mFrontier
Deal found 4/29$218
Tue 5/78:16 pmMDW - PUJ
1 stop13h 08mFrontier
Sat 5/1110:52 amPUJ - MDW
1 stop13h 39mFrontier
Deal found 4/29$220
Wed 5/297:49 amMDW - PUJ
1 stop6h 46mFrontier
Mon 6/310:42 amPUJ - MDW
2 stops35h 49mFrontier
Deal found 4/29$228
Thu 5/302:28 pmMDW - PUJ
1 stop19h 38mFrontier
Mon 6/310:42 amPUJ - MDW
2 stops35h 49mFrontier
Deal found 4/29$230
Fri 5/103:44 pmMDW - PUJ
1 stop22h 51mFrontier
Tue 5/1411:17 amPUJ - MDW
1 stop8h 58mFrontier
Deal found 4/29$233
Thu 5/912:42 pmMDW - PUJ
1 stop20h 36mFrontier
Mon 5/131:07 pmPUJ - MDW
1 stop25h 46mFrontier
Deal found 4/29$235

Midway to Dominican Republic 2024 flight deals

Discover exclusive flight deals for travel between Midway and Dominican Republic in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 2,948,547 searches. Data last updated April 30, 2024.
These are some of the best deals we've found on flights to Dominican Republic in 2024 at this time. For more flight deals, be sure to check back very soon.
Wed 5/297:49 amMDW - PUJ
1 stop6h 46mFrontier
Mon 6/312:01 pmPUJ - MDW
1 stop22h 20mFrontier
Deal found 4/29$209
Thu 5/302:28 pmMDW - PUJ
1 stop19h 38mFrontier
Mon 6/312:01 pmPUJ - MDW
1 stop22h 20mFrontier
Deal found 4/29$211
Mon 5/66:55 amMDW - PUJ
1 stop26h 12mFrontier
Tue 5/1411:17 amPUJ - MDW
1 stop8h 58mFrontier
Deal found 4/29$212
Wed 5/297:49 amMDW - PUJ
1 stop6h 46mFrontier
Mon 6/310:42 amPUJ - MDW
1 stop8h 45mFrontier
Deal found 4/29$218
Tue 5/78:16 pmMDW - PUJ
1 stop13h 08mFrontier
Sat 5/1110:52 amPUJ - MDW
1 stop13h 39mFrontier
Deal found 4/29$220
Wed 5/297:49 amMDW - PUJ
1 stop6h 46mFrontier
Mon 6/310:42 amPUJ - MDW
2 stops35h 49mFrontier
Deal found 4/29$228
Thu 5/302:28 pmMDW - PUJ
1 stop19h 38mFrontier
Mon 6/310:42 amPUJ - MDW
2 stops35h 49mFrontier
Deal found 4/29$230
Fri 5/103:44 pmMDW - PUJ
1 stop22h 51mFrontier
Tue 5/1411:17 amPUJ - MDW
1 stop8h 58mFrontier
Deal found 4/29$233
Thu 5/912:42 pmMDW - PUJ
1 stop20h 36mFrontier
Mon 5/131:07 pmPUJ - MDW
1 stop25h 46mFrontier
Deal found 4/29$235

Midway to Dominican Republic flights leaving soon

Find last-minute flight options from Midway to Dominican Republic for spontaneous travel. Discover available flights and compare prices based on user searches. Secure great deals and offers for spontaneous trips with quick booking options. Over the last 7 days, Cheapflights users made 2,948,547 searches. Data last updated April 30, 2024.
Book one of these great deals on flights from Chicago to Dominican Republic. To prevent any unwanted surprises, users should verify their flight info before booking.
Tue 5/78:16 pmMDW - PUJ
1 stop13h 08mFrontier
Sat 5/1110:52 amPUJ - MDW
1 stop13h 39mFrontier
Deal found 4/29$220
Fri 5/103:44 pmMDW - PUJ
1 stop22h 51mFrontier
Tue 5/1411:17 amPUJ - MDW
1 stop8h 58mFrontier
Deal found 4/29$233
Tue 5/78:16 pmMDW - PUJ
1 stop13h 08mFrontier
Tue 5/1411:17 amPUJ - MDW
1 stop8h 58mFrontier
Deal found 4/29$245
Mon 5/66:55 amMDW - PUJ
1 stop26h 12mFrontier
Fri 5/104:45 pmPUJ - MDW
1 stop27h 42mFrontier
Deal found 4/29$257
Thu 5/910:17 pmMDW - PUJ
1 stop12h 43mFrontier
Mon 5/131:07 pmPUJ - MDW
1 stop25h 46mFrontier
Deal found 4/29$259
Mon 5/65:30 amMDW - PUJ
2 stops27h 15mFrontier
Tue 5/1411:17 amPUJ - MDW
1 stop8h 58mFrontier
Deal found 4/29$261
Fri 5/103:44 pmMDW - PUJ
1 stop22h 51mFrontier
Mon 5/131:07 pmPUJ - MDW
1 stop25h 46mFrontier
Deal found 4/29$266
Thu 5/910:17 pmMDW - PUJ
1 stop12h 43mFrontier
Sun 5/1210:42 amPUJ - MDW
1 stop8h 41mFrontier
Deal found 4/29$269
Thu 5/910:17 pmMDW - PUJ
1 stop12h 43mFrontier
Mon 5/131:07 pmPUJ - MDW
2 stops36h 09mFrontier
Deal found 4/29$287

One-way flights to Dominican Republic from Midway

Search for one-way flight options from Midway to Dominican Republic. Find affordable one-way fares based on user searches. Compare prices and availability to plan your one-way journey according to your preferred dates and budget. Over the last 7 days, Cheapflights users made 2,948,547 searches. Data last updated April 30, 2024.
Users traveling one-way from Chicago to Dominican Republic can select one of these great deals. Users can also find round-trip Chicago to Dominican Republic flights by using the search form above.
Sat 5/185:45 pmMDW - PUJ
1 stop15h 03mFrontier
Deal found 4/29$99
Wed 5/297:49 amMDW - PUJ
1 stop6h 46mFrontier
Deal found 4/29$119
Sat 5/182:35 pmMDW - SDQ
1 stop23h 15mFrontier
Deal found 4/29$129
Thu 5/302:28 pmMDW - PUJ
1 stop19h 38mFrontier
Deal found 4/29$130
Sat 5/185:45 pmMDW - SDQ
2 stops22h 15mFrontier
Deal found 4/29$135
Fri 5/247:23 pmMDW - PUJ
1 stop20h 17mFrontier
Deal found 4/29$142
Sat 5/187:53 amMDW - PUJ
2 stops24h 55mFrontier
Deal found 4/29$150
Thu 5/162:28 pmMDW - PUJ
1 stop19h 38mFrontier
Deal found 4/29$152
Fri 5/247:23 pmMDW - PUJ
1 stop20h 17mFrontier
Deal found 4/30$156

Find flights from Midway to Dominican Republic within your budget

Customize your flight search to find flights from Midway 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, Cheapflights users made 2,948,547 searches. Data last updated April 30, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$209 - $406

Route

Depart

Return

Price

Chicago MidwayPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Wed 5/29

1 stop6h 46m

Punta Cana

Mon 6/3

1 stop22h 20m

$209

Chicago MidwayPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Thu 5/30

1 stop19h 38m

Punta Cana

Mon 6/3

1 stop22h 20m

$211

Chicago MidwayPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Wed 5/29

1 stop6h 46m

Punta Cana

Mon 6/3

1 stop8h 45m

$218

Chicago MidwayPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Wed 5/29

1 stop6h 46m

Punta Cana

Mon 6/3

1 stop8h 45m

$220

Chicago MidwayPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Wed 5/29

1 stop6h 46m

Punta Cana

Mon 6/3

2 stops35h 49m

$228

Chicago MidwayPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Thu 5/30

1 stop19h 38m

Punta Cana

Mon 6/3

2 stops35h 49m

$230

Chicago MidwayPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Fri 5/10

1 stop22h 51m

Punta Cana

Tue 5/14

1 stop8h 58m

$233

Chicago MidwaySanto Domingo Las Americas

MDW - SDQ

MDWSDQ

Chicago Midway

Mon 5/27

1 stop6h 58m

Santo Domingo Las Americas

Mon 6/3

1 stop13h 44m

$350

Chicago MidwaySanto Domingo Las Americas

MDW - SDQ

MDWSDQ

Chicago Midway

Tue 5/7

1 stop6h 05m

Santo Domingo Las Americas

Wed 5/8

1 stop8h 31m

$406

Flights are sorted by cheapest first

Deals found on 4/29

No data available for this route at this time. Please check back soon.

Reviews of airlines servicing Dominican Republic

Get insights into the airlines that provide service to Dominican Republic. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Dominican Republic. Reviews last updated April 30, 2024.
Read through reviews of airlines operating flights from Chicago to Dominican Republic, such as Delta and Frontier. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.1
Very good
10,895 reviews
Check prices

Boarding

8.2

Overall

8.1

Crew

8.6

Comfort

7.9

Food

7.4

Entertainment

8.0

Reviews

1 / 10

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

Delta
8.1
Very good
10,895 reviews
Delta
8.1
Very good
10,895 reviews
Check prices

Boarding

8.2

Overall

8.1

Crew

8.6

Comfort

7.9

Food

7.4

Entertainment

8.0

Reviews

1 / 10

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

Frontier
6.3
Okay
4,123 reviews
Delta
8.1
Very good
10,895 reviews
Check prices

Boarding

8.2

Overall

8.1

Crew

8.6

Comfort

7.9

Food

7.4

Entertainment

8.0

Reviews

1 / 10

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

Related info for your journey

Find useful and relevant information for your journey from Midway to Dominican Republic. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • Can I find flights from Chicago Midway Airport to Dominican Republic for under $300 on Cheapflights?

    Yes, there are multiple flights from Chicago Midway Airport to Dominican Republic for under $300. The cheapest flight booked recently is on Frontier for just $209, but on average you can expect to pay $244.

  • Are there last-minute flights available from Chicago Midway Airport to Dominican Republic for under $300?

    There are currently 20+ open flights from Chicago Midway Airport to Dominican Republic within the next 7 days for less than $300.

  • What are the most popular routes from Chicago Midway Airport to Dominican Republic?

    While some choose either Chicago Midway - Santo Domingo Las Americas or Chicago Midway - Santiago de los Caballeros, Chicago Midway - Punta Cana is the most popular route from Chicago Midway Airport to Dominican Republic.

  • What are the most popular airlines that fly from Chicago Midway Airport to Dominican Republic?

    The most popular airlines flying from Chicago Midway Airport to Dominican Republic are Alaska Airlines, Delta and Frontier. Something to consider prior to booking your flight.

  • What does MDW to PUJ mean?

    Great question - MDW to PUJ just means Chicago Midway Airport to Punta Cana Airport. Now you’ll know what these unique codes when you look for flights! Ready for more IATA code knowledge? These are related airports for your current travel destination: Santo Domingo Las Americas Airport (SDQ), Santiago de los Caballeros Airport (STI), Puerto Plata La Union Airport (POP), La Romana Airport (LRM), Santo Domingo Dr. Joaquin Balaguer Airport (JBQ).

  • Can I find deals for flights from Midway to Dominican Republic that include extra baggage allowance?

    The amount of baggage you can bring on your Midway to Dominican Republic flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Midway to Dominican Republic with specific airlines?

    Yes, Cheapflights allows you to browse and filter Midway to Dominican Republic flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • Can I find deals for flights from Midway to Dominican Republic that include hotel bookings?

    Yes. In addition to deals on Midway to Dominican Republic flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Dominican Republic?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Dominican Republic.

  • Can I find deals for business class flights from Midway to Dominican Republic?

    Yes. Cheapflights offers flight deals from Midway to Dominican Republic by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • Can I find deals for flights from Midway to Dominican Republic that allow pets onboard?

    Many airlines flying from Midway to Dominican Republic offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Midway to Dominican Republic?

    Yes, you can often find last-minute deals on Midway to Dominican Republic flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Chicago Midway Airport to Dominican Republic flight deals updated?

    The Chicago Midway Airport to Dominican Republic flight deals you see on this page were last updated on 4/29.

See more FAQs

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Alternative routes for Midway to Dominican Republic
See prices for flight routes from nearby airports that may be better suited for you.

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Midway to Santiago de los Caballeros flights
Midway to Georgetown flights
O'Hare Intl to Holguín flights

Top 3 airlines flying from Midway to Dominican Republic

Discover the top 3 airlines that operate flights from Midway to Dominican Republic. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,948,547 searches. Data last updated April 30, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$278Average$465FlexibilityNo cancel feeOn-time62%
Search Frontier flights
DeltaCheapest$367Average$746FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
Alaska AirlinesCheapest$503Average$503FlexibilityNo cancel feeOn-time75%
Search Alaska Airlines flights
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Search flights from Midway to Dominican Republic by cabin class

Find flights from Midway to Dominican Republic, based on your preferred cabin class, be it economy, premium economy, business, or first class.
First Class
Business Class
Prem Econ Class
Economy Class

Hourly flight availability from Midway to Dominican Republic

Find hourly flight availability from Midway to Dominican Republic. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 30, 2024.
0%of flight departuresEarly morningMidnight to 6 am
100%of flight departuresMorning6 am to noon
0%of flight departuresAfternoonNoon to 6 pm
0%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Noon
6 PM

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Fly with Cheapflights

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How does Cheapflights help users find flights from Midway to Dominican Republic?

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Why should you use Cheapflights to find cheap flight tickets from Midway to Dominican Republic?

Millions of users choose and trust Cheapflights to book the best flight deals from Midway to Dominican Republic for free. We help you search and compare prices from hundreds of airlines for the right flight just for you.

Can Cheapflights find flights from Midway to Dominican Republic with no change fees?

Yes, we can. To see specific flights from Midway to Dominican Republic with no change fees, users can toggle flexible booking options after using the search form above to find flights.

Can Cheapflights notify me if prices for flights from Midway to Dominican Republic become cheaper?

Yes, Cheapflights offers price alerts on Midway to Dominican Republic flights so you can book your travel at the perfect time. Price Alerts can be enabled by clicking the bell icon next to the flight deals above and providing your email address where you want to receive the alerts.

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