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$133+ Cheap flights from the Dominican Republic to Midway (MDW)

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 2/17. Fares are subject to change and may not be available on all flights or dates of travel.
PUJ — MDW
Nov 26 — Dec 31
Tue 11/26
Tue 12/3
1 adult, Economy
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Cheap flight deals from Dominican Republic to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Dominican Republic (DO0) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated November 21, 2024.

Find flight deals from Dominican Republic to Midway

Cheapest flights from Dominican Republic to Midway
Explore the most affordable flight options available from Dominican Republic to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 21, 2024.

This Mytrip deal was found by Cheapflights users on 11/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/2212:02 pmSDQ - MDW
1 stop9h 40mFrontier
Tue 12/316:49 pmMDW - SDQ
1 stop16h 16mFrontier
Deal found 11/19$356
This Booking.com deal was found by Cheapflights users on 11/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/126:37 pmPUJ - MDW
2 stops24h 35mFrontier
Sun 12/1512:36 pmMDW - PUJ
1 stop20h 55mFrontier
Deal found 11/20$401
This Kiwi.com deal was found by Cheapflights users on 11/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/2211:45 amSDQ - MDW
1 stop14h 33mMultiple Airlines
Sun 1/1910:58 amMDW - SDQ
1 stop23h 57mMultiple Airlines
Deal found 11/19$439
This Delta deal was found by Cheapflights users on 11/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/213:54 pmSDQ - MDW
1 stop8h 12mDelta
Sun 1/199:34 amMDW - SDQ
2 stops13h 22mDelta
Deal found 11/19$606
This Delta deal was found by Cheapflights users on 11/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/63:50 pmPUJ - MDW
1 stop8h 16mDelta
Mon 12/96:00 amMDW - PUJ
1 stop8h 24mDelta
Deal found 11/20$626
This Southwest deal was found by Cheapflights users on 11/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/63:45 pmPUJ - MDW
2 stops17h 35mSouthwest
Mon 12/96:00 amMDW - PUJ
1 stop6h 45mSouthwest
Deal found 11/20$744
This Mytrip deal was found by Cheapflights users on 11/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/61:50 pmPUJ - MDW
2 stops24h 10mMultiple Airlines
Mon 12/912:05 pmMDW - PUJ
3 stops33h 40mMultiple Airlines
Deal found 11/20$760
This WestJet deal was found by Cheapflights users on 11/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/611:00 amPUJ - MDW
2 stops33h 32mWestJet
Mon 12/912:44 pmMDW - PUJ
2 stops23h 20mWestJet
Deal found 11/20$2,250
This LATAM Airlines deal was found by Cheapflights users on 11/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure LATAM Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/52:45 amPUJ - MDW
2 stops21h 21mLATAM Airlines
Mon 12/94:58 pmMDW - PUJ
2 stops20h 07mLATAM Airlines
Deal found 11/20$3,089

Find flights from Dominican Republic to Midway within your budget

Customize your flight search to find flights from Dominican Republic to Midway 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 2,629,791 searches. Data last updated November 21, 2024.

Fly from

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Fly to

Any airport

Route

Depart

Return

Price

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Sun 12/22

12:02 pm-7:42 pm

1 stop9h 40m

Chicago Midway

Tue 12/31

6:49 pm-1:05 pm

1 stop16h 16m

$356

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Thu 12/12

6:37 pm-5:12 pm

2 stops24h 35m

Chicago Midway

Sun 12/15

12:36 pm-11:31 am

1 stop20h 55m

$401

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Sun 12/22

11:45 am-12:18 am

1 stop14h 33m

Chicago Midway

Sun 1/19

10:58 am-12:55 pm

1 stop23h 57m

$439

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Sat 1/25

4:50 pm-10:20 pm

1 stop7h 30m

Chicago Midway

Tue 1/28

6:00 am-2:22 pm

1 stop6h 22m

$497

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Wed 3/12

7:00 am-5:10 pm

2 stops11h 10m

Chicago Midway

Tue 3/25

9:30 am-11:40 pm

2 stops13h 10m

$521

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Sat 1/25

5:00 pm-8:00 pm

Nonstop5h 00m

Chicago Midway

Tue 1/28

5:35 am-2:45 pm

1 stop7h 10m

$639

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Fri 12/6

1:50 pm-12:00 pm

2 stops24h 10m

Chicago Midway

Mon 12/9

12:05 pm-11:45 pm

3 stops33h 40m

$760

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Fri 1/31

9:05 pm-10:36 am

2 stops15h 31m

Chicago Midway

Wed 2/5

12:44 pm-9:51 am

2 stops19h 07m

$2,060

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Fri 1/24

2:45 am-10:20 pm

2 stops21h 35m

Chicago Midway

Tue 1/28

5:07 pm-6:30 pm

2 stops23h 23m

$2,554

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Mon 2/17

3:15 pm-7:02 am

1 stop17h 47m

$133

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/21

Showing 1-10 of 16 results
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Best time to book a flight from Dominican Republic to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Dominican Republic with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Travel insights for flights from Dominican Republic to Midway

Get recent, data-driven insights about flights from Dominican Republic to Midway including ideal travel times, pricing trends, and more.

What is the cheapest time of day to fly from DO to MDW?

Find hourly flight availability from Dominican Republic to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 21, 2024.

When flying from Dominican Republic to Chicago Midway Airport, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated November 21, 2024.
Get a feel of what it's like to fly with Frontier and Delta from Dominican Republic to Chicago by reading reviews from past customers. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
5,015 reviews

Entertainment

7.7

Crew

8.7

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Southwest
8.1
Very good
5,015 reviews
Southwest
8.1
Very good
5,015 reviews

Entertainment

7.7

Crew

8.7

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Delta
8.0
Very good
8,758 reviews
Southwest
8.1
Very good
5,015 reviews

Entertainment

7.7

Crew

8.7

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

LATAM Airlines
7.5
Good
1,939 reviews
Southwest
8.1
Very good
5,015 reviews

Entertainment

7.7

Crew

8.7

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

WestJet
7.3
Good
2,810 reviews
Southwest
8.1
Very good
5,015 reviews

Entertainment

7.7

Crew

8.7

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Frontier
6.1
Okay
3,539 reviews
Southwest
8.1
Very good
5,015 reviews

Entertainment

7.7

Crew

8.7

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Related info for your journey

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

  • What are the cheapest airlines to fly from Dominican Republic to Chicago Midway Airport one-way?

    For one-way options, check prices for Frontier. According to our data, you can fly for as low as $133. Users have also found prices from $199 and $281 on Delta and Southwest, respectively.

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

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

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

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

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

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

  • What is the cheapest month to book a flight from Dominican Republic to Chicago Midway Airport?

    Currently, December is the cheapest month in which you can book a flight from Dominican Republic to Chicago Midway Airport (average of $159). Flying from Dominican Republic to Chicago Midway Airport in July is currently the most expensive (average of $231). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for Dominican Republic to Midway

See prices for flight routes from nearby airports that may be better suited for you.
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