$211+ Cheap flights from Midway (MDW) to Santo Domingo (SDQ)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/24. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SDQ
Nov 7 — Nov 141
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Midway to Santo Domingo with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Midway to Santo Domingo
Cheapest
Best
Last-minute
One-way
Cheapest flights from Midway to Santo DomingoExplore the most affordable flight options available from Midway to Santo Domingo. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 8, 2026.
Explore the most affordable flight options available from Midway to Santo Domingo. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 8, 2026.
This Mytrip deal was found by Cheapflights users on 10/6. 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 10/306:42 pm -
2 stops26h 03m
Thu 11/125:02 pm -
2 stops26h 45m
Deal found 10/6![Multiple Airlines logo]()
$499
This Mytrip deal was found by Cheapflights users on 10/6. 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.
Thu 10/296:16 am -
2 stops15h 56m
Thu 11/55:02 pm -
2 stops26h 45m
Deal found 10/6![Multiple Airlines logo]()
$500
This Mytrip deal was found by Cheapflights users on 10/6. 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.
Thu 11/269:09 am -
2 stops12h 03m
Thu 12/33:55 pm -
3 stops25h 00m
Deal found 10/6![Multiple Airlines logo]()
$515
This Mytrip deal was found by Cheapflights users on 10/6. 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.
Mon 11/96:42 pm -
2 stops25h 03m
Mon 11/167:30 am -
3 stops36h 17m
Deal found 10/6![Multiple Airlines logo]()
$516
This Delta deal was found by Cheapflights users on 10/6. 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.
Tue 10/276:04 am -
1 stop6h 28m
Wed 10/282:57 pm -
1 stop8h 36m
Deal found 10/6![Delta logo]()
$520
This Delta deal was found by Cheapflights users on 10/5. 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.
Mon 10/266:04 am -
2 stops11h 02m
Mon 11/23:57 pm -
1 stop8h 36m
Deal found 10/5![Delta logo]()
$525
This Delta deal was found by Cheapflights users on 10/4. 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 10/246:04 am -
1 stop6h 28m
Sat 10/312:57 pm -
1 stop8h 36m
Deal found 10/4![Delta logo]()
$529
This Mytrip deal was found by Cheapflights users on 10/6. 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.
Thu 11/56:08 am -
2 stops15h 04m
Thu 11/125:02 pm -
2 stops26h 45m
Deal found 10/6![Multiple Airlines logo]()
$530
Best flights from Midway to Santo DomingoDiscover carefully curated flight deals from Midway to Santo Domingo that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 8, 2026.
Discover carefully curated flight deals from Midway to Santo Domingo that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 8, 2026.
This Delta deal was found by Cheapflights users on 10/4. 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.
Tue 10/276:04 am -
1 stop6h 28m
Wed 10/282:57 pm -
1 stop8h 36m
Deal found 10/4![Delta logo]()
$520
This Delta deal was found by Cheapflights users on 10/3. 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 10/316:04 am -
2 stops11h 02m
Tue 11/38:35 pm -
2 stops16h 08m
Deal found 10/3![Delta logo]()
$525
This Delta deal was found by Cheapflights users on 10/4. 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.
Tue 11/36:04 am -
2 stops11h 02m
Tue 11/107:02 am -
2 stops13h 02m
Deal found 10/4![Delta logo]()
$525
This Delta deal was found by Cheapflights users on 10/7. 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.
Tue 10/276:04 am -
1 stop6h 28m
Tue 11/38:35 pm -
2 stops16h 08m
Deal found 10/7![Delta logo]()
$545
This Delta deal was found by Cheapflights users on 10/6. 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 10/236:04 am -
1 stop6h 28m
Fri 10/307:35 pm -
2 stops16h 02m
Deal found 10/6![Delta logo]()
$605
This Delta deal was found by Cheapflights users on 10/7. 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.
Wed 10/146:04 am -
2 stops11h 02m
Wed 10/212:57 pm -
1 stop8h 36m
Deal found 10/7![Delta logo]()
$666
This Delta deal was found by Cheapflights users on 10/3. 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.
Thu 10/296:04 am -
1 stop6h 28m
Tue 11/38:35 pm -
2 stops16h 08m
Deal found 10/3![Delta logo]()
$671
This Delta deal was found by Cheapflights users on 10/7. 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.
Wed 10/216:04 am -
1 stop6h 28m
Sat 10/242:57 pm -
1 stop8h 36m
Deal found 10/7![Delta logo]()
$742
Last-minute flights from Midway to Santo DomingoDiscover last-minute flight deals from Midway to Santo Domingo. Data last updated October 8, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Santo Domingo. Data last updated October 8, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 10/4. 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 10/246:04 am -
1 stop6h 28m
Sat 10/312:57 pm -
1 stop8h 36m
Deal found 10/4![Delta logo]()
$529
This Delta deal was found by Cheapflights users on 10/6. 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.
Mon 10/266:04 am -
1 stop6h 28m
Fri 10/307:35 pm -
2 stops16h 02m
Deal found 10/6![Delta logo]()
$525
This Delta deal was found by Cheapflights users on 10/6. 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.
Tue 10/276:04 am -
1 stop6h 28m
Wed 10/282:57 pm -
1 stop8h 36m
Deal found 10/6![Delta logo]()
$520
This Mytrip deal was found by Cheapflights users on 10/6. 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.
Thu 10/296:16 am -
2 stops15h 56m
Thu 11/55:02 pm -
2 stops26h 45m
Deal found 10/6![Multiple Airlines logo]()
$500
This Mytrip deal was found by Cheapflights users on 10/6. 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 10/306:42 pm -
2 stops26h 03m
Thu 11/125:02 pm -
2 stops26h 45m
Deal found 10/6![Multiple Airlines logo]()
$499
This Mytrip deal was found by Cheapflights users on 10/6. 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.
Thu 11/56:08 am -
2 stops15h 04m
Thu 11/125:02 pm -
2 stops26h 45m
Deal found 10/6![Multiple Airlines logo]()
$530
This Mytrip deal was found by Cheapflights users on 10/6. 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.
Mon 11/96:42 pm -
2 stops25h 03m
Mon 11/167:30 am -
3 stops36h 17m
Deal found 10/6![Multiple Airlines logo]()
$516
This Mytrip deal was found by Cheapflights users on 10/6. 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.
Thu 11/269:09 am -
2 stops12h 03m
Thu 12/33:55 pm -
3 stops25h 00m
Deal found 10/6![Multiple Airlines logo]()
$515
One-way flights from Midway to Santo DomingoSearch for one-way flight options from Midway to Santo Domingo. Find affordable one-way fares based on user searches. Data last updated October 8, 2026.
Search for one-way flight options from Midway to Santo Domingo. Find affordable one-way fares based on user searches. Data last updated October 8, 2026.
This Trip.com deal was found by Cheapflights users on 10/5. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/246:21 am -
2 stops11h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![Multiple Airlines logo]()
$211
This Mytrip deal was found by Cheapflights users on 10/5. 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.
Wed 12/212:28 pm -
2 stops21h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![Frontier logo]()
$240
This FlightHub deal was found by Cheapflights users on 10/5. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/318:07 pm -
1 stop20h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![Frontier logo]()
$241
This Delta deal was found by Cheapflights users on 10/6. 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.
Tue 10/136:04 am -
1 stop6h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/6![Delta logo]()
$243
This Kiwi.com deal was found by Cheapflights users on 10/5. 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.
Sat 12/512:28 pm -
2 stops28h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![Multiple Airlines logo]()
$244
This Delta deal was found by Cheapflights users on 10/5. 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.
Mon 11/2310:34 am -
2 stops13h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![Delta logo]()
$252
This Kiwi.com deal was found by Cheapflights users on 10/5. 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 10/256:24 am -
2 stops11h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![Multiple Airlines logo]()
$255
This Kiwi.com deal was found by Cheapflights users on 10/5. 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.
Tue 12/812:28 pm -
2 stops26h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![Multiple Airlines logo]()
$260
This Kiwi.com deal was found by Cheapflights users on 10/5. 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 10/186:24 am -
2 stops11h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![Multiple Airlines logo]()
$262
This Kiwi.com deal was found by Cheapflights users on 10/7. 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 12/132:04 pm -
2 stops19h 14m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/7![Multiple Airlines logo]()
$263
This Kiwi.com deal was found by Cheapflights users on 10/5. 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.
Mon 12/79:37 pm -
2 stops40h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![Multiple Airlines logo]()
$266
This FlightHub deal was found by Cheapflights users on 10/5. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/308:07 pm -
1 stop20h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![Frontier logo]()
$272
Find flight deals from Midway to Santo Domingo
Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Santo Domingo (SDQ). 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 October 8, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $499 (Mytrip) |
One-way from | $211 (Trip.com) |
Popular in | June |
Cheapest in | February |
Average price | $490 |
Cheapflights Fare Finder
Customize your flight search to find flights from Midway to Santo Domingo 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 7,457,451 searches. Data last updated October 8, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Santo Domingo that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
ChicagoSanto Domingo
MDW Chicago Midway - SDQ Santo Domingo Las Americas
MDWSDQ
Chicago Midway
Tue 10/13
6:04 am-1:32 pm
1 stop6h 28m
Santo Domingo Las Americas
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$243
ChicagoSanto Domingo
MDW Chicago Midway - SDQ Santo Domingo Las Americas
MDWSDQ
Chicago Midway
Sun 12/13
2:04 pm-11:18 am
2 stops19h 14m
Santo Domingo Las Americas
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$263
ChicagoSanto Domingo
MDW Chicago Midway - SDQ Santo Domingo Las Americas
MDWSDQ
Chicago Midway
Thu 12/10
3:50 pm-11:42 am
3 stops17h 52m
Santo Domingo Las Americas
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$302
ChicagoSanto Domingo
MDW Chicago Midway - SDQ Santo Domingo Las Americas
MDWSDQ
Chicago Midway
Wed 10/14
6:04 am-1:32 pm
1 stop6h 28m
Santo Domingo Las Americas
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$303
ChicagoSanto Domingo
MDW Chicago Midway - SDQ Santo Domingo Las Americas
MDWSDQ
Chicago Midway
Fri 10/16
6:44 pm-1:32 pm
2 stops17h 48m
Santo Domingo Las Americas
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$318
ChicagoSanto Domingo
MDW Chicago Midway - SDQ Santo Domingo Las Americas
MDWSDQ
Chicago Midway
Sun 11/1
6:04 am-2:32 pm
1 stop6h 28m
Santo Domingo Las Americas
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$364
ChicagoSanto Domingo
MDW Chicago Midway - SDQ Santo Domingo Las Americas
MDWSDQ
Chicago Midway
Mon 12/28
8:07 pm-3:47 pm
2 stops41h 40m
Santo Domingo Las Americas
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$432
ChicagoSanto Domingo
MDW Chicago Midway - SDQ Santo Domingo Las Americas
MDWSDQ
Chicago Midway
Sun 10/11
6:04 am-1:32 pm
1 stop6h 28m
Santo Domingo Las Americas
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$445
ChicagoSanto Domingo
MDW Chicago Midway - SDQ Santo Domingo Las Americas
MDWSDQ
Chicago Midway
Sun 10/18
6:04 am-1:32 pm
1 stop6h 28m
Santo Domingo Las Americas
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$445
ChicagoSanto Domingo
MDW Chicago Midway - SDQ Santo Domingo Las Americas
MDWSDQ
Chicago Midway
Tue 10/27
6:04 am-1:32 pm
1 stop6h 28m
Santo Domingo Las Americas
Wed 10/28
2:57 pm-10:33 pm
1 stop8h 36m
$520
Showing 1-10 of 17 resultsSorted by cheapest first
Compare providers for flights from Midway to Santo Domingo
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Midway to Santo Domingo in October.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago Midway Airport-Santo Domingo flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-Santo Domingo flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Santo Domingo flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago Midway Airport-Santo Domingo flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago Midway Airport-Santo Domingo flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Midway to Santo Domingo
Have a flexible travel schedule? Discover the best time to fly to Santo Domingo from Midway with our price prediction graph.
MDW-SDQ
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.
Related info for your journey
Find useful and relevant information for your journey from Midway to Santo Domingo. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Santo Domingo?
Book flights to Santo Domingo if you plan to visit one of these locationsJuan Dolio
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Other flights from Midway
Popular flights
Santo Domingo flight routes