MDW - SDQ

$176 Find Cheap Flights from Chicago Midway Airport to Santo Domingo

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Santo Domingo departing on 10/22. 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.
1 adult
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Santo Domingo

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Santo Domingo, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Santo Domingo, as well as popular online travel agencies
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Flight Deals

Cheap Flights from Midway to Santo Domingo (MDW-SDQ)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to Santo Domingo that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to Santo Domingo

Thu, Oct 9 - Mon, Oct 13
Multiple Airlines Logo
8:25 am - 4:29 pmMDW-SDQ
31h 04m2 stops
Multiple Airlines Logo
10:19 am - 11:46 pmSDQ-MDW
14h 27m1 stop
$368Multiple Airlines
Find Deal
Sat, Oct 18 - Sat, Oct 25
Delta Logo
1:11 pm - 12:27 amMDW-SDQ
10h 16m2 stops
Delta Logo
6:05 am - 6:25 pmSDQ-MDW
13h 20m2 stops
$379Delta
Find Deal
Sat, Nov 15 - Wed, Nov 19
Delta Logo
11:05 am - 1:36 amMDW-SDQ
12h 31m2 stops
Delta Logo
6:45 am - 4:39 pmSDQ-MDW
11h 54m2 stops
$388Delta
Find Deal
Thu, Oct 30 - Thu, Nov 6
Delta Logo
9:35 am - 12:27 amMDW-SDQ
13h 52m2 stops
Delta Logo
3:56 pm - 10:14 pmSDQ-MDW
8h 18m1 stop
$407Delta
Find Deal
Thu, Oct 30 - Thu, Nov 6
Frontier Logo
6:20 am - 1:56 pmMDW-SDQ
6h 36m1 stop
Frontier Logo
4:19 pm - 10:03 pmSDQ-MDW
7h 44m1 stop
$414Frontier
Find Deal
Sun, Oct 12 - Sun, Oct 19
Frontier Logo
6:20 am - 2:01 pmMDW-SDQ
6h 41m1 stop
Frontier Logo
3:14 pm - 11:46 pmSDQ-MDW
9h 32m1 stop
$423Frontier
Find Deal
Thu, Nov 13 - Mon, Nov 17
Multiple Airlines Logo
6:26 pm - 4:26 pmMDW-SDQ
20h 00m1 stop
Multiple Airlines Logo
6:10 am - 6:39 pmSDQ-MDW
14h 29m2 stops
$424Multiple Airlines
Find Deal
Mon, Sep 29 - Thu, Oct 2
Multiple Airlines Logo
5:15 pm - 12:15 pmMDW-SDQ
18h 00m2 stops
Multiple Airlines Logo
1:20 pm - 8:53 amSDQ-MDW
20h 33m1 stop
$427Multiple Airlines
Find Deal
Thu, Oct 30 - Thu, Nov 6
Frontier Logo
6:20 am - 1:56 pmMDW-SDQ
6h 36m1 stop
Frontier Logo
4:19 pm - 10:03 pmSDQ-MDW
7h 44m1 stop
$428Frontier
Find Deal
Wed, Jan 21 - Wed, Jan 28
Delta Logo
6:00 am - 2:15 pmMDW-SDQ
6h 15m1 stop
Delta Logo
3:40 pm - 9:46 pmSDQ-MDW
8h 06m1 stop
$429Delta
Find Deal

Everything you should know

Top airlines
Delta
Cheapest • from $379 (round-trip)
Delta
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Cheapest round-trip
$368
Multiple Airlines
Thu 10/9Mon 10/13
MDW - SDQ • 2 stops
Cheapest one-way
$176
Delta
Wed 10/22
MDW - SDQ • 1 stop
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Santo Domingo!
Booking Insights

KAYAK's insights & trends for Midway to Santo Domingo flights

Get data-powered insights and trends into flights from Midway to Santo Domingo to help you find the cheapest flights, the best time to fly and much more.

Which airlines provide the cheapest flights from Chicago Midway Airport to Santo Domingo?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 72 hours.

In the past 3 days, the cheapest round-trip tickets from Chicago Midway Airport to Santo Domingo were found on Delta ($379) and Frontier ($414).

Find deals

Good to know

Low seasonMarch
Cheapest flight$176
Best time to beat the crowds with an average 65% drop in price.
Most popular time to fly with an average 4% increase in price.
Flight from Chicago Midway Airport to Santo Domingo

When to book flights from Midway to Santo Domingo

Are your dates flexible? Find out the best times to travel from Midway to Santo Domingo based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago Midway Airport to Santo Domingo flights

  • What is the cheapest flight from Chicago Midway Airport to Santo Domingo?

    In the last 3 days, the lowest price for a flight from Chicago Midway Airport to Santo Domingo was $176 for a one-way ticket and $368 for a round-trip.

  • Do I need a passport to fly between Chicago Midway Airport and Santo Domingo?

    A passport is required to fly from Chicago Midway Airport to Santo Domingo.

  • Which aircraft models fly most regularly from Chicago Midway Airport to Santo Domingo?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Chicago Midway Airport to Santo Domingo?

    SkyTeam is the only airline alliance operating flights between Chicago Midway Airport and Santo Domingo.

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to Santo Domingo?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago Midway Airport to Santo Domingo.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport to Santo Domingo?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Santo Domingo from Chicago Midway Airport is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago Midway Airport to Santo Domingo?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Santo Domingo with an airline and back to Chicago Midway Airport with another airline. Booking your flights between Chicago Midway Airport and SDQ can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway Airport to Santo Domingo?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Santo Domingo from Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from Midway to Santo Domingo

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Santo Domingo. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Midway to Santo Domingo? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.9
DeltaOverall score based on 7954 reviews
7.9Entertainment
8.2Boarding
7.9Comfort
7.3Food
8.5Crew
Airline reviews

Passengers need to check in big baggage instead of bringing on the plane. That cause inconvenience for everyone. Otherwise flight was good.

8.0 ExcellentTarun, Sep 2025MCO - LHR
Read more Delta reviews

Passengers need to check in big baggage instead of bringing on the plane. That cause inconvenience for everyone. Otherwise flight was good.

Perfect flight both ways. On time, courteous staff, plane comfortable and cool. Best domestic flights I’ve had in awhile.

The food was terrible especially for a 15 hour international flight. The crew was unpleasant as well.

Really low quality food especially for an international flight. The crew also was surprisingly unpleasant except couple of ladies. I know we were not in first class but that’s no reason to treat customers as less.

Flight delayed for two and half hours and then canceled altogether due to mechanical issues. No mechanic onsite to fix so had to send one from LAX.

Quick check in. Everything went smooth. I don't know what can be done about airline food.

Crew was good. The reservation got mixed up and they didn't have my TSA number. I am also a Silver Medallion and wasn't able to use Sky Priority.

Delta made it easy, comfortable and timely. The crew was fantastic.

This route with Delta always has delays or is cancelled. Aircrafts seem smaller and older. I fly Delta quite a bit - haven’t had issues with the international flights. But this route has always been the troublesome one

Nothing special. The crew never went out of their way for anything.

Everything you need to know for your flight from Midway to Santo Domingo

Information on your arrival and departure airports

Chicago Midway Airport (MDW)
Santo Domingo (SDQ)

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