MDW - SDQ

$193 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 6/13. 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.
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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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Flights Deals

Cheap Flights from Midway to Santo Domingo

 
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.

Recent round-trip flight deals from Midway to Santo Domingo

KAYAK's recommended round-trip deals from the most popular airlines that fly from Midway to Santo Domingo.
Discover the best prices for you by selecting your travel dates on KAYAK.
Delta Logo
10:25 am - 12:34 amMDW-SDQ
13h 09m2 stops
Delta Logo
7:00 am - 6:45 pmSDQ-MDW
12h 45m2 stops
$421Delta
Find Deal
Thu, May 29 - Thu, Jun 5
Frontier Logo
6:20 am - 8:48 pmMDW-SDQ
13h 28m2 stops
Frontier Logo
1:49 am - 5:34 pmSDQ-MDW
16h 45m2 stops
$427Frontier
Find Deal
Fri, Jun 13 - Thu, Jun 19
Frontier Logo
6:20 am - 8:48 pmMDW-SDQ
13h 28m2 stops
Frontier Logo
1:49 am - 5:34 pmSDQ-MDW
16h 45m2 stops
$429Frontier
Find Deal
Fri, Jun 13 - Thu, Jun 19
Frontier Logo
6:20 am - 8:48 pmMDW-SDQ
13h 28m2 stops
Frontier Logo
1:49 am - 5:34 pmSDQ-MDW
16h 45m2 stops
$430Frontier
Find Deal
Fri, Jun 13 - Thu, Jun 19
Frontier Logo
6:20 am - 8:45 pmMDW-SDQ
13h 25m2 stops
Frontier Logo
1:48 am - 5:36 pmSDQ-MDW
16h 48m2 stops
$435Frontier
Find Deal
Fri, Aug 15 - Sun, Aug 17
Frontier Logo
2:55 pm - 12:28 amMDW-SDQ
8h 33m1 stop
Frontier Logo
1:48 am - 5:36 pmSDQ-MDW
16h 48m2 stops
$436Frontier
Find Deal
Thu, Aug 14 - Sun, Aug 17
Frontier Logo
4:06 pm - 9:09 amMDW-SDQ
16h 03m1 stop
Frontier Logo
1:48 am - 11:17 pmSDQ-MDW
22h 29m1 stop
$438Frontier
Find Deal
Thu, Aug 14 - Sun, Aug 17
Delta Logo
9:16 am - 12:19 amMDW-SDQ
14h 03m2 stops
Delta Logo
2:41 pm - 9:27 pmSDQ-MDW
7h 46m1 stop
$463Delta
Find Deal
Mon, Jun 2 - Thu, Jun 5
 Logo
9:12 pm - 2:21 amMDW-SDQ
28h 09m1 stop
 Logo
7:29 pm - 10:28 pmSDQ-MDW
27h 59m2 stops
Fri, Jun 13 - Fri, Jun 20
Delta Logo
6:00 am - 1:16 pmMDW-SDQ
6h 16m1 stop
Delta Logo
2:41 pm - 9:27 pmSDQ-MDW
7h 46m1 stop
$491Delta
Find Deal
Mon, Jun 2 - Thu, Jun 5
Useful Info

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 ($421) and Frontier ($427).

Good to know

Low seasonMarch
High seasonSeptember
Cheapest flight$193
Best time to beat the crowds with an average 65% drop in price.
Most popular time to fly and prices are also 29% lower on average.
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 $193 for a one-way ticket and $421 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.

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.
8.0
DeltaOverall score based on 7934 reviews
8.2Boarding
7.9Entertainment
7.9Comfort
7.3Food
8.5Crew
Airline reviews

Our bag was lost so that made unnecessary chaos On our trip

6.0 GoodBarbara, Apr 2025JFK - FCO
Read more Delta reviews

Our bag was lost so that made unnecessary chaos On our trip

Delta is my preferred airline. I've traveled with them for years. On time in most cases, good communication, easy to use app. Most planes are pretty nice. I was on a CRJ 700/900 however, which was pretty badly aged inside and needed a refresh. No infotainment, unreliable wifi, best to download before boarding or bring a book. Food choices are really just snacks on this flight, nice variety but about what you'd expect. Great staff and prompt in departure and early arrival too. Overall quite satisfied.

Crew was friendly Love the entertainment in the seat head rest.

Delta flight was on time, seats were comfortable, and crew was nice.

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

Delayed take-off. Very small plane so very scary with lots of bumps during the flight. Would never fly Delta on short flights in small 80 seaters plane again! Felt relieved when landed.

The worst part was I was NOT allowed in the lounge even though I was holding a first class ticket and have a premium American Express card. I have flown Business or First Class with many airlines. Delta is the ONLY one who does not extend this courtesy to anyone except people who hold the very expensive American Express card. As a result, I won’t fly Delta if I have any other choice.

It was an overnight flight and I desperately needed coffee before we landed, but Delta does only one beverage service, and that is shortly after takeoff, not before landing at 5 am.

A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.

Simply outstanding. Their new lounge for Delta One customers is a cut above the rest.

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

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