MDW - SDQ

$202 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 11/16. 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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Flights 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, Nov 20 - Thu, Nov 27
Frontier Logo
6:00 am - 2:47 pmMDW-SDQ
6h 47m1 stop
Frontier Logo
4:07 pm - 11:06 pmSDQ-MDW
8h 59m1 stop
$403Frontier
Find Deal
Thu, Aug 14 - Sun, Aug 17
Frontier Logo
3:58 pm - 9:09 amMDW-SDQ
16h 11m1 stop
Frontier Logo
11:50 am - 3:06 pmSDQ-MDW
28h 16m1 stop
$419Frontier
Find Deal
Sat, Sep 13 - Sat, Sep 20
Delta Logo
6:00 am - 1:40 pmMDW-SDQ
6h 40m1 stop
Delta Logo
3:06 pm - 9:10 pmSDQ-MDW
7h 04m1 stop
$427Delta
Find Deal
Sat, Oct 18 - Sat, Oct 25
Delta Logo
11:10 am - 12:27 amMDW-SDQ
12h 17m2 stops
Delta Logo
6:05 am - 6:25 pmSDQ-MDW
13h 20m2 stops
$431Delta
Find Deal
Sun, Dec 14 - Thu, Dec 18
Frontier Logo
6:00 am - 2:48 pmMDW-SDQ
6h 48m1 stop
Frontier Logo
3:22 pm - 11:05 pmSDQ-MDW
9h 43m1 stop
$433Frontier
Find Deal
Thu, Sep 18 - Tue, Sep 23
Delta Logo
6:00 am - 1:24 pmMDW-SDQ
6h 24m1 stop
Delta Logo
2:50 pm - 9:36 pmSDQ-MDW
7h 46m1 stop
$470Delta
Find Deal
Fri, Sep 12 - Fri, Sep 19
Delta Logo
12:43 pm - 12:36 amMDW-SDQ
10h 53m2 stops
Delta Logo
6:03 am - 6:35 pmSDQ-MDW
13h 32m2 stops
$474Delta
Find Deal
Thu, Oct 23 - Tue, Oct 28
Delta Logo
6:00 am - 1:41 pmMDW-SDQ
6h 41m1 stop
Delta Logo
2:56 pm - 10:14 pmSDQ-MDW
8h 18m1 stop
$513Delta
Find Deal
Sat, Sep 6 - Sat, Sep 13
Delta Logo
6:00 am - 6:00 pmMDW-SDQ
11h 00m2 stops
Delta Logo
6:03 am - 6:35 pmSDQ-MDW
13h 32m2 stops
$517Delta
Find Deal
Sun, Sep 14 - Sun, Sep 21
Frontier Logo
6:20 am - 5:24 pmMDW-SDQ
10h 04m2 stops
Frontier Logo
6:29 pm - 7:11 amSDQ-MDW
13h 42m2 stops
$538Frontier
Find Deal
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 Frontier ($403) and Delta ($427).

Good to know

Low seasonMarch
Cheapest flight$202
Best time to beat the crowds with an average 66% 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 $202 for a one-way ticket and $403 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.
8.0
DeltaOverall score based on 7980 reviews
7.9Comfort
8.2Boarding
8.5Crew
7.9Entertainment
7.3Food
Airline reviews

Delayed and took off even later than the scheduled delay time

8.0 ExcellentAnonymous, Jul 2025DTW - SEA
Read more Delta reviews

Delayed and took off even later than the scheduled delay time

For a 69 year old with health problems I had the worse experience, no wheelchair when I entered a lady told me to sit and wait while a gentleman told me I had to walk to the Delta station, which I did. I had a carry on and a bag, and I was traveling with my service dog, which was on his carrier and the lady charged me for my carry on luggage, beside all the waiting cause of the delay, I had to walk to get my luggage cause no wheelchair showed up, I am so disappointed. I will get in touch with the company. I got home at 3:00 am, not good for my health situation.

Only issue was with seating. The economy fare we purchased did say there was no guarantee the three people in our party would be seated together, and we were not. At the gate, the agent told us more specifically, the fare we purchased meant we would be seated in middle seats only. This should just be made more obvious.

Great experience on Delta. Staff from baggage check to flight attendants were very courteous and professional. My only issue was a personal preference for pretzels instead of the chips and cookies that were offered.

There was no problems, just a little uncomfortable with seats that do not lay back a little

Always good but we must do something about people in rows ahead of you that don't put their seats back up when they are suppose to. And It's rough to not be able to even lean over to get something out of my purse.

Flight was delayed, 30+ bags had to be gate checked. Crew were very friendly!

Everything was good until we were boarding our connection flight in Atlanta, we were told to gate check our carry-on, but when we got inside the plane, there was plenty of room in the overhead.

Did not know my son and I had different seating arrangements. He was fine, but it was disappointing.

Flight was canceled, and no effort was made to help with rebooking, no hotel vouchers, no car transportation and minimal food voucher and most places for food were closed by the time the voucher was given. Waited for 3 hours for bags. Simply the worst travel experience I have ever had

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

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