SDQ - CHI

$177 Find Cheap Flights from Santo Domingo to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Santo Domingo to Chicago departing on 5/12. 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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These are the airlines KAYAK users have selected most often from within our search results in flight searches from Santo Domingo to Chicago, 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 Santo Domingo to Chicago, as well as popular online travel agencies
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Cheap Flights from Santo Domingo to Chicago

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Santo Domingo to Chicago 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 Santo Domingo to Chicago

KAYAK's recommended round-trip deals from the most popular airlines that fly from Santo Domingo to Chicago.
Discover the best prices for you by selecting your travel dates on KAYAK.
 Logo
10:19 am - 5:41 pmSDQ-ORD
8h 22m1 stop
 Logo
1:43 pm - 4:29 pmORD-SDQ
25h 46m1 stop
Wed, Jun 4 - Tue, Jun 17
Spirit Airlines Logo
3:50 pm - 12:05 amSDQ-ORD
9h 15m1 stop
Spirit Airlines Logo
10:46 am - 2:21 amORD-SDQ
14h 35m1 stop
$335Spirit Airlines
Find Deal
Sat, Jun 7 - Sat, Jun 14
Delta Logo
7:00 am - 6:38 pmSDQ-ORD
12h 38m2 stops
Delta Logo
7:00 am - 5:52 pmORD-SDQ
9h 52m2 stops
$438Delta
Find Deal
Mon, Oct 6 - Wed, Oct 15
Delta Logo
7:00 am - 6:36 pmSDQ-MDW
12h 36m2 stops
Delta Logo
9:30 am - 11:29 pmMDW-SDQ
12h 59m2 stops
$438Delta
Find Deal
Mon, Oct 27 - Thu, Oct 30
Frontier Logo
1:24 pm - 11:44 pmSDQ-ORD
11h 20m2 stops
Frontier Logo
5:01 am - 6:15 pmORD-SDQ
12h 14m2 stops
$447Frontier
Find Deal
Thu, Jul 31 - Fri, Aug 8
American Airlines Logo
12:15 pm - 9:58 pmSDQ-ORD
10h 43m2 stops
American Airlines Logo
8:22 am - 8:47 pmORD-SDQ
11h 25m2 stops
$450American Airlines
Find Deal
Wed, May 21 - Sun, May 25
American Airlines Logo
7:10 pm - 9:05 amSDQ-ORD
14h 55m1 stop
American Airlines Logo
6:57 am - 3:20 pmORD-SDQ
7h 23m1 stop
$452American Airlines
Find Deal
Sun, Jun 8 - Thu, Jun 12
Frontier Logo
1:24 pm - 11:28 pmSDQ-ORD
11h 04m2 stops
Frontier Logo
5:01 am - 6:15 pmORD-SDQ
12h 14m2 stops
$453Frontier
Find Deal
Thu, Jul 3 - Fri, Aug 1
Copa Airlines Logo
11:52 am - 12:34 amSDQ-ORD
13h 42m1 stop
Copa Airlines Logo
7:54 am - 10:27 pmORD-SDQ
13h 33m1 stop
$482Copa Airlines
Find Deal
Sun, Jun 8 - Thu, Jun 12
Copa Airlines Logo
5:21 am - 12:34 amSDQ-ORD
20h 13m1 stop
Copa Airlines Logo
7:54 am - 2:45 amORD-SDQ
17h 51m1 stop
$514Copa Airlines
Find Deal
Wed, Jun 18 - Sun, Jun 22
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KAYAK's insights & trends for Santo Domingo to Chicago flights

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

What’s the cheapest day of the week to fly from Santo Domingo to Chicago?

The average price of all round-trip flights from Santo Domingo to Chicago clicked on KAYAK for each day over the last 12 months.

If your flying dates are flexible, you should consider flying to Chicago on a Saturday, as we generally find the cheapest rates on that day for this route. On the other hand, Wednesday is the most expensive day to fly from Santo Domingo to Chicago. For your return ticket, we recommend flying on a Tuesday and avoiding Fridays for the best deals.

What is the cheapest month to fly from Santo Domingo to Chicago?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Santo Domingo to Chicago, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Santo Domingo to Chicago is September, where tickets cost $389 (return) on average. On the other hand, the most expensive months are August and January, where the average cost of round-trip tickets is $664 and $551 respectively.

How far in advance should I book a flight from Santo Domingo to Chicago?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Santo Domingo to Chicago, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Santo Domingo to Chicago, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 25 weeks before departure.

Good to know

Low seasonMarch
High seasonOctober
Cheapest flight$177
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly with an average 4% increase in price.
Flight from Santo Domingo to Chicago O'Hare Airport

When to book flights from Santo Domingo to Chicago

Are your dates flexible? Find out the best times to travel from Santo Domingo to Chicago 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 flights from Santo Domingo to Chicago

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

    In the last 3 days, the lowest price for a flight from Santo Domingo to Chicago was $177 for a one-way ticket and $320 for a round-trip.

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

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

  • Which airports will I be using when flying from Santo Domingo to Chicago?

    Santo Domingo is served by only 1 airport and there are 2 airports in Chicago. You will leave Santo Domingo from Santo Domingo Las Americas and you will be arriving in Chicago at one of these airports: Chicago Midway or Chicago O'Hare Intl.

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

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

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

    Star Alliance, SkyTeam, and oneworld are the airline alliances operating flights between Santo Domingo and Chicago, with SkyTeam being the most commonly used for this route.

  • Which is the best airline for flights from Santo Domingo to Chicago, Delta or American Airlines?

    The two airlines most popular with KAYAK users for flights from Santo Domingo to Chicago are Delta and American Airlines. With an average price for the route of $426 and an overall rating of 8.0, Delta is the most popular choice. American Airlines is also a great choice for the route, with an average price of $600 and an overall rating of 7.2.

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

    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 Santo Domingo to Chicago.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Santo Domingo 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 Santo Domingo to Chicago?

    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 Chicago with an airline and back to Santo Domingo with another airline.

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

    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 Chicago from Santo Domingo up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Top 3 airlines serving from Santo Domingo to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Santo Domingo to Chicago. 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 Santo Domingo to Chicago? 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 7936 reviews
7.9Comfort
8.2Boarding
7.3Food
8.5Crew
7.9Entertainment
Airline reviews

Fine except the person next to me took up her seat had raised the arm divide so she spilled into my seat. because of her size. Fortunately no one was in the seat on my right so I could use part of it.

10.0 ExcellentAnonymous, Apr 2025AMS - ATL
Read more Delta reviews

Fine except the person next to me took up her seat had raised the arm divide so she spilled into my seat. because of her size. Fortunately no one was in the seat on my right so I could use part of it.

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.

Delta is a cut above the others in customer service.

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.

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.

To start, I’d like to say that every American Airline personnel I interacted with on the ground, especially flight crew, was very friendly and did their best to help me out. Despite this, however, my experience with the airline was an entire mess. The 7:19 PM flight was heavily delayed due to weather, and pushed to 10:30 AM the next morning. Because of this, I had to spend the night inside of the airport. At some point later in the night, I got an email saying that the flight had been canceled. I called the support number, and the representative on the other line told me that the flight was still on and that I didn’t need to rebook. The next morning, no one came to the gate to open the door for the crew until almost 11 AM. By this time the flight crew had been waiting for over an hour, and they had called management to get someone to open the door for them multiple times. Around 11:30, the gate screen had changed to a different flight. I ended up buying a last minute ticket with Southwest airline just to get to Chicago, because the next flight with American wasn’t until 7:19 pm that day. Now, earlier that morning my suitcase had been sent ahead of me to ORD. I went to baggage claim to ask them if I could have my suitcase forwarded to where I was staying. The representative at SDF baggage claim said they could and put the claim in for me. As I was going back through TSA, I got an email that the airline had found my suitcase, but the next step was to send it BACK to SDF. I called the airline support number again, and I made it clear that my suitcase needed to stay in Chicago and to not come back to SDF. The representative told me that they would hold my suitcase at ORD and that it wasn’t going to be forwarded anywhere. Once I got there, I found that they had loaded my suitcase onto a plane to send it back to SDF. Thankfully, I had gotten to the baggage claim counter in time for them to put in a request to bring my suitcase back up. My refund with the airline is processing already, but because of this entire experience and miscommunication at every turn of the way, I will not book with American Airlines in the future.

The plane was late and then sat on the runway for almost 45 minutes before taking off.

Crew professional. Easy bag drop off. On time. Good entertainment.

Everything was great. Boarding, early departure, early arrival, and deplaning were smooth. Smooth flight.

Per usual, flight status, staff courtesy and professionalism were excellent

The only thing is if Wi-Fi is available after you land and taxi to the gate. It takes forever to get to the gate, and having the Wi-Fi continue would be great to bide the time at least 5 minutes before you arrive at the entrance. That is my only comment; otherwise, everything was good.

Had to wait on pilot and crew to depart and had to wait to arrive at the gate because they only had 2 crews working. Delays, delays....Planes just keep getting smaller and tighter and they nickle and dime for everything. When will an airline actually wake up and make flying more enjoyable?

Seating was horrible. Small seats. Access to flight information and extras very iser unfriendly. Kept losing internet after paying for it. Staff in madison was as unprofessional and unhelpful.

Delayed due to no crew. On a major holiday travel day.

Other than being delayed 5.5 hours and having to get a hotel because I missed my connecting flight, it was an okay flight. No in-flight Wi-Fi or entertainment.

The reps working at the airport counter were dumber than a second coat of paint.

My costume jewelry was stolen out of my bag. Got to airport and my bag weighed 45 pounds- 5 pounds over cost me $100 Long lines in tier one. No entertainment No WiFi no free drinks or snacks

Not very good. Paid in excess of $400 for assigned seating for my family and that was not provided. I want that money back.

The seats were hard molded plastic covered in plastic vinyl. And the scam to charge people extra to sit together. Don’t they know we can just ask someone to trade seats. And watching the staff separate young children from parents… super classy. We had to guilt them into offering up our seats. This companies policies suck. Don’t give them your money.

The seats were awful, hard plastic covered in sheet vinyl. The airline tries to scam you into paying extra to get seat together when the flight wasn’t full. They were going to separate a family with young children but my wife who had a row to herself gave up her seat so the young mom could be with her young boys. I’m never giving this airline my money again.

It was a short flight so no food or entertainment….

Seats are uncomfortable but price is good. Guess I can put up with misery for four hours.

I’ve never traveled on Frontier before. If you want basic, no frills, friendly service at great prices then give them a fly!

I guess you get what you pay for. The seats are very uncomfortable and very little space. The snacks were pricey.

Cancelled and declined to find alternatives Earlier flight is 2 days later Sent the cancellation notification very late, wish I knew earlier would have stayed to watch the Miami open final game Very disappointing service

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

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