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Find cheap flights from Chicago Midway Airport to Dominican Republic from $119

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 the Dominican Republic departing on 6/22. 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
0 bags
Wed 6/5
Wed 6/12

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Best Dominican Republic Flight Deals

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Good to know

Low season

April

High season

October

Cheapest flight

$119
Best time to beat the crowds with an average 22% drop in price.
Most popular time to fly with an average 6% increase in price.
Flight from Chicago Midway Airport to Santo Domingo

FAQs - booking Dominican Republic flights

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

    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 Dominican Republic.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Dominican Republic 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 Dominican Republic?

    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 Dominican Republic with an airline and back to Chicago Midway Airport with another airline.

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

    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 Dominican Republic from Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding cheap flights to the Dominican Republic

  • Morning departure is around 98% more expensive than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

Top 3 airlines serving from Midway to the Dominican Republic

 
Need help choosing which airline to fly with from Midway to the Dominican Republic? 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
Alaska AirlinesOverall score based on 9134 reviews
8.6Crew
7.3Entertainment
7.9Comfort
8.2Boarding
7.3Food
Airline reviews

The flight was delayed because the pilots had not arrived on their previous flight yet. The flight was 100% full so it was pretty crowded. I miss having the screens on the back of the seats. It would be great if the Alaska planes had the clip so you can put your phone or tablet on the back of the seat in front of you to not strain your neck. Everything else was very smooth.

10.0 ExcellentAnonymous, May 2024SEA - BOS
Read more about Alaska Airlines reviews

The flight was delayed because the pilots had not arrived on their previous flight yet. The flight was 100% full so it was pretty crowded. I miss having the screens on the back of the seats. It would be great if the Alaska planes had the clip so you can put your phone or tablet on the back of the seat in front of you to not strain your neck. Everything else was very smooth.

Boarded the plain and had to wait 1 hour for crew Captain to arrive from another flight

It was fine since it ensure we went to our destination in time.

Overall good flight, smooth and on time and comfortable. Disappointing that food is not served and you can't purchase the snack packs on the plane.

The space for legs in coach is better than other Airlines you can even cross your legs!!

There was a row with three women who were very loud - talking and laughing. In an open, outdoor setting that's fine. On an airplane, no. The flight attendants told the women they were the fun row. It took the woman sitting in the row ahead of the loud women to tell them they were too loud, but everyone in the general vicinity was irritated. I didn't think it would be possible to be so rowdy for so long. Then when we landed we weren't let off at a gate. We had to be bussed in and the bus contended with airline traffic. After dealing with the loud passengers, this was not what I was expecting. An incredibly disappointing experience with an airline that I have always regarded as one of the better ones.

I bought the cheapest ticket. No meal, no checked luggage so I didn't expect much and was surprised by how good the flight and service was. Alaska is now my favorite airline.

Comfortable seat, plenty of leg room which is so rare, overhead bin comfortably accommodated my carry-on bag. Deli box was tasty, service was good, bathrooms were clean. Uneventful flight, which I appreciate. Departed on time and landed early.

No entertainment, food was cookies & juice,water, soda or coffee.

My baggage was in another flight, anit was delayed for one hour.

Very frustrated with boarding gate crew. She announced the plane was small and they would be limiting us to one item to carry on. Not a problem for me as I understand the tiny planes have limited space!! Not the case here! It was a rather large plane and had plenty of room for bags! So because I don’t want to be one of “those people” who ignores the request to check a carry on I did so asking if I would be able to pick it up at the bottom of the ramp on arrival in Knoxville to which she responded “yes”! Then I watched as every other passenger held onto their 2 items and boarded!! Then when we arrived in Knoxville our 2 carry ons had been put with all the other luggage and we had to go to baggage pick up and wait for all the big checked bags to come off the carousel! So she lied!! Frustrating. Next time I won’t be so nice!

It was a good experience except when boarding a female flight attendant did not go out of her way to assist my teenage daughters in finding space for their carry-ons after their compartments were full.

On time departure, smooth trip, flight attendant told through passengers the gate we would arrive at and the gate our outbound flight was departing from. Early arrival

Checking in at the airport the agent only booked the first keg of my trip and had my checked luggage going to the airport with a layover! Never was issued a boarding pass for the second leg or received sticker fir my checked bag. All was well in the end! Delta agents helped to resolve the situation!!!

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

Big plane, long flight, absolutely no leg room and basically non existent air! I am 5”4’ and always travel Main Cabin, I was miserable on this plane and could barely move when we arrived in Cabo due to the cramped leg area!

From Atlanta to Cabo I would have hoped on a plane that size I would have been able to breathe and wiggle my feet a little! The leg room in that plane is non existent and I am only 5”4’. And the air vent either wasn’t working very well or just could not blow air from the ceiling to the seat area as I was suffocating through the entire flight! And please don’t say I would have been more comfortable in first class because I cannot afford those rates and have always travelled Main Cabin without issues !

The pilots were good. Disappointing when planes don't have electrical ports

I liked the piloting of the aircraft. Very disappointed about lack of electrical ports. Also, although a short flight. there was enough time to hand out snacks to comfort + seats as was done for first class.

Not good 😐 Over priced baggage fees Small hard seats No wifi or entertainment options 😕

Didn't like anything!! Horrible flight. Small seating area and hard seats. Butt was sore after 2 hour flight to Seattle No entertainment or free refreshments No wifi or USB charging receptacles to charge phone entoute like other airliners Luggage rates were 3 times as much as competitors. Difficult to navigate online luggue process to pre pay before flight Overall bad experience WILL NEVER RIDE OR RECOMMEND FRONTIER TO FRIENDS OR FAMILY MEMBERS!!! THIS IS A SHAME!! MOST MESERIBLE FLIGHT OF MY LIFE!! AND I THOUGHT SPIRIT WAS 👎 YOU GOT THEM BEAD HANDS DOWN!!

Flight was a little late taking off. Seats are too upright, no ports to charge devices, no wifi, no entertainment

Six hour delay. Poor customer service. No voucher. Bad communication. Missed important appointments.

Our flight was delayed an hour, then when we got to board our flight finally, we were waiting in our seats for take off for 45 minutes before it was communicated that there was a maintenance issue therefore we waited on the plane for over an hour while that was resolved. We did not get to Phoenix until almost 3 hours after we were originally supposed to. This was the first and last time I will be flying Frontier.

Flight was canceled with little warning. Flight was rebooked through Ontario, California and connecting flight was delayed by over three hours. Frontier is living up to their Greyhound of the skies reputation for sure.

I purchased a carry on bag online…was supposed to cost $72 but after a whole slew of bs charges, the total was over $175.00. Because of these hidden charges, I will not even consider flying Frontier ever again. It’s just not worth the hassle. I’m scratching this company off my list forever.

Flight was OK. Seats were good no cell phone charges on the plane no TVs or entertainment.

There were 3 leg for the trip and each leg was delayed by 90 minutes or more. The boarding process takes forever with people waiting on the jetway even though most folks do not have carry-on. The whole process is poorly managed.

Flight cancelled and was told by a rude gate agent that they don’t accommodate on other airlines. Had to wait 5 hours for a connecting flight that had a 7 hour layover. Would not allow bags to be checked early so we couldn’t go through security .Had to rent a car for the afternoon to store bags and get a meal. Also incurred a hotel fee. No apology or reason given for the cancellation- just rudeness.

Book cheap flights from Chicago to the Dominican Republic

Recent round-trip flight deals

5/20Mon
1 stopFrontier
13h 19mMDW-PUJ
5/21Tue
1 stopFrontier
25h 11mPUJ-MDW
$212
6/6Thu
1 stopFrontier
17h 46mMDW-PUJ
6/11Tue
1 stopFrontier
14h 21mPUJ-MDW
$223
8/21Wed
1 stopFrontier
12h 49mMDW-PUJ
8/26Mon
1 stopFrontier
9h 01mPUJ-MDW
$224
5/29Wed
1 stopFrontier
20h 33mMDW-PUJ
6/3Mon
1 stopFrontier
8h 45mPUJ-MDW
$227
5/16Thu
1 stopFrontier
19h 38mMDW-PUJ
5/23Thu
1 stopFrontier
25h 11mPUJ-MDW
$234
5/20Mon
1 stop
13h 19mMDW-PUJ
5/21Tue
2 stops
16h 55mPUJ-MDW
$371
9/1Sun
1 stopDelta
8h 03mMDW-PUJ
9/5Thu
1 stopDelta
17h 49mPUJ-MDW
$440
9/21Sat
2 stopsDelta
18h 02mMDW-STI
9/24Tue
2 stopsDelta
19h 17mSTI-MDW
$441
5/18Sat
2 stopsDelta
14h 23mMDW-SDQ
5/26Sun
1 stopDelta
18h 25mSDQ-MDW
$468
10/2Wed
2 stopsDelta
19h 17mMDW-STI
10/30Wed
2 stopsDelta
19h 26mSTI-MDW
$483

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Recent one-way flight deals

6/22Sat
1 stopFrontier
23h 03mMDW-SDQ
$119
5/26Sun
1 stopFrontier
13h 04mMDW-PUJ
$123
7/14Sun
1 stopFrontier
12h 49mMDW-PUJ
$134
6/4Tue
1 stopFrontier
23h 38mMDW-PUJ
$142
6/4Tue
2 stopsFrontier
23h 02mMDW-PUJ
$144
9/14Sat
2 stops
15h 16mMDW-SDQ
$158
9/25Wed
1 stopDelta
6h 23mMDW-SDQ
$190
5/14Tue
2 stopsDelta
17h 55mMDW-SDQ
$192
8/31Sat
2 stopsDelta
16h 45mMDW-PUJ
$206
9/22Sun
2 stopsDelta
17h 37mMDW-PUJ
$256

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Last minute flights from Midway to the Dominican Republic

Last minute flight, train and bus deals

5/7Tue
multi-stopFrontier
17h 43mMDW-SDQ
5/9Thu
multi-stopFrontier
13h 24mSDQ-MDW
$315
5/11Sat
multi-stopFrontier
26h 22mMDW-PUJ
5/13Mon
multi-stopFrontier
25h 46mPUJ-MDW
$324
5/9Thu
multi-stopFrontier
12h 43mMDW-PUJ
5/13Mon
multi-stopFrontier
25h 46mPUJ-MDW
$334
5/7Tue
multi-stopFrontier
13h 08mMDW-PUJ
5/8Wed
multi-stopFrontier
25h 20mPUJ-MDW
$335
5/7Tue
multi-stopDelta
8h 00mMDW-PUJ
5/8Wed
multi-stopDelta
16h 30mPUJ-MDW
$435
5/7Tue
multi-stopDelta
6h 25mMDW-PUJ
5/8Wed
multi-stopDelta
19h 16mPUJ-MDW
$440
5/8Wed
multi-stop
21h 03mMDW-SDQ
5/10Fri
multi-stop
16h 14mSDQ-MDW
$600
5/8Wed
multi-stop
21h 03mMDW-SDQ
5/10Fri
multi-stop
10h 56mSDQ-MDW
$1,014
5/7Tue
multi-stopLATAM Airlines
21h 19mMDW-PUJ
5/8Wed
multi-stopLATAM Airlines
19h 22mPUJ-MDW
$3,356
5/7Tue
multi-stopLATAM Airlines
21h 19mMDW-PUJ
5/8Wed
multi-stopLATAM Airlines
19h 22mPUJ-MDW
$3,758

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Chicago Midway Airport - Dominican Republic Flights

Departure:

Chicago Midway Airport (MDW)United States

Return flight deals:

Dominican Republic - Chicago Midway Airport

Cabin classes: