Find flights
When to book
FAQs & Tips
Direct Flights
Airlines
Deals

$129 Find cheap flights from Caribbean Islands to Chicago Midway Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Midway departing on 6/6. 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
to. 6/20
to. 6/27

Search hundreds of travel sites at once for deals on flights to Chicago Midway Airport

In the last 7 days travelers have searched 42,596,105 times on KAYAK, and here is why:

Save 21% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Bundle and saveSave money when you bundle your flight + hotel.

Good to know

Low season

March

High season

December

Cheapest flight

$129
Best time to beat the crowds but there is an average 65% increase in price.
Most popular time to fly and prices are also 4% lower on average.
Flight from Santo Domingo to Chicago Midway Airport

FAQs for booking Caribbean Islands to Chicago Midway Airport flights

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

    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 Caribbean Islands to Chicago Midway Airport.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from Caribbean Islands 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 Caribbean Islands to Chicago Midway Airport?

    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 Midway Airport with an airline and back to Caribbean Islands with another airline.

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

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

See more FAQs

Prefer to fly non-stop from Caribbean Islands to Chicago Midway Airport?

Find which airlines fly direct from Caribbean Islands to Midway, which days they fly and book direct flights.

Nonstop departures

Caribbean Islands to Chicago Midway

Monday

Aeromexico, Air France, Allegiant Air, +11 more

Aeromexico, Air France, +12 more

Tuesday

Aeromexico, Air France, Delta, +9 more

Aeromexico, Air France, +10 more

Wednesday

Aeromexico, Air France, Delta, +9 more

Aeromexico, Air France, +10 more

Thursday

Aeromexico, Air France, Allegiant Air, +10 more

Aeromexico, Air France, +11 more

Friday

Aeromexico, Air France, Allegiant Air, +11 more

Aeromexico, Air France, +12 more

Saturday

Aeromexico, Air France, Delta, +9 more

Aeromexico, Air France, +10 more

Sunday

Aeromexico, Air France, Allegiant Air, +10 more

Aeromexico, Air France, +11 more

See more direct flights

Nonstop returns

Chicago Midway to Caribbean Islands

Monday

Aeromexico, Air France, Allegiant Air, +11 more

Aeromexico, Air France, +12 more

Tuesday

Aeromexico, Air France, Delta, +9 more

Aeromexico, Air France, +10 more

Wednesday

Aeromexico, Air France, Delta, +9 more

Aeromexico, Air France, +10 more

Thursday

Aeromexico, Air France, Allegiant Air, +10 more

Aeromexico, Air France, +11 more

Friday

Aeromexico, Air France, Allegiant Air, +11 more

Aeromexico, Air France, +12 more

Saturday

Aeromexico, Air France, Delta, +9 more

Aeromexico, Air France, +10 more

Sunday

Aeromexico, Air France, Allegiant Air, +10 more

Aeromexico, Air France, +11 more

See more direct flights
See more direct flights

Top airline flying from Caribbean Islands to Midway

 
Need help choosing which airline to fly with from Caribbean Islands to Midway? 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.
6.2
FrontierOverall score based on 4049 reviews
4.9Entertainment
7.1Crew
5.2Food
5.8Comfort
6.6Boarding
Airline reviews

Plane could have been more on time. More leg room .

2.0 MediocreAnonymous, May 2024PDX - DEN
Read more about Frontier reviews

Plane could have been more on time. More leg room .

I arrived 1 hour prior to boarding, and they said I was too late for a domestic flight. First time I heard that :-(

Check in online was easy. Seats aren’t very comfortable

Fecal matter in seat back pocket. Presumably from a kids diaper.

Worst airline to travel with. They treat you like a prisoner in a jailhouse barking out orders and threats. Nickle and dime you to the same price or higher than a respectable airline like one of the big 3 . Might as well fly with standard airlines

Well I mean u get what u pay for so 🤷‍♂️

Over an hour delay in departure but I was notified beforehand. Another delay on tarmac upon arrival at LGA. We ended up departing the plane almost 2 hours later than expected

I fly Frontier because it’s affordable. I understand that the seats are tight and not the most comfortable…but that’s part of it. The problem with this flight was that there was a group of travelers directly behind me at the back of the plane who were ridiculously loud and obnoxious the entire flight. I’m pretty sure they were drunk and I could periodically smell an odd odor that I believe was one of them using a smokeless vape pen. The stewards had to remind them to keep quiet during the pre-flight instruction, but that was it. They never said another thing to them for the rest of the flight. It was a miserable.

I checked a bag because it was $5 less than carry on. They managed to lose my bag on a 2.5 hr direct flight! Frontier has no airport staff at baggage claim to help. As soon as I got home around 11 pm I tried to use their online system to file the claim for lost bag - system wouldn't take the # on my baggage claim ticket - said it was not the correct number. Also said that I had not checked a bag, which wasn't true - even my online boarding pass showed that I had checked a bag. Wasted about an hour on that process with no luck. Tried again in the morning - same thing. So tried online chat with Frontier bot - waited 35-40" twice to be connected to a baggage agent and it never happened. Eventually drove to PDX after work and waited 2 hrs for the Frontier ticket agents to arrive prior to the next Frontier flight out of PDX and FINALLY got some help from one of them, to take me to lost luggage area where I was able to retrive my bag. Probably took 4-5 hrs. of my time and endless frustration to get my bag. This was my first -- and LAST -- experience flying Frontier Airlines. Check-in was also extremely difficult and time consuming. The flight itself (and staff) were fine but everything else about the experience was a total disaster! The fact that Frontier literally has NO WAY to connect to a human voice for customer service (in this case for lost luggage) is the WORST!!!!!

Frontier is a crappy airline nothing about it is honest

Book cheap flights from Caribbean Islands to Chicago

Recent round-trip flight deals

7/25to.
1 stopFrontier
23h 46mPUJ-MDW
7/29ma.
1 stopFrontier
15h 14mMDW-PUJ
$222
7/23ti.
1 stopFrontier
27h 01mPUJ-MDW
7/29ma.
1 stopFrontier
15h 14mMDW-PUJ
$234
6/17ma.
1 stopFrontier
14h 41mSDQ-MDW
6/20to.
1 stopFrontier
13h 47mMDW-SDQ
$237
7/25to.
1 stopFrontier
23h 46mPUJ-MDW
7/30ti.
1 stopFrontier
11h 17mMDW-PUJ
$255
10/24to.
1 stopDelta
9h 50mSJU-MDW
10/27sø.
1 stopDelta
9h 04mMDW-SJU
$397
10/24to.
1 stopDelta
7h 48mSDQ-MDW
10/29ti.
1 stopDelta
6h 23mMDW-SDQ
$422
5/31fr.
1 stop
26h 56mSDQ-MDW
6/5on.
1 stop
7h 53mMDW-SDQ
$436
8/1to.
1 stop
16h 36mNAS-MDW
8/5ma.
1 stop
10h 09mMDW-NAS
$471
6/11ti.
2 stopsWestJet
23h 15mMBJ-MDW
6/20to.
2 stopsWestJet
22h 29mMDW-MBJ
$1,728
10/22ti.
2 stopsLATAM Airlines
32h 47mPUJ-MDW
10/27sø.
2 stopsLATAM Airlines
27h 00mMDW-PUJ
$2,240

Search by stops

Search by airline

Search by price

Recent one-way flight deals

6/6to.
1 stopFrontier
12h 22mSDQ-MDW
$129
6/4ti.
1 stopFrontier
14h 15mPUJ-MDW
$131
8/21on.
1 stopFrontier
8h 58mSJU-MDW
$135
6/14fr.
1 stopFrontier
12h 53mSJU-MDW
$139
6/14fr.
1 stopFrontier
23h 01mPUJ-MDW
$140
6/12on.
1 stopDelta
7h 26mNAS-MDW
$225
6/13to.
2 stops
17h 45mSJU-MDW
$228
6/7fr.
2 stopsDelta
18h 48mSDQ-MDW
$236
7/7sø.
2 stops
17h 44mSJU-MDW
$236
8/26ma.
2 stopsLATAM Airlines
20h 36mPUJ-MDW
$1,157

Search by stops

Search by airline

Search by price

Last minute flights from Caribbean Islands to Midway

Last minute flight, train and bus deals

5/25lø.
multi-stopFrontier
7h 31mSJU-MDW
6/1lø.
multi-stopFrontier
8h 24mMDW-SJU
$349
5/24fr.
multi-stopFrontier
28h 46mSJU-MDW
6/1lø.
multi-stopFrontier
8h 24mMDW-SJU
$364
5/22on.
multi-stopFrontier
19h 41mSJU-MDW
5/30to.
multi-stopFrontier
8h 05mMDW-SJU
$404
5/22on.
multi-stopFrontier
9h 39mSJU-MDW
5/26sø.
multi-stopFrontier
12h 07mMDW-SJU
$428
5/22on.
multi-stopFrontier
9h 39mSJU-MDW
5/24fr.
multi-stopFrontier
23h 04mMDW-SJU
$434
5/23to.
multi-stopFrontier
13h 28mSJU-MDW
5/27ma.
multi-stopFrontier
12h 21mMDW-SJU
$448
5/25lø.
multi-stop
14h 59mMBJ-MDW
6/14fr.
multi-stop
20h 49mMDW-MBJ
$588
5/23to.
multi-stopDelta
9h 55mPUJ-MDW
6/21fr.
multi-stopDelta
18h 22mMDW-PUJ
$865
5/23to.
multi-stopDelta
10h 12mSJU-MDW
5/29on.
multi-stopDelta
6h 38mMDW-SJU
$904
5/24fr.
multi-stopDelta
7h 51mSXM-MDW
5/27ma.
multi-stopDelta
6h 40mMDW-SXM
$916

Search by stops

Search by airline

Search by price