Cheap flights from Chicago to Caribbean Islands from $68
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Caribbean Islands departing on 10/1. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
Round-trip
1 adult
Economy
0 bags
From?
To?
dom. 7/7
dom. 7/14
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Below you can see the best fares for your round-trip flight route over the next six months. All fares were found on momondo this week. Browse the quickest and cheapest flights from Chicago to Caribbean Islands by changing tabs
Frontier![Frontier]()
Jul 24![Frontier]()
Jul 30
MDW9:31 amChicago Midway
16h 41m
1 stop
SJU3:12 amSan Juan Luis Munoz Marin Intl
SJU8:41 pmSan Juan Luis Munoz Marin Intl
12h 55m
1 stop
MDW8:36 amChicago Midway
Spirit Airlines![Spirit Airlines]()
Jul 6![Spirit Airlines]()
Jul 14
ORD5:11 pmChicago O'Hare Intl
4h 47m
SJU10:58 pmSan Juan Luis Munoz Marin Intl
SJU6:40 amSan Juan Luis Munoz Marin Intl
5h 09m
ORD10:49 amChicago O'Hare Intl
Multiple Airlines![Multiple Airlines]()
Sep 10![Multiple Airlines]()
Sep 16
ORD5:05 amChicago O'Hare Intl
13h 03m
1 stop
SJU7:08 pmSan Juan Luis Munoz Marin Intl
SJU1:25 amSan Juan Luis Munoz Marin Intl
10h 08m
1 stop
ORD10:33 amChicago O'Hare Intl
American Airlines![American Airlines]()
Sep 15![American Airlines]()
Sep 19
ORD5:20 amChicago O'Hare Intl
9h 24m
1 stop
PUJ3:44 pmPunta Cana
PUJ2:04 pmPunta Cana
10h 55m
1 stop
ORD11:59 pmChicago O'Hare Intl
Frontier![Frontier]()
Jul 31![Frontier]()
Aug 3
MDW3:36 pmChicago Midway
8h 54m
1 stop
SJU1:30 amSan Juan Luis Munoz Marin Intl
SJU10:15 pmSan Juan Luis Munoz Marin Intl
12h 30m
1 stop
MDW9:45 amChicago Midway
Find the cheapest one-way flights from Chicago to Caribbean Islands
If you're looking for one-way flights from Chicago to Caribbean Islands, view some of our deals below provided by Frontier, Spirit Airlines and United Airlines
Spirit Airlines![Spirit Airlines]()
Oct 1
ORD7:05 amChicago O'Hare Intl
11h 03m
1 stop
SJU7:08 pmSan Juan Luis Munoz Marin Intl
Find the cheapest direct flights from Chicago to Caribbean Islands
Spirit Airlines![Spirit Airlines]()
Jul 6![Spirit Airlines]()
Jul 14
ORD5:11 pmChicago O'Hare Intl
4h 47m
SJU10:58 pmSan Juan Luis Munoz Marin Intl
SJU6:40 amSan Juan Luis Munoz Marin Intl
5h 09m
ORD10:49 amChicago O'Hare Intl
Frontier![Frontier]()
Jul 15![Frontier]()
Jul 18
ORD5:15 amChicago O'Hare Intl
4h 46m
PUJ11:01 amPunta Cana
PUJ1:04 pmPunta Cana
5h 03m
ORD5:07 pmChicago O'Hare Intl
United Airlines![United Airlines]()
Sep 4![United Airlines]()
Sep 14
ORD8:55 amChicago O'Hare Intl
4h 47m
SJU2:42 pmSan Juan Luis Munoz Marin Intl
SJU3:55 pmSan Juan Luis Munoz Marin Intl
5h 03m
ORD7:58 pmChicago O'Hare Intl
American Airlines![American Airlines]()
Aug 20![American Airlines]()
Aug 24
ORD8:38 amChicago O'Hare Intl
4h 35m
PUJ2:13 pmPunta Cana
PUJ5:00 pmPunta Cana
5h 00m
ORD9:00 pmChicago O'Hare Intl
Spirit Airlines![Spirit Airlines]()
Jul 6![Spirit Airlines]()
Jul 14
ORD5:11 pmChicago O'Hare Intl
4h 47m
SJU10:58 pmSan Juan Luis Munoz Marin Intl
SJU6:40 amSan Juan Luis Munoz Marin Intl
5h 09m
ORD10:49 amChicago O'Hare Intl
Search last-minute flights to Caribbean Islands from Chicago
Find and compare round-trip flight prices for your last-minute flight from Chicago to Caribbean Islands
Spirit Airlines![Spirit Airlines]()
Jul 16![Spirit Airlines]()
Aug 6
ORD9:15 pmChicago O'Hare Intl
14h 16m
1 stop
SJU12:31 pmSan Juan Luis Munoz Marin Intl
SJU9:15 pmSan Juan Luis Munoz Marin Intl
12h 59m
1 stop
ORD9:14 amChicago O'Hare Intl
Multiple Airlines![Multiple Airlines]()
Jul 6![Multiple Airlines]()
Jul 26
ORD5:11 pmChicago O'Hare Intl
4h 47m
SJU10:58 pmSan Juan Luis Munoz Marin Intl
SJU5:57 pmSan Juan Luis Munoz Marin Intl
8h 02m
1 stop
ORD12:59 amChicago O'Hare Intl
Frontier![Frontier]()
Jul 9![Frontier]()
Jul 13
MDW7:37 pmChicago Midway
11h 36m
1 stop
SJU8:13 amSan Juan Luis Munoz Marin Intl
SJU3:08 amSan Juan Luis Munoz Marin Intl
7h 37m
1 stop
MDW9:45 amChicago Midway
Spirit Airlines![Spirit Airlines]()
Jul 16![Spirit Airlines]()
Aug 6
ORD11:48 amChicago O'Hare Intl
4h 47m
SJU5:35 pmSan Juan Luis Munoz Marin Intl
SJU9:15 pmSan Juan Luis Munoz Marin Intl
12h 59m
1 stop
ORD9:14 amChicago O'Hare Intl
Delta![Delta]()
Jul 8![Delta]()
Jul 10
ORD7:59 pmChicago O'Hare Intl
14h 56m
1 stop
NAS11:55 amNassau Intl
NAS3:58 pmNassau Intl
7h 48m
1 stop
ORD10:46 pmChicago O'Hare Intl
Spirit Airlines flights from Chicago to Caribbean Islands
Our best Spirit Airlines deals on Chicago to Caribbean Islands flight tickets
Spirit Airlines![Spirit Airlines]()
Jul 16![Spirit Airlines]()
Aug 6
ORD9:15 pmChicago O'Hare Intl
14h 16m
1 stop
SJU12:31 pmSan Juan Luis Munoz Marin Intl
SJU9:15 pmSan Juan Luis Munoz Marin Intl
12h 59m
1 stop
ORD9:14 amChicago O'Hare Intl
Spirit Airlines![Spirit Airlines]()
Jul 16![Spirit Airlines]()
Aug 6
ORD11:48 amChicago O'Hare Intl
4h 47m
SJU5:35 pmSan Juan Luis Munoz Marin Intl
SJU9:15 pmSan Juan Luis Munoz Marin Intl
12h 59m
1 stop
ORD9:14 amChicago O'Hare Intl
Frontier flights from Chicago to Caribbean Islands
Our best Frontier deals on Chicago to Caribbean Islands flight tickets
Frontier![Frontier]()
Jul 24![Frontier]()
Jul 30
MDW9:31 amChicago Midway
16h 41m
1 stop
SJU3:12 amSan Juan Luis Munoz Marin Intl
SJU8:41 pmSan Juan Luis Munoz Marin Intl
12h 55m
1 stop
MDW8:36 amChicago Midway
Frontier![Frontier]()
Jul 31![Frontier]()
Aug 3
MDW3:36 pmChicago Midway
8h 54m
1 stop
SJU1:30 amSan Juan Luis Munoz Marin Intl
SJU10:15 pmSan Juan Luis Munoz Marin Intl
12h 30m
1 stop
MDW9:45 amChicago Midway
How to get the cheapest flight ticket from Chicago to Caribbean Islands
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the cheapest airline that flies to Caribbean Islands from Chicago?
Frontier. Aeromexico, Copa Airlines, and Frontier are the most popular carriers operating from Chicago to Caribbean Islands
What is the cheapest Chicago to Caribbean Islands flight route?
Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl. Fly from Chicago O'Hare Intl to San Juan Luis Munoz Marin Intl for the best Chicago - Caribbean Islands flight prices
Can stopping save me money on Chicago to Caribbean Islands flights?
You could potentially save up to 11% on your flight if you consider stops on a Chicago to Caribbean Islands flight.
Cheap Chicago to Caribbean Islands flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Chicago to Caribbean Islands
Best Price Found | $68 |
|---|---|
Fastest flight time | 3h 23m |
Direct flights | Every day |
Airports in Caribbean Islands | 5 airports |
When did momondo last update prices for flights from Chicago to Caribbean Islands?
Prices for flights from Chicago to Caribbean Islands were last updated today.
How many operators does momondo search for flights from Chicago to Caribbean Islands?
There are 12 operators available for flights from Chicago to Caribbean Islands as of July 2024.
How old do you have to be to fly from Chicago to Caribbean Islands?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago to Caribbean Islands.
What documentation or ID do you need to fly to Caribbean Islands?
The travel and health documents you'll need for your trip to Caribbean Islands may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Caribbean Islands. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
Best airlines flying from Chicago to Caribbean Islands
Compare and see reviews for airlines that fly from Chicago to Caribbean Islands with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $90 | Free Cancellation | Rating 6.2 3,903 reviews | |||
| PriceFrom $133 | Free Cancellation | Rating 6.4 8,476 reviews | |||
| PriceFrom $134 | Free Cancellation | Rating 8.0 9,947 reviews | |||
| PriceFrom $136 | Free Cancellation | Rating 7.6 4,131 reviews | |||
| PriceFrom $169 | Free Cancellation | Rating 7.4 10,000 reviews | |||
| PriceFrom $262 | Free Cancellation | Rating 7.5 2,309 reviews | |||
| PriceFrom $283 | Free Cancellation | Rating 7.0 7,225 reviews | |||
| PriceFrom $288 | Free Cancellation | Rating 8.0 9,353 reviews | |||
| PriceFrom $296 | Free Cancellation | Rating 7.3 10,000 reviews | |||
| PriceFrom $400 | Free Cancellation | Rating 6.9 7,414 reviews |
Why use momondo?
Why should I use momondo to find a flight deal from Chicago to Caribbean Islands?
momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Chicago to Caribbean Islands. momondo saves you time and could save you money on your trip.
Can I find flights from Chicago to Caribbean Islands with flexible booking policies on momondo?
All flight searches from Chicago to Caribbean Islands on momondo can be filtered to show those which offer flexible booking policies.
How can momondo help me find flights from Chicago to Caribbean Islands?
momondo provides multiple filters to help you find the best flight to Caribbean Islands from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.
I’m not ready to book a flight from Chicago to Caribbean Islands right now. Can momondo alert me if prices change?
If you are simply researching potential flights to Caribbean Islands, momondo offers a useful price alert feature which will track prices for flights to Caribbean Islands from Chicago and alert you when they change.
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