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Cheap flights from Caribbean to Chicago from $101

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Caribbean to Chicago departing on 8/7. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Caribbean to Chicago

Cheap round-trip flights

Spirit Airlines Logo
10:14 pm - 8:55 amSJU-ORD
11h 41m1 stop
Spirit Airlines Logo
5:05 am - 9:09 pmORD-SJU
15h 04m1 stop
$203Spirit Airlines
Find Deal
jue., ago. 7 - dom., ago. 10
Spirit Airlines Logo
11:59 am - 10:48 pmSJU-ORD
11h 49m1 stop
Spirit Airlines Logo
6:44 pm - 11:04 amORD-SJU
15h 20m1 stop
$212Spirit Airlines
Find Deal
vie., sep. 5 - dom., sep. 7
Frontier Logo
3:32 am - 3:17 pmBQN-ORD
12h 45m1 stop
Frontier Logo
8:49 pm - 10:56 amORD-BQN
13h 07m1 stop
$258Frontier
Find Deal
vie., sep. 19 - vie., oct. 3
Frontier Logo
12:59 am - 12:20 pmSJU-ORD
12h 21m1 stop
Frontier Logo
7:46 pm - 8:59 amORD-SJU
12h 13m1 stop
$258Frontier
Find Deal
mié., ago. 27 - sáb., ago. 30
American Airlines Logo
2:00 pm - 6:30 pmMBJ-ORD
4h 30mnonstop
American Airlines Logo
8:30 am - 12:31 pmORD-MBJ
4h 01mnonstop
$334American Airlines
Find Deal
mié., ago. 20 - dom., ago. 24
American Airlines Logo
2:00 pm - 6:30 pmMBJ-ORD
4h 30mnonstop
American Airlines Logo
6:00 am - 12:03 pmORD-MBJ
6h 03m1 stop
$338American Airlines
Find Deal
mié., ago. 20 - dom., ago. 24
Delta Logo
3:59 pm - 10:37 pmPUJ-ORD
7h 38m1 stop
Delta Logo
5:30 am - 1:20 pmORD-PUJ
6h 50m1 stop
$350Delta
Find Deal
vie., sep. 5 - dom., sep. 14
Delta Logo
1:10 pm - 10:37 pmPUJ-ORD
10h 27m1 stop
Delta Logo
5:30 am - 1:20 pmORD-PUJ
6h 50m1 stop
$360Delta
Find Deal
vie., sep. 5 - dom., sep. 14
United Airlines Logo
12:15 am - 9:38 amBQN-ORD
10h 23m1 stop
United Airlines Logo
2:20 pm - 11:09 pmORD-BQN
7h 49m1 stop
$391United Airlines
Find Deal
lun., sep. 15 - mar., sep. 23
United Airlines Logo
12:15 am - 2:50 pmBQN-ORD
15h 35m2 stops
United Airlines Logo
7:24 am - 11:09 pmORD-BQN
14h 45m2 stops
$418United Airlines
Find Deal
mié., ago. 20 - lun., ago. 25

Spirit Airlines flights from Caribbean to Chicago O'Hare Intl Airport

Our best Spirit Airlines deals on Caribbean to Chicago O'Hare Intl Airport flight tickets
Spirit Airlines
Aug 7
SJU10:14 pmSan Juan Luis Munoz Marin Intl
11h 41m
1 stop
ORD8:55 amChicago O'Hare Intl
Aug 10
ORD5:05 amChicago O'Hare Intl
15h 04m
1 stop
SJU9:09 pmSan Juan Luis Munoz Marin Intl
$203
Find similar
Spirit Airlines
Sep 5
SJU11:59 amSan Juan Luis Munoz Marin Intl
11h 49m
1 stop
ORD10:48 pmChicago O'Hare Intl
Sep 7
ORD6:44 pmChicago O'Hare Intl
15h 20m
1 stop
SJU11:04 amSan Juan Luis Munoz Marin Intl
$212
Find similar
Spirit Airlines
Aug 15
SJU7:40 pmSan Juan Luis Munoz Marin Intl
5h 03m
ORD11:43 pmChicago O'Hare Intl
Aug 19
ORD6:56 amChicago O'Hare Intl
16h 01m
1 stop
SJU11:57 pmSan Juan Luis Munoz Marin Intl
$217
Find similar

Copa Airlines flights from Caribbean to Chicago O'Hare Intl Airport

Our best Copa Airlines deals on Caribbean to Chicago O'Hare Intl Airport flight tickets
Copa Airlines
Aug 6
SDQ11:54 amSanto Domingo Las Americas
12h 52m
1 stop
ORD11:46 pmChicago O'Hare Intl
Aug 9
ORD3:07 pmChicago O'Hare Intl
10h 36m
1 stop
SDQ2:43 amSanto Domingo Las Americas
$510
Find similar
Copa Airlines
Nov 26
POS2:26 pmPort of Spain Piarco Intl
11h 39m
1 stop
ORD12:05 amChicago O'Hare Intl
Nov 30
ORD2:07 pmChicago O'Hare Intl
9h 41m
1 stop
POS1:48 amPort of Spain Piarco Intl
$744
Find similar

See travel insights to Chicago from

How to get the cheapest flight ticket from Caribbean to Chicago O'Hare Intl Airport

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 month to fly to Chicago O'Hare Intl Airport?

The month of August is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Caribbean averaging around $255.

What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Friday when prices can be found for as low as $342. This is often the case because there is less demand to fly during this day of the week. On the other hand, Monday is the most expensive day to depart from Caribbean because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $478.

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

Flying to Chicago O'Hare Intl Airport from Caribbean in the evening is the least expensive time of day to depart. momondo users have found prices as low as $242 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $479. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Caribbean to Chicago O'Hare Intl flight route?

Fly from San Juan Luis Munoz Marin Intl to Chicago O'Hare Intl for the best Caribbean - Chicago O'Hare Intl flight prices

How far in advance should I book a flight to Chicago O'Hare Intl Airport?

You are more likely to see cheaper flights to Chicago O'Hare Intl Airport from Caribbean when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport for around $318 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago O'Hare Intl Airport from Caribbean for as low as $252 on momondo.

What cabin class options are available on Caribbean to Chicago O'Hare Intl flights?

There are 4 cabin classes available to choose from on Caribbean to Chicago O'Hare Intl flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Cheap Caribbean to Chicago O'Hare Intl Airport flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Caribbean to Chicago O'Hare Intl Airport

Best Price Found

$101

Fastest flight time

3h 56m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Caribbean in the past 72 hours is $101. The best round-trip flight deal from Caribbean to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $203.
The fastest flight from Caribbean to Chicago O'Hare Intl Airport takes 3h 56m
Direct flights go from Caribbean to Chicago O'Hare Intl Airport every day.
Search flight deals

  • When did momondo last update prices for flights from Caribbean to Chicago O'Hare Intl Airport?

    Prices for flights from Caribbean to Chicago O'Hare Intl Airport were last updated today.

  • How many operators does momondo search for flights from Caribbean to Chicago O'Hare Intl Airport?

  • How old do you have to be to fly from Caribbean to Chicago O'Hare Intl Airport?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Caribbean to Chicago O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The necessary travel and health documents for your Chicago O'Hare Intl Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Caribbean to Chicago O'Hare Intl Airport?

Best airlines flying from Caribbean to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from Caribbean to Chicago O'Hare Intl Airport with momondo
Airline
Rating
Free Cancellation
Price
Spirit AirlinesPriceFrom $137Free CancellationRating
6.3
8,034 reviews
Search Spirit Airlines flights
FrontierPriceFrom $137Free CancellationRating
5.9
3,244 reviews
Search Frontier flights
DeltaPriceFrom $162Free CancellationRating
8.0
7,967 reviews
Search Delta flights
United AirlinesPriceFrom $218Free CancellationRating
7.4
8,880 reviews
Search United Airlines flights
SouthwestPriceFrom $257Free CancellationRating
8.0
4,233 reviews
Search Southwest flights
American AirlinesPriceFrom $329Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lake Geneva
Rockford
Schaumburg
South Haven
Merrillville
Gurnee
Naperville
Rosemont
Kenosha
New Buffalo
Joliet
Oak Brook
Racine
Hammond
Tinley Park
Elgin
Aurora
Orland Park
Janesville
Benton Harbor

Why use momondo?

Why should I use momondo to find a flight deal from Caribbean to Chicago?

It is quick and easy to find Caribbean to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

Can I find flights from Caribbean to Chicago with flexible booking policies on momondo?

All flight searches from Caribbean to Chicago on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Caribbean to Chicago?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Caribbean to Chicago.

I’m not ready to book a flight from Caribbean to Chicago right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Caribbean to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Chicago and let you know when they change.

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