Cheap NZD 209 Flights From Chicago to Jamaica
Easily compare flights from Chicago to Jamaica and find the cheapest tickets available!
Flying From Chicago to Jamaica: What You Need to Know
| Cheapest one-way flight price | NZD 208 |
|---|---|
| Cheapest round-trip ticket price | NZD 648 |
| Off-season for travel | April |
| Peak season for travel | June |
| Popular airline | United Airlines |
| Cheapest month | October |
Compare multiple airlines at once to find the best flight deals from Chicago to Jamaica.
Airlines Flying From Chicago to Jamaica
Search Flights From Chicago to Jamaica
Easily compare flights from Chicago to Jamaica and find the cheapest tickets available!
Find the Cheapest Flights to Jamaica From Chicago
Looking for cheap flights from Chicago to Jamaica? Check out prices for the next 90 days, starting at just NZD 209 for a one-way ticket and NZD 593 for a round trip.
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Round-trip
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One way
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Cheapest nonstop
Tue, Jul 8ORD|MBJChicagoMontego BayDirect | American Airlines
Tue, Jul 15MBJ|ORDMontego BayChicagoDirect | American AirlinesNZD 783 NZD 97720% OFF20% OFFNZD 977 NZD 783 -
Sat, Jun 7ORD|MBJChicagoMontego BayDirect | United Airlines
Fri, Jun 13MBJ|ORDMontego BayChicagoDirect | United AirlinesNZD 791 NZD 97719% OFF19% OFFNZD 977 NZD 791 -
Tue, Jul 15ORD|MBJChicagoMontego Bay1 stops | Spirit Airlines
Tue, Jul 22MBJ|ORDMontego BayChicago1 stops | Spirit AirlinesNZD 593 NZD 97739% OFF39% OFFNZD 977 NZD 593 -
Sat, Jun 28ORD|MBJChicagoMontego Bay1 stops | Spirit Airlines
Wed, Jul 2MBJ|ORDMontego BayChicago1 stops | Caribbean AirlinesNZD 59839% OFFNZD 977 NZD 598
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Tue, Jun 24ORD|MBJChicagoMontego Bay1 stops | Spirit Airlines
Thu, Jun 26MBJ|ORDMontego BayChicago1 stops | Spirit AirlinesNZD 61637% OFFNZD 977 NZD 616
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Wed, Jul 2ORD|MBJChicagoMontego Bay1 stops | Spirit Airlines
Wed, Jul 9MBJ|ORDMontego BayChicago1 stops | United AirlinesNZD 61837% OFFNZD 977 NZD 618
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Tue, Jun 17ORD|MBJChicagoMontego Bay1 stops | Spirit Airlines
Tue, Jun 24MBJ|ORDMontego BayChicago1 stops | Spirit AirlinesNZD 62037% OFFNZD 977 NZD 620
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Wed, Jun 11ORD|MBJChicagoMontego Bay1 stops | Spirit Airlines
Wed, Jun 18MBJ|ORDMontego BayChicago1 stops | Spirit AirlinesNZD 62236% OFFNZD 977 NZD 622
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Fri, Jun 20ORD|MBJChicagoMontego Bay1 stops | Spirit Airlines
Thu, Jun 26MBJ|ORDMontego BayChicago1 stops | Spirit AirlinesNZD 62636% OFFNZD 977 NZD 626
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Tue, Jun 10ORD|MBJChicagoMontego Bay1 stops | Spirit Airlines
Tue, Jun 17MBJ|ORDMontego BayChicago1 stops | Spirit AirlinesNZD 63036% OFFNZD 977 NZD 630
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Tue, Jun 17ORD|KINChicagoKingston1 stops | Spirit Airlines
Tue, Jun 24KIN|ORDKingstonChicago1 stops | Spirit AirlinesNZD 63435% OFFNZD 977 NZD 634
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Sat, Jun 14ORD|MBJChicagoMontego Bay1 stops | Spirit Airlines
Wed, Jun 18MBJ|ORDMontego BayChicago1 stops | Caribbean AirlinesNZD 63835% OFFNZD 977 NZD 638
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Mon, Jun 9CHI|MBJChicagoMontego Bay1 stops | Normal Airline
Wed, Jun 11MBJ|CHIMontego BayChicagoDirect | Normal AirlineFind More FlightsFind More Flights
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Cheapest nonstop
Sun, Jun 29ORD|MBJChicagoMontego BayDirect | American AirlinesNZD 365 NZD 46421% OFF21% OFFNZD 464 NZD 365
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Sat, Jun 14ORD|MBJChicagoMontego BayDirect | American AirlinesNZD 376 NZD 46419% OFF19% OFFNZD 464 NZD 376
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Tue, Jun 10ORD|KINChicagoKingston1 stops | Spirit AirlinesNZD 209 NZD 46455% OFF55% OFFNZD 464 NZD 209
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Sat, Jun 28ORD|MBJChicagoMontego Bay1 stops | Spirit AirlinesNZD 21055% OFFNZD 464 NZD 210
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Sat, Jun 14ORD|KINChicagoKingston1 stops | Spirit AirlinesNZD 23450% OFFNZD 464 NZD 234
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Fri, Jun 13RFD|MBJChicagoMontego Bay1 stops | Allegiant AirNZD 23450% OFFNZD 464 NZD 234 -
Wed, Jun 25ORD|KINChicagoKingston1 stops | Spirit AirlinesNZD 24248% OFFNZD 464 NZD 242
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Fri, Jun 27RFD|MBJChicagoMontego Bay1 stops | Allegiant AirNZD 24248% OFFNZD 464 NZD 242
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Tue, Jun 24ORD|KINChicagoKingston1 stops | Spirit AirlinesNZD 24348% OFFNZD 464 NZD 243
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Sun, Jun 15ORD|MBJChicagoMontego Bay1 stops | Spirit AirlinesNZD 24747% OFFNZD 464 NZD 247
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Wed, Jul 2ORD|MBJChicagoMontego Bay1 stops | Spirit AirlinesNZD 24747% OFFNZD 464 NZD 247
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Sat, Jun 28ORD|KINChicagoKingston1 stops | Spirit AirlinesNZD 24747% OFFNZD 464 NZD 247
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Mon, Jun 9CHI|MBJChicagoMontego Bay1 stops | Normal AirlineFind More FlightsFind More Flights
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Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.
FAQs: Flights From Chicago to Jamaica
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What is the cheapest Chicago to Jamaica flight route?
The cheapest round-trip flight from Chicago to Jamaica is on the route from Chicago to Montego Bay, with prices starting at NZD 655 for a round trip between 2025-03-02 and 2025-03-08. -
When is it the cheapest time to fly from Chicago to Jamaica?
According to our flights calendar over the next 90 days, it seems the cheapest date is on 2025-04-08 for one-way flights. -
How long does it take to fly to Jamaica from Chicago?
Based on our flight data, the average flight time from Chicago to Jamaica is approximately 4 hours based on our most popular routes from Chicago to Montego Bay. The time may also vary depending on your destination. -
What is the cheapest airline that flies to Jamaica from Chicago?
The cheapest airline flying to Jamaica from Chicago is Spirit Airlines serving route from Chicago to Montego Bay. -
Where can I fly to Jamaica from Chicago?
There are direct flights from Chicago to Jamaica. Montego Bay, Kingston, and Ocho Rios are all popular destinations in Jamaica.