Flight Routes from Chicago to Montego Bay

Compare cheap outbound and return flights from Chicago (CHI) to Montego Bay (MBJ) and find the best offer from numerous airlines and travel agencies.

Trip type
Cheapest roundtrip flight
from€480
Fastest flight
non-stop flights
23x / week
Flight distance
2,761 km
Time difference
Airports in Chicago
  1. O'Hare International Airport, IL
  2. Midway International Airport, IL
  3. Rockford, IL

Cheap flight offers from Chicago to Montego Bay

sorted by price and recency
  1. –
    American Airlines
    –
    CHI–MBJ
    1 stopover
    American Airlines
    –
    MBJ–CHI
    non-stop flight
    €1,081
  2. –
    American Airlines
    –
    CHI–MBJ
    1 stopover
    American Airlines
    –
    MBJ–CHI
    non-stop flight
    €638
  3. –
    Air Canada
    –
    CHI–MBJ
    1 stopover
    Air Canada
    –
    MBJ–CHI
    1 stopover
    €629
  4. –
    Air Canada
    –
    CHI–MBJ
    1 stopover
    Air Canada
    –
    MBJ–CHI
    1 stopover
    €624
  5. –
    American Airlines
    –
    CHI–MBJ
    1 stopover
    American Airlines
    –
    MBJ–CHI
    non-stop flight
    €480
  6. –
    Aeroméxico
    –
    CHI–MBJ
    2 stopovers
    Westjet
    –
    MBJ–CHI
    2 stopovers
    €3,471

Flight schedule from Chicago (CHI) to Montego Bay (MBJ)

Select a travel date in the flight schedule for the route from Chicago (CHI) to Montego Bay (MBJ) and compare affordable flight deals.

offers
Active filtersnone
Matching outbound flightsCHI–MBJ · 5 of 5
fromto
dep.arr.
durationstopovers
  1. November 8 – 14, 2026
  2. November 15 – 21, 2026
  3. November 22 – 28, 2026
    1. MDWMBJ
      nonstop
      1. Southwest Airlines
    2. ORDMBJ
      nonstop
      1. United Airlines
    3. ORDMBJ
      nonstop
      1. American Airlines
    4. ORDMBJ
      nonstop
      1. American Airlines
    5. ORDMBJ
      nonstop
      1. American Airlines

      Tips and tricks to help you find cheap flights from Chicago to Montego Bay

      Favorite airline: Spirit Airlines
      Spirit Airlines is the most popular airline for flights from Chicago to Montego Bay.
      Spirit Airlines
      29 %
      American Airlines
      19 %
      United Airlines
      19 %
      Stopover flights are the cheapest connection
      Direct flights on this route are $297.00 more expensive on average than flights with a stopover.
      non stop flight
      1 stop
      2 stops
      04h 05min
      14h 22min
      08h 19min
      618 US$
      321 US$
      405 US$
      Favourite connection: via Fort Lauderdale
      On this route, flights with a stopover in Fort Lauderdale are the most popular.
      Route
      bookings
      1 stopover Fort Lauderdale-Hollywood International Airport, FL
      14h 22min, from 321 US$
      41 %
      1 stopover Toronto - Lester B. Pearson International Airport
      14h 25min, from 531 US$
      19 %
      1 stopover Orlando International Airport, FL
      06h 00min, from 381 US$
      14 %

      Important flight information

      Discover more flights around Chicago and Montego Bay

      Departure airport Airport Chicago-IL, all airports (CHI)
      Arrival airport Airport Montego Bay (MBJ)
      Destination country Flights to Jamaica
      Departure airport - Destination country Chicago-IL, all airports - Jamaica
      Alternative flights to Montego Bay
      Flight destinations with a similar price
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