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Flight Deals from Chicago O Hare Airport to Montego Bay from $130

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Stops

  • Up to 1 stop
    $327
  • Up to 2 stops
    $520

Airlines

  • Air Canada
    $496
  • American Airlines
    $524
  • Delta Air Lines
    $550
  • Frontier Airlines
    $446
  • JetBlue
    $545
  • Spirit Airlines
    $327
  • United Airlines
    $523

Cabin Class

  • Economy
    $327

Departure Airports

  • Chicago O Hare Airport
    $327

Arrival Airports

  • Sangster International Airport
    $327

Layover Airports

  • Charlotte Douglas International Airport
    $524
  • Dallas Fort Worth International Airport
    $589
  • Fort Lauderdale Hollywood International Airport
    $327
  • General Edward Lawrence Logan International Airport
    $633
  • George Bush Intercontinental Houston Airport
    $559
  • Hartsfield Jackson Atlanta International Airport
    $446
  • Miami International Airport
    $530
  • Montreal Trudeau Airport
    $520
  • New York John F Kennedy Airport
    $530
  • New York LaGuardia Airport
    $530
  • Newark Liberty Airport
    $568
  • Orlando International Airport
    $542
  • Ottawa Macdonald-Cartier International Airport
    $583
  • Philadelphia International Airport
    $529
  • Reagan Washington National Airport
    $530
  • Toronto Pearson Airport
    $496
  • Washington Dulles Airport
    $523

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Spirit Airlines Logo
Spirit Airlines

06/07/25

ORD
5h 57m
FLL

06/07/25

MBJ
Spirit Airlines Logo
Spirit Airlines

06/11/25

MBJ
10h 57m
FLL

06/11/25

ORD
$327
Free cancellation within 83 hours of booking
Spirit Airlines Logo
Spirit Airlines

06/11/25

ORD
5h 57m
FLL

06/11/25

MBJ
Spirit Airlines Logo
Spirit Airlines

06/25/25

MBJ
11h 38m
FLL

06/25/25

ORD
$327
Free cancellation within 83 hours of booking
Frontier Airlines Logo
Frontier Airlines

05/29/25

ORD
13h 24m
ATL

05/30/25

MBJ
Frontier Airlines Logo
Frontier Airlines

06/02/25

MBJ
13h 3m
ATL

06/02/25

ORD
$446
Free cancellation within 83 hours of booking
Frontier Airlines Logo
Frontier Airlines

05/25/25

ORD
13h 24m
ATL

05/26/25

MBJ
Frontier Airlines Logo
Frontier Airlines

05/28/25

MBJ
7h 36m
ATL

05/28/25

ORD
$446
Free cancellation within 83 hours of booking
Air Canada Logo
Air Canada

05/26/25

ORD
14h 50m
YYZ

05/27/25

MBJ
Air Canada Logo
Air Canada

06/04/25

MBJ
24h 50m
YYZ

06/05/25

ORD
$496
Free cancellation within 83 hours of booking
Air Canada Logo
Air Canada

05/27/25

ORD
14h 50m
YYZ

05/28/25

MBJ
Air Canada Logo
Air Canada

06/13/25

MBJ
24h 50m
YYZ

06/14/25

ORD
$508
Free cancellation within 83 hours of booking
Air Canada Logo
Air Canada

06/12/25

ORD
19h 20m
YYZ

06/13/25

MBJ
Air Canada Logo
Air Canada

06/19/25

MBJ
21h 47m
YYZ
YUL

06/20/25

ORD
$520
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

05/25/25

ORD
4h 7m
Direct

05/25/25

MBJ
United Airlines Logo
United Airlines

05/28/25

MBJ
7h 18m
IAD

05/28/25

ORD
$523
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/25/25

ORD
6h 35m
CLT

05/25/25

MBJ
American Airlines Logo
American Airlines

05/28/25

MBJ
4h 35m
Direct

05/28/25

ORD
$524
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

06/07/25

ORD
16h 35m
CLT

06/08/25

MBJ
American Airlines Logo
American Airlines

06/11/25

MBJ
10h 17m
CLT

06/11/25

ORD
$526
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

05/25/25

ORD
6h 18m
IAD

05/25/25

MBJ
United Airlines Logo
United Airlines

05/28/25

MBJ
7h 18m
IAD

05/28/25

ORD
$528
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/27/25

ORD
4h
Direct

05/27/25

MBJ
American Airlines Logo
American Airlines

05/31/25

MBJ
17h 36m
PHL

06/01/25

ORD
$529
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

06/07/25

ORD
15h 30m
DCA
CLT

06/08/25

MBJ
American Airlines Logo
American Airlines

06/11/25

MBJ
9h 22m
MIA

06/11/25

ORD
$530
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

06/10/25

ORD
9h 20m
LGA
CLT

06/10/25

MBJ
American Airlines Logo
American Airlines

06/25/25

MBJ
22h 56m
CLT
JFK

06/26/25

ORD
$530
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

06/10/25

ORD
9h 51m
CLT

06/10/25

MBJ
American Airlines Logo
American Airlines

06/25/25

MBJ
22h 56m
CLT
JFK

06/26/25

ORD
$530
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/25/25

ORD
12h 53m
DCA
CLT

05/26/25

MBJ
American Airlines Logo
American Airlines

05/28/25

MBJ
4h 35m
Direct

05/28/25

ORD
$534
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/27/25

ORD
6h 35m
CLT

05/27/25

MBJ
American Airlines Logo
American Airlines

05/31/25

MBJ
17h 36m
PHL

06/01/25

ORD
$534
Free cancellation within 83 hours of booking
Spirit Airlines Logo
Spirit Airlines

06/18/25

ORD
24h 16m
MCO
FLL

06/19/25

MBJ
Spirit Airlines Logo
Spirit Airlines

06/22/25

MBJ
20h 43m
FLL

06/23/25

ORD
$542
Free cancellation within 83 hours of booking
JetBlue Logo
JetBlue

06/13/25

ORD
9h 25m
JFK

06/13/25

MBJ
JetBlue Logo
JetBlue

06/16/25

MBJ
17h 9m
JFK

06/17/25

ORD
$545
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

06/04/25

ORD
6h 7m
ATL

06/04/25

MBJ
Delta Air Lines Logo
Delta Air Lines

06/18/25

MBJ
7h 7m
ATL

06/18/25

ORD
$550
Free cancellation within 83 hours of booking
Air Canada Logo
Air Canada

05/29/25

ORD
21h 15m
YYZ

05/30/25

MBJ
Air Canada Logo
Air Canada

06/07/25

MBJ
21h 47m
YYZ
YUL

06/08/25

ORD
$554
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

06/06/25

ORD
8h 25m
MIA

06/06/25

MBJ
American Airlines Logo
American Airlines

06/10/25

MBJ
16h
MIA

06/11/25

ORD
$557
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

05/24/25

ORD
15h 50m
IAH

05/25/25

MBJ
United Airlines Logo
United Airlines

05/29/25

MBJ
15h 50m
IAD

05/30/25

ORD
$559
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

05/29/25

ORD
15h 25m
EWR

05/30/25

MBJ
United Airlines Logo
United Airlines

06/16/25

MBJ
19h 47m
EWR

06/17/25

ORD
$568
Free cancellation within 83 hours of booking
Air Canada Logo
Air Canada

06/18/25

ORD
16h 55m
YOW
YYZ

06/19/25

MBJ
Air Canada Logo
Air Canada

06/22/25

MBJ
19h 54m
YYZ

06/23/25

ORD
$583
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/29/25

ORD
18h
DFW

05/30/25

MBJ
American Airlines Logo
American Airlines

06/02/25

MBJ
18h 19m
MIA

06/03/25

ORD
$589
Free cancellation within 83 hours of booking
Frontier Airlines Logo
Frontier Airlines

06/18/25

ORD
9h 42m
ATL

06/18/25

MBJ
Frontier Airlines Logo
Frontier Airlines

06/22/25

MBJ
15h 3m
ATL
DFW

06/23/25

ORD
$611
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

06/14/25

ORD
9h 26m
IAH

06/14/25

MBJ
United Airlines Logo
United Airlines

06/23/25

MBJ
29h 45m
EWR

06/24/25

ORD
$614
Free cancellation within 83 hours of booking
JetBlue Logo
JetBlue

06/18/25

ORD
9h 25m
JFK

06/18/25

MBJ
JetBlue Logo
JetBlue

06/22/25

MBJ
17h
BOS

06/23/25

ORD
$633
Free cancellation within 83 hours of booking
Air Canada Logo
Air Canada

06/18/25

ORD
16h 55m
YOW
YYZ

06/19/25

MBJ
Air Canada Logo
Air Canada

06/22/25

MBJ
19h 54m
YYZ
YUL

06/23/25

ORD
$634
Free cancellation within 83 hours of booking

Top Deals on flights from Chicago O Hare Airport to Montego Bay

Chicago, US (CHI) - Montego Bay, JM (MBJ)

Spirit Airlines Logo
Spirit Airlines

May 28

ORD
5h 57m
FLL

May 28

MBJ

as low as

$130

Chicago, US (CHI) - Montego Bay, JM (MBJ)

Spirit Airlines Logo
Spirit Airlines

May 25

ORD
18h 27m
MCO
FLL

May 26

MBJ

as low as

$162

Chicago, US (CHI) - Montego Bay, JM (MBJ)

Frontier Airlines Logo
Frontier Airlines

May 24

ORD
13h 54m
ATL

May 25

MBJ

as low as

$199

Chicago, US (CHI) - Montego Bay, JM (MBJ)

American Airlines Logo
American Airlines

May 25

ORD
6h 45m
MIA

May 25

MBJ

as low as

$200

Chicago, US (CHI) - Montego Bay, JM (MBJ)

American Airlines Logo
American Airlines

May 28

ORD
4h
Direct

May 28

MBJ

as low as

$226

Chicago, US (CHI) - Montego Bay, JM (MBJ)

COPA Airlines Logo
COPA Airlines

Jun 3

ORD
20h 8m
PTY

Jun 4

MBJ

as low as

$229

Chicago, US (CHI) - Montego Bay, JM (MBJ)

American Airlines Logo
American Airlines

May 18

ORD
9h 35m
DFW

May 18

MBJ

as low as

$230

Chicago, US (CHI) - Montego Bay, JM (MBJ)

JetBlue Logo
JetBlue

May 25

ORD
7h 13m
JFK

May 25

MBJ

as low as

$235

Chicago, US (CHI) - Montego Bay, JM (MBJ)

United Airlines Logo
United Airlines

May 25

ORD
4h 7m
Direct

May 25

MBJ

as low as

$236

Chicago, US (CHI) - Montego Bay, JM (MBJ)

American Airlines Logo
American Airlines

May 25

ORD
16h 19m
DCA
CLT

May 26

MBJ

as low as

$236

Chicago, US (CHI) - Montego Bay, JM (MBJ)

United Airlines Logo
United Airlines

May 25

ORD
6h 18m
IAD

May 25

MBJ

as low as

$240

Chicago, US (CHI) - Montego Bay, JM (MBJ)

United Airlines Logo
United Airlines

May 28

ORD
7h 10m
EWR

May 28

MBJ

as low as

$245

Frequently Asked Questions

What is the typical flight duration from Chicago O Hare Airport to Montego Bay?
The typical flight duration from Chicago O Hare Airport to Montego Bay ranges between 5 to 7 hours. This timeframe often includes one or more connecting flights, though non-stop segments may take around 4 hours if available. Weather conditions, layover durations, and different routing options may affect the total journey time. Travelers should confirm their itinerary details, as schedules can vary seasonally and by airline. This information helps in planning transit timings and ensuring a smoother transition from Chicago to the Jamaican destination.
Are there any direct flights from Chicago O Hare Airport to Montego Bay?
No, direct flights from Chicago O Hare Airport to Montego Bay are currently very limited. Most itineraries require at least one stopover in major transit hubs such as Miami or Atlanta, which extends the overall travel time. This means travelers should be prepared for a connection when scheduling their trips. It is advisable to check multiple airlines and booking platforms as routes can change seasonally, and occasionally a direct option might become available. Always review your travel plans carefully to avoid unexpected delays.
What are the best transportation options from Montego Bay airport to popular tourist attractions?
The best transportation options include prepaid taxis, ride-sharing services, rental cars, and hotel shuttles. Prepaid taxis usually cost between $15 to $30 depending on the distance to key attractions, while organized shuttle services may range from $20 to $40. For more flexibility, rental cars are available from around $40 to $70 per day. Private transfer services can also be arranged for added comfort and convenience. It’s beneficial to pre-arrange your transportation or compare rates in advance to ensure a smooth journey to popular tourist sites.
What are the must-see attractions in Montego Bay for travelers arriving from Chicago O Hare Airport?
Key attractions include the famous Doctor’s Cave Beach known for its clear, turquoise waters, and the historic Rose Hall Great House that offers fascinating cultural insights. The Hip Strip provides a vibrant mix of local shops, nightlife, and dining options, while local craft markets offer unique souvenirs. Beyond these, nature reserves and nearby excursions to waterfalls provide enriching outdoor experiences. This itinerary ensures that visitors get a well-rounded taste of local history, scenic beauty, and cultural richness soon after their arrival from Chicago O Hare Airport.
What are the top dining options in Montego Bay for visitors from Chicago O Hare Airport?
Montego Bay offers a diverse culinary scene ranging from traditional Jamaican cuisine to international dishes. Local favorites include Scotchies for authentic jerk chicken and pork, as well as the unique Houseboat Grill for a one-of-a-kind dining experience. Upscale options such as Sugar Mill offer a refined meal in a historic setting. Meals typically range from $15 to $50 per person, depending on the venue and menu. Visitors are encouraged to explore both beachfront spots and local eateries to savor the full spectrum of Jamaican flavors after arrival.
Is there a specific time of year when Montego Bay is best visited by travelers from Chicago O Hare Airport?
Yes, the dry season between December and April is considered ideal because of the mild weather and lower chances of rain. This period provides optimal conditions for beach outings and outdoor activities. For cost-conscious travelers, shoulder months like May and November also offer pleasant weather, albeit with slightly fewer facilities available. It is best to avoid the hurricane season, which runs from June to November, as weather disruptions can occur. Checking seasonal trends and booking in advance can ensure a more enjoyable travel experience.
What are the customs requirements for travelers flying from Chicago O Hare Airport to Montego Bay?
Travelers are required to present a valid passport with a minimum of six months’ validity beyond the intended stay. Most tourists do not need a visa for short visits, but it is important to check the current entry requirements well in advance. Upon arrival, you must complete customs declaration forms and may be asked to declare items that exceed duty-free limits. It is advisable to review current regulations from both airline services and government sources to stay updated on any changes, ensuring a smooth passage through customs.
What are the best family-friendly activities in Montego Bay for travelers arriving from Chicago O Hare Airport?
Families can enjoy a range of activities including beach outings, water sports, and adventure parks such as Mystic Mountain, which offers zip-lining and bobsled experiences. Interactive dolphin or wildlife encounters are also popular and engaging for kids. Additionally, scheduled cultural tours and nature trails provide educational insights into local Jamaican heritage and landscapes. Costs for these experiences generally range from $20 to $60 per person. Planning ahead and booking tickets online, when possible, ensures hassle-free participation in these family-friendly attractions.
Are there any local festivals in Montego Bay that travelers from Chicago O Hare Airport should not miss?
Yes, one notable festival is Reggae Sumfest, typically celebrated in July, which is a major event showcasing Jamaican music, dance, and culture. Additionally, local independence celebrations and seasonal cultural events offer opportunities for immersive experiences in local traditions. These festivals provide an engaging blend of entertainment and cultural expression, often accompanied by street food vendors and artisan stalls. Ticket prices vary from free events to cost ranges of $20 to $50 for major concerts. Check official schedules and event details prior to your visit for the best experience.
What are the best shopping areas in Montego Bay for travelers from Chicago O Hare Airport?
The Hip Strip is one of the top shopping areas, offering a blend of duty-free shops, boutiques, and local craft markets. Here visitors can find handmade jewelry, art, and traditional souvenirs with prices typically ranging from $5 to $50. In addition to the Hip Strip, local markets and specialized artisan centers provide a more authentic and budget-friendly shopping experience. It is recommended to compare items and negotiate prices in local markets. Overall, shoppers can enjoy a mix of modern and traditional retail options when exploring the area after their flight.
What health precautions should travelers from Chicago O Hare Airport take before visiting Montego Bay?
Travelers should ensure their routine immunizations are current, particularly for hepatitis A and typhoid, and consult with a travel health professional regarding recommended vaccinations. It is also wise to carry travel insurance that includes medical coverage. Given the tropical climate, using insect repellent and wearing breathable clothing help prevent mosquito-borne illnesses. Drinking bottled water and cautiously selecting street food are recommended for avoiding gastrointestinal issues. Preparing a basic first aid kit and understanding local health facilities can further ensure a safe and hassle-free travel experience.
What are the best car rental options in Montego Bay for travelers from Chicago O Hare Airport?
Montego Bay offers several reputable car rental services including international companies like Avis, Hertz, and Budget, as well as local agencies. Rates generally range from $40 to $80 per day, depending on vehicle type and rental terms. It is beneficial to compare rates and read reviews to ensure a good deal and quality service. Insurance coverage is essential, so clarify all terms before confirming a booking. A rental car provides the flexibility to explore various attractions at your own pace, making it an appealing option for travelers seeking convenience and freedom.
Are there any budget-friendly hotels in Montego Bay for visitors from Chicago O Hare Airport?
Yes, there are numerous budget-friendly accommodations ranging from modest guesthouses to small boutique hotels with prices typically between $50 to $100 per night. Many of these options offer basic amenities, secure lodging, and are conveniently located near popular attractions and dining areas. It is advisable to read guest reviews and check for special packages or deals that might include transportation or breakfast. Booking in advance can secure a better rate, ensuring that visitors have comfortable and affordable accommodations during their stay.
What unique cultural experiences can travelers from Chicago O Hare Airport enjoy in Montego Bay?
Travelers can participate in local craft workshops, attend reggae music sessions, and join culinary tours that highlight traditional Jamaican cuisine. Visiting heritage sites and engaging with local artisans offer deep cultural insights and memorable experiences. Interactive dance lessons or community festivals allow visitors to experience local traditions firsthand. Cultural tours are typically priced between $20 and $50 per person. This variety of authentic activities provides opportunities to understand and appreciate the vibrant local culture, making for a richer travel experience directly upon arrival.
What are the airport amenities in Montego Bay for travelers arriving from Chicago O Hare Airport?
Montego Bay airport features a range of modern amenities designed for convenience and comfort. Travelers can enjoy duty-free shopping, various dining options offering both local and international cuisines, and well-maintained lounges for relaxation. Additional services include ATM machines, currency exchange counters, and travel information kiosks to assist with onward transportation arrangements. High-speed Wi-Fi access and comfortable seating areas are also available. These amenities ensure that those arriving have a smooth transition into the attractions and experiences that await them in this vibrant destination.

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