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Flight Deals from Montego Bay to Chicago O Hare Airport from $180

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Stops

  • Nonstop
    from $547
  • Up to 1 stop
    $307

Airlines

  • Air Canada
    $531
  • American Airlines
    $494
  • COPA Airlines
    $529
  • Delta Air Lines
    $470
  • Frontier Airlines
    $440
  • JetBlue
    $447
  • Spirit Airlines
    $307
  • United Airlines
    $462

Cabin Class

  • Economy
    $307

Departure Airports

  • Sangster International Airport
    $307

Arrival Airports

  • Chicago O Hare Airport
    $307

Layover Airports

  • Charlotte Douglas International Airport
    $498
  • Fort Lauderdale Hollywood International Airport
    $307
  • General Edward Lawrence Logan International Airport
    $447
  • George Bush Intercontinental Houston Airport
    $499
  • Hartsfield Jackson Atlanta International Airport
    $440
  • Miami International Airport
    $521
  • New York John F Kennedy Airport
    $447
  • Newark Liberty Airport
    $479
  • Philadelphia International Airport
    $580
  • Tocumen International Airport
    $529
  • Toronto Pearson Airport
    $531
  • Washington Dulles Airport
    $462

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Spirit Airlines Logo
Spirit Airlines

06/24/25

MBJ
11h 38m
FLL

06/24/25

ORD
Spirit Airlines Logo
Spirit Airlines

07/08/25

ORD
16h 29m
FLL

07/09/25

MBJ
$307
Free cancellation within 83 hours of booking
Spirit Airlines Logo
Spirit Airlines

06/07/25

MBJ
11h 58m
FLL

06/08/25

ORD
Spirit Airlines Logo
Spirit Airlines

06/21/25

ORD
5h 57m
FLL

06/21/25

MBJ
$332
Free cancellation within 83 hours of booking
Spirit Airlines Logo
Spirit Airlines

06/02/25

MBJ
11h 58m
FLL

06/03/25

ORD
Spirit Airlines Logo
Spirit Airlines

06/16/25

ORD
5h 57m
FLL

06/16/25

MBJ
$392
Free cancellation within 83 hours of booking
Frontier Airlines Logo
Frontier Airlines

06/07/25

MBJ
14h 57m
ATL

06/08/25

ORD
Frontier Airlines Logo
Frontier Airlines

06/21/25

ORD
13h 42m
ATL

06/22/25

MBJ
$440
Free cancellation within 83 hours of booking
JetBlue Logo
JetBlue

06/17/25

MBJ
12h 46m
JFK

06/17/25

ORD
JetBlue Logo
JetBlue

07/01/25

ORD
29h 8m
BOS

07/02/25

MBJ
$447
Free cancellation within 83 hours of booking
Frontier Airlines Logo
Frontier Airlines

06/01/25

MBJ
14h 42m
ATL

06/02/25

ORD
Frontier Airlines Logo
Frontier Airlines

06/15/25

ORD
26h 57m
ATL

06/16/25

MBJ
$459
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

06/19/25

MBJ
7h 18m
IAD

06/19/25

ORD
United Airlines Logo
United Airlines

07/03/25

ORD
21h 14m
IAD

07/04/25

MBJ
$462
Free cancellation within 83 hours of booking
Frontier Airlines Logo
Frontier Airlines

06/12/25

MBJ
14h 56m
ATL

06/13/25

ORD
Frontier Airlines Logo
Frontier Airlines

06/26/25

ORD
13h 42m
ATL

06/27/25

MBJ
$470
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

06/12/25

MBJ
7h 8m
ATL

06/12/25

ORD
Delta Air Lines Logo
Delta Air Lines

06/26/25

ORD
6h 9m
ATL

06/26/25

MBJ
$470
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

06/24/25

MBJ
9h 20m
EWR

06/24/25

ORD
United Airlines Logo
United Airlines

07/08/25

ORD
6h 18m
IAD

07/08/25

MBJ
$479
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

06/17/25

MBJ
7h 18m
IAD

06/17/25

ORD
United Airlines Logo
United Airlines

07/01/25

ORD
6h 18m
IAD

07/01/25

MBJ
$479
Free cancellation within 83 hours of booking
JetBlue Logo
JetBlue

06/24/25

MBJ
12h 46m
JFK

06/24/25

ORD
JetBlue Logo
JetBlue

07/08/25

ORD
9h 6m
JFK

07/08/25

MBJ
$481
Free cancellation within 83 hours of booking
JetBlue Logo
JetBlue

06/07/25

MBJ
11h 12m
JFK

06/07/25

ORD
JetBlue Logo
JetBlue

06/21/25

ORD
9h 25m
JFK

06/21/25

MBJ
$481
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

06/17/25

MBJ
21h 42m
JFK

06/18/25

ORD
American Airlines Logo
American Airlines

07/01/25

ORD
3h 58m
Direct

07/01/25

MBJ
$494
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

06/07/25

MBJ
7h 17m
ATL

06/07/25

ORD
Delta Air Lines Logo
Delta Air Lines

06/21/25

ORD
6h 9m
ATL

06/21/25

MBJ
$495
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

06/17/25

MBJ
21h 42m
JFK

06/18/25

ORD
American Airlines Logo
American Airlines

07/01/25

ORD
6h 51m
CLT

07/01/25

MBJ
$498
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

06/21/25

MBJ
9h 41m
IAH

06/22/25

ORD
United Airlines Logo
United Airlines

07/05/25

ORD
4h 7m
Direct

07/05/25

MBJ
$499
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

06/07/25

MBJ
15h 44m
EWR

06/08/25

ORD
United Airlines Logo
United Airlines

06/21/25

ORD
4h 7m
Direct

06/21/25

MBJ
$499
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

06/07/25

MBJ
15h 44m
EWR

06/08/25

ORD
United Airlines Logo
United Airlines

06/21/25

ORD
17h
IAH

06/22/25

MBJ
$504
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

06/21/25

MBJ
9h 41m
IAH

06/22/25

ORD
United Airlines Logo
United Airlines

07/05/25

ORD
16h 30m
IAH

07/06/25

MBJ
$504
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

06/02/25

MBJ
9h 54m
MIA

06/02/25

ORD
American Airlines Logo
American Airlines

06/16/25

ORD
12h 30m
CLT

06/17/25

MBJ
$521
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

06/07/25

MBJ
8h 54m
CLT

06/07/25

ORD
American Airlines Logo
American Airlines

06/21/25

ORD
12h 30m
CLT

06/22/25

MBJ
$521
Free cancellation within 83 hours of booking
COPA Airlines Logo
COPA Airlines

06/09/25

MBJ
25h 33m
PTY

06/10/25

ORD
COPA Airlines Logo
COPA Airlines

06/23/25

ORD
20h 8m
PTY

06/24/25

MBJ
$529
Free cancellation within 83 hours of booking
Air Canada Logo
Air Canada

06/16/25

MBJ
24h 50m
YYZ

06/17/25

ORD
Air Canada Logo
Air Canada

06/30/25

ORD
14h 50m
YYZ

07/01/25

MBJ
$531
Free cancellation within 83 hours of booking
Air Canada Logo
Air Canada

06/01/25

MBJ
19h 54m
YYZ

06/02/25

ORD
Air Canada Logo
Air Canada

06/15/25

ORD
14h 45m
YYZ

06/16/25

MBJ
$536
Free cancellation within 83 hours of booking
Air Canada Logo
Air Canada

06/19/25

MBJ
24h 49m
YYZ

06/20/25

ORD
Air Canada Logo
Air Canada

06/22/25

ORD
14h 45m
YYZ

06/23/25

MBJ
$536
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

06/21/25

MBJ
4h 29m
Direct

06/21/25

ORD
United Airlines Logo
United Airlines

07/05/25

ORD
4h 7m
Direct

07/05/25

MBJ
$547
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

06/12/25

MBJ
4h 37m
Direct

06/12/25

ORD
American Airlines Logo
American Airlines

06/26/25

ORD
18h 30m
MIA

06/27/25

MBJ
$549
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

06/19/25

MBJ
4h 37m
Direct

06/19/25

ORD
American Airlines Logo
American Airlines

07/03/25

ORD
16h 43m
MIA

07/04/25

MBJ
$558
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

06/09/25

MBJ
18h 20m
PHL

06/10/25

ORD
American Airlines Logo
American Airlines

06/23/25

ORD
12h 30m
CLT

06/24/25

MBJ
$580
Free cancellation within 83 hours of booking

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

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

Spirit Airlines Logo
Spirit Airlines

May 28

MBJ
10h 57m
FLL

May 28

ORD

as low as

$180

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

United Airlines Logo
United Airlines

May 28

MBJ
7h 18m
IAD

May 28

ORD

as low as

$247

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

American Airlines Logo
American Airlines

Aug 28

MBJ
4h 30m
Direct

Aug 28

ORD

as low as

$247

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

Frontier Airlines Logo
Frontier Airlines

May 15

MBJ
9h 10m
ATL

May 15

ORD

as low as

$250

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

United Airlines Logo
United Airlines

May 7

MBJ
8h 18m
IAH

May 7

ORD

as low as

$251

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

United Airlines Logo
United Airlines

Aug 28

MBJ
9h 8m
EWR

Aug 28

ORD

as low as

$253

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

American Airlines Logo
American Airlines

Aug 28

MBJ
7h 58m
PHL

Aug 28

ORD

as low as

$257

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

Delta Air Lines Logo
Delta Air Lines

Jul 31

MBJ
7h 10m
ATL

Aug 1

ORD

as low as

$258

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

American Airlines Logo
American Airlines

Jul 2

MBJ
10h 47m
MIA

Jul 2

ORD

as low as

$258

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

COPA Airlines Logo
COPA Airlines

May 31

MBJ
25h 33m
PTY

Jun 1

ORD

as low as

$287

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

American Airlines Logo
American Airlines

Aug 20

MBJ
6h 39m
CLT

Aug 20

ORD

as low as

$288

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

JetBlue Logo
JetBlue

Aug 11

MBJ
17h
BOS

Aug 12

ORD

as low as

$291

Frequently Asked Questions

What is the typical flight duration from Montego Bay to Chicago O Hare Airport?
The typical flight duration from Montego Bay to Chicago O Hare Airport generally ranges between 4 to 6 hours, depending on wind conditions and the specific route chosen. Direct flights tend to be on the shorter end of the range, while connecting flights may extend your total travel time. It’s wise to factor in potential delays and layovers when planning your schedule. This estimated range should help you coordinate your itinerary and plan ground transportation upon arrival, ensuring a smooth transition from Montego Bay to your Chicago destination.
Are there any direct flights from Montego Bay to Chicago O Hare Airport?
Yes, direct flights are sometimes available between Montego Bay and Chicago O Hare Airport, although the frequency can vary based on seasonal demand and airline scheduling. Travelers should verify current flight timetables as some routes are seasonal or operated on specific days of the week. A direct flight can significantly reduce travel time and minimize layovers, enhancing overall comfort. Checking with your preferred carrier in advance and booking early can increase your chance of securing a direct option for a smoother and more efficient journey.
What are the best transportation options from Chicago O Hare Airport to downtown Chicago?
After arriving at Chicago O Hare Airport, travelers have several efficient transportation options to downtown Chicago. The Blue Line CTA train offers a cost-effective and reliable method with fares typically ranging from $5 to $10, and the trip takes around 45 minutes. Additionally, taxis and ride-sharing services are readily available with prices generally between $30 to $50, depending on traffic. Airport shuttles provide door-to-door service with rates between $20 to $40 per person. Consider your budget, schedule, and comfort when choosing the best option for a smooth transit to the city center.
What are the must-see attractions in Chicago for travelers arriving from Montego Bay?
Travelers arriving from Montego Bay should not miss several iconic Chicago attractions. Highlights include visiting the Willis Tower Skydeck for panoramic views, exploring Millennium Park with its famed Cloud Gate sculpture, and enjoying the vibrant atmosphere at Navy Pier. The Art Institute of Chicago is another must-see destination for art enthusiasts. Additionally, strolling through historic neighborhoods offers a taste of local culture. Planning your itinerary around these attractions will provide a comprehensive and enriching experience of Chicago’s diverse and dynamic urban landscape.
Which local dishes should travelers from Montego Bay try when visiting Chicago?
Visitors from Montego Bay should be sure to indulge in Chicago’s renowned culinary offerings. Iconic dishes include deep-dish pizza and Chicago-style hot dogs, available at celebrated local eateries. Additionally, Italian beef sandwiches and a variety of locally crafted desserts offer a taste of the city’s diverse food scene. Exploring neighborhood restaurants and food festivals will let you experience authentic flavors and unique regional twists. Sampling these dishes provides not only a delicious culinary adventure but also an opportunity to immerse yourself in the rich culture and history of Chicago’s dining traditions.
Are there any family-friendly activities in Chicago for visitors from Montego Bay?
Yes, Chicago is filled with family-friendly activities that cater to visitors from Montego Bay. Interactive experiences at museums such as the Field Museum and the Museum of Science and Industry are perfect for engaging children and adults alike. Outdoor attractions like Millennium Park and Lincoln Park Zoo offer relaxed environments for picnics and educational fun. Many events throughout the year are designed with families in mind, ensuring safe and inclusive entertainment. It is recommended to plan your itinerary ahead to maximize both indoor and outdoor activities for a well-rounded family getaway.
What are the best budget-friendly hotels in Chicago for travelers from Montego Bay?
Budget-conscious visitors from Montego Bay will find several comfortable yet affordable hotel options in Chicago. Chains like Best Western and Holiday Inn Express, along with local boutique hotels, typically offer nightly rates ranging from $80 to $150. These accommodations are often conveniently located near public transportation and main attractions, such as Millennium Park or the Magnificent Mile. Booking in advance and checking travel deal websites can secure even better rates. Reading recent reviews also helps to ensure that your stay is both pleasant and financially accessible during your Chicago adventure.
What cultural etiquette should travelers from Montego Bay be aware of when visiting Chicago?
Travelers from Montego Bay visiting Chicago should note that cultural etiquette emphasizes respect for personal space and local customs. In public areas, moderate volume in conversations is appreciated, and tipping is customary—usually 15% to 20% in restaurants and for taxi services. When visiting cultural landmarks or upscale neighborhoods, dressing appropriately can show respect. Embracing the city’s multicultural environment by being considerate and open-minded will enrich interactions with locals. Familiarizing yourself with these etiquette guidelines will help ensure a courteous and enjoyable stay in Chicago.
What are the top shopping districts in Chicago for souvenirs for travelers from Montego Bay?
Chicago offers a variety of shopping districts perfect for finding unique souvenirs. The Magnificent Mile is renowned for its mix of high-end retailers and accessible boutiques, while neighborhoods like Wicker Park and Bucktown feature artisan shops and vintage finds reflective of local creativity. Additionally, downtown markets and seasonal pop-up events often showcase handmade crafts and culturally diverse items. These areas provide ample choices to suit varying budgets and tastes. Exploring these vibrant shopping districts is an excellent way to bring a piece of Chicago’s local culture back home with you from your trip.
Is there a specific time of year when Chicago is best visited by travelers from Montego Bay?
Yes, the ideal times to visit Chicago for travelers from Montego Bay are during the spring and early fall. Specifically, the periods between April to June and September to October offer mild temperatures, reduced tourist crowds, and a host of outdoor events. These seasons provide comfortable weather for exploring local landmarks and enjoying festivals without the extremes found in winter or the busyness of summer. Timing your visit during these months can enhance your sightseeing opportunities and overall experience by balancing pleasant weather with vibrant local activity.
What are the health and safety tips for travelers from Montego Bay visiting Chicago?
Travelers from Montego Bay should adopt standard health and safety measures when exploring Chicago. Always secure personal belongings, especially in crowded public spaces like transit hubs and popular attractions. Utilize trusted transportation options and remain aware of your surroundings during nighttime travel. Acquiring travel insurance is a prudent step in case medical or emergency situations arise. Additionally, keeping a list of local emergency contacts and staying updated on weather forecasts can enhance your preparedness. These proactive measures will help ensure a secure and enjoyable visit to Chicago.
Are there any seasonal events in Chicago that travelers from Montego Bay should not miss?
Yes, Chicago hosts a range of seasonal events that are highly recommended for visitors from Montego Bay. In the summer, the Chicago Air and Water Show and various outdoor food festivals create a vibrant atmosphere along the lakefront. The fall season brings cultural celebrations and art fairs, and winter features festive markets and ice skating events in prominent parks. Each season provides unique experiences that highlight Chicago’s dynamic social and cultural scene. Checking the event calendar before your trip can help you plan to attend these special events and enrich your overall visit.
What unique airport amenities are available at Chicago O Hare Airport for travelers arriving from Montego Bay?
Chicago O Hare Airport provides an array of unique amenities to enhance the experience of travelers arriving from Montego Bay. The airport features diverse dining options ranging from quick bites to full-service meals, typically costing between $10 and $30. Comfortable airport lounges offer relaxing spaces for both work and leisure, complemented by free Wi-Fi and numerous charging stations. Travelers can also enjoy local art installations and a variety of retail shops. These well-thought-out amenities promote a stress-free transition from flight to ground transport and add a cultural touch reflective of the city’s vibrant character.
What are the best seating options for families traveling from Montego Bay to Chicago?
Families traveling from Montego Bay to Chicago should consider selecting airline seating options that prioritize comfort and convenience. Many carriers offer family-preferred seating arrangements such as adjoining seats, bulkhead rows, or seats with extra legroom, typically available when booking in advance. Some airlines even provide child-friendly features like seat belt extenders or bassinets on certain flights. Requesting these options ahead of time can ensure that everyone travels comfortably and stays together during the flight. This proactive approach helps make the journey less stressful and more enjoyable for the entire family.
What are the customs requirements for travelers flying from Montego Bay to Chicago?
Travelers flying from Montego Bay to Chicago must adhere to U.S. customs regulations. Essential documents include a valid passport, and depending on your nationality, you may need a visa or an approved ESTA. It’s crucial to declare items subject to duty and be aware of limits on food, alcohol, and currency. Reviewing the latest U.S. Customs and Border Protection guidelines prior to departure is recommended. Following these protocols ensures a smooth and efficient process at Chicago O Hare Airport, helping you avoid any unnecessary delays during your entry into the United States.

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