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Flight Deals from Montego Bay to Chicago from $180

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Stops

  • Up to 1 stop
    $307

Airlines

  • Air Canada
    $531
  • American Airlines
    $494
  • COPA Airlines
    $529
  • Delta Air Lines
    $463
  • Frontier Airlines
    $440
  • JetBlue
    $447
  • Spirit Airlines
    $307
  • United Airlines
    $462

Cabin Class

  • Economy
    $307

Departure Airports

  • Sangster International Airport
    $307

Arrival Airports

  • Chicago Midway Airport
    $440
  • 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
    $490
  • 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

06/02/25

MBJ
15h 7m
ATL

06/03/25

ORD
Frontier Airlines Logo
Frontier Airlines

06/16/25

ORD
9h 42m
ATL

06/16/25

MBJ
$440
Free cancellation within 83 hours of booking
Frontier Airlines Logo
Frontier Airlines

05/31/25

MBJ
13h 22m
ATL

05/31/25

MDW
Frontier Airlines Logo
Frontier Airlines

06/14/25

MDW
8h 23m
ATL

06/14/25

MBJ
$440
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

05/29/25

MBJ
12h 21m
ATL

05/29/25

MDW
Frontier Airlines Logo
Frontier Airlines

06/12/25

MDW
17h 3m
ATL

06/13/25

MBJ
$450
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
Delta Air Lines Logo
Delta Air Lines

05/28/25

MBJ
8h 25m
ATL

05/28/25

MDW
Delta Air Lines Logo
Delta Air Lines

06/11/25

MDW
9h 25m
ATL

06/11/25

MBJ
$463
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
Frontier Airlines Logo
Frontier Airlines

06/20/25

MBJ
14h
ATL

06/20/25

MDW
Frontier Airlines Logo
Frontier Airlines

07/04/25

MDW
16h 9m
PHL

07/05/25

MBJ
$490
Free cancellation within 83 hours of booking
Frontier Airlines Logo
Frontier Airlines

06/13/25

MBJ
14h
ATL

06/13/25

MDW
Frontier Airlines Logo
Frontier Airlines

06/27/25

MDW
16h 12m
PHL

06/28/25

MBJ
$490
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

06/07/25

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
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
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

Top Deals on flights from Montego Bay to Chicago

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

Spirit Airlines Logo
Spirit Airlines

Jun 4

MBJ
10h 57m
FLL

Jun 4

ORD

as low as

$180

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)

United Airlines Logo
United Airlines

May 28

MBJ
15h 50m
IAD

May 29

ORD

as low as

$247

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

Frontier Airlines Logo
Frontier Airlines

Jun 4

MBJ
7h 28m
ATL

Jun 4

MDW

as low as

$250

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
8h 11m
MIA

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)

 Logo

Jul 2

MBJ
4h 10m
Direct

Jul 2

MDW

as low as

$262

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

 Logo

Jul 2

MBJ
11h
MCO

Jul 2

MDW

as low as

$272

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

COPA Airlines Logo
COPA Airlines

Aug 18

MBJ
12h 8m
PTY

Aug 19

ORD

as low as

$287

Frequently Asked Questions

What is the typical flight duration from Montego Bay to Chicago?
The typical flight duration from Montego Bay (MBJ) to Chicago (CHI) usually ranges between 4 to 6 hours for non-stop flights. When opting for connecting flights, durations can extend from 7 to 9 hours depending on layover times and routing. Factors such as weather or air traffic may impact the total travel time. It is advisable to check updated flight schedules well in advance and allow extra time for airport procedures, ensuring a smooth transition from departure to arrival.
Are there any direct flights from Montego Bay to Chicago?
Yes, there are direct flights available from Montego Bay to Chicago, though availability may vary based on season and airline schedules. Direct services can significantly reduce travel time by eliminating layovers. It is wise to monitor flight listings as some airlines might only offer a limited number of non-stop options. Checking with your preferred carrier or travel agency prior to booking can help confirm current schedules and ensure that you secure the most convenient option for your travel dates.
What are the best transportation options from Chicago airport to downtown?
When arriving in Chicago, travelers have several reliable transportation options. Taxis and rideshare services like Uber or Lyft provide direct, hassle-free rides with fares typically ranging from $25 to $45, depending on traffic and distance. Alternatively, the CTA Blue Line offers a budget-friendly option at about $5 per ride, connecting the airport to downtown in around 30 to 45 minutes. Additionally, airport shuttles and rental car services provide further flexibility based on your itinerary and luggage requirements.
What are the must-see attractions in Chicago for travelers arriving from Montego Bay?
Visitors should not miss iconic landmarks such as Millennium Park, the Art Institute, and Willis Tower when exploring Chicago. Other attractions include Navy Pier, offering boat tours, and diverse cultural neighborhoods that highlight local art and music. These spots provide a deeper understanding of the city’s vibrant history and modern charm. Planning your itinerary to include both historical sites and contemporary attractions ensures a balanced exploration. Detailed maps and guided tours can add extra value to your visit, making every moment memorable.
Which local dishes should travelers from Montego Bay try when visiting Chicago?
Chicago is renowned for its distinctive culinary offerings. Travelers should try local specialties such as the city's famous deep-dish pizza, authentic Chicago-style hot dogs, and Italian beef sandwiches. Many local diners and neighborhood eateries serve these iconic dishes with a unique twist that reflects the city’s diverse food culture. Besides these, explore ethnic neighborhoods for global cuisines and modern fusion flavors. Sampling these dishes not only provides a taste of Chicago’s gastronomic traditions but also highlights the city’s dynamic blend of culinary influences.
What are the best family-friendly activities in Chicago for visitors from Montego Bay?
Chicago is packed with family-friendly activities that cater to all ages. Popular spots include attractions like the Shedd Aquarium, the Field Museum, and Lincoln Park Zoo, where interactive exhibits and educational tours engage both children and adults. Outdoor activities in parks and lakefront areas are ideal for leisure days. Many venues offer family passes or discounts during off-peak times. Planning a day with a mix of indoor and outdoor attractions ensures that families can enjoy a balanced, enriching experience while exploring the city’s vibrant culture and scientific achievements.
Are there any seasonal events in Chicago that travelers from Montego Bay should not miss?
Yes, Chicago hosts a range of vibrant seasonal events that showcase its cultural diversity. In the summer, events like the Taste of Chicago and various outdoor music festivals highlight local food and performances. In winter, festive markets, ice-skating rinks, and holiday events create a magical atmosphere. Spring and fall bring art fairs, neighborhood festivals, and food events that offer a glimpse into local traditions. It is recommended to review local event calendars before your visit to plan your itinerary around these culturally rich and entertaining festivities.
What are the most affordable dining options in Chicago for travelers from Montego Bay?
Budget-conscious travelers can enjoy a wide variety of affordable dining choices in Chicago. Local diners, food trucks, and casual ethnic restaurants offer diverse menus at prices typically ranging between $10 and $20 per meal. Neighborhoods such as Wicker Park and parts of the Near West Side feature unique and reasonably priced eateries where you can savor local specialties like hot dogs, deep-dish pizza, and Italian beef sandwiches. Exploring food markets and pop-up culinary events can also provide delicious and economical dining experiences, ensuring you enjoy both quality and flavor without overspending.
What are the customs requirements for travelers flying from Montego Bay to Chicago?
Travelers arriving in Chicago from Montego Bay should ensure they have all necessary documentation in order prior to departure. Essential requirements include a valid passport and, if applicable, a visa or ESTA approval. US Customs and Border Protection mandates that you complete an entry declaration form upon arrival and be ready to answer questions regarding your visit. Carry proof of onward travel and accommodation details as additional evidence of your itinerary. It is important to stay updated on evolving guidelines by consulting official US and travel advisory websites before embarking on your journey.
Is there a specific time of year when Chicago is best visited by travelers from Montego Bay?
Yes, the period from late spring to early fall, typically May through September, is often regarded as the best time to visit Chicago. During these months, the weather is mild and conducive to outdoor activities, and the city hosts multiple festivals and cultural events. Additionally, longer daylight hours allow for extended sightseeing and the enjoyment of vibrant outdoor spaces. However, depending on what you want to experience, winter also offers unique attractions, albeit with colder weather. Always check seasonal forecasts and event schedules as you plan your visit.
What are the best shopping areas in Chicago for souvenirs for travelers from Montego Bay?
Chicago boasts several shopping districts perfect for finding unique souvenirs. The Magnificent Mile offers a blend of upscale shops and local boutiques, while neighborhoods such as Wicker Park and the West Loop present quirky, artisanal stores with locally crafted items. Look for Chicago-themed memorabilia, vintage pieces, or original artwork that reflect the cultural diversity of the city. Prices in these areas generally range from $10 to $100, catering to a variety of budgets. Exploring these areas on foot can also give you a richer insight into the city’s vibrant local culture.
What health precautions should travelers from Montego Bay take when visiting Chicago?
Travelers should take several practical health precautions when planning their visit. Ensure that all routine vaccinations are up-to-date, especially the flu shot, since seasonal weather variations can affect health. It is also smart to carry any personal medications and a basic first-aid kit. Consider travel insurance that covers health emergencies and check for any updated advisories or COVID-19 guidelines. Additionally, be prepared for Chicago’s sometimes unpredictable weather by packing appropriate clothing. Consulting with a healthcare provider prior to travel can help tailor these recommendations to your specific needs.
What unique cultural experiences can travelers from Montego Bay enjoy in Chicago?
Chicago offers a wealth of unique cultural experiences that extend beyond typical sightseeing. Visit neighborhoods rich in history and diverse culinary traditions or attend live music performances in renowned jazz and blues clubs. Art enthusiasts can explore world-class museums and contemporary galleries that showcase innovative works alongside classic masterpieces. Additionally, local theater productions, street festivals, and community markets highlight the city’s dynamic cultural fabric. These immersive experiences not only provide insight into Chicago’s artistic spirit but also create memorable interactions with local residents and traditions.
What are the best car rental options in Chicago for travelers from Montego Bay?
Chicago features a variety of reputable car rental companies such as Enterprise, Hertz, and Budget, offering extensive fleets to suit diverse travel needs. Daily rental rates typically range from $40 to $100 depending on vehicle type and rental duration, with compact cars being on the lower end and SUVs on the higher end. Booking in advance can secure the best rates and may include supplemental extras like insurance or additional driver options. It is recommended to compare deals online and read reviews to select a service that meets your specific travel itinerary and parking requirements.
Are there any special airport amenities in Chicago for travelers arriving from Montego Bay?
Yes, Chicago’s airports cater well to international travelers with a range of special amenities. Facilities include expedited customs lanes, comfortable lounges, and clearly marked information desks. Complimentary WiFi, charging stations, and quality dining and shopping options enhance your transit experience. Additionally, services like baggage assistance and concierge support help streamline the arrival process. Checking an airport guide upon arrival can help you navigate available amenities efficiently, ensuring that your transition from international travel is both pleasant and stress-free.

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