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Flight Deals from Montreal to Chicago from $151

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Stops

  • Nonstop
    from $251
  • Up to 1 stop
    $256
  • Up to 2 stops
    $311

Airlines

  • Air Canada
    $251
  • American Airlines
    $278
  • Delta Air Lines
    $276
  • Porter Airlines
    $261
  • United Airlines
    $251
  • WestJet
    $351

Cabin Class

  • Economy
    $251

Departure Airports

  • Montreal Trudeau Airport
    $251

Arrival Airports

  • Chicago Midway Airport
    $261
  • Chicago O Hare Airport
    $251

Layover Airports

  • Calgary International Airport
    $357
  • Charlotte Douglas International Airport
    $278
  • Detroit Metropolitan Airport
    $276
  • Hartsfield Jackson Atlanta International Airport
    $351
  • Minneapolis-St Paul International/Wold-Chamberlain Airport
    $351
  • New York LaGuardia Airport
    $261
  • Ottawa Macdonald-Cartier International Airport
    $256
  • Philadelphia International Airport
    $316
  • Reagan Washington National Airport
    $266
  • Salt Lake City International Airport
    $357
  • Toronto Island Airport
    $261
  • Toronto Pearson Airport
    $263
  • Washington Dulles Airport
    $266

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On average save $240 per traveler
Air Canada Logo
Air Canada

05/27/25

YUL
1h 32m
Direct

05/27/25

ORD
Air Canada Logo
Air Canada

06/04/25

ORD
3h 21m
Direct

06/04/25

YUL
$251
Free cancellation within 83 hours of booking
Air Canada Logo
Air Canada

05/24/25

YUL
1h 32m
Direct

05/24/25

ORD
Air Canada Logo
Air Canada

05/29/25

ORD
3h 19m
Direct

05/29/25

YUL
$251
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

06/06/25

YUL
1h 32m
Direct

06/06/25

ORD
United Airlines Logo
United Airlines

06/07/25

ORD
3h 31m
Direct

06/07/25

YUL
$251
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

06/01/25

YUL
1h 32m
Direct

06/01/25

ORD
United Airlines Logo
United Airlines

06/15/25

ORD
3h 21m
Direct

06/15/25

YUL
$251
Free cancellation within 83 hours of booking
Air Canada Logo
Air Canada

05/23/25

YUL
1h 32m
Direct

05/23/25

ORD
Air Canada Logo
Air Canada

05/31/25

ORD
7h 25m
YOW

05/31/25

YUL
$256
Free cancellation within 83 hours of booking
Air Canada Logo
Air Canada

05/27/25

YUL
5h 53m
YOW

05/27/25

ORD
Air Canada Logo
Air Canada

06/04/25

ORD
3h 21m
Direct

06/04/25

YUL
$256
Free cancellation within 83 hours of booking
Porter Airlines Logo
Porter Airlines

05/29/25

YUL
5h 39m
YTZ

05/29/25

MDW
Porter Airlines Logo
Porter Airlines

06/02/25

MDW
6h 20m
YTZ

06/02/25

YUL
$261
Free cancellation within 83 hours of booking
Air Canada Logo
Air Canada

06/06/25

YUL
1h 44m
Direct

06/06/25

ORD
Air Canada Logo
Air Canada

06/20/25

ORD
5h 44m
LGA

06/20/25

YUL
$261
Free cancellation within 83 hours of booking
Porter Airlines Logo
Porter Airlines

05/21/25

YUL
6h 9m
YTZ

05/21/25

MDW
Porter Airlines Logo
Porter Airlines

05/25/25

MDW
6h 20m
YTZ

05/25/25

YUL
$261
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

06/06/25

YUL
1h 32m
Direct

06/06/25

ORD
United Airlines Logo
United Airlines

06/20/25

ORD
6h 44m
LGA

06/20/25

YUL
$261
Free cancellation within 83 hours of booking
Air Canada Logo
Air Canada

06/04/25

YUL
1h 32m
Direct

06/04/25

ORD
Air Canada Logo
Air Canada

06/09/25

ORD
5h 26m
YYZ

06/10/25

YUL
$263
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

05/23/25

YUL
1h 44m
Direct

05/23/25

ORD
United Airlines Logo
United Airlines

06/06/25

ORD
5h 26m
YYZ

06/07/25

YUL
$263
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

05/24/25

YUL
6h 27m
DCA

05/24/25

ORD
United Airlines Logo
United Airlines

06/07/25

ORD
3h 31m
Direct

06/07/25

YUL
$266
Free cancellation within 83 hours of booking
Air Canada Logo
Air Canada

05/27/25

YUL
5h 53m
YOW

05/27/25

ORD
Air Canada Logo
Air Canada

06/04/25

ORD
6h 57m
IAD

06/04/25

YUL
$266
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

05/25/25

YUL
6h 25m
DCA

05/25/25

ORD
United Airlines Logo
United Airlines

06/08/25

ORD
3h 19m
Direct

06/08/25

YUL
$266
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

05/23/25

YUL
3h 16m
DTW

05/23/25

ORD
Delta Air Lines Logo
Delta Air Lines

06/06/25

ORD
7h 15m
DTW

06/06/25

YUL
$276
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/23/25

YUL
1h 35m
Direct

05/23/25

ORD
American Airlines Logo
American Airlines

06/06/25

ORD
6h 39m
CLT

06/06/25

YUL
$278
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

05/24/25

YUL
6h 27m
DCA

05/24/25

ORD
United Airlines Logo
United Airlines

06/07/25

ORD
6h 57m
IAD

06/07/25

YUL
$292
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/25/25

YUL
1h 35m
Direct

05/25/25

ORD
American Airlines Logo
American Airlines

06/08/25

ORD
3h 20m
Direct

06/08/25

YUL
$300
Free cancellation within 83 hours of booking
Air Canada Logo
Air Canada

06/14/25

YUL
9h 9m
YOW
YYZ

06/14/25

ORD
Air Canada Logo
Air Canada

06/16/25

ORD
5h 26m
YYZ

06/17/25

YUL
$311
Free cancellation within 83 hours of booking
Air Canada Logo
Air Canada

06/03/25

YUL
5h 25m
YOW
YYZ

06/03/25

ORD
Air Canada Logo
Air Canada

06/15/25

ORD
7h 21m
YYZ

06/15/25

YUL
$311
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/25/25

YUL
6h 5m
PHL

05/25/25

ORD
American Airlines Logo
American Airlines

06/08/25

ORD
3h 20m
Direct

06/08/25

YUL
$316
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/23/25

YUL
6h 5m
PHL

05/23/25

ORD
American Airlines Logo
American Airlines

06/06/25

ORD
6h 39m
CLT

06/06/25

YUL
$322
Free cancellation within 83 hours of booking
WestJet Logo
WestJet

06/10/25

YUL
10h 40m
LGA

06/10/25

ORD
WestJet Logo
WestJet

06/14/25

ORD
12h 34m
ATL

06/14/25

YUL
$351
Free cancellation within 83 hours of booking
WestJet Logo
WestJet

05/28/25

YUL
14h 20m
ATL

05/28/25

ORD
WestJet Logo
WestJet

06/01/25

ORD
12h 16m
MSP

06/01/25

YUL
$351
Free cancellation within 83 hours of booking
WestJet Logo
WestJet

05/30/25

YUL
11h 30m
MSP

05/30/25

MDW
WestJet Logo
WestJet

06/03/25

MDW
22h 51m
ATL

06/04/25

YUL
$351
Free cancellation within 83 hours of booking
WestJet Logo
WestJet

06/13/25

YUL
15h 9m
YYC
SLC

06/13/25

ORD
WestJet Logo
WestJet

06/19/25

ORD
14h 13m
DTW

06/19/25

YUL
$357
Free cancellation within 83 hours of booking
WestJet Logo
WestJet

05/31/25

YUL
11h 37m
MSP

05/31/25

MDW
WestJet Logo
WestJet

06/06/25

MDW
15h 23m
MSP
YYC

06/07/25

YUL
$357
Free cancellation within 83 hours of booking
WestJet Logo
WestJet

06/13/25

YUL
15h 9m
YYC
SLC

06/13/25

ORD
WestJet Logo
WestJet

06/19/25

ORD
10h 52m
ATL
YYZ

06/20/25

YUL
$368
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

05/17/25

YUL
5h 20m
ATL

05/17/25

ORD
Delta Air Lines Logo
Delta Air Lines

05/31/25

ORD
5h 34m
LGA

05/31/25

YUL
$391
Free cancellation within 83 hours of booking

Top Deals on flights from Montreal to Chicago

Montreal, CA (YMQ) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 24

YUL
1h 35m
Direct

May 24

ORD

as low as

$151

Montreal, CA (YMQ) - Chicago, US (CHI)

United Airlines Logo
United Airlines

May 30

YUL
1h 44m
Direct

May 30

ORD

as low as

$151

Montreal, CA (YMQ) - Chicago, US (CHI)

Delta Air Lines Logo
Delta Air Lines

Jun 3

YUL
8h 43m
ATL

Jun 3

MDW

as low as

$163

Montreal, CA (YMQ) - Chicago, US (CHI)

Delta Air Lines Logo
Delta Air Lines

Jun 12

YUL
2h 41m
DTW

Jun 12

MDW

as low as

$163

Montreal, CA (YMQ) - Chicago, US (CHI)

United Airlines Logo
United Airlines

May 31

YUL
13h 55m
DCA

Jun 1

ORD

as low as

$167

Montreal, CA (YMQ) - Chicago, US (CHI)

United Airlines Logo
United Airlines

Jun 13

YUL
9h 30m
IAD

Jun 13

ORD

as low as

$167

Montreal, CA (YMQ) - Chicago, US (CHI)

United Airlines Logo
United Airlines

May 22

YUL
10h 49m
EWR

May 22

ORD

as low as

$167

Montreal, CA (YMQ) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 21

YUL
4h 33m
PHL

May 21

ORD

as low as

$167

Montreal, CA (YMQ) - Chicago, US (CHI)

United Airlines Logo
United Airlines

May 24

YUL
12h 4m
LGA

May 25

ORD

as low as

$167

Montreal, CA (YMQ) - Chicago, US (CHI)

Delta Air Lines Logo
Delta Air Lines

May 26

YUL
7h
MSP

May 26

MDW

as low as

$167

Montreal, CA (YMQ) - Chicago, US (CHI)

American Airlines Logo
American Airlines

Jun 3

YUL
6h 37m
CLT

Jun 3

ORD

as low as

$167

Montreal, CA (YMQ) - Chicago, US (CHI)

Air Canada Logo
Air Canada

May 21

YUL
1h 32m
Direct

May 21

ORD

as low as

$168

Frequently Asked Questions

What is the typical flight duration from Montreal to Chicago?
The typical flight duration from Montreal to Chicago ranges between 2 to 3 hours for a direct flight, although weather conditions or slight routing differences may extend the journey closer to 3.5 hours. Travelers should be aware that connecting flights will add additional time to the total travel duration. Direct flights are generally the preferred option for those looking to save time. Planning ahead by checking updated timings from your airline can ensure a smooth experience for visitors journeying from Montreal to Chicago.
Are there any direct flights from Montreal to Chicago?
Yes, direct flights between Montreal and Chicago are available. These non-stop services usually run several times daily, offering a convenient and time-efficient option for travelers. Direct flights typically last between 2 and 3 hours, which makes them ideal when you want a quick transfer from Montreal to Chicago. It is a good idea to check current schedules, as flight frequencies and pricing can vary by season and demand. Booking in advance can also often secure better rates and seat options.
What are the best transportation options from Chicago airport to downtown?
Chicago’s airports offer a variety of transportation options to reach downtown. The CTA Blue Line provides an economical and efficient service, with costs ranging from $5 to $10 per person. Alternatively, rideshare services and taxis are available, with fares typically ranging from $30 to $50, depending on traffic and time of day. For added convenience, shuttle services and rental cars are also accessible. Evaluating your budget and time schedule can help travelers from Montreal select the most practical option for your trip to Chicago.
What are the must-see attractions in Chicago for travelers arriving from Montreal?
Chicago offers a wealth of must-see attractions for visitors coming from Montreal. Highlights include the iconic Millennium Park with its reflective art installations, the breathtaking views from the Willis Tower Skydeck, and the engaging exhibits at the Art Institute of Chicago. Additionally, Navy Pier and the vibrant neighborhoods provide cultural enrichment and scenic views along the lakefront. Each site offers unique experiences and diverse activities that cater to a variety of interests. It's advisable to allocate a full day for exploring the downtown area to fully enjoy these urban wonders.
Which local dishes should travelers from Montreal try when visiting Chicago?
Travelers visiting Chicago from Montreal should indulge in local culinary specialties. Chicago is renowned for its deep-dish pizza, a hearty meal marked by a thick crust, generous cheese, and scrumptious toppings. Additionally, Chicago-style hot dogs, known for their unique toppings and mustard-based seasoning, and Italian beef sandwiches are must-tries. Local diners also offer a variety of classic American comfort foods. Exploring these dishes provides an authentic taste of the city’s lively food culture while offering a delicious contrast to Montreal’s culinary scene.
What are the best family-friendly activities in Chicago for visitors from Montreal?
Chicago welcomes families with an array of kid-friendly activities and attractions. The Shedd Aquarium and Field Museum offer interactive exhibits that educate and entertain visitors of all ages. For outdoor fun, Lincoln Park Zoo and Millennium Park provide ample space to explore and engage with nature and public art. Moreover, numerous science centers and kid-oriented museums are available throughout the city. These activities provide a balanced mix of learning and leisure, ensuring that families from Montreal have a memorable and enjoyable visit to Chicago.
Are there any seasonal events in Chicago that travelers from Montreal should not miss?
Yes, Chicago hosts a range of seasonal events that visitors from Montreal should consider adding to their itinerary. In the summer months, festivals like the Taste of Chicago and outdoor concerts create vibrant atmospheres, while autumn brings cultural fairs and art shows. In the winter, the city transforms with holiday markets such as the Christkindlmarket and festive light displays. These seasonal events offer unique opportunities to experience local traditions and community gatherings, making your trip to Chicago culturally enriching and exciting at any time of year.
What are the most affordable dining options in Chicago for travelers from Montreal?
Affordable dining in Chicago can be found throughout the city in both casual eateries and local diners. Options include family-run pizza parlors, street food vendors offering hot dogs and ethnic dishes, and neighborhood cafes with daily specials. Meals in these venues generally range from $10 to $20 per person. Areas like Pilsen or Chinatown often feature budget-friendly menus paired with authentic local flavors. This variety of affordable dining options allows travelers from Montreal to explore the city’s culinary diversity without straining their travel budget.
What are the best shopping districts in Chicago for souvenirs for travelers from Montreal?
Chicago offers several vibrant shopping districts ideal for finding unique souvenirs and gifts. The Magnificent Mile is a prime destination featuring upscale shops, international brands, and specialty boutiques. Other neighborhoods like Wicker Park and River North offer local artisan markets and vintage stores for more distinctive items. Prices can vary broadly, with souvenirs typically ranging from $10 to $50. Each district provides a unique shopping experience, ensuring that visitors from Montreal can find memorable keepsakes that reflect Chicago’s cultural and urban vibe.
What cultural etiquette should travelers from Montreal be aware of when visiting Chicago?
Yes, travelers should be mindful of local cultural etiquette when visiting Chicago. It is customary to greet store clerks and service staff courteously and to tip around 15-20% in dining establishments. Punctuality and clarity in communication are appreciated in both professional and social settings. Additionally, respecting personal space and being aware of local customs, especially in crowded public spaces, can enhance your interactions. Such etiquette helps ensure a respectful and positive experience for visitors from Montreal as they explore Chicago's diverse cultural landscape.
What are the best car rental options in Chicago for travelers from Montreal?
For travelers looking for car rental options in Chicago, major companies such as Hertz, Enterprise, and Avis offer competitive deals with daily rates typically ranging from $40 to $80. These companies provide a variety of vehicles, from compact cars to larger SUVs, catering to different travel needs. Booking in advance online often secures lower rates and confirms availability. Additionally, local rental services sometimes offer attractive packages for short-term use. It is wise to compare offers and read customer reviews to ensure reliability and good service during your visit from Montreal to Chicago.
Is there a specific time of year when Chicago is best visited by travelers from Montreal?
The optimal times for visiting Chicago are during the spring (April to June) and fall (September to early November). These seasons boast mild weather, fewer crowds, and more competitive accommodation prices compared to summer peak times. Travelers from Montreal will appreciate temperate conditions perfect for outdoor sightseeing and cultural events, such as local festivals, art shows, and outdoor markets. While winter offers notable attractions too, the cold weather may deter some visitors. This makes spring and fall the most appealing periods for an immersive and comfortable experience in Chicago.
What are the customs requirements for travelers flying from Montreal to Chicago?
Travelers flying from Montreal to Chicago should prepare to adhere to customs requirements that include carrying a valid passport and, if applicable, an ESTA or visa for entry into the United States. The customs process can take anywhere from 30 minutes to over an hour, depending on peak hours and individual circumstances. It’s important to declare any items subject to duty and adhere to limits on duty-free purchases. Prior research on the latest customs policies is advised, as regulations can change. Being well-prepared ensures a smooth border crossing and stress-free entry into Chicago.
What unique airport amenities are available in Chicago for travelers arriving from Montreal?
Chicago’s airports are known for their modern amenities that enhance the travel experience. Amenities include comfortable lounges, high-speed free Wi-Fi, and an array of dining and retail options featuring local flavors and international brands. Travelers can also enjoy art installations, relaxation zones, and family-friendly play areas. Many terminals offer charging stations and even spa services. These conveniences help ease the transition from the flight, providing both comfort and entertainment as visitors from Montreal prepare to explore the lively surroundings of Chicago.
What are the best travel tips for first-time travelers flying from Montreal to Chicago?
For first-time travelers, it is essential to prepare by arriving at the airport early to account for security checks and customs procedures. Ensure that all travel documents, such as passports and any necessary visas or ESTA authorizations, are in order. Familiarize yourself with the layout of Chicago’s airports and available transportation options to streamline your journey. Additionally, research the key attractions and local dining spots in Chicago ahead of time. Practical planning, including booking transportation and car rentals in advance, can relieve stress and ensure a seamless experience.