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Flight Deals from Montreal Trudeau Airport 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
  • Vancouver International Airport
    $389
  • Washington Dulles Airport
    $266

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On average save $240 per traveler
United Airlines Logo
United Airlines

05/24/25

YUL
1h 32m
Direct

05/24/25

ORD
United Airlines Logo
United Airlines

06/07/25

ORD
3h 8m
Direct

06/07/25

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

05/28/25

ORD
3h 15m
Direct

05/28/25

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
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
Air Canada Logo
Air Canada

05/24/25

YUL
1h 39m
Direct

05/24/25

ORD
Air Canada Logo
Air Canada

05/29/25

ORD
7h 25m
YOW

05/29/25

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

05/25/25

YUL
1h 32m
Direct

05/25/25

ORD
Air Canada Logo
Air Canada

05/29/25

ORD
7h 25m
YOW

05/29/25

YUL
$256
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

06/06/25

YUL
6h 9m
YTZ

06/06/25

MDW
Porter Airlines Logo
Porter Airlines

06/15/25

MDW
6h 20m
YTZ

06/15/25

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

06/09/25

YUL
6h 9m
YTZ

06/09/25

MDW
Porter Airlines Logo
Porter Airlines

06/11/25

MDW
6h 20m
YTZ

06/11/25

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

05/30/25

YUL
1h 32m
Direct

05/30/25

ORD
Air Canada Logo
Air Canada

06/14/25

ORD
7h 56m
YYZ

06/15/25

YUL
$263
Free cancellation within 83 hours of booking
Air Canada Logo
Air Canada

06/11/25

YUL
1h 32m
Direct

06/11/25

ORD
Air Canada Logo
Air Canada

06/18/25

ORD
7h 21m
YYZ

06/18/25

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
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
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
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

06/03/25

YUL
6h 9m
YYZ

06/03/25

ORD
Air Canada Logo
Air Canada

06/15/25

ORD
11h 41m
YYZ
YOW

06/15/25

YUL
$311
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
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
11h 20m
MSP

06/10/25

MDW
WestJet Logo
WestJet

06/14/25

MDW
9h 21m
DTW

06/14/25

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

05/19/25

YUL
14h 28m
ATL

05/19/25

MDW
WestJet Logo
WestJet

05/23/25

MDW
27h 7m
MSP

05/24/25

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

05/31/25

YUL
3h 51m
DTW

05/31/25

ORD
WestJet Logo
WestJet

06/06/25

ORD
27h 55m
ATL

06/07/25

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

05/31/25

YUL
16h 17m
YYC
ATL

05/31/25

ORD
WestJet Logo
WestJet

06/06/25

ORD
27h 55m
ATL

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
14h 13m
DTW

06/19/25

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
WestJet Logo
WestJet

05/23/25

YUL
15h 6m
MSP

05/23/25

ORD
WestJet Logo
WestJet

05/25/25

ORD
15h 28m
MSP
YVR

05/26/25

YUL
$389
Free cancellation within 83 hours of booking

Top Deals on flights from Montreal Trudeau Airport to Chicago

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

American Airlines Logo
American Airlines

Jun 6

YUL
1h 35m
Direct

Jun 6

ORD

as low as

$151

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

United Airlines Logo
United Airlines

May 22

YUL
1h 39m
Direct

May 22

ORD

as low as

$151

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

Delta Air Lines Logo
Delta Air Lines

Jun 3

YUL
6h 28m
DTW

Jun 3

MDW

as low as

$163

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

Delta Air Lines Logo
Delta Air Lines

Jun 4

YUL
8h 43m
ATL

Jun 4

MDW

as low as

$163

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)

United Airlines Logo
United Airlines

May 26

YUL
12h 37m
EWR

May 26

ORD

as low as

$167

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

United Airlines Logo
United Airlines

May 24

YUL
6h 27m
DCA

May 24

ORD

as low as

$167

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

American Airlines Logo
American Airlines

Jun 3

YUL
4h 54m
PHL

Jun 3

ORD

as low as

$167

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

United Airlines Logo
United Airlines

May 22

YUL
12h 30m
LGA

May 22

ORD

as low as

$167

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

United Airlines Logo
United Airlines

May 31

YUL
4h 20m
IAD

May 31

ORD

as low as

$167

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

Air Canada Logo
Air Canada

May 22

YUL
1h 32m
Direct

May 22

ORD

as low as

$168

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

Porter Airlines Logo
Porter Airlines

Jun 4

YUL
6h 9m
YTZ

Jun 4

MDW

as low as

$173

Frequently Asked Questions

What is the typical flight duration from Montreal Trudeau Airport to Chicago?
The flight duration between Montreal Trudeau Airport and Chicago generally ranges from 2 to 3 hours for non-stop routes, though flights with connections may take 4 to 5 hours. Travelers should also factor in boarding times and potential weather delays. It’s advisable to arrive early at the airport for check-in and security. This detailed information benefits both Montreal and Chicago flyers, supporting smooth travel planning and realistic expectations about in-flight time variations.
Are there any direct flights from Montreal Trudeau Airport to Chicago?
Yes, there are direct flight options available from Montreal Trudeau Airport to Chicago. Direct routes typically take around 2 to 3 hours, providing a convenient and time-efficient choice for travelers. However, schedules may vary seasonally and airline offerings might change, so it’s advisable to verify the latest schedules with your booking provider. This option is popular among those traveling between Montreal and Chicago, offering a seamless journey without the hassle of layovers.
What are the best transportation options from Chicago airport to downtown?
Travelers arriving at Chicago airports have several dependable transportation options to reach downtown. Options include the CTA Blue Line train, which takes between 45 and 60 minutes, taxis and ride-sharing services costing around $30 to $50, and shuttle bus services that can vary in price. Car rentals are also available if you prefer to explore on your own schedule. These options cater well to visitors from Montreal by offering flexibility, convenience, and varied price ranges for a smooth transition from the airport to the city center.
What are the must-see attractions in Chicago for travelers arriving from Montreal?
Travelers from Montreal should consider exploring several iconic attractions in Chicago. Highlights include Millennium Park with its famous Cloud Gate sculpture, the Art Institute of Chicago, and the Willis Tower Skydeck for panoramic views. Navy Pier offers a mix of entertainment and dining, while the Museum Campus houses fascinating cultural institutions. Each destination provides a unique experience, so planning your itinerary can maximize your visit by balancing art, history, and modern urban attractions in the vibrant city.
Which local dishes should travelers from Montreal try when visiting Chicago?
Visitors from Montreal should sample authentic Chicago cuisine during their stay. Notable dishes include the classic deep-dish pizza with its buttery crust and generous toppings, the Italian beef sandwich often served with a side of au jus, and the renowned Chicago-style hot dog garnished with sport peppers and a pickle spear. Dining experiences can range from $10 to $30 per meal in casual eateries. These distinctive flavors offer a tasty exploration of local culinary traditions that make Chicago’s food scene truly memorable.
Are there any family-friendly activities in Chicago for visitors from Montreal?
Yes, Chicago offers an array of family-friendly activities ideal for travelers from Montreal. Families can visit the Shedd Aquarium to see a variety of marine life, explore the interactive exhibits at the Chicago Children’s Museum, or spend a day at the Lincoln Park Zoo which offers free admission. Other engaging spots include the Field Museum and various parks along the lakefront. These activities provide affordable fun with admission fees typically ranging from free to $25 per ticket, ensuring diverse experiences for visitors of all ages.
What are the best budget-friendly hotels in Chicago for travelers from Montreal?
Travelers from Montreal who seek affordable accommodations in Chicago can choose from several budget-friendly hotels. Options such as chain hotels and boutique inns are often available in central areas like the Loop or near public transit hubs. Prices typically range from $100 to $200 per night, depending on the season and location. It’s recommended to book in advance and read recent reviews to ensure quality and accessibility. These practical choices help manage travel expenses while still offering convenient access to Chicago’s top attractions.
What cultural etiquette should travelers from Montreal be aware of when visiting Chicago?
Travelers from Montreal should note that Chicago’s cultural etiquette emphasizes friendliness, punctuality, and respect for personal space. Tipping is customary in restaurants and for other services, typically ranging from 15% to 20%. Being clear and direct in conversation is appreciated, and small talk is common. Visitors should also be aware that local residents value efficiency and courteous behavior in busy settings like public transit. Understanding these norms can enhance interactions and provide a smoother experience while navigating social and business environments in Chicago.
What are the top shopping districts in Chicago for visitors from Montreal?
Chicago boasts several prime shopping districts that appeal to visitors from Montreal seeking a diverse retail experience. The Magnificent Mile is renowned for its upscale boutiques, international brands, and department stores. Additionally, areas like State Street and trendy neighborhoods such as Wicker Park offer unique local shops and vintage finds. Expect price ranges from affordable to luxury, with many options for window shopping or finding that special souvenir. These districts provide both shopping enthusiasts and casual visitors a vibrant atmosphere and a variety of purchasing opportunities.
Is there a specific time of year when Chicago is best visited by travelers from Montreal?
Travelers from Montreal will find that Chicago is best visited during the spring (April to June) and fall (September to early November) seasons. During these periods, the weather is usually mild with temperatures ranging from 60°F to 75°F, ideal for sightseeing and outdoor activities. Spring brings blooming parks and fewer crowds, while fall offers pleasant weather and vibrant cityscapes. Summer is popular but can be hotter and more crowded. Planning your trip during these shoulder seasons ensures comfortable weather and potentially lower travel costs.
What health precautions should travelers from Montreal consider before flying to Chicago?
Travelers from Montreal should consider several health precautions when heading to Chicago. It is wise to check that routine vaccinations are current and to review any travel-specific advisories, particularly during flu season or other health alerts. Carry a travel medical kit with essentials like hand sanitizer and basic medications. Additionally, it is beneficial to ensure you have updated travel insurance covering medical issues abroad. With Chicago’s urban setting, staying hydrated and wearing comfortable clothing during transit can further enhance your overall travel experience.
Are there any seasonal events in Chicago that travelers from Montreal should not miss?
Yes, Chicago hosts several seasonal events that are well worth experiencing for visitors from Montreal. In the summer, the Taste of Chicago and outdoor music festivals attract crowds, while winter brings festive activities like the Christkindlmarket and Winter WonderFest. Additionally, the fall season features cultural festivals and art walks, and spring often offers street fairs and sporting events. Attending these events provides immersive local experiences with diverse entertainment, food, and cultural exhibitions, allowing travelers to experience the city’s vibrant community firsthand.
What are the best solo travel activities in Chicago for travelers arriving from Montreal?
Solo travelers from Montreal visiting Chicago can engage in a variety of enriching activities. A visit to world-class museums, such as the Art Institute of Chicago or the Field Museum, allows for reflective exploration of art and culture. City walking tours and bike rentals offer an excellent way to discover distinct neighborhoods with local eateries and shops. Additionally, relaxing by the lakefront or attending independent film screenings can provide a tailored travel experience. These activities give solo adventurers a balanced mix of urban exploration, cultural insights, and peaceful escapes.
What unique airport amenities can travelers expect at Chicago airport?
Travelers arriving at Chicago airports can enjoy a range of unique amenities designed for comfort and convenience. Modern terminals feature complimentary Wi-Fi, a variety of dining options with meals usually priced between $10 to $25, and numerous retail stores offering local and international brands. Many terminals also provide dedicated rest zones, charging stations for devices, and art installations that reflect the city’s cultural heritage. Whether you’re seeking a quiet space to work or a lively spot for a snack, these amenities help enhance the overall travel experience for visitors from Montreal and other destinations.
What are the customs requirements for travelers flying from Montreal to Chicago?
Travelers flying from Montreal to Chicago must adhere to U.S. customs and border regulations. A valid passport is required, and some visitors may also need to apply for an ESTA under the Visa Waiver Program if applicable. Customs procedures typically involve completing declaration forms and going through an immigration check upon arrival, which can take anywhere from 30 minutes to over an hour depending on crowd levels. It is advised to review the latest guidelines before departure and to have all necessary documents ready to ensure a smooth transition between Montreal and Chicago.