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Flight Deals from Toronto to Chicago Midway Airport from $115

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Stops

  • Nonstop
    from $155
  • Up to 1 stop
    $309
  • Up to 2 stops
    $320

Airlines

  • Air Transat
    $187
  • Delta Air Lines
    $339
  • Porter Airlines
    $155
  • WestJet
    $309

Cabin Class

  • Economy
    $155

Departure Airports

  • Toronto Island Airport
    $155
  • Toronto Pearson Airport
    $309

Arrival Airports

  • Chicago Midway Airport
    $155

Layover Airports

  • Calgary International Airport
    $320
  • Detroit Metropolitan Airport
    $309
  • Edmonton Airport
    $320
  • Hartsfield Jackson Atlanta International Airport
    $315
  • Minneapolis-St Paul International/Wold-Chamberlain Airport
    $309
  • Salt Lake City International Airport
    $329
  • Vancouver International Airport
    $320
  • Winnipeg / James Armstrong Richardson International Airport
    $320

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

05/28/25

YTZ
49m
Direct

05/28/25

MDW
Porter Airlines Logo
Porter Airlines

06/04/25

MDW
2h 42m
Direct

06/04/25

YTZ
$155
Free cancellation within 83 hours of booking
Porter Airlines Logo
Porter Airlines

05/20/25

YTZ
49m
Direct

05/20/25

MDW
Porter Airlines Logo
Porter Airlines

06/04/25

MDW
2h 42m
Direct

06/04/25

YTZ
$155
Free cancellation within 83 hours of booking
Porter Airlines Logo
Porter Airlines

05/29/25

YTZ
49m
Direct

05/29/25

MDW
Porter Airlines Logo
Porter Airlines

06/05/25

MDW
2h 42m
Direct

06/05/25

YTZ
$155
Free cancellation within 83 hours of booking
Porter Airlines Logo
Porter Airlines

05/24/25

YTZ
50m
Direct

05/24/25

MDW
Porter Airlines Logo
Porter Airlines

05/25/25

MDW
2h 42m
Direct

05/25/25

YTZ
$155
Free cancellation within 83 hours of booking
Air Transat Logo
Air Transat

06/02/25

YTZ
50m
Direct

06/02/25

MDW
Air Transat Logo
Air Transat

06/11/25

MDW
2h 42m
Direct

06/11/25

YTZ
$187
Free cancellation within 83 hours of booking
Air Transat Logo
Air Transat

05/24/25

YTZ
50m
Direct

05/24/25

MDW
Air Transat Logo
Air Transat

06/08/25

MDW
2h 42m
Direct

06/08/25

YTZ
$187
Free cancellation within 83 hours of booking
Air Transat Logo
Air Transat

05/27/25

YTZ
50m
Direct

05/27/25

MDW
Air Transat Logo
Air Transat

06/08/25

MDW
2h 42m
Direct

06/08/25

YTZ
$187
Free cancellation within 83 hours of booking
Air Transat Logo
Air Transat

06/04/25

YTZ
50m
Direct

06/04/25

MDW
Air Transat Logo
Air Transat

06/06/25

MDW
2h 42m
Direct

06/06/25

YTZ
$187
Free cancellation within 83 hours of booking
WestJet Logo
WestJet

05/26/25

YYZ
6h 45m
MSP

05/26/25

MDW
WestJet Logo
WestJet

05/26/25

MDW
5h 43m
DTW

05/26/25

YYZ
$309
Free cancellation within 83 hours of booking
WestJet Logo
WestJet

05/27/25

YYZ
17h 54m
MSP

05/28/25

MDW
WestJet Logo
WestJet

06/08/25

MDW
11h 58m
DTW

06/08/25

YYZ
$315
Free cancellation within 83 hours of booking
WestJet Logo
WestJet

05/20/25

YYZ
6h 45m
MSP

05/20/25

MDW
WestJet Logo
WestJet

06/10/25

MDW
10h 5m
MSP

06/10/25

YYZ
$315
Free cancellation within 83 hours of booking
WestJet Logo
WestJet

05/19/25

YYZ
11h 15m
MSP

05/19/25

MDW
WestJet Logo
WestJet

05/31/25

MDW
12h 50m
ATL

05/31/25

YYZ
$315
Free cancellation within 83 hours of booking
WestJet Logo
WestJet

06/07/25

YYZ
7h 48m
ATL

06/07/25

MDW
WestJet Logo
WestJet

06/08/25

MDW
5h 41m
DTW

06/08/25

YYZ
$315
Free cancellation within 83 hours of booking
WestJet Logo
WestJet

05/28/25

YYZ
11h 15m
MSP

05/28/25

MDW
WestJet Logo
WestJet

06/08/25

MDW
6h 15m
DTW

06/08/25

YYZ
$315
Free cancellation within 83 hours of booking
WestJet Logo
WestJet

05/22/25

YYZ
6h 45m
MSP

05/22/25

MDW
WestJet Logo
WestJet

05/31/25

MDW
20h 53m
ATL

06/01/25

YYZ
$315
Free cancellation within 83 hours of booking
WestJet Logo
WestJet

05/30/25

YYZ
11h 15m
MSP

05/30/25

MDW
WestJet Logo
WestJet

06/03/25

MDW
14h 41m
MSP
YVR

06/04/25

YYZ
$320
Free cancellation within 83 hours of booking
WestJet Logo
WestJet

06/07/25

YYZ
14h 58m
ATL

06/07/25

MDW
WestJet Logo
WestJet

06/11/25

MDW
13h 22m
MSP
YYC

06/12/25

YYZ
$320
Free cancellation within 83 hours of booking
WestJet Logo
WestJet

05/20/25

YYZ
9h 57m
ATL

05/20/25

MDW
WestJet Logo
WestJet

06/10/25

MDW
12h 4m
MSP
YWG

06/10/25

YYZ
$320
Free cancellation within 83 hours of booking
WestJet Logo
WestJet

05/22/25

YYZ
11h 15m
MSP

05/22/25

MDW
WestJet Logo
WestJet

05/31/25

MDW
15h 15m
MSP
YEG

06/01/25

YYZ
$320
Free cancellation within 83 hours of booking
WestJet Logo
WestJet

05/26/25

YYZ
11h 15m
YYC
MSP

05/26/25

MDW
WestJet Logo
WestJet

06/09/25

MDW
12h 21m
MSP

06/09/25

YYZ
$320
Free cancellation within 83 hours of booking
WestJet Logo
WestJet

05/28/25

YYZ
6h 45m
MSP

05/28/25

MDW
WestJet Logo
WestJet

06/08/25

MDW
16h 4m
MSP
YEG

06/09/25

YYZ
$320
Free cancellation within 83 hours of booking
WestJet Logo
WestJet

05/25/25

YYZ
11h 15m
YYC
MSP

05/25/25

MDW
WestJet Logo
WestJet

05/27/25

MDW
20h 53m
ATL

05/28/25

YYZ
$320
Free cancellation within 83 hours of booking
WestJet Logo
WestJet

05/24/25

YYZ
14h 43m
YYC
ATL

05/24/25

MDW
WestJet Logo
WestJet

05/30/25

MDW
14h 24m
ATL

05/31/25

YYZ
$320
Free cancellation within 83 hours of booking
WestJet Logo
WestJet

05/21/25

YYZ
15h 12m
ATL

05/21/25

MDW
WestJet Logo
WestJet

05/23/25

MDW
15h 15m
MSP
YEG

05/24/25

YYZ
$324
Free cancellation within 83 hours of booking
WestJet Logo
WestJet

05/25/25

YYZ
11h 15m
YYC
MSP

05/25/25

MDW
WestJet Logo
WestJet

05/27/25

MDW
11h 40m
MSP
YWG

05/27/25

YYZ
$325
Free cancellation within 83 hours of booking
WestJet Logo
WestJet

06/09/25

YYZ
15h 11m
YYC
ATL

06/10/25

MDW
WestJet Logo
WestJet

06/13/25

MDW
16h 4m
MSP
YEG

06/14/25

YYZ
$325
Free cancellation within 83 hours of booking
WestJet Logo
WestJet

05/30/25

YYZ
11h 15m
YYC
MSP

05/30/25

MDW
WestJet Logo
WestJet

06/03/25

MDW
14h 41m
MSP
YVR

06/04/25

YYZ
$325
Free cancellation within 83 hours of booking
WestJet Logo
WestJet

05/19/25

YYZ
15h 10m
YVR
ATL

05/20/25

MDW
WestJet Logo
WestJet

05/31/25

MDW
14h 22m
SLC
YYC

06/01/25

YYZ
$329
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

05/14/25

YYZ
2h 55m
DTW

05/14/25

MDW
Delta Air Lines Logo
Delta Air Lines

05/17/25

MDW
5h 43m
DTW

05/17/25

YYZ
$339
Free cancellation within 83 hours of booking
WestJet Logo
WestJet

05/12/25

YYZ
9h 45m
YWG
MSP

05/12/25

MDW
WestJet Logo
WestJet

05/27/25

MDW
11h 40m
MSP
YWG

05/27/25

YYZ
$345
Free cancellation within 83 hours of booking

Top Deals on flights from Toronto to Chicago Midway Airport

Toronto, CA (YTO) - Chicago, US (CHI)

Porter Airlines Logo
Porter Airlines

Aug 3

YTZ
50m
Direct

Aug 3

MDW

as low as

$115

Toronto, CA (YTO) - Chicago, US (CHI)

Porter Airlines Logo
Porter Airlines

Aug 17

YTZ
50m
Direct

Aug 17

MDW

as low as

$115

Toronto, CA (YTO) - Chicago, US (CHI)

Air Transat Logo
Air Transat

Sep 3

YTZ
49m
Direct

Sep 3

MDW

as low as

$132

Toronto, CA (YTO) - Chicago, US (CHI)

Air Transat Logo
Air Transat

Jun 30

YTZ
49m
Direct

Jun 30

MDW

as low as

$132

Toronto, CA (YTO) - Chicago, US (CHI)

Delta Air Lines Logo
Delta Air Lines

Jun 18

YYZ
5h 59m
DTW

Jun 18

MDW

as low as

$155

Toronto, CA (YTO) - Chicago, US (CHI)

Delta Air Lines Logo
Delta Air Lines

May 28

YYZ
2h 55m
DTW

May 28

MDW

as low as

$155

Toronto, CA (YTO) - Chicago, US (CHI)

Delta Air Lines Logo
Delta Air Lines

Jun 25

YYZ
4h 36m
MSP

Jun 25

MDW

as low as

$155

Toronto, CA (YTO) - Chicago, US (CHI)

Delta Air Lines Logo
Delta Air Lines

May 27

YYZ
5h 15m
MSP

May 27

MDW

as low as

$155

Toronto, CA (YTO) - Chicago, US (CHI)

WestJet Logo
WestJet

Aug 7

YYZ
4h 40m
MSP

Aug 7

MDW

as low as

$201

Toronto, CA (YTO) - Chicago, US (CHI)

WestJet Logo
WestJet

May 30

YYZ
8h 2m
ATL

May 30

MDW

as low as

$201

Toronto, CA (YTO) - Chicago, US (CHI)

WestJet Logo
WestJet

Jun 2

YYZ
8h 2m
ATL

Jun 2

MDW

as low as

$202

Toronto, CA (YTO) - Chicago, US (CHI)

WestJet Logo
WestJet

May 29

YYZ
9h 45m
YWG
MSP

May 29

MDW

as low as

$206

Frequently Asked Questions

What is the typical flight duration from Toronto to Chicago Midway Airport?
The typical flight duration from Toronto to Chicago Midway Airport usually ranges between 1.5 to 2.5 hours, depending on the specific route and weather conditions. Keep in mind that while the in-air time is short, additional time will be needed for boarding, security, and taxiing on the runway. Travelers should factor in a cushion of extra time when planning their schedules. Advanced booking and checking the flight status before departure can help manage any potential delays effectively.
Are there any direct flights from Toronto to Chicago Midway Airport?
Yes, there are direct flights available from Toronto to Chicago Midway Airport. Several airlines offer non-stop services that cater specifically to travelers seeking a quick and hassle-free trip. These flights typically provide competitive prices and shorter overall travel times, making them a convenient option for those flying between the two cities. It is advisable to compare flight times and pricing ranges, which generally vary between moderate and premium levels, to select the best option for your schedule and budget.
What are the best transportation options from Chicago Midway Airport to downtown Chicago?
Travelers arriving from Toronto to Chicago Midway Airport have a variety of transportation choices to reach downtown. The CTA Orange Line train is a popular option, taking between 20 to 35 minutes and costing around $5 to $10. Alternatively, taxis and rideshare services like Uber or Lyft offer door-to-door picks that may range from $30 to $50, depending on traffic conditions. For those traveling light or on a budget, local bus services can also be convenient, though they may take a bit longer.
What are the must-see attractions in Chicago for travelers arriving from Toronto?
Visitors from Toronto to Chicago Midway Airport should not miss exploring landmarks such as Millennium Park with its iconic Cloud Gate sculpture, Navy Pier for scenic lake views, and the Art Institute of Chicago renowned for its collections. Additionally, walking along the Magnificent Mile offers a vibrant city experience with shops and eateries. Each landmark provides a unique glimpse into Chicago’s arts, culture, and history, allowing travelers to fully immerse themselves in the local charm and bustling urban environment.
Which local dishes should travelers from Toronto try when visiting Chicago?
Travelers arriving from Toronto to Chicago Midway Airport should definitely sample local culinary specialties that define the city’s food scene. Iconic suggestions include the famous deep-dish pizza with its hearty crust and rich tomato sauce, the savory Italian beef sandwich served with sweet peppers, and the original Chicago-style hot dog topped with sport peppers and celery salt. These dishes reflect the city’s vibrant and diverse culinary heritage, and many local eateries and restaurants offer authentic preparations that provide a true taste of Chicago’s flavor.
What are the best family-friendly activities in Chicago for visitors from Toronto?
Families traveling from Toronto to Chicago can celebrate a wide array of kid-friendly activities near Chicago Midway Airport. Popular options include visiting the Field Museum for its intriguing natural history exhibitions, exploring the interactive exhibits at the Museum of Science and Industry, and enjoying the Shedd Aquarium’s aquatic displays. In addition, Navy Pier offers rides, games, and boat tours. These attractions provide educational and entertaining experiences for family members of all ages while ensuring a memorable and engaging visit in the vibrant settings of Chicago.
Are there any seasonal events in Chicago that travelers from Toronto should not miss?
Yes, Chicago offers plenty of seasonal events that visitors from Toronto can enjoy throughout the year. During the summer months, events such as the Taste of Chicago and outdoor concerts in the parks provide a festive atmosphere ideal for both families and solo travelers. In the winter, the Christkindlmarket and ice skating at Millennium Park create a charming holiday experience. Spring and fall festivals also offer local food, craft fairs, and cultural performances, ensuring there is always a dynamic event to enhance your Chicago visit.
What are the most affordable dining options in Chicago for travelers from Toronto?
For those traveling from Toronto to Chicago on a budget, the city offers diverse and affordable dining options. Neighborhoods like Pilsen and Chinatown are known for their authentic, reasonably priced eateries serving everything from tacos to dim sum. Local diners and casual bistros provide meals typically ranging from $10 to $25, while food trucks and local markets offer a variety of street foods at even lower prices. Exploring these areas can grant an enjoyable culinary experience without compromising quality or the authenticity of Chicago’s vibrant food scene.
What are the best car rental options in Chicago for travelers from Toronto?
Travelers arriving from Toronto to Chicago Midway Airport will find several reputable car rental services available directly at the terminal or nearby rental centers. Major companies such as Enterprise, Hertz, and Avis typically offer competitive rates with daily prices ranging from $40 to $100, depending on the vehicle class and rental duration. It is recommended to book in advance to secure the best rates and availability. Comparing rates and checking for promotions can further help optimize your budget, while ensuring you have a reliable mode of transportation during your stay.
What cultural tips should travelers from Toronto be aware of when visiting Chicago?
Travelers from Toronto should embrace Chicago’s diverse cultural landscape by recognizing local customs and social norms. In Chicago, it is customary to tip around 15-20% in restaurants and cafes. Familiarize yourself with local etiquette such as maintaining a friendly yet respectful tone in public interactions and being mindful of personal space in crowded areas. Additionally, while the city is welcoming, understanding transportation etiquette on public transit and appreciating the local accent and pace can enhance your experience and ease cultural navigation while exploring Chicago.
Is there a specific time of year when Chicago is best visited by travelers from Toronto?
While Chicago has appeal year-round, many travelers from Toronto find that late spring to early autumn, specifically between May and September, is the best time to visit. The weather is generally mild and pleasant, perfect for outdoor activities, festivals, and lakefront walks. Summer events and cultural festivals keep the city vibrant. However, visitors should note that winter, from December to February, can be harsh with chilly temperatures, although it offers its own festive charm with holiday markets and seasonal landmarks.
What are the customs requirements for travelers flying from Toronto to Chicago Midway Airport?
Travelers flying from Toronto to Chicago Midway Airport need to prepare for international customs and immigration procedures. U.S. Customs and Border Protection requires a valid passport, and in some cases, an Electronic System for Travel Authorization (ESTA) or visa for non-U.S. citizens. Additionally, travelers should be aware of restrictions on bringing in food, agricultural products, and certain items. Preparation in advance by verifying travel documents and checking the latest customs guidelines can streamline the process, helping you to avoid unexpected delays and ensuring a smoother entry experience into the United States.
What are the unique airport amenities at Chicago Midway Airport for travelers arriving from Toronto?
Chicago Midway Airport offers a range of unique amenities that can enhance your travel experience coming from Toronto. Facilities include complimentary Wi-Fi, a variety of dining and shopping options, and comfortable seating areas near departure gates. Travelers can also find modern business lounges, charging stations, and free information kiosks that provide local news and weather updates. Additionally, the airport’s layout is designed to simplify navigation, and its proximity to public transit adds convenience. These amenities ensure that even during layovers or delays, passengers remain well-supported and comfortable.
What are the best shopping areas in Chicago for travelers from Toronto looking for souvenirs?
After arriving from Toronto at Chicago Midway, travelers looking for souvenirs should explore iconic shopping districts in Chicago such as the Magnificent Mile and Water Tower Place. These areas are renowned for a mix of high-end boutiques, local artisan shops, and flagship stores that offer unique memorabilia. Neighborhood markets in areas like Lincoln Park also showcase local crafts and specialty items. These shopping hubs not only provide diverse products but also allow visitors to enjoy vibrant urban atmospheres and potentially discover exclusive deals and seasonal offers during their visit.
Are there any health precautions travelers from Toronto should take before visiting Chicago?
Travelers from Toronto planning a trip to Chicago should consider some basic health precautions to ensure a smooth visit. It is recommended to check for any regional advisories or vaccine recommendations well in advance. While Chicago offers excellent healthcare facilities, having travel insurance that covers health emergencies, with costs ranging from moderate to premium, is advisable. Additionally, staying aware of seasonal weather-related illnesses or allergens common in urban environments can help in taking proactive steps, such as packing necessary medications and practicing good hygiene practices during your stay.