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Toronto to Chicago Flights

Flight only Hotel only Flight + Hotel

Flight type

Round-trip One-way
Age of children at time of trip

We will search for applicable airfare discounts. Must have 1 adult for each infant in lap

Selected fares from Toronto to Chicago

Departure Arrival Travel dates Round-trip
YTO CHI Sun, Nov 23 - Tue, Nov 25 $232
YTO CHI Thu, Nov 6 - Sat, Nov 8 $255
YTO CHI Sun, Oct 19 - Thu, Oct 23 $269
YTO CHI Sun, Nov 23 - Wed, Nov 26 $277
YTO CHI Sun, Oct 12 - Thu, Oct 16 $292
YTO CHI Sun, Nov 23 - Wed, Nov 26 $294
YTO CHI Sat, Sep 27 - Wed, Oct 8 $753
YTO CHI Sat, Sep 20 - Sun, Sep 21 $2,380

Toronto and Chicago airports and terminals

Airports in Toronto ON, CA
map of airports in Toronto
  • 1

    Toronto Airport (YYZ)

    Distance from City Center: 12.9 miles

    Terminals and carriers for flights from YYZ to CHI

    Terminal Carriers
    Terminal 1 Air Canada, All Nippon Airways, United Airlines
    Terminal 3 American Airlines, British Airways, Finnair, Iberia, US Airways
  • 2

    Toronto Island (YTZ)

    Distance from City Center: 2.2 miles

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Airports in Chicago IL, US
map of airports in Chicago
  • 1

    Midway Airport (MDW)

    Distance from City Center: 9.5 miles

  • 2

    O'Hare Airport (ORD)

    Distance from City Center: 15.1 miles

    Terminals and carriers for flights from YTO to ORD

    Terminal Carriers
    Terminal 1 Air Canada, United Airlines
    Terminal 2 Air Canada, All Nippon Airways, United Airlines
    Terminal 3 American Airlines, British Airways, Finnair, Iberia, US Airways
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Cheap flights from Toronto to Chicago

Sun Mon Tue Wed Thu Fri Sat
1 2 3 4
5 6 7
$232
8 9 10 11
12 13
$232
14 15 16
$232
17 18
19
$232
20 21
$232
22 23 24 25
26
$232
27 28
$232
29 30
$232
31

Highlighted price = Cheapest round-trip flights

Prices are round trip per person (conditions apply)

Featured Chicago Airport Hotels

Hotel only $119

Hilton Chicago O'Hare Airport

4 stars
3.9 / 5 122 reviews

O'Hare International Airport Map

Park & Fly - Includes up to 3 nights valet parking

...This O'Hare airport hotel is located in Terminal 2 and is within walking distance to all O'Hare Airport's domestic terminals.... More

Hotel only $137

Holiday Inn Express & Suites CHICAGO-MIDWAY AIRPORT

3 stars
4.1 / 5 42 reviews

6500 South Cicero Avenue Map

Exceptional Hotel Near Chicago Midway Airport Searching for hotels near the best sights in downtown Chicago?... More

Hotel only $144

Hilton Garden Inn Chicago/Midway Airport

3 stars
3.6 / 5 14 reviews

6530 S. Cicero Avenue Map

Complimentary wired and Wi-Fi Internet Access

...Advance Purchase Rate online!The Hilton Garden Inn Chicago Midway Airport in Chicago is located on the Midway Hotel Center campus just two blocks south of the Chicago Midway Airport and the... More

Hotel only $135

Hampton Inn Chicago-Midway Airport

2 stars
3.8 / 5 17 reviews

6540 S. Cicero Ave. Map

Free On The HouseT hot breakfast, Wi-Fi

...And no matter what time your flight got in or is going out, we're here to pick you up or drop you off.... land here and let your vacation take off...welcome to the Hampton Inn Chicago-Midway... More

Hotel only $179

Chicago Marriott Midway

3 stars
3.7 / 5 7 reviews

6520 South Cicero Avenue Map

Rate includes breakfast

...WiFi-equipped guest rooms at our Chicago Midway Airport hotel are recently renovated and offer soundproof windows, 32" flat-screen TVs and room service.... Perfect for business travel and... More

Hotel only $109

Sheraton Chicago O’Hare Airport Hotel

4 stars
4.0 / 5 109 reviews

6501 N. Mannheim Road Map

Save 40% on your stay

...Complimentary shuttle service to and from O'Hare Airport is available 24 hours a day.... Our all-suite hotel is conveniently located minutes from O'Hare International Airport, Donald E. Stephens... More

October

Cheapest weekend flights in October from Toronto to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Oct 16 Toronto (YYZ) Chicago (ORD) United Airlines $232
Earn $2.32
Return Sat, Oct 18 Chicago (ORD) Toronto (YYZ) United Airlines

Lowest roundtrip airfare in October from Toronto to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Oct 16 Toronto (YYZ) Chicago (ORD) United Airlines $232
Earn $2.32
Return Wed, Oct 29 Chicago (ORD) Toronto (YYZ) United Airlines

Best one-week trip in October from Toronto to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Mon, Oct 27 Toronto (YTZ) Chicago (MDW) Porter Airlines $338
Earn $3.38
Return Mon, Nov 3 Chicago (MDW) Toronto (YTZ) Porter Airlines
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November

Cheapest weekend flights in November from Toronto to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Nov 27 Toronto (YYZ) Chicago (ORD) United Airlines $232
Earn $2.32
Return Sat, Nov 29 Chicago (ORD) Toronto (YYZ) United Airlines

Lowest roundtrip airfare in November from Toronto to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Nov 27 Toronto (YYZ) Chicago (ORD) United Airlines $232
Earn $2.32
Return Sat, Nov 29 Chicago (ORD) Toronto (YYZ) United Airlines

Best one-week trip in November from Toronto to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Fri, Nov 7 Toronto (YTZ) Chicago (MDW) Porter Airlines $303
Earn $3.03
Return Fri, Nov 14 Chicago (MDW) Toronto (YTZ) Porter Airlines
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December

Cheapest weekend flights in December from Toronto to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Dec 4 Toronto (YYZ) Chicago (MDW) Delta Air Lines $255
Earn $2.55
Return Sat, Dec 6 Chicago (MDW) Toronto (YYZ) Delta Air Lines

Lowest roundtrip airfare in December from Toronto to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Tue, Dec 2 Toronto (YYZ) Chicago (ORD) United Airlines $232
Earn $2.32
Return Thu, Dec 4 Chicago (ORD) Toronto (YYZ) United Airlines

Best one-week trip in December from Toronto to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Fri, Dec 26 Toronto (YTZ) Chicago (MDW) Porter Airlines $380
Earn $3.80
Return Fri, Jan 2 Chicago (MDW) Toronto (YTZ) Porter Airlines
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Travel from Toronto to Chicago

Travelers from Toronto often enjoy visiting Chicago for weekend trips or longer vacations to experience the exciting attractions, enlightening cultural events, and incredible shopping opportunities the Windy City has to offer. When planning a trip from Toronto to Chicago, search Orbitz.com for great deals on flights, hotels, and tickets to local attractions.

Leaving Toronto

When heading to Chicago, you'll fly out of Toronto Pearson International Airport, which is located about 17 miles from downtown. Taxis, buses, and the LINK train are all popular ways to get to the airport from central Toronto. Alternately, you can hop on the Express airport shuttle, which makes regular stops throughout the downtown area. If you plan to drive yourself to the airport, you can choose from the value parking garage or the value parking lot, both located just minutes from the terminals on the LINK line.

Visiting Chicago

Chicago has two airports: Chicago O'Hare International Airport and Chicago Midway International Airport. Both airports are served by public buses, and O'Hare has a stop for the CTA Blue line. You can also head into town via taxi or rent a car at the car rental facilities located at both airports. Once in Chicago, check out the Chicago Historical Society museum to get a better idea of the history and culture of the city, then head out to explore. Visit Navy Pier and Lincoln Park Zoo, or relax at Hyde Park before heading out to the theater district to catch a performance. Summer is a popular time to visit Chicago due to the pleasant weather; temperatures average in the low 80s during the day and in the 60s at night. Winters can be cold, with highs near freezing temperature and lows in the 20s, but prices drop significantly during this time.

Your Trip to Chicago

Whether you spend your Chicago vacation investigating the many museums of the city, shopping on the Magnificent Mile, or soaking up culture at local art galleries, you are sure to have a blast in the Windy City. Whatever your vacation budget, check Orbitz.com for great deals on air tickets from Toronto to Chicago, vacation packages, and all of your travel needs.

Interesting facts about flights from Toronto to Chicago

    • 42 direct flights are operating from Toronto to Chicago today.
    • Today's average time for a direct flight is 1h 44m.
    • American Airlines flight 4228 (1:10 AM GMT, Embraer 175) is today's earliest available flight from Toronto to Chicago.
    • Air Canada flight 7409 (4:00 PM GMT, Embraer 175) is today's latest available flight from Toronto to Chicago.
    • Today's shortest direct flight from Toronto to Chicago (Air Canada flight 5141, Airbus Industrie A320) takes 1h 39m.
    • Today's longest direct flight from Toronto to Chicago (United Airlines flight 3670, Canadair Regional Jet 700) takes 1h 57m.
    • Flights from Toronto Airport (YYZ), Toronto Island (YTZ) to Midway Airport (MDW), O'Hare Airport (ORD) are available for this route.

Aircraft options between Toronto and Chicago

Equipment Carrier
Embraer 170/175/190/195 British Airways
Embraer 170 Air Canada, United Airlines
Boeing 737-700 Passenger United Airlines
Embraer RJ135/RJ140/RJ145 United Airlines, Air Canada, US Airways
Airbus Industrie A319 United Airlines, Air Canada
Canadair Regional Jet 700 American Airlines, United Airlines, Air Canada, US Airways, All Nippon Airways
Airbus Industrie A320 United Airlines, Air Canada
Embraer RJ140 American Airlines, US Airways
Boeing 737 Passenger Air Canada
Canadair CRJ Series 705 Air Canada, United Airlines
Boeing 737-900 Passenger United Airlines, Air Canada
Boeing 737-800 Passenger Air Canada, United Airlines
Embraer 190 Air Canada, United Airlines
Canadair Regional Jet United Airlines, Air Canada, US Airways
Embraer RJ145 American Airlines, US Airways, Finnair, Iberia
Embraer 175 Air Canada, United Airlines, American Airlines, US Airways