A river with a yellow boat, surrounded by tall buildings and a bridge.

Flights from Toronto Pearson Intl. Airport (YYZ) to Chicago, IL (CHI-All Airports)
Flights to Illinois
United States of America
Flights
Expedia.ca

Popular airlines from Toronto Pearson Intl. Airport (YYZ) to Chicago

Porter Airlines
WestJet
Delta
American Airlines
Air Canada
United

Be in the know
Get alerts if flight prices drop or rise*
Book smarter
Save up to 30% on select hotels after you book a flight*
Earn twice
Earn your airline miles on top of our rewards
Sign in

Cheap Flights from Toronto to Chicago (YYZ-CHI)

Prices were available within the past 7 days and start at CA $269 for one-way flights and CA $464 for roundtrip, for the period specified. Prices and availability are subject to change.

All deals

One way

Roundtrip

Tue, Nov 24 - Tue, Nov 24

YYZ

Toronto

MDW

Chicago

CA $464

Roundtrip

Found 7 hours ago

Select Delta flight, departing Tue, Nov 24 from Toronto to Chicago, returning Tue, Nov 24, priced at CA $464 Found 7 hours ago

Thu, Nov 19 - Sun, Nov 22

YYZ

Toronto

ORD

Chicago

CA $464

Roundtrip

Just found

Select Air Canada flight, departing Thu, Nov 19 from Toronto to Chicago, returning Sun, Nov 22, priced at CA $464 Just found

Fri, Nov 13 - Mon, Nov 16

YYZ

Toronto

ORD

Chicago

CA $469

Roundtrip

Just found

Select United flight, departing Fri, Nov 13 from Toronto to Chicago, returning Mon, Nov 16, priced at CA $469 Just found

Thu, Nov 19 - Sun, Nov 22

YYZ

Toronto

ORD

Chicago

CA $472

Roundtrip

Just found

Select Delta flight, departing Thu, Nov 19 from Toronto to Chicago, returning Sun, Nov 22, priced at CA $472 Just found

Fri, Nov 20 - Mon, Nov 23

YYZ

Toronto

ORD

Chicago

CA $473

Roundtrip

Just found

Select Air Canada flight, departing Fri, Nov 20 from Toronto to Chicago, returning Mon, Nov 23, priced at CA $473 Just found

Fri, Nov 13 - Mon, Nov 16

YYZ

Toronto

ORD

Chicago

CA $477

Roundtrip

Just found

Select United flight, departing Fri, Nov 13 from Toronto to Chicago, returning Mon, Nov 16, priced at CA $477 Just found

Thu, Nov 5 - Sun, Nov 8

YYZ

Toronto

ORD

Chicago

CA $480

Roundtrip

Just found

Select Air Canada flight, departing Thu, Nov 5 from Toronto to Chicago, returning Sun, Nov 8, priced at CA $480 Just found

Mon, Nov 2 - Wed, Nov 4

YYZ

Toronto

ORD

Chicago

CA $483

Roundtrip

Just found

Select Air Canada flight, departing Mon, Nov 2 from Toronto to Chicago, returning Wed, Nov 4, priced at CA $483 Just found

Thu, Nov 19 - Sun, Nov 22

YYZ

Toronto

ORD

Chicago

CA $592

Roundtrip

Just found

Select American Airlines flight, departing Thu, Nov 19 from Toronto to Chicago, returning Sun, Nov 22, priced at CA $592 Just found

Sat, Dec 26 - Sat, Jan 2

YYZ

Toronto

ORD

Chicago

CA $697

Roundtrip

Just found

Select Porter Airlines flight, departing Sat, Dec 26 from Toronto to Chicago, returning Sat, Jan 2, priced at CA $697 Just found

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city centre is 23 minutes. Flights from CA $563

ORD

O'Hare Intl.

Cheapest

23 min

Flights from CA $563

Select flight to Midway Intl. MDW. Closest option available. Average driving time to city centre is 16 minutes. Flights from CA $608

MDW

Midway Intl.

Closest

16 min

Flights from CA $608

Travel information

Origin airport	Toronto Pearson Intl. Airport
Destination airport	Chicago O'Hare International Airport
Distance	701 km away
Airlines serving	Porter Airlines, American Airlines, Delta, WestJet, Air Canada, United
Popular airline	Porter Airlines
Roundtrip price	CA $464
Average flight time	2 hours 2 mins

Explore a world of travel with Expedia

Flights

Flights from Phoenix (PHX) to Chicago (CHI)
Standard Link for Flights from Phoenix (PHX) to Chicago (CHI)
Flights from Rome (RME) to Chicago (CHI)
Standard Link for Flights from Rome (RME) to Chicago (CHI)
Flights from Minneapolis (MSP) to Chicago (CHI)
Standard Link for Flights from Minneapolis (MSP) to Chicago (CHI)
Flights from Tampa (TPA) to Chicago (CHI)
Standard Link for Flights from Tampa (TPA) to Chicago (CHI)
Flights from Prince Albert (YPA) to Chicago (CHI)
Standard Link for Flights from Prince Albert (YPA) to Chicago (CHI)
Flights from Kitchener (YKF) to Chicago (CHI)
Standard Link for Flights from Kitchener (YKF) to Chicago (CHI)
Flights from Peoria (PIA) to Chicago (CHI)
Standard Link for Flights from Peoria (PIA) to Chicago (CHI)
Flights from Oshawa (YOO) to Chicago (CHI)
Standard Link for Flights from Oshawa (YOO) to Chicago (CHI)
Flights from Hartford (BDL) to Chicago (CHI)
Standard Link for Flights from Hartford (BDL) to Chicago (CHI)
Flights from Boise (BOI) to Chicago (CHI)
Standard Link for Flights from Boise (BOI) to Chicago (CHI)
Flights from Kamloops (YKA) to Chicago (CHI)
Standard Link for Flights from Kamloops (YKA) to Chicago (CHI)
Flights from Milwaukee (MKE) to Chicago (CHI)
Standard Link for Flights from Milwaukee (MKE) to Chicago (CHI)
Flights from Santo Domingo (SDQ) to Chicago (CHI)
Standard Link for Flights from Santo Domingo (SDQ) to Chicago (CHI)
Flights from Edmonton (YEG) to Chicago (ORD)
Standard Link for Flights from Edmonton (YEG) to Chicago (ORD)
Flights from Fredericton (YFC) to Chicago (CHI)
Standard Link for Flights from Fredericton (YFC) to Chicago (CHI)
Flights from Hyderabad (HYD) to Chicago (CHI)
Standard Link for Flights from Hyderabad (HYD) to Chicago (CHI)
Flights from New Orleans (MSY) to Chicago (CHI)
Standard Link for Flights from New Orleans (MSY) to Chicago (CHI)
Flights from Regina (YQR) to Chicago (CHI)
Standard Link for Flights from Regina (YQR) to Chicago (CHI)
Flights from San Antonio (SAT) to Chicago (CHI)
Standard Link for Flights from San Antonio (SAT) to Chicago (CHI)
Flights from Gander (YQX) to Chicago (CHI)
Standard Link for Flights from Gander (YQX) to Chicago (CHI)
Flights from Edmonton (YEA) to Chicago (CHI)
Standard Link for Flights from Edmonton (YEA) to Chicago (CHI)
Flights from Toronto (YYZ) to Chicago (ORD)
Standard Link for Flights from Toronto (YYZ) to Chicago (ORD)
Flights from Syracuse (SYR) to Chicago (CHI)
Standard Link for Flights from Syracuse (SYR) to Chicago (CHI)
Flights from Beirut (BEY) to Chicago (CHI)
Standard Link for Flights from Beirut (BEY) to Chicago (CHI)
Flights from Los Angeles (LAX) to Chicago (CHI)
Standard Link for Flights from Los Angeles (LAX) to Chicago (CHI)
Flights from Calgary (YYC) to Chicago (CHI)
Standard Link for Flights from Calgary (YYC) to Chicago (CHI)
Flights from Detroit (DTW) to Chicago (ORD)
Standard Link for Flights from Detroit (DTW) to Chicago (ORD)
Flights from Flin Flon (YFO) to Chicago (CHI)
Standard Link for Flights from Flin Flon (YFO) to Chicago (CHI)
Flights from St. Louis (STL) to Chicago (CHI)
Standard Link for Flights from St. Louis (STL) to Chicago (CHI)
Flights from Vancouver (YVR) to Chicago (ORD)
Standard Link for Flights from Vancouver (YVR) to Chicago (ORD)
Flights from Evanston (EVW) to Chicago (CHI)
Standard Link for Flights from Evanston (EVW) to Chicago (CHI)
Flights from Niagara Falls (IAG) to Chicago (CHI)
Standard Link for Flights from Niagara Falls (IAG) to Chicago (CHI)
Flights from Windsor (YQG) to Chicago (CHI)
Standard Link for Flights from Windsor (YQG) to Chicago (CHI)
Flights from Buffalo (BUF) to Chicago (CHI)
Standard Link for Flights from Buffalo (BUF) to Chicago (CHI)
Flights from Detroit (DTW) to Chicago (CHI)
Standard Link for Flights from Detroit (DTW) to Chicago (CHI)
Flights from Manhattan (MHK) to Chicago (CHI)
Standard Link for Flights from Manhattan (MHK) to Chicago (CHI)
Flights from St. John's (YYT) to Chicago (CHI)
Standard Link for Flights from St. John's (YYT) to Chicago (CHI)
Flights from Salt Lake City (SLC) to Chicago (CHI)
Standard Link for Flights from Salt Lake City (SLC) to Chicago (CHI)
Flights from Montreal (YMQ) to Chicago (CHI)
Standard Link for Flights from Montreal (YMQ) to Chicago (CHI)
Flights from Myrtle Beach (MYR) to Chicago (CHI)
Standard Link for Flights from Myrtle Beach (MYR) to Chicago (CHI)
Flights from Owen Sound (YOS) to Chicago (CHI)
Standard Link for Flights from Owen Sound (YOS) to Chicago (CHI)
Flights from Ottawa (YOW) to Chicago (CHI)
Standard Link for Flights from Ottawa (YOW) to Chicago (CHI)
Flights from Whitehorse (YXY) to Chicago (CHI)
Standard Link for Flights from Whitehorse (YXY) to Chicago (CHI)
Flights from Brampton Island (BMP) to Chicago (CHI)
Standard Link for Flights from Brampton Island (BMP) to Chicago (CHI)
Flights from San Diego (SAN) to Chicago (CHI)
Standard Link for Flights from San Diego (SAN) to Chicago (CHI)
Flights from Terrace (YXT) to Chicago (CHI)
Standard Link for Flights from Terrace (YXT) to Chicago (CHI)
Flights from Winnipeg (YWG) to Chicago (ORD)
Standard Link for Flights from Winnipeg (YWG) to Chicago (ORD)
Flights from Detroit (DTT) to Chicago (CHI)
Standard Link for Flights from Detroit (DTT) to Chicago (CHI)
Flights from Cleveland (CLE) to Chicago (CHI)
Standard Link for Flights from Cleveland (CLE) to Chicago (CHI)
Flights from Presque Isle (PQI) to Chicago (CHI)
Standard Link for Flights from Presque Isle (PQI) to Chicago (CHI)
Flights from Poughkeepsie (POU) to Chicago (CHI)
Standard Link for Flights from Poughkeepsie (POU) to Chicago (CHI)
Flights from Blaine (BWS) to Chicago (CHI)
Standard Link for Flights from Blaine (BWS) to Chicago (CHI)
Flights from Halifax (YHZ) to Chicago (CHI)
Standard Link for Flights from Halifax (YHZ) to Chicago (CHI)
Flights from Zürich (ZRH) to Chicago (CHI)
Standard Link for Flights from Zürich (ZRH) to Chicago (CHI)
Flights from Chennai (MAA) to Chicago (CHI)
Standard Link for Flights from Chennai (MAA) to Chicago (CHI)
Flights from Little Rock (LIT) to Chicago (CHI)
Standard Link for Flights from Little Rock (LIT) to Chicago (CHI)
Flights from Nanaimo (YCD) to Chicago (CHI)
Standard Link for Flights from Nanaimo (YCD) to Chicago (CHI)
Flights from Traverse City (TVC) to Chicago (CHI)
Standard Link for Flights from Traverse City (TVC) to Chicago (CHI)
Flights from Chatham (XCM) to Chicago (CHI)
Standard Link for Flights from Chatham (XCM) to Chicago (CHI)
Flights from Moncton (YQM) to Chicago (CHI)
Standard Link for Flights from Moncton (YQM) to Chicago (CHI)
Flights from Carlsbad (CNM) to Chicago (CHI)
Standard Link for Flights from Carlsbad (CNM) to Chicago (CHI)
Flights from Argyle (SVD) to Chicago (CHI)
Standard Link for Flights from Argyle (SVD) to Chicago (CHI)
Flights from New York (JFK) to Chicago (CHI)
Standard Link for Flights from New York (JFK) to Chicago (CHI)
Flights from Benton Harbor (BEH) to Chicago (CHI)
Standard Link for Flights from Benton Harbor (BEH) to Chicago (CHI)
Flights from Montreal (YUL) to Chicago (ORD)
Standard Link for Flights from Montreal (YUL) to Chicago (ORD)
Flights from Edmonton (YEG) to Chicago (CHI)
Standard Link for Flights from Edmonton (YEG) to Chicago (CHI)
Flights from Trois-Rivieres (YRQ) to Chicago (CHI)
Standard Link for Flights from Trois-Rivieres (YRQ) to Chicago (CHI)
Flights from Gary (GYY) to Chicago (CHI)
Standard Link for Flights from Gary (GYY) to Chicago (CHI)
Flights from Burlington (BTV) to Chicago (CHI)
Standard Link for Flights from Burlington (BTV) to Chicago (CHI)
Flights from Cincinnati (CVG) to Chicago (CHI)
Standard Link for Flights from Cincinnati (CVG) to Chicago (CHI)
Flights from Cambridge (CGE) to Chicago (CHI)
Standard Link for Flights from Cambridge (CGE) to Chicago (CHI)
Flights from Sept-Iles (YZV) to Chicago (CHI)
Standard Link for Flights from Sept-Iles (YZV) to Chicago (CHI)
Flights from Punta Cana (PUJ) to Chicago (CHI)
Standard Link for Flights from Punta Cana (PUJ) to Chicago (CHI)
Flights from Kelowna (YLW) to Chicago (CHI)
Standard Link for Flights from Kelowna (YLW) to Chicago (CHI)
Flights from Dhaka (DAC) to Chicago (CHI)
Standard Link for Flights from Dhaka (DAC) to Chicago (CHI)
Flights from Montreal (YUL) to Chicago (CHI)
Standard Link for Flights from Montreal (YUL) to Chicago (CHI)
Flights from Kolkata (CCU) to Chicago (CHI)
Standard Link for Flights from Kolkata (CCU) to Chicago (CHI)
Flights from Whitby (NCA) to Chicago (CHI)
Standard Link for Flights from Whitby (NCA) to Chicago (CHI)
Flights from Singapore (SIN) to Chicago (CHI)
Standard Link for Flights from Singapore (SIN) to Chicago (CHI)
Flights from Newark Liberty Intl. Airport (EWR) to Chicago (CHI)
Standard Link for Flights from Newark Liberty Intl. Airport (EWR) to Chicago (CHI)
Flights from Toronto (YTO) to Chicago (CHI)
Standard Link for Flights from Toronto (YTO) to Chicago (CHI)
Flights from Memphis (MEM) to Chicago (CHI)
Standard Link for Flights from Memphis (MEM) to Chicago (CHI)
Flights from Ottawa (YOW) to Chicago (ORD)
Standard Link for Flights from Ottawa (YOW) to Chicago (ORD)
Flights from Boston (BOS) to Chicago (CHI)
Standard Link for Flights from Boston (BOS) to Chicago (CHI)
Flights from Hamilton (YHM) to Chicago (CHI)
Standard Link for Flights from Hamilton (YHM) to Chicago (CHI)
Flights from Debrecen (DEB) to Chicago (CHI)
Standard Link for Flights from Debrecen (DEB) to Chicago (CHI)
Flights from Calgary (YYC) to Chicago (ORD)
Standard Link for Flights from Calgary (YYC) to Chicago (ORD)
Flights from Sheboygan (SBM) to Chicago (CHI)
Standard Link for Flights from Sheboygan (SBM) to Chicago (CHI)
Flights from Panama City (PTY) to Chicago (CHI)
Standard Link for Flights from Panama City (PTY) to Chicago (CHI)
Flights from Seattle (SEA) to Chicago (CHI)
Standard Link for Flights from Seattle (SEA) to Chicago (CHI)
Flights from Victoria (YYJ) to Chicago (CHI)
Standard Link for Flights from Victoria (YYJ) to Chicago (CHI)
Flights from Laval (LVA) to Chicago (CHI)
Standard Link for Flights from Laval (LVA) to Chicago (CHI)
Flights from Berlin (BER) to Chicago (CHI)
Standard Link for Flights from Berlin (BER) to Chicago (CHI)
Flights from Vancouver (YVR) to Chicago (CHI)
Standard Link for Flights from Vancouver (YVR) to Chicago (CHI)
Flights from Winnipeg (YWG) to Chicago (CHI)
Standard Link for Flights from Winnipeg (YWG) to Chicago (CHI)
Flights from St. Catharines (YCM) to Chicago (CHI)
Standard Link for Flights from St. Catharines (YCM) to Chicago (CHI)
Flights from Chicago (ORD) to Chicago (CHI)
Standard Link for Flights from Chicago (ORD) to Chicago (CHI)
Flights from Pittsburgh (PIT) to Chicago (CHI)
Standard Link for Flights from Pittsburgh (PIT) to Chicago (CHI)
Flights from Fort Frances (YAG) to Chicago (CHI)
Standard Link for Flights from Fort Frances (YAG) to Chicago (CHI)
Flights from Wilmington (ILM) to Chicago (CHI)
Standard Link for Flights from Wilmington (ILM) to Chicago (CHI)

*Available to Expedia members.

CA $269 Cheap Flights from Toronto (YYZ) to Chicago (CHI)

Popular airlines from Toronto Pearson Intl. Airport (YYZ) to Chicago

Be in the know

Book smarter

Earn twice

Cheap Flights from Toronto to Chicago (YYZ-CHI)

Alternative airports near Chicago

Travel information

Explore a world of travel with Expedia