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

Flights from Trudeau International Airport (YUL) to Chicago, IL (CHI-All Airports)
Flights to Illinois
United States of America
Flights
Expedia.ca

Popular airlines from Trudeau International Airport (YUL) to Chicago

Porter Airlines
Delta
WestJet
American Airlines
Air Canada
Air Transat
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 Montreal to Chicago (YUL-CHI)

Prices were available within the past 7 days and start at CA $253 for one-way flights and CA $414 for roundtrip, for the period specified. Prices and availability are subject to change.

All deals

One way

Roundtrip

Sat, Nov 7 - Sat, Nov 7

YUL

Montreal

MDW

Chicago

CA $414

Roundtrip

Found 1 day ago

Select Delta flight, departing Sat, Nov 7 from Montreal to Chicago, returning Sat, Nov 7, priced at CA $414 Found 1 day ago

Tue, Oct 27 - Tue, Oct 27

YUL

Montreal

ORD

Chicago

CA $415

Roundtrip

Found 3 hours ago

Select Delta flight, departing Tue, Oct 27 from Montreal to Chicago, returning Tue, Oct 27, priced at CA $415 Found 3 hours ago

Wed, Dec 2 - Fri, Dec 4

YUL

Montreal

ORD

Chicago

CA $422

Roundtrip

Found 18 hours ago

Select Delta flight, departing Wed, Dec 2 from Montreal to Chicago, returning Fri, Dec 4, priced at CA $422 Found 18 hours ago

Fri, Nov 20 - Fri, Nov 20

YUL

Montreal

MDW

Chicago

CA $445

Roundtrip

Found 1 day ago

Select Delta flight, departing Fri, Nov 20 from Montreal to Chicago, returning Fri, Nov 20, priced at CA $445 Found 1 day ago

Fri, Dec 11 - Fri, Dec 11

YUL

Montreal

MDW

Chicago

CA $453

Roundtrip

Found 1 day ago

Select Delta flight, departing Fri, Dec 11 from Montreal to Chicago, returning Fri, Dec 11, priced at CA $453 Found 1 day ago

Wed, Nov 18 - Wed, Nov 25

YUL

Montreal

ORD

Chicago

CA $453

Roundtrip

Just found

Select Delta flight, departing Wed, Nov 18 from Montreal to Chicago, returning Wed, Nov 25, priced at CA $453 Just found

Fri, Nov 27 - Sun, Nov 29

YUL

Montreal

ORD

Chicago

CA $476

Roundtrip

Just found

Select United flight, departing Fri, Nov 27 from Montreal to Chicago, returning Sun, Nov 29, priced at CA $476 Just found

Wed, Nov 18 - Wed, Nov 25

YUL

Montreal

ORD

Chicago

CA $476

Roundtrip

Just found

Select Air Canada flight, departing Wed, Nov 18 from Montreal to Chicago, returning Wed, Nov 25, priced at CA $476 Just found

Thu, Oct 29 - Tue, Nov 3

YUL

Montreal

ORD

Chicago

CA $476

Roundtrip

Just found

Select American Airlines flight, departing Thu, Oct 29 from Montreal to Chicago, returning Tue, Nov 3, priced at CA $476 Just found

Tue, Dec 8 - Thu, Dec 17

YUL

Montreal

ORD

Chicago

CA $550

Roundtrip

Found 1 day ago

Select Porter Airlines flight, departing Tue, Dec 8 from Montreal to Chicago, returning Thu, Dec 17, priced at CA $550 Found 1 day ago

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 $501

ORD

O'Hare Intl.

Cheapest

23 min

Flights from CA $501

Select flight to Midway Intl. MDW. Closest option available. Average driving time to city centre is 16 minutes. Flights from CA $740

MDW

Midway Intl.

Closest

16 min

Flights from CA $740

Find the cheapest month to fly from Montreal (YUL) to Chicago (CHI)

January is typically the cheapest month to fly

From CA $394 - CA $621 per traveller.

Travel information

Origin airport	Trudeau International Airport
Destination airport	Chicago Midway Airport
Distance	1,195 km away
Airlines serving	Delta, WestJet, Porter Airlines
Popular airline	Delta
Roundtrip price	CA $414

Explore a world of travel with Expedia

Flights

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

*Available to Expedia members.

CA $253 Cheap Flights from Montreal (YUL) to Chicago (CHI)

Popular airlines from Trudeau International Airport (YUL) to Chicago

Be in the know

Book smarter

Earn twice

Cheap Flights from Montreal to Chicago (YUL-CHI)

Alternative airports near Chicago

Find the cheapest month to fly from Montreal (YUL) to Chicago (CHI)

January is typically the cheapest month to flyJanuary is typically the cheapest month to fly

Travel information

Explore a world of travel with Expedia

January is typically the cheapest month to fly