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

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

Popular airlines from Pittsburgh International Airport (PIT) to Chicago

Delta
American Airlines
United
JetBlue Airways
Southwest Airlines
Alaska Airlines
Frontier Airlines

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 Pittsburgh to Chicago (PIT-CHI)

Prices were available within the past 7 days and start at CA $97 for one-way flights and CA $192 for roundtrip, for the period specified. Prices and availability are subject to change.

All deals

One way

Roundtrip

Sat, Feb 20 - Mon, Feb 22

PIT

Pittsburgh

ORD

Chicago

CA $192

Roundtrip

Found 4 days ago

Select American Airlines flight, departing Sat, Feb 20 from Pittsburgh to Chicago, returning Mon, Feb 22, priced at CA $192 Found 4 days ago

Thu, Aug 27 - Thu, Sept 3

PIT

Pittsburgh

ORD

Chicago

CA $193

Roundtrip

Found 23 hours ago

Select American Airlines flight, departing Thu, Aug 27 from Pittsburgh to Chicago, returning Thu, Sept 3, priced at CA $193 Found 23 hours ago

Sat, Feb 20 - Mon, Feb 22

PIT

Pittsburgh

ORD

Chicago

CA $206

Roundtrip

Found 4 days ago

Select Delta flight, departing Sat, Feb 20 from Pittsburgh to Chicago, returning Mon, Feb 22, priced at CA $206 Found 4 days ago

Thu, Aug 27 - Thu, Sept 3

PIT

Pittsburgh

ORD

Chicago

CA $208

Roundtrip

Found 23 hours ago

Select American Airlines flight, departing Thu, Aug 27 from Pittsburgh to Chicago, returning Thu, Sept 3, priced at CA $208 Found 23 hours ago

Sat, Feb 20 - Mon, Feb 22

PIT

Pittsburgh

ORD

Chicago

CA $220

Roundtrip

Found 4 days ago

Select Delta flight, departing Sat, Feb 20 from Pittsburgh to Chicago, returning Mon, Feb 22, priced at CA $220 Found 4 days ago

Thu, Aug 27 - Thu, Sept 3

PIT

Pittsburgh

MDW

Chicago

CA $221

Roundtrip

Found 23 hours ago

Select Delta flight, departing Thu, Aug 27 from Pittsburgh to Chicago, returning Thu, Sept 3, priced at CA $221 Found 23 hours ago

Thu, Aug 27 - Thu, Sept 3

PIT

Pittsburgh

ORD

Chicago

CA $221

Roundtrip

Found 23 hours ago

Select Delta flight, departing Thu, Aug 27 from Pittsburgh to Chicago, returning Thu, Sept 3, priced at CA $221 Found 23 hours ago

Sat, Feb 20 - Mon, Feb 22

PIT

Pittsburgh

ORD

Chicago

CA $242

Roundtrip

Found 4 days ago

Select American Airlines flight, departing Sat, Feb 20 from Pittsburgh to Chicago, returning Mon, Feb 22, priced at CA $242 Found 4 days ago

Thu, Aug 27 - Thu, Sept 3

PIT

Pittsburgh

ORD

Chicago

CA $274

Roundtrip

Found 23 hours ago

Select JetBlue Airways flight, departing Thu, Aug 27 from Pittsburgh to Chicago, returning Thu, Sept 3, priced at CA $274 Found 23 hours ago

Wed, Nov 11 - Sun, Nov 15

PIT

Pittsburgh

ORD

Chicago

CA $474

Roundtrip

Found 1 day ago

Select United flight, departing Wed, Nov 11 from Pittsburgh to Chicago, returning Sun, Nov 15, priced at CA $474 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 $436

ORD

O'Hare Intl.

Cheapest

23 min

Flights from CA $436

Select flight to Midway Intl. MDW. Closest option available. Average driving time to city centre is 16 minutes. Flights from CA $568

MDW

Midway Intl.

Closest

16 min

Flights from CA $568

Travel information

Origin airport	Pittsburgh International Airport
Destination airport	Chicago Midway Airport
Distance	642 km away
Airlines serving	Southwest Airlines, Delta, Frontier Airlines
Popular airline	Southwest Airlines
Roundtrip price	CA $192
Average flight time	1 hour 25 mins

Explore a world of travel with Expedia

Flights

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

*Available to Expedia members.

CA $97 Cheap Flights from Pittsburgh (PIT) to Chicago (CHI)

Flight 1

Popular airlines from Pittsburgh International Airport (PIT) to Chicago

Be in the know

Book smarter

Earn twice

Cheap Flights from Pittsburgh to Chicago (PIT-CHI)

Alternative airports near Chicago

Travel information

Explore a world of travel with Expedia