FlightsFrom Toronto

To Chicago

Cheap Flights from Toronto to Chicago

Browse current best options from Toronto. Become a member to unlock all deals and get alerts when new deals appear.

Deals from

Toronto

RatePunk searches hundreds of travel sites at once for deals on flights to Chicago

Prices updated 24 days ago

486,190 searches this week

171 airlines compared

80%+ AI score for best value

Fares are subject to change and may not be available for all dates. (Data last updated May 29, 2026.)

Today’s best flight deals from Toronto to Chicago

Explore current cheapest deals departing from Toronto to Chicago

September 4 - September 7

Cheapest

YTZ - Chicago

$221

$173

Round trip

September 4 - September 6

YTZ - Chicago

$221

$174

Round trip

October 14 - October 18

Best

YTZ - Chicago

$275

$175

Round trip

September 11 - September 13

YTZ - Chicago

$227

$176

Round trip

October 15 - October 18

Best

YTZ - Chicago

$275

$176

Round trip

September 14 - September 20

YTZ - Chicago

$220

$178

Round trip

September 9 - September 15

YTZ - Chicago

$221

$178

Round trip

September 3 - September 6

YTZ - Chicago

$218

$180

Round trip

September 3 - September 7

YTZ - Chicago

$218

$180

Round trip

September 2 - September 7

Earliest

YTZ - Chicago

$217

$180

Round trip

Unlock all 500+ flight deals to Chicago and get alerts when great deals appear

Route Intelligence — 486,190 Searches this Week

Insights for flights from Toronto to Chicago

Fares for flights from Toronto to Chicago typically range from $189–$495, with a median of $282. Right now, prices are above the typical level, but 41% of recent fares were still classified as a good price. New deals appear almost daily, offering frequent opportunities to find cheap flights from Toronto to Chicago.
When is the cheapest time to fly from Toronto to Chicago? The data indicates that November is typically the most affordable month, with a median fare of $179. Other cost-effective options include April, with a median of $225, and February, where the median fare is $238.
A typical journey from Toronto to Chicago takes about 3h 50m, including connections. This route is classified as a short-haul flight, covering a distance of 696 kilometers.
For flights from Toronto to Chicago, 50.9% of itineraries are non-stop, meaning a meaningful share are non-stop, the rest connect once. When a connection is involved, the median number of stopovers is 2.

How much is a round trip from Toronto to Chicago

Regular price: $178 - $360

Prices are currently below the regular range for flights from Toronto to Chicago.

The regular price range for flights from Toronto to Chicago is between $178 and $360. The current lowest deal is $173 with Porter Airlines for travel from Sep 4-Sep 7.

now $173

Low $178

High $360

The cheapest time to fly from Toronto to Chicago

The cheapest month to fly from Toronto to Chicago is November, with a median price of $179. The most expensive month is October, with a median price of $626. Prices are generally lower from January to November.

November

Cheapest

Flights from $179

October

Most Expensive

Flights from $626

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec

Direct flights from Toronto to Chicago

Airline logo

Porter Airlines

Last-minute flights going from Toronto to Chicago

Wed, Jul 1

⌛ Last-Minute

YTZ - Chicago

Porter Airlines

Toronto (YTZ) - Chicago (MDW)

Porter Airlines

$636

$187

One-way

Wed, Jul 1

⌛ Last-Minute

YTZ - Chicago

Porter Airlines

Toronto (YTZ) - Chicago (MDW)

Porter Airlines

$588

$192

One-way

Wed, Jul 1

⌛ Last-Minute

YTZ - Chicago

Porter Airlines

Toronto (YTZ) - Chicago (MDW)

Porter Airlines

$588

$193

One-way

Wed, Jul 1

⌛ Last-Minute

YTZ - Chicago

Porter Airlines

Toronto (YTZ) - Chicago (MDW)

Porter Airlines

$637

$195

One-way

Wed, Jul 1

⌛ Last-Minute

YTZ - Chicago

Porter Airlines

Toronto (YTZ) - Chicago (MDW)

Porter Airlines

$638

$195

One-way

Wed, Jul 1

⌛ Last-Minute

YTZ - Chicago

Porter Airlines

Toronto (YTZ) - Chicago (MDW)

Porter Airlines

$600

$195

One-way

Biggest price drops on these dates for flights from Toronto to Chicago

4 nights

Jul 2 - Jul 6

$637  →  $185

71%

2 nights

Jul 2 - Jul 4

$636  →  $185

71%

2 nights

Jul 1 - Jul 3

$636  →  $187

71%

3 nights

Jul 1 - Jul 4

$638  →  $195

69%

Popular Airports to fly from Toronto to Chicago

Toronto - Chicago route insights

💸 Price insights

Recent fares are above the typical level

Recent fares from YTO to CHI are above the typical level, with 41% good prices.

📅 Best time to fly

November is historically cheapest at $179

Historically, November is the cheapest month to fly from YTO to CHI, with a median price of $179.

⏱️ Flight duration

Direct flights take 3h 50m

The median flight time for this short-haul route is 3 hours 50 minutes.

✈️ Airlines & availability

Mixed availability of direct flights

Around 50.9% of recent deals for this route are direct, with others having 2 stopovers.

🏆 Airline highlight

Porter Airlines offers direct flights

Porter Airlines has recently offered direct flights on the YTO to CHI route.

🎯 Booking tip

Deals are frequent for this route

Deals for flights from YTO to CHI are frequent, with over 1 deal per day.

Toronto main airports to depart from

Billy Bishop Toronto City (YTZ)

Cheapest

Consider Billy Bishop Toronto City for flights to Chicago, offering a convenient departure point.

📍 ~3 km from city center (reachable by car or bus)

💸 Flights from ~$173

Toronto Pearson International (YYZ)

Toronto Pearson International is a major hub for flights to Chicago, providing many options.

📍 ~25 km from city center (reachable by car or train)

💸 Flights from ~$190

Chicago main airports to arrive at

O Hare International (ORD)

Cheapest

O'Hare International Airport is a good option for flights from Toronto to Chicago.

📍 ~25 km from Chicago (reachable by car)

💸 Flights from ~$173

Chicago Midway International (MDW)

Chicago Midway International Airport is a convenient choice for flights from Toronto to Chicago.

📍 ~15 km from Chicago (reachable by car)

💸 Flights from ~$185

Chicago Rockford International (RFD)

Chicago Rockford International Airport offers another arrival option for flights from Toronto to Chicago.

📍 ~100 km from Chicago (reachable by car)

💸 Flights from ~$322

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

Consider Milwaukee for excellent proximity to Chicago with high-frequency flight options and direct rail access.

📍 ~135 km from Chicago (reachable by rail)

💸 Flights from ~$410

South Bend International (SBN)

South Bend is a close alternative to Chicago, offering direct commuter rail links and easier security.

📍 ~120 km from Chicago (reachable by rail)

💸 Flights from ~$347

Gerald R. Ford International (GRR)

Cheapest

Grand Rapids is a major regional hub, useful for travelers on the eastern side of the Chicago metro area.

📍 ~235 km from Chicago (reachable by car)

💸 Flights from ~$318

Dane County Regional (MSN)

Madison offers reliable regional service and less congestion compared to major Chicago airports.

📍 ~200 km from Chicago (reachable by car)

💸 Flights from ~$409

Fort Wayne International (FWA)

Fort Wayne provides stable regional service, ideal for travelers in the southeastern Chicago suburbs.

📍 ~240 km from Chicago (reachable by car)

💸 Flights from ~$344

Business & First Class Flight Deals to Chicago

Discover luxury on the budget with premium cabin class on flights from Toronto to Chicago.

Elite

Best Elite deals to Chicago

Exclusive daily First Class, Business Class, and Premium Economy flight deals, refreshed every 24 hours.

From YTZ

Elite

Sep 14

Chicago, United States

81% AI deal score

$742

$352

Save $390

From YTZ

Elite

Jul 03

Chicago, United States

80% AI deal score

$635

$352

Save $283

From YTZ

Elite

Jul 02

Chicago, United States

80% AI deal score

$635

$352

Save $283

From YTZ

Elite

Sep 01

Chicago, United States

80% AI deal score

$703

$352

Save $351

From YTZ

Elite

Sep 08

Chicago, United States

80% AI deal score

$710

$352

Save $358

From YTZ

Elite

Sep 14

Chicago, United States

80% AI deal score

$715

$352

Save $363

From YTZ

Elite

Sep 07

Chicago, United States

80% AI deal score

$710

$352

Save $358

From YTZ

Elite

Sep 01

Chicago, United States

80% AI deal score

$701

$352

Save $349

From YTZ

Elite

Sep 06

Chicago, United States

80% AI deal score

$696

$352

Save $344

From YTZ

Elite

Sep 06

Chicago, United States

80% AI deal score

$727

$352

Save $375

From YTZ

Elite

Sep 06

Chicago, United States

80% AI deal score

$695

$352

Save $343

From YTZ

Elite

Sep 14

Chicago, United States

80% AI deal score

$730

$352

Save $378

From YTZ

Elite

Sep 01

Chicago, United States

80% AI deal score

$704

$352

Save $352

From YTZ

Elite

Sep 06

Chicago, United States

80% AI deal score

$730

$352

Save $378

From YTZ

Elite

Sep 06

Chicago, United States

80% AI deal score

$692

$352

Save $340

From YTZ

Elite

Sep 13

Chicago, United States

80% AI deal score

$726

$352

Save $374

From YTZ

Elite

Sep 04

Chicago, United States

80% AI deal score

$704

$352

Save $352

From YTZ

Elite

Sep 02

Chicago, United States

80% AI deal score

$698

$352

Save $346

From YTZ

Elite

Sep 07

Chicago, United States

80% AI deal score

$711

$352

Save $359

From YTZ

Elite

Sep 07

Chicago, United States

80% AI deal score

$711

$352

Save $359

From YTZ

Elite

Sep 08

Chicago, United States

80% AI deal score

$711

$352

Save $359

From YTZ

Elite

Sep 06

Chicago, United States

80% AI deal score

$700

$352

Save $348

From YTZ

Elite

Sep 03

Chicago, United States

80% AI deal score

$704

$352

Save $352

From YTZ

Elite

Sep 09

Chicago, United States

80% AI deal score

$704

$352

Save $352

From YTZ

Elite

Sep 07

Chicago, United States

80% AI deal score

$711

$352

Save $359

From YTZ

Elite

Sep 10

Chicago, United States

80% AI deal score

$704

$352

Save $352

From YTZ

Elite

Sep 03

Chicago, United States

80% AI deal score

$701

$352

Save $349

From YTZ

Elite

Sep 12

Chicago, United States

80% AI deal score

$714

$352

Save $362

From YTZ

Elite

Sep 12

Chicago, United States

80% AI deal score

$713

$352

Save $361

From YTZ

Elite

Sep 14

Chicago, United States

80% AI deal score

$727

$360

Save $367

From YTZ

Elite

Aug 11

Chicago, United States

79% AI deal score

$799

$395

Save $404

From YTZ

Elite

Aug 05

Chicago, United States

79% AI deal score

$772

$395

Save $377

From YTZ

Elite

Aug 26

Chicago, United States

79% AI deal score

$774

$402

Save $372

From YTZ

Elite

Aug 31

Chicago, United States

79% AI deal score

$770

$402

Save $368

From YTZ

Elite

Aug 31

Chicago, United States

79% AI deal score

$769

$402

Save $367

From YTZ

Elite

Aug 19

Chicago, United States

79% AI deal score

$775

$402

Save $373

From YTZ

Elite

Aug 31

Chicago, United States

79% AI deal score

$798

$402

Save $396

From YTZ

Elite

Aug 19

Chicago, United States

79% AI deal score

$775

$402

Save $373

From YYZ

Elite

Jul 02

Chicago, United States

78% AI deal score

$1,370

$484

Save $886

From YYZ

Elite

Oct 29

Chicago, United States

77% AI deal score

$1,362

$706

Save $656

From YYZ

Elite

Oct 30

Chicago, United States

77% AI deal score

$1,329

$706

Save $623

From YYZ

Elite

Oct 02

Chicago, United States

77% AI deal score

$1,354

$706

Save $648

From YYZ

Elite

Oct 16

Chicago, United States

77% AI deal score

$1,362

$706

Save $656

From YTZ

Elite

Jul 18

Chicago, United States

77% AI deal score

$656

$395

Save $261

From YTZ

Elite

Jul 18

Chicago, United States

77% AI deal score

$656

$395

Save $261

From YYZ

Elite

Aug 13

Chicago, United States

76% AI deal score

$1,216

$484

Save $732

From YYZ

Elite

Jun 23

Chicago, United States

76% AI deal score

$1,193

$679

Save $514

From YYZ

Elite

Jul 27

Chicago, United States

75% AI deal score

$1,095

$683

Save $412

From YYZ

Elite

Jul 23

Chicago, United States

75% AI deal score

$1,095

$683

Save $412

From YYZ

Elite

Jul 16

Chicago, United States

75% AI deal score

$1,067

$683

Save $384

From YYZ

Elite

Jul 30

Chicago, United States

75% AI deal score

$1,068

$683

Save $385

From YYZ

Elite

Jul 30

Chicago, United States

75% AI deal score

$1,097

$683

Save $414

From YYZ

Elite

Jul 24

Chicago, United States

75% AI deal score

$1,067

$683

Save $384

From YYZ

Elite

Jul 14

Chicago, United States

75% AI deal score

$1,097

$688

Save $409

From YYZ

Elite

Jul 19

Chicago, United States

75% AI deal score

$1,118

$484

Save $634

From YTZ

Elite

Jun 29

Chicago, United States

75% AI deal score

$596

$400

Save $196

From YTZ

Elite

Jun 28

Chicago, United States

75% AI deal score

$617

$400

Save $217

From YYZ

Elite

Jul 21

Chicago, United States

74% AI deal score

$1,022

$683

Save $339

From YYZ

Elite

Jul 17

Chicago, United States

74% AI deal score

$1,054

$683

Save $371

From YYZ

Elite

Jul 11

Chicago, United States

74% AI deal score

$1,031

$683

Save $348

From YYZ

Elite

Jul 23

Chicago, United States

74% AI deal score

$1,067

$687

Save $380

From YYZ

Elite

Aug 15

Chicago, United States

73% AI deal score

$938

$683

Save $255

From YYZ

Elite

Jul 23

Chicago, United States

73% AI deal score

$1,029

$689

Save $340

From YYZ

Elite

Aug 15

Chicago, United States

73% AI deal score

$952

$643

Save $309

From YYZ

Elite

Aug 07

Chicago, United States

72% AI deal score

$925

$683

Save $242

From YYZ

Elite

Aug 15

Chicago, United States

72% AI deal score

$924

$683

Save $241

From YYZ

Elite

Nov 10

Chicago, United States

72% AI deal score

$1,021

$674

Save $347

From YYZ

Elite

Jul 14

Chicago, United States

72% AI deal score

$810

$687

Save $123

From YYZ

Elite

Jul 10

Chicago, United States

71% AI deal score

$1,081

$749

Save $332

From YYZ

Elite

Jul 10

Chicago, United States

70% AI deal score

$1,108

$801

Save $307

From YYZ

Elite

Nov 21

Chicago, United States

69% AI deal score

$1,000

$778

Save $222

From YYZ

Elite

Aug 13

Chicago, United States

68% AI deal score

$879

$683

Save $196

From YYZ

Elite

Aug 14

Chicago, United States

68% AI deal score

$879

$683

Save $196

From YYZ

Elite

Sep 03

Chicago, United States

67% AI deal score

$900

$683

Save $217

From YYZ

Elite

Aug 13

Chicago, United States

67% AI deal score

$857

$683

Save $174

From YYZ

Elite

Aug 12

Chicago, United States

67% AI deal score

$853

$687

Save $166

From YYZ

Elite

Aug 13

Chicago, United States

66% AI deal score

$826

$687

Save $139

From YYZ

Elite

Sep 04

Chicago, United States

66% AI deal score

$880

$694

Save $186

From YYZ

Elite

Jul 16

Chicago, United States

66% AI deal score

$757

$683

Save $74

From YYZ

Elite

Jul 08

Chicago, United States

66% AI deal score

$758

$683

Save $75

From YYZ

Elite

Jul 01

Chicago, United States

49% AI deal score

$1,128

$876

Save $252

From YYZ

Elite

Sep 13

Chicago, United States

48% AI deal score

$966

$778

Save $188

From YYZ

Elite

Jul 25

Chicago, United States

48% AI deal score

$1,100

$884

Save $216

From YYZ

Elite

Jul 23

Chicago, United States

48% AI deal score

$1,297

$1,015

Save $282

From YYZ

Elite

Sep 06

Chicago, United States

47% AI deal score

$961

$801

Save $160

From YYZ

Elite

Sep 04

Chicago, United States

46% AI deal score

$966

$839

Save $127

From YYZ

Elite

Sep 16

Chicago, United States

45% AI deal score

$889

$801

Save $88

From YYZ

Elite

Aug 12

Chicago, United States

44% AI deal score

$683

From YYZ

Elite

Sep 15

Chicago, United States

44% AI deal score

$966

$884

Save $82

From YYZ

Elite

Jun 22

Chicago, United States

42% AI deal score

$920

From YYZ

Elite

Jun 23

Chicago, United States

38% AI deal score

$920

From YYZ

Elite

Jul 10

Chicago, United States

38% AI deal score

$930

From YYZ

Elite

Jun 19

Chicago, United States

38% AI deal score

$1,508

From YYZ

Elite

Jun 25

Chicago, United States

37% AI deal score

$1,038

From YYZ

Elite

Jun 24

Chicago, United States

36% AI deal score

$1,102

From YYZ

Elite

Jul 11

Chicago, United States

35% AI deal score

$1,152

From YYZ

Elite

Jun 24

Chicago, United States

33% AI deal score

$1,508

From YYZ

Elite

Jul 19

Chicago, United States

31% AI deal score

$1,419

From YYZ

Elite

Jun 25

Chicago, United States

31% AI deal score

$1,448

From YYZ

Elite

Jul 30

Chicago, United States

31% AI deal score

$1,470

Frequently Asked Questions About Flights to Chicago

Historically, the optimal booking window for flights from Toronto to Chicago is typically 14-27 days before departure. During this period, the average price observed was $294. Booking within 7-13 days of departure saw an average price of $390, while waiting until 0-6 days before departure resulted in a significantly higher average price of $662. Conversely, booking more than 60 days out also showed higher average prices, around $415.

A good price for a flight from Toronto to Chicago is considered to be around $189 or less, based on historical data from the trailing 90 days. The median price for this route was $282. Prices typically ranged up to $495 for the upper quartile of fares observed during this period.

Historically, November has been the cheapest month to fly from Toronto to Chicago, with a median price of $179. Other historically inexpensive months include April, with a median price of $225, and February, with a median price of $238. The annual median price for this route, across the trailing 270 days, was $282.