Find flight deals from Toronto to Chicago

Cheapest flights from Toronto to Chicago
Explore the most affordable flight options available from Toronto to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 14 May 2025.

Sat 28/67:55 a.m.YTZ - MDW

Nonstop1h 50mPorter Airlines

Sat 5/79:40 a.m.MDW - YTZ

Nonstop1h 40mPorter Airlines

Deal found 14/5C$ 236

Fri 27/67:55 a.m.YTZ - MDW

Nonstop1h 50mPorter Airlines

Fri 4/79:40 a.m.MDW - YTZ

Nonstop1h 40mPorter Airlines

Deal found 13/5C$ 237

Fri 6/64:05 p.m.YTZ - MDW

Nonstop1h 49mPorter Airlines

Fri 13/69:40 a.m.MDW - YTZ

Nonstop1h 40mPorter Airlines

Deal found 14/5C$ 239

Fri 15/86:35 p.m.YYZ - ORD

Nonstop1h 54mAir Canada

Mon 18/83:50 p.m.ORD - YYZ

Nonstop1h 45mAir Canada

Deal found 14/5C$ 240

Wed 11/67:55 a.m.YTZ - MDW

Nonstop1h 50mPorter Airlines

Mon 23/69:40 a.m.MDW - YTZ

Nonstop1h 40mPorter Airlines

Deal found 14/5C$ 240

Wed 13/87:55 a.m.YTZ - MDW

Nonstop1h 50mPorter Airlines

Thu 21/85:20 p.m.MDW - YTZ

Nonstop1h 42mPorter Airlines

Deal found 14/5C$ 242

Fri 15/89:00 a.m.YYZ - ORD

1 stop6h 51mAir Canada

Mon 18/88:25 p.m.ORD - YYZ

Nonstop1h 45mAir Canada

Deal found 14/5C$ 243

Sun 17/87:55 a.m.YTZ - MDW

Nonstop1h 50mPorter Airlines

Thu 21/85:20 p.m.MDW - YTZ

Nonstop1h 42mPorter Airlines

Deal found 14/5C$ 243

Fri 25/78:15 a.m.YYZ - ORD

Nonstop1h 54mAir Canada

Sun 27/78:25 p.m.ORD - YYZ

Nonstop1h 45mAir Canada

Deal found 14/5C$ 244

Sun 15/67:55 a.m.YTZ - MDW

Nonstop1h 50mPorter Airlines

Wed 18/65:50 p.m.MDW - YTZ

Nonstop1h 42mPorter Airlines

Deal found 14/5C$ 244

Wed 25/67:55 a.m.YTZ - MDW

Nonstop1h 50mPorter Airlines

Wed 2/79:40 a.m.MDW - YTZ

Nonstop1h 42mPorter Airlines

Deal found 12/5C$ 246

Wed 13/83:35 p.m.YTZ - MDW

Nonstop1h 49mPorter Airlines

Mon 18/85:20 p.m.MDW - YTZ

Nonstop1h 42mPorter Airlines

Deal found 14/5C$ 247

Best flights from Toronto to Chicago
Discover carefully curated flight deals from Toronto to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 14 May 2025.

Sat 28/67:55 a.m.YTZ - MDW

Nonstop1h 50mPorter Airlines

Sat 5/79:40 a.m.MDW - YTZ

Nonstop1h 40mPorter Airlines

Deal found 14/5C$ 236

Fri 25/78:15 a.m.YYZ - ORD

Nonstop1h 54mAir Canada

Sun 27/78:25 p.m.ORD - YYZ

Nonstop1h 45mAir Canada

Deal found 14/5C$ 244

Wed 23/77:00 a.m.YYZ - ORD

Nonstop1h 59mMultiple Airlines

Tue 29/710:40 a.m.ORD - YYZ

1 stop5h 49mMultiple Airlines

Deal found 13/5C$ 267

Mon 21/73:35 p.m.YTZ - MDW

Nonstop1h 49mAir Transat

Sat 26/79:40 a.m.MDW - YTZ

Nonstop1h 40mAir Transat

Deal found 14/5C$ 268

Thu 12/611:00 a.m.YYZ - ORD

Nonstop2h 01mUnited Airlines

Mon 16/69:14 p.m.ORD - YYZ

Nonstop1h 44mUnited Airlines

Deal found 14/5C$ 270

Thu 3/73:45 p.m.YYZ - ORD

1 stop9h 12mAmerican Airlines

Fri 11/78:45 p.m.ORD - YYZ

1 stop18h 49mAmerican Airlines

Deal found 14/5C$ 300

Wed 23/76:30 a.m.YYZ - MDW

1 stop6h 59mKLM

Tue 29/76:20 p.m.MDW - YYZ

1 stop3h 38mKLM

Deal found 14/5C$ 302

Mon 11/812:15 p.m.YYZ - MDW

1 stop7h 13mDelta

Wed 20/89:30 a.m.MDW - YYZ

1 stop4h 51mDelta

Deal found 13/5C$ 304

Fri 27/67:55 a.m.YTZ - MDW

Nonstop1h 50mPorter Airlines

Fri 4/79:40 a.m.MDW - YTZ

Nonstop1h 40mPorter Airlines

Deal found 13/5C$ 237

Sat 14/61:04 p.m.YYZ - MDW

1 stop5h 08mWestJet

Sat 14/67:21 p.m.MDW - YYZ

1 stop15h 34mWestJet

Deal found 14/5C$ 475

Sun 3/88:15 a.m.YYZ - ORD

Nonstop1h 54mAir Canada

Wed 6/88:25 p.m.ORD - YYZ

Nonstop1h 45mAir Canada

Deal found 13/5C$ 249

Fri 6/64:05 p.m.YTZ - MDW

Nonstop1h 49mPorter Airlines

Fri 13/69:40 a.m.MDW - YTZ

Nonstop1h 40mPorter Airlines

Deal found 14/5C$ 239

Direct flights from Toronto to Chicago
Explore direct flight options from Toronto to Chicago based on user searches, and compare prices and availability for your desired travel dates. Data last updated 14 May 2025.

Sat 28/67:55 a.m.YTZ - MDW

Nonstop1h 50mPorter Airlines

Sat 5/79:40 a.m.MDW - YTZ

Nonstop1h 40mPorter Airlines

Deal found 14/5C$ 236

Fri 27/67:55 a.m.YTZ - MDW

Nonstop1h 50mPorter Airlines

Fri 4/79:40 a.m.MDW - YTZ

Nonstop1h 40mPorter Airlines

Deal found 13/5C$ 237

Fri 6/64:05 p.m.YTZ - MDW

Nonstop1h 49mPorter Airlines

Fri 13/69:40 a.m.MDW - YTZ

Nonstop1h 40mPorter Airlines

Deal found 14/5C$ 239

Wed 11/67:55 a.m.YTZ - MDW

Nonstop1h 50mPorter Airlines

Sat 14/69:40 a.m.MDW - YTZ

Nonstop1h 42mPorter Airlines

Deal found 14/5C$ 240

Thu 12/67:55 a.m.YTZ - MDW

Nonstop1h 50mPorter Airlines

Mon 16/69:40 a.m.MDW - YTZ

Nonstop1h 40mPorter Airlines

Deal found 13/5C$ 242

Thu 12/67:55 a.m.YTZ - MDW

Nonstop1h 50mPorter Airlines

Sun 15/69:40 a.m.MDW - YTZ

Nonstop1h 42mPorter Airlines

Deal found 13/5C$ 243

Fri 25/78:15 a.m.YYZ - ORD

Nonstop1h 54mAir Canada

Sun 27/78:25 p.m.ORD - YYZ

Nonstop1h 45mAir Canada

Deal found 14/5C$ 244

Fri 27/64:05 p.m.YTZ - MDW

Nonstop1h 49mPorter Airlines

Sun 29/69:40 a.m.MDW - YTZ

Nonstop1h 42mPorter Airlines

Deal found 13/5C$ 244

Wed 25/67:55 a.m.YTZ - MDW

Nonstop1h 50mPorter Airlines

Wed 2/79:40 a.m.MDW - YTZ

Nonstop1h 42mPorter Airlines

Deal found 12/5C$ 246

Fri 1/87:55 a.m.YTZ - MDW

Nonstop1h 50mPorter Airlines

Sun 3/89:40 a.m.MDW - YTZ

Nonstop1h 40mPorter Airlines

Deal found 13/5C$ 247

Sun 3/88:15 a.m.YYZ - ORD

Nonstop1h 54mAir Canada

Wed 6/88:25 p.m.ORD - YYZ

Nonstop1h 45mAir Canada

Deal found 13/5C$ 249

Fri 1/87:55 a.m.YTZ - MDW

Nonstop1h 50mPorter Airlines

Sun 3/89:40 a.m.MDW - YTZ

Nonstop1h 40mPorter Airlines

Deal found 14/5C$ 249

Last-minute flights from Toronto to Chicago
Discover last-minute flight deals from Toronto to Chicago. Data last updated 14 May 2025 and is based on user searches.

Fri 23/57:55 a.m.YTZ - MDW

Nonstop1h 50mPorter Airlines

Sun 1/69:40 a.m.MDW - YTZ

Nonstop1h 42mPorter Airlines

Deal found 12/5C$ 377

Fri 23/57:55 a.m.YTZ - MDW

Nonstop1h 50mPorter Airlines

Fri 30/59:40 a.m.MDW - YTZ

Nonstop1h 42mPorter Airlines

Deal found 13/5C$ 383

Fri 23/57:55 a.m.YTZ - MDW

Nonstop1h 50mPorter Airlines

Mon 26/55:50 p.m.MDW - YTZ

Nonstop1h 42mPorter Airlines

Deal found 13/5C$ 427

Fri 23/57:55 a.m.YTZ - MDW

Nonstop1h 50mPorter Airlines

Mon 26/55:50 p.m.MDW - YTZ

Nonstop1h 42mPorter Airlines

Deal found 13/5C$ 432

Fri 23/57:00 a.m.YYZ - ORD

Nonstop1h 59mUnited Airlines

Mon 26/59:35 a.m.ORD - YYZ

Nonstop1h 40mUnited Airlines

Deal found 12/5C$ 443

Fri 23/59:00 p.m.YYZ - ORD

Nonstop2h 05mUnited Airlines

Fri 30/512:05 p.m.ORD - YYZ

1 stop5h 55mUnited Airlines

Deal found 13/5C$ 444

Sat 24/57:55 a.m.YTZ - MDW

Nonstop1h 50mPorter Airlines

Mon 26/59:40 a.m.MDW - YTZ

Nonstop1h 42mPorter Airlines

Deal found 12/5C$ 378

Sat 24/57:55 a.m.YTZ - MDW

Nonstop1h 50mPorter Airlines

Sat 31/59:40 a.m.MDW - YTZ

Nonstop1h 42mPorter Airlines

Deal found 14/5C$ 380

Sat 24/59:00 a.m.YYZ - ORD

Nonstop1h 59mAir Canada

Sat 31/57:04 a.m.ORD - YYZ

Nonstop1h 54mAir Canada

Deal found 14/5C$ 415

Sat 24/57:25 a.m.YTZ - ORD

1 stop4h 59mAir Canada

Sat 31/58:40 a.m.ORD - YTZ

1 stop5h 10mAir Canada

Deal found 14/5C$ 420

Sat 24/57:00 a.m.YYZ - ORD

1 stop5h 24mAir Canada

Wed 28/59:14 p.m.ORD - YYZ

Nonstop1h 44mAir Canada

Deal found 14/5C$ 422

Sat 24/56:15 a.m.YYZ - ORD

1 stop4h 37mAir Canada

Sat 31/510:40 a.m.ORD - YYZ

1 stop5h 48mAir Canada

Deal found 14/5C$ 429

One-way flights from Toronto to Chicago
Search for one-way flight options from Toronto to Chicago. Find affordable one-way fares based on user searches. Data last updated 14 May 2025.

Thu 5/611:35 a.m.YHM - ORD

1 stop4h 30mAir Canada

Deal found 14/5C$ 158

Thu 5/65:40 a.m.YHM - ORD

1 stop4h 30mAir Canada

Deal found 13/5C$ 161

Tue 3/66:15 a.m.YYZ - ORD

1 stop4h 37mAir Canada

Deal found 14/5C$ 165

Tue 1/73:35 p.m.YTZ - MDW

Nonstop1h 49mAir Transat

Deal found 13/5C$ 165

Thu 5/66:15 a.m.YYZ - ORD

1 stop4h 37mAir Canada

Deal found 14/5C$ 166

Fri 18/73:35 p.m.YTZ - MDW

Nonstop1h 49mAir Transat

Deal found 13/5C$ 166

Thu 5/66:15 a.m.YYZ - ORD

1 stop4h 37mAir Canada

Deal found 13/5C$ 168

Tue 27/57:55 a.m.YTZ - MDW

Nonstop1h 50mPorter Airlines

Deal found 13/5C$ 168

Mon 9/67:25 a.m.YTZ - ORD

1 stop4h 59mAir Canada

Deal found 14/5C$ 169

Mon 9/69:00 p.m.YYZ - ORD

Nonstop2h 05mAir Canada

Deal found 14/5C$ 170

Tue 12/86:15 a.m.YYZ - ORD

1 stop4h 37mAir Canada

Deal found 14/5C$ 172

Tue 27/53:35 p.m.YTZ - MDW

Nonstop1h 49mPorter Airlines

Deal found 13/5C$ 172

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Cheap flights from Toronto to Chicago – Compare and Save

Find flight deals from Toronto to Chicago

Cheapest flights from Toronto to ChicagoExplore the most affordable flight options available from Toronto to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 14 May 2025.

Explore the most affordable flight options available from Toronto to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 14 May 2025.

100% Free

Book with Flexibility

Travel Smart

Cheapest flights from Toronto to Chicago
Explore the most affordable flight options available from Toronto to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 14 May 2025.