Travel options for:
Toronto to Chicago
  • Fly Toronto Island to Chicago Midway

    $105 - $365
    1. Toronto

      11 min - every 10 minutes - line 509

      $3

    2. Toronto Island (YTZ)

      1 h 45 min - non-stop

      $100 - $360

    3. Chicago Midway (MDW)

      24 min - every 15 minutes

      $3

      • Chicago
  • Fly Toronto to Chicago O'Hare

    $111 - $352
    1. Toronto

      25 min - every 10 minutes

    2. Toronto (YYZ)

      1 h 42 min - non-stop

      $100 - $350

    3. Chicago O'Hare (ORD)

      42 min - every 10 minutes

      $3

      • Chicago
  • Bus to Buffalo, fly to Chicago Midway

    $147 - $448
    1. Toronto

      2 h 40 min - 3 times a day

      $11 - $21

    2. Buffalo, NY

      15 min - 4 times a day

      $2 - $24

    3. Buffalo (BUF)

      1 h 35 min - non-stop

      $130 - $400

    4. Chicago Midway (MDW)

      24 min - every 15 minutes

      $3

      • Chicago
  • Bus to Buffalo, fly to Chicago O'Hare

    $137 - $418
    1. Toronto

      2 h 40 min - 3 times a day

      $11 - $21

    2. Buffalo, NY

      15 min - 4 times a day

      $2 - $24

    3. Buffalo (BUF)

      1 h 43 min - non-stop

      $120 - $370

    4. Chicago O'Hare (ORD)

      42 min - every 10 minutes

      $3

      • Chicago
  • Train

    $106 - $207
    1. Toronto

      4 h 15 min - hourly

      $55 - $75

    2. Windsor

      10 min - 7.5 miles

      $1 - $2

    3. Detroit Amtrak

      5 h 18 min - once daily

      $50 - $130

      • Chicago Union Station Amtrak
  • Bus

    $45 - $120
    1. Toronto, ON

      10 h 45 min - once daily

      $45 - $120

      • Chicago, IL
  • Drive

    $65 - $100
    1. Toronto

      8 h 50 min - 522 miles

      $65 - $100

      • Chicago
  • Accommodation
  • Best Price Guarantee
  • Car Hire
  • Compare Best Rates
  • Things to do
  • View attractions

From Union Station line 509 tram to Toronto Island airport, fly to Chicago Midway airport, then subway to Chicago. 4 h 25 min $175. From UP Express Union Station train to Toronto airport, fly to Chicago O'Hare airport, then subway to Chicago. 4 h 53 min $168. From Toronto, ON bus to Buffalo, NY, bus to Buffalo airport, fly to Chicago Midway airport, then subway to Chicago. 6 h 27 min $223. From Toronto, ON bus to Buffalo, NY, bus to Buffalo airport, fly to Chicago O'Hare airport, then subway to Chicago. 6 h 52 min $203. From Toronto train to Windsor, drive to Detroit Amtrak, then train to Chicago Union Station Amtrak. 10 h 43 min $161. From Toronto, ON bus to Chicago, IL. 10 h 45 min $82. From Toronto drive to Chicago. 8 h 50 min $84.