Travel options for:
Winnipeg to Chicago
  • Fly to Chicago O'Hare

    $205 - $488
    1. Winnipeg

      21 min - hourly - line 15

      $3

    2. Winnipeg (YWG)

      2 h 25 min - non-stop

      $200 - $480

    3. Chicago O'Hare (ORD)

      42 min - every 10 minutes

      $2 - $5

  • Fly to Chicago Midway

    $215 - $477
    1. Winnipeg

      21 min - hourly - line 15

      $3

    2. Winnipeg (YWG)

      4 h 10 min - 1 stopover

      $210 - $470

    3. Chicago Midway (MDW)

      24 min - every 15 minutes

      $2 - $4

  • Fly to South Bend, train

    $224 - $1,618
    1. Winnipeg

      21 min - hourly - line 15

      $3

    2. Winnipeg (YWG)

      4 h 23 min - 1 stopover

      $210 - $1,600

    3. South Bend (SBN)

      2 h 26 min - hourly

      $11 - $15

  • Bus, Amtrak Thruway

    1. Southbound Memorial at

      32 min - hourly - line 20

      $3

    2. Westbound Wellington at

      6 min - 1797 feet

    3. Winnipeg, MB

      21 h 50 min - once daily

      $75 - $180

    4. Sault Ste Marie, ON

      12 min - 9.4 miles

      $1 - $2

    5. Sault Ste. Marie, MI

      7 h 53 min - once daily

    6. Rockford, MI

      23 min - once daily - line 81

      $2 - $5

    7. Grand Rapids, MI

      3 h 2 min - once daily

      $35 - $65

  • Bus

    $158 - $383
    1. Northbound Vaughan at Portage

      21 min - hourly - line 15

      $3

    2. Westbound Wellington at

      6 min - 1883 feet

    3. Winnipeg, MB

      30 h 30 min - once daily

      $110 - $260

    4. Toronto, ON

      10 h 45 min - once daily

      $45 - $120

  • Train via Detroit Amtrak

    $306 - $486
    1. Winnipeg

      35 h 39 min - 3 times a week

      $200 - $280

    2. Toronto

      4 h 9 min - hourly

      $50 - $75

    3. Windsor

      10 min - 7.5 miles

      $1 - $2

    4. Detroit Amtrak

      5 h 18 min - once daily

      $50 - $130

  • Train

    $315 - $554
    1. Winnipeg

      37 h 55 min - 3 times a week

      $200 - $280

    2. Toronto

      5 h 11 min - every 3 hours

      $35 - $55

    3. Buffalo Depew Station Amtrak

      10 h 46 min - once daily

      $75 - $220

  • Drive

    $110 - $170
    1. Winnipeg

      14 h 33 min - 868.7 miles

      $110 - $170

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From Northbound Vaughan at Portage North line 15 bus to Winnipeg airport, fly to Chicago O'Hare airport, then subway to Chicago. 5 h 32 min $267. From Northbound Vaughan at Portage North line 15 bus to Winnipeg airport, fly to Chicago Midway airport, then subway to Chicago. 7 h $266. From Northbound Vaughan at Portage North line 15 bus to Winnipeg airport, fly to South Bend airport, then train to Chicago. 9 h 26 min $715. From Southbound Memorial at Broadway line 20 bus to Westbound Wellington at Airport Terminal, walk to Winnipeg, MB, bus to Sault Ste Marie, ON, drive to Sault Ste. Marie, MI, Amtrak Thruway to Rockford, MI, line 81 bus to Grand Rapids, MI, then bus to Chicago, IL. 37 h 59 min. From Northbound Vaughan at Portage North line 15 bus to Westbound Wellington at Airport Terminal, walk to Winnipeg, MB, bus to Toronto, ON, then bus to Chicago, IL. 43 h 42 min $262. From Winnipeg train to Toronto, train to Windsor, drive to Detroit Amtrak, then train to Chicago Union Station Amtrak. 46 h 35 min $403. From Winnipeg train to Toronto, train to Buffalo Depew Station Amtrak, then train to Chicago Union Station Amtrak. 2 days 7 h $447. From Winnipeg drive to Chicago. 14 h 33 min $140.