Meet in the middle between Toronto and Chicago

Cheapest 15 destinations to meet between Toronto and Chicago

Meet in the middle flights
  • $271.18 to Thunder Bay, Canada

    Total for 2 peoplereturn flightsquoted 2 days ago
    FromPrice
    Toronto$761 person
    Chicago$1961 person
  • $314.19 to Toronto, Canada

    Total for 2 peoplereturn flightsquoted 14 days ago
    FromPrice
    Chicago$3151 person
    TorontoFree1 person
  • $488.6 to Fort Lauderdale, United States

    Total for 2 peoplereturn flightsquoted 5 days ago
    FromPrice
    Toronto$1491 person
    Chicago$3401 person
  • $516.4 to Abbotsford, Canada

    Total for 2 peoplereturn flightsquoted 2 days ago
    FromPrice
    Toronto$2391 person
    Chicago$2781 person
  • $632.22 to Cancun, Mexico

    Total for 2 peoplereturn flightsquoted 2 days ago
    FromPrice
    Toronto$3471 person
    Chicago$2861 person
  • $655.78 to Guatemala City, Guatemala

    Total for 2 peoplereturn flightsquoted 2 days ago
    FromPrice
    Toronto$3161 person
    Chicago$3411 person
  • $667.53 to San Juan, Puerto Rico

    Total for 2 peoplereturn flightsquoted 2 days ago
    FromPrice
    Toronto$3921 person
    Chicago$2761 person
  • $729.31 to San Salvador, El Salvador

    Total for 2 peoplereturn flightsquoted 3 days ago
    FromPrice
    Toronto$4131 person
    Chicago$3181 person
  • $786.67 to Havana, Cuba

    Total for 2 peoplereturn flightsquoted 3 days ago
    FromPrice
    Toronto$4061 person
    Chicago$3811 person
  • $799.87 to Bogota, Colombia

    Total for 2 peoplereturn flightsquoted 3 days ago
    FromPrice
    Toronto$4831 person
    Chicago$3181 person
  • $806.78 to Managua, Nicaragua

    Total for 2 peoplereturn flightsquoted 15 days ago
    FromPrice
    Toronto$3521 person
    Chicago$4551 person
  • $813.60 to San Pedro Sula, Honduras

    Total for 2 peoplereturn flightsquoted 4 days ago
    FromPrice
    Toronto$3971 person
    Chicago$4181 person
  • $870.96 to Santo Domingo, Dominican Republic

    Total for 2 peoplereturn flightsquoted 3 days ago
    FromPrice
    Toronto$4221 person
    Chicago$4501 person
  • $884.73 to Port Of Spain, Trinidad and Tobago

    Total for 2 peoplereturn flightsquoted 2 days ago
    FromPrice
    Toronto$4071 person
    Chicago$4781 person
  • $901.17 to Toronto, Canada

    Total for 2 peoplereturn flightsquoted 14 days ago
    FromPrice
    Toronto$5871 person
    Chicago$3151 person
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