Meet in the middle between Toronto and Chicago

Cheapest 15 destinations to meet between Toronto and Chicago

Meet in the middle flights
  • $264.76 to Thunder Bay, Canada

    Total for 2 peoplereturn flightsquoted 20 days ago
    FromPrice
    Toronto$701 person
    Chicago$1961 person
  • $297.60 to Toronto, Canada

    Total for 2 peoplereturn flightsquoted 2 days ago
    FromPrice
    Chicago$2981 person
    TorontoFree1 person
  • $354.98 to Halifax, Canada

    Total for 2 peoplereturn flightsquoted 10 days ago
    FromPrice
    Toronto$651 person
    Chicago$2901 person
  • $399.60 to Boston, United States

    Total for 2 peoplereturn flightsquoted 9 days ago
    FromPrice
    Toronto$1711 person
    Chicago$2291 person
  • $505.30 to Abbotsford, Canada

    Total for 2 peoplereturn flightsquoted 7 days ago
    FromPrice
    Toronto$1991 person
    Chicago$3071 person
  • $511.71 to Fort Lauderdale, United States

    Total for 2 peoplereturn flightsquoted 17 days ago
    FromPrice
    Toronto$2981 person
    Chicago$2141 person
  • $545.85 to Orlando, United States

    Total for 2 peoplereturn flightsquoted 13 days ago
    FromPrice
    Toronto$3261 person
    Chicago$2211 person
  • $597.83 to Montreal, Canada

    Total for 2 peoplereturn flightsquoted 3 days ago
    FromPrice
    Toronto$3161 person
    Chicago$2831 person
  • $708.12 to Aguadilla, Puerto Rico

    Total for 2 peoplereturn flightsquoted 12 days ago
    FromPrice
    Toronto$3351 person
    Chicago$3741 person
  • $794.26 to Vancouver, Canada

    Total for 2 peoplereturn flightsquoted 6 days ago
    FromPrice
    Toronto$3181 person
    Chicago$4771 person
  • $800.26 to Cancun, Mexico

    Total for 2 peoplereturn flightsquoted 2 days ago
    FromPrice
    Toronto$3961 person
    Chicago$4051 person
  • $841.7 to San Juan, Puerto Rico

    Total for 2 peoplereturn flightsquoted 2 days ago
    FromPrice
    Toronto$5241 person
    Chicago$3181 person
  • $889.85 to St Croix Island, US Virgin Islands

    Total for 2 peoplereturn flightsquoted 24 days ago
    FromPrice
    Toronto$3731 person
    Chicago$5171 person
  • $907.79 to Cartagena, Colombia

    Total for 2 peoplereturn flightsquoted 4 days ago
    FromPrice
    Toronto$4521 person
    Chicago$4571 person
  • $941.68 to Guatemala City, Guatemala

    Total for 2 peoplereturn flightsquoted 2 days ago
    FromPrice
    Toronto$4191 person
    Chicago$5241 person
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