Meet in the middle between Toronto and Chicago

Cheapest 15 destinations to meet between Toronto and Chicago

Meet in the middle flights
  • $226.23 to Toronto, Canada

    Total for 2 peoplereturn flightsquoted 20 days ago
    FromPrice
    Chicago$2271 person
    TorontoFree1 person
  • $525.3 to Cancun, Mexico

    Total for 2 peoplereturn flightsquoted 20 days ago
    FromPrice
    Toronto$2461 person
    Chicago$2811 person
  • $583.31 to Guatemala City, Guatemala

    Total for 2 peoplereturn flightsquoted 20 days ago
    FromPrice
    Toronto$2481 person
    Chicago$3361 person
  • $685.30 to San Salvador, El Salvador

    Total for 2 peoplereturn flightsquoted 20 days ago
    FromPrice
    Toronto$3401 person
    Chicago$3461 person
  • $706.99 to San Juan, Puerto Rico

    Total for 2 peoplereturn flightsquoted 19 days ago
    FromPrice
    Toronto$3991 person
    Chicago$3091 person
  • $788.30 to Havana, Cuba

    Total for 2 peoplereturn flightsquoted 20 days ago
    FromPrice
    Toronto$3511 person
    Chicago$4391 person
  • $824.68 to Managua, Nicaragua

    Total for 2 peoplereturn flightsquoted 20 days ago
    FromPrice
    Toronto$3711 person
    Chicago$4541 person
  • $828.2 to San Jose, Costa Rica

    Total for 2 peoplereturn flightsquoted 19 days ago
    FromPrice
    Toronto$3491 person
    Chicago$4811 person
  • $830.90 to Paris, France

    Total for 2 peoplereturn flightsquoted 19 days ago
    FromPrice
    Toronto$4131 person
    Chicago$4191 person
  • $853.99 to Providenciales, Turks and Caicos Islands

    Total for 2 peoplereturn flightsquoted 18 days ago
    FromPrice
    Toronto$3801 person
    Chicago$4751 person
  • $855.85 to Port Of Spain, Trinidad and Tobago

    Total for 2 peoplereturn flightsquoted 19 days ago
    FromPrice
    Toronto$3411 person
    Chicago$5161 person
  • $872.54 to Rio De Janeiro, Brazil

    Total for 2 peoplereturn flightsquoted 20 days ago
    FromPrice
    Toronto$4111 person
    Chicago$4621 person
  • $892.25 to Nassau, Bahamas

    Total for 2 peoplereturn flightsquoted 19 days ago
    FromPrice
    Toronto$3621 person
    Chicago$5311 person
  • $900.66 to Hamilton, Bermuda

    Total for 2 peoplereturn flightsquoted 20 days ago
    FromPrice
    Toronto$4511 person
    Chicago$4511 person
  • $908.2 to Oranjestad, Aruba

    Total for 2 peoplereturn flightsquoted 18 days ago
    FromPrice
    Toronto$3671 person
    Chicago$5421 person
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