Meet in the middle between Toronto and Chicago

Cheapest 15 destinations to meet between Toronto and Chicago

Meet in the middle flights
  • $224.92 to Toronto, Canada

    Total for 2 peoplereturn flightsquoted 8 days ago
    FromPrice
    Chicago$2251 person
    TorontoFree1 person
  • $508.70 to Cancun, Mexico

    Total for 2 peoplereturn flightsquoted 6 days ago
    FromPrice
    Toronto$2461 person
    Chicago$2641 person
  • $567.65 to Guatemala City, Guatemala

    Total for 2 peoplereturn flightsquoted 6 days ago
    FromPrice
    Toronto$2481 person
    Chicago$3201 person
  • $644.32 to San Salvador, El Salvador

    Total for 2 peoplereturn flightsquoted 6 days ago
    FromPrice
    Toronto$3401 person
    Chicago$3051 person
  • $680.96 to San Juan, Puerto Rico

    Total for 2 peoplereturn flightsquoted 6 days ago
    FromPrice
    Toronto$3991 person
    Chicago$2831 person
  • $726.5 to Havana, Cuba

    Total for 2 peoplereturn flightsquoted 6 days ago
    FromPrice
    Toronto$3511 person
    Chicago$3761 person
  • $807.74 to Managua, Nicaragua

    Total for 2 peoplereturn flightsquoted 8 days ago
    FromPrice
    Toronto$3711 person
    Chicago$4371 person
  • $810.43 to San Jose, Costa Rica

    Total for 2 peoplereturn flightsquoted 6 days ago
    FromPrice
    Toronto$3491 person
    Chicago$4631 person
  • $830.53 to Paris, France

    Total for 2 peoplereturn flightsquoted 8 days ago
    FromPrice
    Toronto$4131 person
    Chicago$4181 person
  • $835.43 to Port Of Spain, Trinidad and Tobago

    Total for 2 peoplereturn flightsquoted 6 days ago
    FromPrice
    Toronto$3411 person
    Chicago$4951 person
  • $855.49 to Providenciales, Turks and Caicos Islands

    Total for 2 peoplereturn flightsquoted 7 days ago
    FromPrice
    Toronto$3801 person
    Chicago$4761 person
  • $857.14 to Nassau, Bahamas

    Total for 2 peoplereturn flightsquoted 6 days ago
    FromPrice
    Toronto$3621 person
    Chicago$4961 person
  • $862.64 to Rio De Janeiro, Brazil

    Total for 2 peoplereturn flightsquoted 6 days ago
    FromPrice
    Toronto$4111 person
    Chicago$4521 person
  • $878.62 to Oranjestad, Aruba

    Total for 2 peoplereturn flightsquoted 6 days ago
    FromPrice
    Toronto$3671 person
    Chicago$5131 person
  • $900 to Hamilton, Bermuda

    Total for 2 peoplereturn flightsquoted 6 days ago
    FromPrice
    Toronto$4511 person
    Chicago$4501 person
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