Meet in the middle between Toronto and Chicago

Cheapest 15 destinations to meet between Toronto and Chicago

Meet in the middle flights
  • $226.37 to Toronto, Canada

    Total for 2 peoplereturn flightsquoted 10 days ago
    FromPrice
    Chicago$2271 person
    TorontoFree1 person
  • $614.77 to Cancun, Mexico

    Total for 2 peoplereturn flightsquoted 13 days ago
    FromPrice
    Toronto$3521 person
    Chicago$2641 person
  • $660.74 to Guatemala City, Guatemala

    Total for 2 peoplereturn flightsquoted 11 days ago
    FromPrice
    Toronto$3421 person
    Chicago$3201 person
  • $695.55 to San Juan, Puerto Rico

    Total for 2 peoplereturn flightsquoted 10 days ago
    FromPrice
    Toronto$4141 person
    Chicago$2821 person
  • $700.27 to San Salvador, El Salvador

    Total for 2 peoplereturn flightsquoted 11 days ago
    FromPrice
    Toronto$3981 person
    Chicago$3041 person
  • $749.4 to Havana, Cuba

    Total for 2 peoplereturn flightsquoted 11 days ago
    FromPrice
    Toronto$3731 person
    Chicago$3771 person
  • $791.66 to Managua, Nicaragua

    Total for 2 peoplereturn flightsquoted 11 days ago
    FromPrice
    Toronto$3591 person
    Chicago$4341 person
  • $813.34 to Toronto, Canada

    Total for 2 peoplereturn flightsquoted 10 days ago
    FromPrice
    Toronto$5871 person
    Chicago$2271 person
  • $848.58 to Port Of Spain, Trinidad and Tobago

    Total for 2 peoplereturn flightsquoted 12 days ago
    FromPrice
    Toronto$3581 person
    Chicago$4921 person
  • $856.26 to San Jose, Costa Rica

    Total for 2 peoplereturn flightsquoted 10 days ago
    FromPrice
    Toronto$3961 person
    Chicago$4621 person
  • $862.64 to Rio De Janeiro, Brazil

    Total for 2 peoplereturn flightsquoted 15 days ago
    FromPrice
    Toronto$4111 person
    Chicago$4521 person
  • $913.2 to London, United Kingdom

    Total for 2 peoplereturn flightsquoted 14 days ago
    FromPrice
    Toronto$4761 person
    Chicago$4381 person
  • $915.89 to Providenciales, Turks and Caicos Islands

    Total for 2 peoplereturn flightsquoted 11 days ago
    FromPrice
    Toronto$4421 person
    Chicago$4751 person
  • $919.72 to San Pedro Sula, Honduras

    Total for 2 peoplereturn flightsquoted 10 days ago
    FromPrice
    Toronto$4651 person
    Chicago$4561 person
  • $938.10 to Philipsburg, St Maarten

    Total for 2 peoplereturn flightsquoted 12 days ago
    FromPrice
    Toronto$4221 person
    Chicago$5171 person
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