Meet in the middle between Toronto and Chicago

Cheapest 15 destinations to meet between Toronto and Chicago

Meet in the middle flights
  • $246.82 to Thunder Bay, Canada

    Total for 2 peoplereturn flightsquoted 22 days ago
    FromPrice
    Toronto$521 person
    Chicago$1961 person
  • $302.67 to Toronto, Canada

    Total for 2 peoplereturn flightsquoted 22 days ago
    FromPrice
    Chicago$3031 person
    TorontoFree1 person
  • $354.98 to Halifax, Canada

    Total for 2 peoplereturn flightsquoted 28 days ago
    FromPrice
    Toronto$651 person
    Chicago$2901 person
  • $440.47 to Boston, United States

    Total for 2 peoplereturn flightsquoted 21 days ago
    FromPrice
    Toronto$2331 person
    Chicago$2081 person
  • $504.24 to Montreal, Canada

    Total for 2 peoplereturn flightsquoted 22 days ago
    FromPrice
    Toronto$2411 person
    Chicago$2651 person
  • $510.69 to Fort Lauderdale, United States

    Total for 2 peoplereturn flightsquoted 22 days ago
    FromPrice
    Toronto$2531 person
    Chicago$2581 person
  • $525.50 to Orlando, United States

    Total for 2 peoplereturn flightsquoted 28 days ago
    FromPrice
    Toronto$2951 person
    Chicago$2321 person
  • $575.64 to Las Vegas, United States

    Total for 2 peoplereturn flightsquoted 21 days ago
    FromPrice
    Toronto$3131 person
    Chicago$2641 person
  • $691.65 to Phoenix, United States

    Total for 2 peoplereturn flightsquoted 22 days ago
    FromPrice
    Toronto$4391 person
    Chicago$2541 person
  • $729.43 to Vancouver, Canada

    Total for 2 peoplereturn flightsquoted 28 days ago
    FromPrice
    Toronto$2311 person
    Chicago$4991 person
  • $806.27 to San Juan, Puerto Rico

    Total for 2 peoplereturn flightsquoted 21 days ago
    FromPrice
    Toronto$4591 person
    Chicago$3481 person
  • $821.3 to Cancun, Mexico

    Total for 2 peoplereturn flightsquoted 21 days ago
    FromPrice
    Toronto$4161 person
    Chicago$4061 person
  • $861.90 to Montego Bay, Jamaica

    Total for 2 peoplereturn flightsquoted 22 days ago
    FromPrice
    Toronto$4221 person
    Chicago$4411 person
  • $871.85 to Punta Cana, Dominican Republic

    Total for 2 peoplereturn flightsquoted 21 days ago
    FromPrice
    Toronto$4571 person
    Chicago$4161 person
  • $920.37 to Toronto, Canada

    Total for 2 peoplereturn flightsquoted 22 days ago
    FromPrice
    Toronto$6181 person
    Chicago$3031 person
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