Meet in the middle between New York and Chicago

Cheapest 15 destinations to meet between New York and Chicago

Meet in the middle flights
  • $388.53 to Quebec, Canada

    Total for 2 peoplereturn flightsquoted 15 days ago
    FromPrice
    New York$1661 person
    Chicago$2231 person
  • $397.33 to Toronto, Canada

    Total for 2 peoplereturn flightsquoted 15 days ago
    FromPrice
    New York$1731 person
    Chicago$2251 person
  • $498.56 to Cancun, Mexico

    Total for 2 peoplereturn flightsquoted 15 days ago
    FromPrice
    New York$2351 person
    Chicago$2641 person
  • $501.89 to San Juan, Puerto Rico

    Total for 2 peoplereturn flightsquoted 15 days ago
    FromPrice
    New York$2201 person
    Chicago$2831 person
  • $576.13 to Guadalajara, Mexico

    Total for 2 peoplereturn flightsquoted 20 days ago
    FromPrice
    New York$3661 person
    Chicago$2111 person
  • $598.35 to San Salvador, El Salvador

    Total for 2 peoplereturn flightsquoted 15 days ago
    FromPrice
    New York$2941 person
    Chicago$3051 person
  • $638.63 to St Croix Island, US Virgin Islands

    Total for 2 peoplereturn flightsquoted 22 days ago
    FromPrice
    New York$2601 person
    Chicago$3801 person
  • $645.9 to Guatemala City, Guatemala

    Total for 2 peoplereturn flightsquoted 16 days ago
    FromPrice
    New York$3261 person
    Chicago$3201 person
  • $652.33 to Santiago, Dominican Republic

    Total for 2 peoplereturn flightsquoted 22 days ago
    FromPrice
    New York$4161 person
    Chicago$2371 person
  • $683 to Punta Cana, Dominican Republic

    Total for 2 peoplereturn flightsquoted 15 days ago
    FromPrice
    New York$2831 person
    Chicago$4011 person
  • $740.96 to Bogota, Colombia

    Total for 2 peoplereturn flightsquoted 16 days ago
    FromPrice
    New York$4691 person
    Chicago$2731 person
  • $777.68 to Managua, Nicaragua

    Total for 2 peoplereturn flightsquoted 17 days ago
    FromPrice
    New York$3411 person
    Chicago$4371 person
  • $782.4 to Port Au Prince, Haiti

    Total for 2 peoplereturn flightsquoted 17 days ago
    FromPrice
    New York$4071 person
    Chicago$3761 person
  • $791.29 to San Jose, Costa Rica

    Total for 2 peoplereturn flightsquoted 15 days ago
    FromPrice
    New York$3291 person
    Chicago$4631 person
  • $793.10 to Hamilton, Bermuda

    Total for 2 peoplereturn flightsquoted 17 days ago
    FromPrice
    New York$3441 person
    Chicago$4501 person
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