Meet in the middle between Chicago and Portland

Cheapest 15 destinations to meet between Chicago and Portland

Meet in the middle flights
  • $108.32 to Las Vegas, United States

    Total for 2 peoplereturn flightsquoted 2 days ago
    FromPrice
    Chicago$491 person
    Portland$611 person
  • $455.96 to Guadalajara, Mexico

    Total for 2 peoplereturn flightsquoted 16 days ago
    FromPrice
    Chicago$2111 person
    Portland$2461 person
  • $656.95 to Cancun, Mexico

    Total for 2 peoplereturn flightsquoted 18 days ago
    FromPrice
    Chicago$2811 person
    Portland$3771 person
  • $756.36 to San Juan, Puerto Rico

    Total for 2 peoplereturn flightsquoted 13 days ago
    FromPrice
    Chicago$2991 person
    Portland$4581 person
  • $853.80 to Bogota, Colombia

    Total for 2 peoplereturn flightsquoted 13 days ago
    FromPrice
    Chicago$2751 person
    Portland$5791 person
  • $867.58 to Havana, Cuba

    Total for 2 peoplereturn flightsquoted 13 days ago
    FromPrice
    Chicago$3881 person
    Portland$4801 person
  • $949.17 to Guatemala City, Guatemala

    Total for 2 peoplereturn flightsquoted 13 days ago
    FromPrice
    Chicago$3211 person
    Portland$6291 person
  • $988.76 to Lima, Peru

    Total for 2 peoplereturn flightsquoted 13 days ago
    FromPrice
    Chicago$4221 person
    Portland$5681 person
  • $989.3 to Santo Domingo, Dominican Republic

    Total for 2 peoplereturn flightsquoted 11 days ago
    FromPrice
    Chicago$5631 person
    Portland$4271 person
  • $991.68 to Montego Bay, Jamaica

    Total for 2 peoplereturn flightsquoted 13 days ago
    FromPrice
    Chicago$5001 person
    Portland$4931 person
  • $994.48 to Managua, Nicaragua

    Total for 2 peoplereturn flightsquoted 13 days ago
    FromPrice
    Chicago$4461 person
    Portland$5491 person
  • $1,010.99 to Guayaquil, Ecuador

    Total for 2 peoplereturn flightsquoted 15 days ago
    FromPrice
    Chicago$4651 person
    Portland$5471 person
  • $1,020.1 to San Jose, Costa Rica

    Total for 2 peoplereturn flightsquoted 13 days ago
    FromPrice
    Chicago$4641 person
    Portland$5571 person
  • $1,047.74 to Reykjavik, Iceland

    Total for 2 peoplereturn flightsquoted 13 days ago
    FromPrice
    Chicago$4561 person
    Portland$5931 person
  • $1,054.61 to Port Of Spain, Trinidad and Tobago

    Total for 2 peoplereturn flightsquoted 15 days ago
    FromPrice
    Chicago$5051 person
    Portland$5501 person
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