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Where to fly in October from Chicago

October: 14 destinations from Chicago, round trips from $186.

  1. Dubai AE · DXB93°F
    ✈ ≈15 h · direct · 🌊 beach
    round trip from $540Flights →
  2. Sharjah AE · SHJ93°F
    ✈ ≈15 h · direct · 🌊 beach
    round trip from $834Flights →
  3. Phoenix US · PHX91°F
    ✈ ≈3.5 h · direct
    round trip from $237Flights →
  4. Bangkok TH · BKK90°F
    ✈ ≈17.5 h · direct
    round trip from $779Flights →
  5. Los Cabos MX · SJD88°F
    ✈ ≈4.5 h · direct · 🌊 beach
    round trip from $357Flights →
  6. Manila PH · MNL88°F
    ✈ ≈16.5 h · direct · 🌊 beach
    round trip from $675Flights →
  7. Cairo EG · CAI86°F
    ✈ ≈12.5 h · direct
    round trip from $639Flights →
  8. Miami US · MIA84°F
    ✈ ≈3 h · direct · 🌊 beach
    round trip from $186Flights →
  9. Las Vegas US · LAS84°F
    ✈ ≈3.5 h · direct
    round trip from $198Flights →
  10. Da Nang VN · DAD84°F
    ✈ ≈17 h · direct · 🌊 beach
    round trip from $1,180Flights →
  11. Seychelles SC · SEZ84°F
    ✈ ≈18 h · direct · 🌊 beach
    round trip from $1,450Flights →
  12. Los Angeles US · LAX82°F
    ✈ ≈4 h · direct · 🌊 beach
    round trip from $199Flights →
  13. Guadalajara MX · GDL81°F
    ✈ ≈4 h · direct
    round trip from $335Flights →
  14. New Orleans US · MSY79°F
    ✈ ≈2.5 h · direct
    round trip from $273Flights →
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