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Where to fly in January from Chicago

January: 12 destinations from Chicago, round trips from $369.

  1. Phuket TH · HKT90°F
    ✈ ≈18 h · direct · 🌊 beach
    round trip from $1,050Flights →
  2. Kuala Lumpur MY · KUL90°F
    ✈ ≈18.5 h · direct
    round trip from $1,190Flights →
  3. Cancún MX · CUN79°F
    ✈ ≈3.5 h · direct · 🌊 beach
    round trip from $400Flights →
  4. Honolulu US · HNL79°F
    ✈ ≈9 h · direct · 🌊 beach
    round trip from $532Flights →
  5. Kolkata IN · CCU79°F
    ✈ ≈16 h · direct
    round trip from $1,250Flights →
  6. San José CR · SJO77°F
    ✈ ≈5 h · direct
    round trip from $369Flights →
  7. Da Nang VN · DAD77°F
    ✈ ≈17 h · direct · 🌊 beach
    round trip from $1,640Flights →
  8. Málaga ES · AGP59°F
    ✈ ≈9 h · direct · 🌊 beach
    round trip from $707Flights →
  9. Madrid ES · MAD50°F
    ✈ ≈9 h · direct
    round trip from $542Flights →
  10. Milan IT · MIL45°F
    ✈ ≈9.5 h · direct
    round trip from $640Flights →
  11. Tashkent UZ · TAS45°F
    ✈ ≈13.5 h · direct
    round trip from $863Flights →
  12. Anchorage US · ANC21°F
    ✈ ≈6.5 h · direct
    round trip from $409Flights →
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