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Where to fly in January from Chicago

January: 14 destinations from Chicago, round trips from $299.

  1. Ho Chi Minh City VN · SGN90°F
    ✈ ≈17.5 h · direct
    round trip from $879Flights →
  2. Phuket TH · HKT90°F
    ✈ ≈18 h · direct · 🌊 beach
    round trip from $974Flights →
  3. Manila PH · MNL86°F
    ✈ ≈16.5 h · direct · 🌊 beach
    round trip from $673Flights →
  4. Bali ID · DPS86°F
    ✈ ≈19.5 h · direct · 🌊 beach
    round trip from $1,150Flights →
  5. Cartagena CO · CTG84°F
    ✈ ≈5 h · direct · 🌊 beach
    round trip from $391Flights →
  6. Punta Cana DO · PUJ82°F
    ✈ ≈4.5 h · direct · 🌊 beach
    round trip from $514Flights →
  7. San Juan US · SJU82°F
    ✈ ≈4.5 h · direct · 🌊 beach
    round trip from $664Flights →
  8. Puerto Vallarta MX · PVR79°F
    ✈ ≈4 h · direct · 🌊 beach
    round trip from $401Flights →
  9. Cancún MX · CUN79°F
    ✈ ≈3.5 h · direct · 🌊 beach
    round trip from $567Flights →
  10. Honolulu US · HNL79°F
    ✈ ≈9 h · direct · 🌊 beach
    round trip from $692Flights →
  11. Miami US · MIA75°F
    ✈ ≈3 h · direct · 🌊 beach
    round trip from $299Flights →
  12. San José CR · SJO75°F
    ✈ ≈5 h · direct
    round trip from $567Flights →
  13. Dubai AE · DXB75°F
    ✈ ≈15 h · direct · 🌊 beach
    round trip from $885Flights →
  14. Sharjah AE · SHJ75°F
    ✈ ≈15 h · direct · 🌊 beach
    round trip from $1,080Flights →
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