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Where to fly in May from Chicago

May: 13 destinations from Chicago, round trips from $348.

  1. Phoenix US · PHX95°F
    ✈ ≈3.5 h · direct
    round trip from $348Flights →
  2. Bangkok TH · BKK95°F
    ✈ ≈17.5 h · direct
    round trip from $973Flights →
  3. Punta Cana DO · PUJ88°F
    ✈ ≈4.5 h · direct · 🌊 beach
    round trip from $403Flights →
  4. Montego Bay JM · MBJ88°F
    ✈ ≈4 h · direct · 🌊 beach
    round trip from $456Flights →
  5. Tashkent UZ · TAS82°F
    ✈ ≈13.5 h · direct
    round trip from $930Flights →
  6. Antalya TR · AYT79°F
    ✈ ≈12 h · direct · 🌊 beach
    round trip from $987Flights →
  7. Madrid ES · MAD77°F
    ✈ ≈9 h · direct
    round trip from $643Flights →
  8. Rome IT · ROM75°F
    ✈ ≈10 h · direct
    round trip from $531Flights →
  9. Lisbon PT · LIS72°F
    ✈ ≈8.5 h · direct · 🌊 beach
    round trip from $969Flights →
  10. Almaty KZ · ALA72°F
    ✈ ≈13.5 h · direct
    round trip from $1,070Flights →
  11. Batumi GE · BUS68°F
    ✈ ≈12 h · direct · 🌊 beach
    round trip from $882Flights →
  12. Saint Petersburg RU · LED64°F
    ✈ ≈9.5 h · direct
    round trip from $1,780Flights →
  13. Moscow RU · MOW63°F
    ✈ ≈10.5 h · direct
    round trip from $1,670Flights →
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