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Departures

Cheap flights from Chicago

The lowest fares found recently to 24 destinations, from $82 return. Pick a place, or let the map and the months below show you where to go.

  • ORDO'Hare
  • MDWMidway
DestinationDatesFrom
ATLAtlanta Thu 12 Nov – Tue 17 Nov $82 LASLas Vegas Sat 12 Dec – Sun 13 Dec $129 TPATPA Wed 2 Dec – Wed 16 Dec $130 ORLOrlando Mon 16 Nov – Mon 23 Nov $145 WASWashington Fri 27 Nov – Sun 29 Nov $154 PHLPHL Fri 15 Jan – Mon 18 Jan $163

Lowest fares found recently · return

Month by month

The cheapest place to fly from Chicago each month

  1. Oct2026 FLL from $31
  2. Nov2026 FLL from $42
  3. Dec2026 FLL from $44
  4. Jan2027 FLL from $65
  5. Feb2027 FLL from $112
  6. Mar2027 TPA from $89
  7. Apr2027 FLL from $43
  8. May2027 Las Vegas from $153
  9. Jun2027 Atlanta from $164

Map

Where you can fly from Chicago

Chicago

Tap a price to see the fare. Map: Natural Earth · Places: GeoNames (CC BY 4.0)

All destinations from Chicago

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Central America & Caribbean

North America

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Long weekends

Your next breaks

See every long weekend
  • 7NovTake 2 days off, get 5 days awayVeterans DayFind flights
  • 26NovTake 1 day off, get 4 days awayThanksgiving DayFind flights
  • 25Dec3 days off without taking leaveChristmas DayFind flights

FAQ

Flying from Chicago

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Help center Contact us
01Where can I fly cheaply from Chicago?

Among recently found fares from Chicago, Atlanta is the cheapest at $82 return. Other low fares include Las Vegas ($129), TPA ($130), Orlando ($145). Prices change often, so check live prices for your dates.

02Which airports can I fly from in Chicago?

Searching from Chicago compares O'Hare (ORD), Midway (MDW) at once, so you see the cheapest airport automatically.

03Are these prices final?

No. They are the lowest fares found recently. When you open a deal, the partner shows the live price, including taxes and fees, before you pay.

04Can I get cheap flights from Chicago by email?

Yes. Subscribe to the deals email and choose this city, or set a price alert on a route you like.