Cheap flights from Chicago
The cheapest round trips from Chicago right now are Miami ($107), Orlando ($138), and Los Angeles ($147). We check fares from ORD twice a day.
Join to get alerts- Airports we check
- ORD
- Destinations priced
- 27 destinations
- Cheapest today
- Miami · $107
- Updated
- November 11, 2026
Flying from Chicago
Chicago O'Hare is a hub for United and American, with nonstop flights to Europe, Asia and Latin America, and Midway is busy with low-cost flights. Being in the middle of the country makes both coasts easy to reach.
Cheapest destinations from Chicago
Cheapest round trip per city, from fares seen on November 11, 2026.
The cheapest trip for each month
The lowest round trip from Chicago by departure month.
Questions about flights from Chicago
What is the cheapest place to fly from Chicago?
Miami, from $107 round trip for travel in December 2026. Next are Orlando ($138) and Los Angeles ($147).
What is the cheapest month to fly from Chicago?
December 2026: that's when we found the lowest fare, $107 round trip to Miami.
Which cheap flights from Chicago are nonstop?
Among the cheapest fares we found, these were nonstop: Miami ($107), Los Angeles ($147), Las Vegas ($167), New York ($182), San Juan ($211), and Mexico City ($240).
Fares like these don't wait
Members get an alert when a fare from their city drops far below normal, with the dates and a link to book.
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Fares are the cheapest round trips we found for these routes, checked once a day. Prices change fast, so always check the final price before you book.