Cheap flights from Chicago to Miami
The cheapest round trip from Chicago to Miami that travelers found recently is $209 with a carry-on: a $209 fare on JetBlue, which usually includes a carry-on. It leaves Sun, Jan 3 and comes back Sun, Jan 10.
Live prices for Sun, Jan 3 to Sun, Jan 10
Cheapest trips travelers found recently
| Leave | Return | Airline | Airports | Stops | Fare | Carry-on (est.) | Total | Live prices |
|---|---|---|---|---|---|---|---|---|
| Sun, Jan 3 | Sun, Jan 10 | JetBlue | ORD → FLL | Nonstop | $209 | Included | $209 | Live price |
| Fri, Nov 6 | Sun, Nov 8 | JetBlue | ORD → FLL | Nonstop | $228 | Included | $228 | Live price |
| Fri, Jan 1 | Fri, Jan 8 | JetBlue | ORD → FLL | Nonstop | $240 | Included | $240 | Live price |
| Sat, Jan 2 | Sat, Jan 9 | JetBlue | ORD → FLL | Nonstop | $247 | Included | $247 | Live price |
| Thu, Oct 15 | Tue, Oct 27 | Frontier | MDW → MIA | 1 stop | $145 | +$110 | $255 | Live price |
| Thu, Oct 15 | Wed, Oct 28 | Frontier | MDW → MIA | 1 stop | $145 | +$110 | $255 | Live price |
| Mon, Nov 9 | Mon, Nov 16 | Frontier | ORD → FLL | 1 stop | $161 | +$110 | $271 | Live price |
| Fri, Nov 20 | Sun, Nov 29 | Frontier | MDW → MIA | 1 stop | $183 | +$110 | $293 | Live price |
| Thu, Nov 19 | Mon, Nov 23 | Frontier | ORD → FLL | Nonstop | $198 | +$110 | $308 | Live price |
| Fri, Feb 26 | Tue, Mar 2 | Frontier | ORD → MIA | 1 stop | $211 | +$110 | $321 | Live price |
Round-trip prices per person, from real fares travelers found in the last few days. Carry-on fees are our estimate for each airline, both ways. Prices change fast: check the live price before you book.
Cheapest month to fly
| Month | Cheapest trip | From | Live prices |
|---|---|---|---|
| October 2026 | Thu, Oct 15 to Tue, Oct 27, 12 nights | $255 | Live price |
| November 2026 | Fri, Nov 6 to Sun, Nov 8, 2 nights | $228 | Live price |
| December 2026 | Fri, Dec 11 to Mon, Dec 14, 3 nights | $334 | Live price |
| January 2027 | Sun, Jan 3 to Sun, Jan 10, 7 nights | $209 | Live price |
| February 2027 | Fri, Feb 26 to Tue, Mar 2, 4 nights | $321 | Live price |
Bag fees on this route
What the airlines flying Chicago to Miami usually charge for one bag each way. Budget airlines often sell the cheapest fares and charge the most for bags, so compare the total, not the fare.
| Airline | Carry-on, each way | Checked bag, each way |
|---|---|---|
| Frontier | $55 | $50 |
| JetBlue | Included | $40 |
Our estimates: fees depend on the fare type and when you pay. Check the airline's own price when you book.
How these prices work
These are real round-trip fares that travelers found on Aviasales recently, not a live search, so they can change or sell out. Dipt adds an estimate of each airline's carry-on fee, so a cheap fare with expensive bags doesn't look cheaper than it is. "Live price" opens Dipt's live flight search for those dates, where you book with the airline or travel site you pick. Dipt may earn a commission when you book, at no extra cost to you (how Dipt makes money).
Not sure where to go? Tell Dipt your budget and vibe and it finds the trip.
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