Cheap flights from Miami to Chicago
The cheapest round trip from Miami to Chicago that travelers found recently is $335 with a carry-on: a $225 fare on Frontier plus about $110 for a carry-on both ways. It leaves Sun, Oct 25 and comes back Fri, Oct 30.
Live prices for Sun, Oct 25 to Fri, Oct 30
Cheapest trips travelers found recently
| Leave | Return | Airline | Airports | Stops | Fare | Carry-on (est.) | Total | Live prices |
|---|---|---|---|---|---|---|---|---|
| Sun, Oct 25 | Fri, Oct 30 | Frontier | MIA → MDW | 1 stop | $225 | +$110 | $335 | Live price |
| Fri, Oct 16 | Sat, Oct 17 | Frontier | FLL → ORD | Nonstop | $269 | +$110 | $379 | Live price |
| Tue, Nov 24 | Sun, Nov 29 | Frontier | FLL → ORD | Nonstop | $304 | +$110 | $414 | Live price |
| Thu, Oct 22 | Sat, Oct 24 | Frontier | MIA → MDW | 1 stop | $316 | +$110 | $426 | Live price |
| Thu, Oct 15 | Sat, Oct 17 | Frontier | FLL → ORD | Nonstop | $323 | +$110 | $433 | Live price |
| Fri, Oct 16 | Sun, Oct 18 | Frontier | MIA → MDW | 1 stop | $330 | +$110 | $440 | 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 | Sun, Oct 25 to Fri, Oct 30, 5 nights | $335 | Live price |
| November 2026 | Tue, Nov 24 to Sun, Nov 29, 5 nights | $414 | Live price |
Bag fees on this route
What the airlines flying Miami to Chicago 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 |
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).
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