Cheap flights from Chicago to Miami from $86 MDW, ORD, RFD → MIA

Found recently, and the cheapest we hold

What have prices looked like?

Over 49 days, 24 Sept to 11 Nov, the cheapest return we saw each day was $117 to $252.

Those were the prices on those days, not today's.

Could nearby dates be cheaper?

We hold no other 3-night return fares leaving within 3 days of 12 Dec to compare.

Every date we hold

339 fares on 24 departure dates

Which month looks cheapest?

December 2026 is the cheapest month — from $138.

Found recently, and the cheapest we hold

What have prices looked like?

Over 49 days, 24 Sept to 11 Nov, the cheapest one-way we saw each day was $69 to $118.

Those were the prices on those days, not today's.

Could nearby dates be cheaper?

No. We hold one-way fares on 1 other departure date within 3 days of 5 Dec, and it is not cheaper.

Every date we hold

92 fares on 23 departure dates

Which month looks cheapest?

January 2027 is the cheapest month — from $85.

Return

Fares 30 to 59 days before departure were typically 42% lower than 0 to 6 days before departure.

From the cheapest return each day between 24 Sept and 11 Nov (49 days), grouped by how many days ahead the flight left; one adult in economy.

Each range covers different departure dates, so this compares typical fares, not the same trip priced twice.

Prices reflect recent searches — current fares may differ.

One-way

Fares 14 to 29 days before departure were typically 29% lower than 0 to 6 days before departure.

From the cheapest one-way each day between 24 Sept and 11 Nov (49 days), grouped by how many days ahead the flight left; one adult in economy.

Each range covers different departure dates, so this compares typical fares, not the same trip priced twice.

Prices reflect recent searches — current fares may differ.

How much is a return flight from Chicago to Miami?

The cheapest return found recently is $191 with Frontier Airlines, 12 Dec to 15 Dec, found 2 days ago. The cheapest return we hold, of any age, is $138 with Frontier Airlines, 12 Dec to 19 Dec, found 7 days ago. The cheapest return fare on each of 24 departure dates is usually $220 to $406.

How much is a one-way flight from Chicago to Miami?

The cheapest one-way found recently is $86 with Frontier Airlines, 5 Dec, found 2 days ago. The cheapest one-way we hold, of any age, is $85 with Frontier Airlines, 16 Jan 2027, found 6 days ago. The cheapest one-way fare on each of 23 departure dates is usually $103 to $177.

What is the cheapest month to fly from Chicago to Miami?

December 2026 is the cheapest month for a return, from $138, 12 Dec to 19 Dec, found 7 days ago. January 2027 is the cheapest month for a one-way, from $85, 16 Jan 2027, found 6 days ago.

Every date in December 2026

How far ahead should I book a flight from Chicago to Miami?

In 49 days of prices between 24 Sept and 11 Nov, return fares 30 to 59 days before departure were typically 42% lower than 0 to 6 days before departure. One-way fares 14 to 29 days before departure were typically 29% lower than 0 to 6 days before departure.

Is there a direct flight from Chicago to Miami?

Yes, the cheapest nonstop return found recently is $519 with United Airlines, 12 Dec to 14 Dec, found 2 days ago. The cheapest nonstop one-way found recently is $100 with United Airlines, 5 Dec, found 2 days ago.

Every nonstop date from Chicago to Miami

How long is the flight from Chicago to Miami?

The cheapest nonstop one-way found recently, with United Airlines on 5 Dec, takes 3 h 20 min from O'Hare International Airport (ORD) to Miami International Airport (MIA). The cheapest one-way found recently, with Frontier Airlines on 5 Dec, takes 6 h 32 min with 1 stop.

Which airlines have the cheapest flights from Chicago to Miami?

Between 19 Nov and 3 Sept 2027, Frontier Airlines has the cheapest return on 19 of the 24 departure dates we hold, American Airlines on 2 and United Airlines on 2. Between 20 Nov and 11 May 2027, Frontier Airlines has the cheapest one-way on 12 of the 23 departure dates we hold, United Airlines on 5 and Southwest Airlines on 3.