Cheap flights from Chicago to Orlando from $107 MDW, ORD, RFD → MCO, SFB

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 $124 to $176.

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

Could nearby dates be cheaper?

We hold no other 5-night return fares leaving within 3 days of 7 Jan 2027 to compare.

Every date we hold

218 fares on 15 departure dates

Which month looks cheapest?

January 2027 is the cheapest month — from $134.

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 $57 to $100.

At $107, the cheapest one-way found recently is above that range.

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

Could nearby dates be cheaper?

Yes. Among one-way fares leaving within 3 days of 22 Dec, 23 Dec costs $101: $6 less than the cheapest found recently.

Frontier Airlines · O'Hare International Airport (ORD) → Orlando International Airport (MCO) · 1 stop · found 6 days ago

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Every date we hold

132 fares on 14 departure dates

Which month looks cheapest?

November 2026 is the cheapest month — from $81.

Return

Fares 14 to 29 days before departure were typically 36% 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 30 to 59 days before departure were typically 43% 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 Orlando?

The cheapest return found recently is $137 with Frontier Airlines, 7 Jan 2027 to 12 Jan 2027, found yesterday. The cheapest return we hold, of any age, is $134 with Allegiant Air, 9 Jan 2027 to 17 Jan 2027, found 5 days ago. The cheapest return fare on each of 15 departure dates is usually $183 to $305.

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

The cheapest one-way found recently is $107 with Frontier Airlines, 22 Dec, found 2 days ago. The cheapest one-way we hold, of any age, is $81 with Allegiant Air, 27 Nov, found 6 days ago. The cheapest one-way fare on each of 14 departure dates is usually $100 to $128.

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

January 2027 is the cheapest month for a return, from $134, 9 Jan 2027 to 17 Jan 2027, found 5 days ago. November 2026 is the cheapest month for a one-way, from $81, 27 Nov, found 6 days ago.

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

In 49 days of prices between 24 Sept and 11 Nov, return fares 14 to 29 days before departure were typically 36% lower than 0 to 6 days before departure. One-way fares 30 to 59 days before departure were typically 43% lower than 0 to 6 days before departure.

Is there a direct flight from Chicago to Orlando?

Yes, the cheapest nonstop return found recently is $177 with Allegiant Air, 11 Dec to 14 Dec, found 2 days ago. The cheapest nonstop one-way found recently is $130 with Frontier Airlines, 21 Dec, found 2 days ago.

Every nonstop date from Chicago to Orlando

How long is the flight from Chicago to Orlando?

The cheapest nonstop one-way found recently, with Frontier Airlines on 21 Dec, takes 2 h 50 min from Chicago Midway International Airport (MDW) to Orlando International Airport (MCO). The cheapest one-way found recently, with Frontier Airlines on 22 Dec, takes 6 h 2 min with 1 stop.

Which airlines have the cheapest flights from Chicago to Orlando?

Between 13 Nov and 3 Apr 2027, Frontier Airlines has the cheapest return on 8 of the 15 departure dates we hold, and Allegiant Air on 7. Between 16 Nov and 11 Feb 2027, Frontier Airlines has the cheapest one-way on 11 of the 14 departure dates we hold, and Allegiant Air on 3.