Cheap flights from Orlando to Chicago from $130 MCO, SFB → MDW, ORD, RFD

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 $104 to $207.

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

Could nearby dates be cheaper?

We hold no other 4-night return fares leaving within 3 days of 14 Jan 2027 to compare.

Every date we hold

169 fares on 10 departure dates

Which month looks cheapest?

December 2026 is the cheapest month — from $152.

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 $46 to $124.

At $130, 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 18 Dec, 15 Dec costs $67: $63 less than the cheapest found recently.

Frontier Airlines · Orlando International Airport (MCO) → O'Hare International Airport (ORD) · 1 stop · found 8 days ago

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Every date we hold

47 fares on 9 departure dates

Which month looks cheapest?

January 2027 is the cheapest month — from $48.

Return

Fares 14 to 29 days before departure were typically 38% 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 27% 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 Orlando to Chicago?

The cheapest return found recently is $156 with Frontier Airlines, 14 Jan 2027 to 18 Jan 2027, found yesterday. The cheapest return we hold, of any age, is $152 with Frontier Airlines, 8 Dec to 15 Dec, found 7 days ago. The cheapest return fare on each of 10 departure dates is usually $160 to $247.

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

The cheapest one-way found recently is $130 with Frontier Airlines, 18 Dec, found 2 days ago. The cheapest one-way we hold, of any age, is $48 with Allegiant Air, 14 Jan 2027, found 6 days ago. The cheapest one-way fare on each of 9 departure dates is usually $100 to $130.

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

December 2026 is the cheapest month for a return, from $152, 8 Dec to 15 Dec, found 7 days ago. January 2027 is the cheapest month for a one-way, from $48, 14 Jan 2027, found 6 days ago.

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

In 49 days of prices between 24 Sept and 11 Nov, return fares 14 to 29 days before departure were typically 38% lower than 0 to 6 days before departure. One-way fares 14 to 29 days before departure were typically 27% lower than 0 to 6 days before departure.

Is there a direct flight from Orlando to Chicago?

Yes, the cheapest nonstop return found recently is $237 with Frontier Airlines, 21 Nov to 23 Nov, found 2 days ago. The cheapest nonstop one-way found recently is $130 with Frontier Airlines, 18 Dec, found 2 days ago.

Every nonstop date from Orlando to Chicago

How long is the flight from Orlando to Chicago?

The cheapest nonstop one-way found recently, with Frontier Airlines on 18 Dec, takes 3 h 1 min from Orlando International Airport (MCO) to Chicago Midway International Airport (MDW).

Which airlines have the cheapest flights from Orlando to Chicago?

Between 19 Nov and 14 Jan 2027, Frontier Airlines has the cheapest return on 9 of the 10 departure dates we hold, and Allegiant Air on 1. Between 21 Nov and 3 Mar 2027, Frontier Airlines has the cheapest one-way on 6 of the 9 departure dates we hold, and Allegiant Air on 3.