Cheap flights from Miami to Chicago from $100 MIA → 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 $151 to $266.

At $343, the cheapest return found recently is above that range.

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 24 Nov to compare.

Every date we hold

24 fares on 4 departure dates

Which month looks cheapest?

January 2027 is the cheapest month — from $212.

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 $62 to $142.

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 19 Dec, 16 Dec costs $90: $10 less than the cheapest found recently.

Frontier Airlines · Miami International Airport (MIA) → Chicago Midway International Airport (MDW) · 1 stop · found 5 days ago

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Every date we hold

36 fares on 11 departure dates

Which month looks cheapest?

December 2026 is the cheapest month — from $90.

Return

Fares 30 to 59 days before departure were typically 41% 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 18% lower than 14 to 29 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 Miami to Chicago?

The cheapest return found recently is $343 with Frontier Airlines, 24 Nov to 29 Nov, found 4 days ago. The cheapest return we hold, of any age, is $212 with Frontier Airlines, 8 Jan 2027 to 15 Jan 2027, found 6 days ago. The cheapest return fare on each of 4 departure dates is usually $213 to $336.

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

The cheapest one-way found recently is $100 with United Airlines, 19 Dec, found 2 days ago. The cheapest one-way we hold, of any age, is $90 with Frontier Airlines, 15 Dec, found 6 days ago. The cheapest one-way fare on each of 11 departure dates is usually $93 to $113.

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

January 2027 is the cheapest month for a return, from $212, 8 Jan 2027 to 15 Jan 2027, found 6 days ago. December 2026 is the cheapest month for a one-way, from $90, 15 Dec, found 6 days ago.

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

In 49 days of prices between 24 Sept and 11 Nov, return fares 30 to 59 days before departure were typically 41% lower than 0 to 6 days before departure. One-way fares 30 to 59 days before departure were typically 18% lower than 14 to 29 days before departure.

Is there a direct flight from Miami to Chicago?

Yes, the cheapest nonstop return found recently is $638 with American Airlines, 19 Dec to 27 Dec, found 6 days ago. The cheapest nonstop one-way found recently is $100 with United Airlines, 19 Dec, found 2 days ago.

Every nonstop date from Miami to Chicago

How long is the flight from Miami to Chicago?

The cheapest nonstop one-way found recently, with United Airlines on 19 Dec, takes 3 h 36 min from Miami International Airport (MIA) to O'Hare International Airport (ORD).

Which airlines have the cheapest flights from Miami to Chicago?

Between 23 Nov and 8 Jan 2027, Frontier Airlines has the cheapest return on 3 of the 4 departure dates we hold, and United Airlines on 1. Between 15 Dec and 6 Jul 2027, Frontier Airlines has the cheapest one-way on 6 of the 11 departure dates we hold, United Airlines on 4 and Southwest Airlines on 1.