Cheap flights from Kansas City to Chicago from $193 MCI → MDW, ORD

Found recently, and the cheapest we hold

It is also the cheapest return we hold, of any age.

What have prices looked like?

Over 39 days, 26 Sept to 11 Nov, the cheapest return we saw each day was $224 to $414.

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

Could nearby dates be cheaper?

We hold no other 2-night return fares leaving within 3 days of 27 Dec to compare.

Every date we hold

2 fares on 2 departure dates

Which month looks cheapest?

December 2026 is the cheapest month — from $340.

Found recently, and the cheapest we hold

What have prices looked like?

Over 48 days, 24 Sept to 11 Nov, the cheapest one-way we saw each day was $80 to $179.

At $193, 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 20 Nov, 17 Nov costs $92: $101 less than the cheapest found recently.

American Airlines · Kansas City International Airport (MCI) → O'Hare International Airport (ORD) · nonstop · found 6 days ago

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Every date we hold

3 fares on 3 departure dates

Return

Fares 60 to 89 days before departure were typically 32% lower than 0 to 6 days before departure.

From the cheapest return each day between 26 Sept and 11 Nov (39 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 7 to 13 days before departure were typically 18% lower than 0 to 6 days before departure.

From the cheapest one-way each day between 24 Sept and 11 Nov (48 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 Kansas City to Chicago?

The cheapest return found recently is $340 with American Airlines, 27 Dec to 29 Dec, found 5 days ago.

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

The cheapest one-way found recently is $193 with Frontier Airlines, 20 Nov, found 3 days ago. The cheapest one-way we hold, of any age, is $92 with American Airlines, 17 Nov, found 6 days ago. The cheapest one-way fare on each of 3 departure dates is usually $126 to $176.

What is the cheapest month to fly from Kansas City to Chicago?

December 2026 is the cheapest month for a return, from $340, 27 Dec to 29 Dec, found 5 days ago.

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

In 39 days of prices between 26 Sept and 11 Nov, return fares 60 to 89 days before departure were typically 32% lower than 0 to 6 days before departure. In 48 days of prices between 24 Sept and 11 Nov, one-way fares 7 to 13 days before departure were typically 18% lower than 0 to 6 days before departure.

Is there a direct flight from Kansas City to Chicago?

Yes, the cheapest nonstop return found recently is $340 with American Airlines, 27 Dec to 29 Dec, found 5 days ago. The cheapest nonstop one-way found recently is $92 with American Airlines, 17 Nov, found 6 days ago.

How long is the flight from Kansas City to Chicago?

The cheapest nonstop one-way found recently, with American Airlines on 17 Nov, takes 1 h 46 min from Kansas City International Airport (MCI) to O'Hare International Airport (ORD). The cheapest one-way found recently, with Frontier Airlines on 20 Nov, takes 8 h 36 min with 1 stop.

Which airlines have the cheapest flights from Kansas City to Chicago?

Between 14 Nov and 20 Nov, Frontier Airlines has the cheapest one-way on 2 of the 3 departure dates we hold, and American Airlines on 1.