Cheap flights from Minneapolis to Chicago from $61 MSP → MDW, ORD

Found recently, and the cheapest we hold

What have prices looked like?

Over 48 days, 24 Sept to 11 Nov, the cheapest return we saw each day was $126 to $285.

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

Could nearby dates be cheaper?

No. We hold 1-night return fares on 2 other departure dates within 3 days of 27 Nov, and none is cheaper.

Every date we hold

8 fares on 8 departure dates

Which month looks cheapest?

December 2026 is the cheapest month — from $168.

Found recently, and the cheapest we hold

It is also the cheapest one-way we hold, of any age.

What have prices looked like?

Over 49 days, 24 Sept to 11 Nov, the cheapest one-way we saw each day was $50 to $116.

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 8 Dec, and it is not cheaper.

Every date we hold

7 fares on 7 departure dates

Which month looks cheapest?

December 2026 is the cheapest month — from $61.

Return

Fares 14 to 29 days before departure were typically 52% lower than 0 to 6 days before departure.

From the cheapest return 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.

One-way

Fares 30 to 59 days before departure were typically 50% 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 Minneapolis to Chicago?

The cheapest return found recently is $230 with Sun Country Airlines, 27 Nov to 28 Nov, found 3 days ago. The cheapest return we hold, of any age, is $168 with Sun Country Airlines, 23 Dec to 26 Dec, found 4 days ago. The cheapest return fare on each of 8 departure dates is usually $197 to $311.

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

The cheapest one-way found recently is $61 with Southwest Airlines, 8 Dec, found 2 days ago. The cheapest one-way fare on each of 7 departure dates is usually $89 to $136.

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

December 2026 is the cheapest month for a return, from $168, 23 Dec to 26 Dec, found 4 days ago. It is the cheapest month for a one-way too, from $61, 8 Dec, found 2 days ago.

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

In 48 days of prices between 24 Sept and 11 Nov, return fares 14 to 29 days before departure were typically 52% lower than 0 to 6 days before departure. In 49 days of prices between 24 Sept and 11 Nov, one-way fares 30 to 59 days before departure were typically 50% lower than 0 to 6 days before departure.

Is there a direct flight from Minneapolis to Chicago?

Yes, the cheapest nonstop return found recently is $230 with Sun Country Airlines, 27 Nov to 28 Nov, found 3 days ago. The cheapest nonstop one-way found recently is $61 with Southwest Airlines, 8 Dec, found 2 days ago.

How long is the flight from Minneapolis to Chicago?

The cheapest nonstop one-way found recently, with Southwest Airlines on 8 Dec, takes 1 h 35 min from Minneapolis-St. Paul International Airport (MSP) to Chicago Midway International Airport (MDW).

Which airlines have the cheapest flights from Minneapolis to Chicago?

Between 13 Nov and 1 Apr 2027, Sun Country Airlines has the cheapest return on 5 of the 8 departure dates we hold, American Airlines on 2 and Frontier Airlines on 1. Between 18 Nov and 15 Jun 2027, Southwest Airlines has the cheapest one-way on 3 of the 7 departure dates we hold, American Airlines on 2 and Frontier Airlines on 1.