Cheap flights from Long Beach to Chicago from $267 LGB → MDW, ORD

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 $214 to $411.

At $501, the cheapest return found recently is above that range.

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

Could nearby dates be cheaper?

No. We hold 4-night return fares on 1 other departure date within 3 days of 30 Dec, and it is not cheaper.

Every date we hold

68 fares on 14 departure dates

Which month looks cheapest?

December 2026 is the cheapest month — from $344.

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 $124 to $221.

At $267, 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?

We hold no other one-way fares leaving within 3 days of 15 Mar 2027 to compare.

Every date we hold

7 fares on 7 departure dates

Which month looks cheapest?

December 2026 is the cheapest month — from $135.

Return

Fares 14 to 29 days before departure were typically 51% 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 34% lower than 7 to 13 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 Long Beach to Chicago?

The cheapest return found recently is $501 with Southwest Airlines, 30 Dec to 3 Jan 2027, found 2 days ago. The cheapest return we hold, of any age, is $344 with Southwest Airlines, 15 Dec to 3 Jan 2027, found 3 days ago. The cheapest return fare on each of 14 departure dates is usually $412 to $512.

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

The cheapest one-way found recently is $267 with Southwest Airlines, 15 Mar 2027, found 2 days ago. The cheapest one-way we hold, of any age, is $135 with Alaska Airlines, 2 Dec, found 4 days ago. The cheapest one-way fare on each of 7 departure dates is usually $194 to $246.

What is the cheapest month to fly from Long Beach to Chicago?

December 2026 is the cheapest month for a return, from $344, 15 Dec to 3 Jan 2027, found 3 days ago. It is the cheapest month for a one-way too, from $135, 2 Dec, found 4 days ago.

Every date in December 2026

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

In 49 days of prices between 24 Sept and 11 Nov, return fares 14 to 29 days before departure were typically 51% lower than 0 to 6 days before departure. One-way fares 30 to 59 days before departure were typically 34% lower than 7 to 13 days before departure.

Is there a direct flight from Long Beach to Chicago?

Yes, the cheapest nonstop return found recently is $501 with Southwest Airlines, 30 Dec to 3 Jan 2027, found 2 days ago. The cheapest nonstop one-way found recently is $267 with Southwest Airlines, 15 Mar 2027, found 2 days ago.

Every nonstop date from Long Beach to Chicago

How long is the flight from Long Beach to Chicago?

The cheapest nonstop one-way found recently, with Southwest Airlines on 15 Mar 2027, takes 3 h 50 min from Long Beach Airport (LGB) to Chicago Midway International Airport (MDW).

Which airlines have the cheapest flights from Long Beach to Chicago?

Between 18 Nov and 19 Mar 2027, Southwest Airlines has the cheapest return on 11 of the 14 departure dates we hold, and Alaska Airlines on 3. Between 2 Dec and 15 Mar 2027, Southwest Airlines has the cheapest one-way on 5 of the 7 departure dates we hold, and Alaska Airlines on 2.