Cheap flights from Chicago to San Diego from $229 MDW, ORD, RFD → CLD, SAN

Found recently, and the cheapest we hold

What have prices looked like?

Over 47 days, 24 Sept to 11 Nov, the cheapest return we saw each day was $190 to $507.

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

Could nearby dates be cheaper?

We hold no other 8-night return fares leaving within 3 days of 3 Dec to compare.

Every date we hold

129 fares on 7 departure dates

Which month looks cheapest?

December 2026 is the cheapest month — from $258.

Found recently, and the cheapest we hold

What have prices looked like?

Over 46 days, 24 Sept to 11 Nov, the cheapest one-way we saw each day was $85 to $323.

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 28 Dec to compare.

Every date we hold

6 fares on 2 departure dates

Which month looks cheapest?

January 2027 is the cheapest month — from $145.

Return

Fares 90 to 179 days before departure were typically 42% lower than 0 to 6 days before departure.

From the cheapest return each day between 24 Sept and 11 Nov (47 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 37% lower than 14 to 29 days before departure.

From the cheapest one-way each day between 24 Sept and 11 Nov (46 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 Chicago to San Diego?

The cheapest return found recently is $283 with Frontier Airlines, 3 Dec to 11 Dec, found 2 days ago. The cheapest return we hold, of any age, is $258 with Frontier Airlines, 17 Dec to 24 Dec, found 8 days ago. The cheapest return fare on each of 7 departure dates is usually $274 to $488.

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

The cheapest one-way found recently is $229 with Frontier Airlines, 28 Dec, found 3 days ago. The cheapest one-way we hold, of any age, is $145 with Frontier Airlines, 15 Jan 2027, found 4 days ago.

What is the cheapest month to fly from Chicago to San Diego?

December 2026 is the cheapest month for a return, from $258, 17 Dec to 24 Dec, found 8 days ago. January 2027 is the cheapest month for a one-way, from $145, 15 Jan 2027, found 4 days ago.

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

In 47 days of prices between 24 Sept and 11 Nov, return fares 90 to 179 days before departure were typically 42% lower than 0 to 6 days before departure. In 46 days of prices between 24 Sept and 11 Nov, one-way fares 30 to 59 days before departure were typically 37% lower than 14 to 29 days before departure.

Is there a direct flight from Chicago to San Diego?

Yes, the cheapest nonstop return found recently is $372 with Southwest Airlines, 3 Dec to 11 Dec, found 2 days ago. The cheapest nonstop one-way found recently is $193 with Southwest Airlines, 15 Jan 2027, found 4 days ago.

How long is the flight from Chicago to San Diego?

The cheapest nonstop one-way found recently, with Southwest Airlines on 15 Jan 2027, takes 4 h 20 min from Chicago Midway International Airport (MDW) to San Diego International Airport (SAN). The cheapest one-way found recently, with Frontier Airlines on 28 Dec, takes 6 h 54 min with 1 stop.

Which airlines have the cheapest flights from Chicago to San Diego?

Between 1 Dec and 3 Jan 2027, Frontier Airlines has the cheapest return on 4 of the 7 departure dates we hold, and Allegiant Air on 3.