Cheap flights from San Jose, California to Chicago from $196 SJC → 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 $188 to $479.

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

Could nearby dates be cheaper?

We hold no other 3-night return fares leaving within 3 days of 1 Jul 2027 to compare.

Every date we hold

65 fares on 5 departure dates

Which month looks cheapest?

December 2026 is the cheapest month — from $255.

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 $135 to $197.

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 24 Dec to compare.

Every date we hold

4 fares on 4 departure dates

Which month looks cheapest?

April 2027 is the cheapest month — from $193.

Return

Fares 14 to 29 days before departure were typically 55% 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

The cheapest fares were 60 to 89 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 San Jose to Chicago?

The cheapest return found recently is $448 with Alaska Airlines, 1 Jul 2027 to 4 Jul 2027, found 3 days ago. The cheapest return we hold, of any age, is $255 with Frontier Airlines, 7 Dec to 10 Dec, found 7 days ago. The cheapest return fare on each of 5 departure dates is usually $380 to $536.

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

The cheapest one-way found recently is $196 with Alaska Airlines, 24 Dec, found 4 days ago. The cheapest one-way we hold, of any age, is $193 with Alaska Airlines, 17 Apr 2027, found 7 days ago. The cheapest one-way fare on each of 4 departure dates is usually $193 to $206.

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

December 2026 is the cheapest month for a return, from $255, 7 Dec to 10 Dec, found 7 days ago. April 2027 is the cheapest month for a one-way, from $193, 17 Apr 2027, found 7 days ago.

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

In 49 days of prices between 24 Sept and 11 Nov, return fares 14 to 29 days before departure were typically 55% lower than 0 to 6 days before departure. One-way fares were cheapest 60 to 89 days before departure.

Is there a direct flight from San Jose to Chicago?

Yes, the cheapest nonstop return found recently is $536 with United Airlines, 30 Dec to 3 Jan 2027, found 3 days ago.

How long is the flight from San Jose to Chicago?

The cheapest one-way found recently, with Alaska Airlines on 24 Dec, takes 14 h 59 min with 1 stop.

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

Between 7 Dec and 1 Jul 2027, United Airlines has the cheapest return on 2 of the 5 departure dates we hold, Alaska Airlines on 2 and Frontier Airlines on 1. Between 24 Dec and 19 Apr 2027, Alaska Airlines has the cheapest one-way on all 4 departure dates we hold.