Cheap flights from Oakland to Chicago from $216 OAK → 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 $220 to $409.

At $460, the cheapest return 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 3-night return fares leaving within 3 days of 1 Jul 2027 to compare.

Every date we hold

39 fares on 6 departure dates

Which month looks cheapest?

December 2026 is the cheapest month — from $310.

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 $128 to $208.

At $216, 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 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 $208.

Return

Fares 14 to 29 days before departure were typically 32% 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 14 to 29 days before departure were typically 15% 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 Oakland to Chicago?

The cheapest return found recently is $460 with Alaska Airlines, 1 Jul 2027 to 4 Jul 2027, found 3 days ago. The cheapest return we hold, of any age, is $310 with Southwest Airlines, 7 Dec to 10 Dec, found 7 days ago. The cheapest return fare on each of 6 departure dates is usually $437 to $519.

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

The cheapest one-way found recently is $216 with Southwest Airlines, 24 Dec, found 4 days ago. The cheapest one-way we hold, of any age, is $208 with Alaska Airlines, 17 Apr 2027, found 7 days ago. The cheapest one-way fare on each of 4 departure dates is usually $208 to $224.

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

December 2026 is the cheapest month for a return, from $310, 7 Dec to 10 Dec, found 7 days ago. April 2027 is the cheapest month for a one-way, from $208, 17 Apr 2027, found 7 days ago.

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

In 49 days of prices between 24 Sept and 11 Nov, return fares 14 to 29 days before departure were typically 32% lower than 0 to 6 days before departure. One-way fares 14 to 29 days before departure were typically 15% lower than 7 to 13 days before departure.

Is there a direct flight from Oakland to Chicago?

Yes, the cheapest nonstop return found recently is $638 with Southwest Airlines, 1 Jul 2027 to 4 Jul 2027, found 3 days ago. The cheapest nonstop one-way found recently is $216 with Southwest Airlines, 24 Dec, found 4 days ago.

How long is the flight from Oakland to Chicago?

The cheapest nonstop one-way found recently, with Southwest Airlines on 24 Dec, takes 4 h 5 min from Metropolitan Oakland International Airport (OAK) to Chicago Midway International Airport (MDW).

Which airlines have the cheapest flights from Oakland to Chicago?

Between 23 Nov and 1 Jul 2027, Southwest Airlines has the cheapest return on 3 of the 6 departure dates we hold, and Alaska Airlines on 3. Between 24 Dec and 19 Apr 2027, Alaska Airlines has the cheapest one-way on 3 of the 4 departure dates we hold, and Southwest Airlines on 1.