Cheap flights from Chicago to Honolulu from $324 MDW, ORD, RFD → HNL

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 $492 to $637.

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

Could nearby dates be cheaper?

We hold no other 5-night return fares leaving within 3 days of 1 Feb 2027 to compare.

Every date we hold

129 fares on 16 departure dates

Which month looks cheapest?

January 2027 is the cheapest month — from $512.

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 39 days, 24 Sept to 11 Nov, the cheapest one-way we saw each day was $197 to $589.

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 23 Mar 2027 to compare.

Every date we hold

2 fares on 1 departure dates

Return

Fares 30 to 59 days before departure were typically 20% 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

Not enough history yet: in 39 days of one-way prices, 24 Sept to 11 Nov, fewer than 3 booking ranges had prices on 7 days or more.

How much is a return flight from Chicago to Honolulu?

The cheapest return found recently is $593 with Alaska Airlines, 1 Feb 2027 to 6 Feb 2027, found 2 days ago. The cheapest return we hold, of any age, is $512 with Alaska Airlines, 19 Jan 2027 to 27 Jan 2027, found 7 days ago. The cheapest return fare on each of 16 departure dates is usually $573 to $775.

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

The cheapest one-way found recently is $324 with Alaska Airlines, 23 Mar 2027, found 2 days ago.

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

January 2027 is the cheapest month for a return, from $512, 19 Jan 2027 to 27 Jan 2027, found 7 days ago.

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

In 49 days of prices between 24 Sept and 11 Nov, return fares 30 to 59 days before departure were typically 20% lower than 0 to 6 days before departure.

Is there a direct flight from Chicago to Honolulu?

Yes, the cheapest nonstop return found recently is $670 with United Airlines, 1 Feb 2027 to 7 Feb 2027, found 2 days ago.

Every nonstop date from Chicago to Honolulu

How long is the flight from Chicago to Honolulu?

The cheapest one-way found recently, with Alaska Airlines on 23 Mar 2027, takes 11 h 25 min with 1 stop.

Which airlines have the cheapest flights from Chicago to Honolulu?

Between 14 Nov and 15 May 2027, Alaska Airlines has the cheapest return on 8 of the 16 departure dates we hold, American Airlines on 4 and Southwest Airlines on 3.