Alaska Airlines is selling cheap flights from Chicago to Maui for as low as $254 return! That works out to a cost of just 3 Cents Per Mile for this 8300 mile journey.

The fare only includes carry-on luggage, so you need to pay extra if you want to check bags.

Our data shows the lowest prices are available in October 2021. See the link(s) below for dates and prices.

Sample date(s) with booking link

Oct 5 – Oct 12 ($279)

Oct 12 – Oct 19 ($255)

Oct 13 – Oct 20 ($289)

Oct 13 – Oct 21 ($254)

Oct 14 – Oct 19 ($255)

Oct 14 – Oct 21 ($255)

Oct 14 – Oct 26 ($255)

Oct 21 – Oct 28 ($314)

Oct 22 – Oct 31 ($284)

Oct 26 – Oct 31 ($290)

Are you looking for an apartment to rent for your stay in Maui? Check out what has to offer!

We post many cheap flights like this one from Chicago to Maui every single day, so have a look at our Travel Deals page, or check out the related posts below!

Note: Prices are valid at the time of publishing this post, but may change in the future.

COVID-19 Note: During these uncertain times, please make sure to check the relevant Coronavirus restrictions for your destination before you book and before you fly. We recommend also checking the refund policy of the airline, as well as purchasing travel insurance for your trip.