CA $462 Cheap Flights from Chicago (MDW) to Honolulu (HNL)

You can find one-way and return flights from MDW to HNL with Expedia. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see our cheapest fares first, and use the Price Tracking tool to receive alerts when MDW to HNL ticket fares go up or down.

The cheapest months to fly from MDW to HNL are typically during off-peak season when demand is low. Traveling in off-peak or shoulder months is usually a good way to secure cheap tickets, just remember to avoid flying during holidays if you are able to. Use the calendar view in your search to see which months have low fares on this route.

Enter MDW to HNL and your travel dates, then apply the 'Nonstop' filter to see only direct flights.

Southwest Airlines is one of the cheapest airlines offering connecting return flights from Chicago, IL (MDW-Midway Intl.) to Honolulu, HI (HNL-Daniel K. Inouye Intl.), with prices starting from around CA$584 for flights that can be booked for departure within the next year, typically with a layover in Sky Harbor Intl. (PHX). These prices are per adult for economy/coach class. Use Expedia's search tool to compare the prices and schedules of airlines that fly this route to find the best option for your plans and budget.

To find a cheap flight from Chicago, IL (MDW-Midway Intl.) to Honolulu, HI (HNL-Daniel K. Inouye Intl.), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.

The best time to fly is usually mid-week (Tuesday or Wednesday) and during early morning hours as flights tend to be cheaper, less crowded, and generally more on-time. Avoid major holidays and peak vacation seasons for smoother travel. Combining off-peak days and hours often gives the best combination of cost, comfort, and convenience.

There are approximately 61 connecting flights per day from Chicago Midway International Airport (MDW) to Honolulu Daniel K. Inouye International Airport (HNL). Some common connection points include Sky Harbor International Airport (PHX), Harry Reid International Airport (LAS), and Hartsfield-Jackson Atlanta International Airport (ATL).

The earliest flight from Chicago, IL (MDW-Midway Intl.) to Honolulu, HI (HNL-Daniel K. Inouye Intl.) typically departs around 5:00 AM. This flight is operated by Southwest Airlines. This is a seasonal service, active only in December. An early departure like this can help you make the most of your time at your destination. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.

You'll typically find the most flights from Chicago, IL (MDW-Midway Intl.) to Honolulu, HI (HNL-Daniel K. Inouye Intl.) on a Sunday, with around 37 flights available. This gives you plenty of options for your travel plans. Sunday offers notably more flight options compared to other days of the week. Major airlines on this route include Southwest Airlines and Delta.

The most popular departure times for flights from Chicago, IL (MDW-Midway Intl.) to Honolulu, HI (HNL-Daniel K. Inouye Intl.) are in the early morning, from 6am to 9am. Many major carriers, including Southwest Airlines and Delta, offer flights during this window. Many travellers prefer these early morning flights as they allow you to arrive at your destination with plenty of time to start your day.

There are no nonstop flights from Chicago, IL (MDW-Midway Intl.) to Honolulu, HI (HNL-Daniel K. Inouye Intl.). The distance between these two airports is approximately 6,833 kilometres. Flights with one stop typically take around 16 hours. If you opt for flights with two or more stops, your travel time will be longer, also averaging around 16 hours. Keep in mind that actual flight times can vary due to factors like routing, weather, and wind patterns, so it's always a good idea to allow for some extra time when planning your trip.

You can fly first class between MDW and HNL. First class cabins are available on Delta.

It's easy to earn miles on a Chicago, IL (MDW-Midway Intl.) to Honolulu, HI (HNL-Daniel K. Inouye Intl.) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

If you're planning to travel to Honolulu from Midway Intl. (MDW), you can fly directly into Daniel K. Inouye Intl. (HNL). Some flights may connect through major hubs like Hartsfield-Jackson Atlanta Intl. (ATL), Harry Reid International Airport (LAS), or Detroit Metropolitan Wayne County (DTW) before reaching Honolulu. Compare routes and airports on Expedia to find the best flight options for your travel plans.

Typically, booking a last minute flight from Chicago, IL (MDW-Midway Intl.) to Honolulu, HI (HNL-Daniel K. Inouye Intl.) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.

Securing a Chicago, IL (MDW-Midway Intl.) to Honolulu, HI (HNL-Daniel K. Inouye Intl.) flight and hotel package is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.

If you booked your Chicago, IL (MDW-Midway Intl.) to Honolulu, HI (HNL-Daniel K. Inouye Intl.) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.