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Cheap Flights from Chicago (MDW) to Honolulu (HNL)

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      Travellers and cabin class, 1 Adult, Economy

      Compare Chicago Midway to Honolulu International flight deals

      Find the cheapest month or even day of the year to fly to Honolulu International

      Book the best Honolulu International fare with no extra fees

      Flight deals from Chicago Midway to Honolulu International

      Looking for a cheap last-minute deal or the best return flight from Chicago Midway Airport to Honolulu International Airport? If you want to travel next month, return fares start from $737. Find the lowest prices on one-way and return tickets right here.
      Honolulu.$612 per passenger.Departing Tue, 17 Nov, returning Wed, 17 Feb.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Tue, 17 Nov, arriving in Honolulu International.Inbound indirect flight with Southwest Airlines, departs from Honolulu International on Wed, 17 Feb, arriving in Chicago Midway.Price includes taxes and charges.From $612, select.
      Honolulu.$637 per passenger.Departing Tue, 8 Dec, returning Fri, 11 Dec.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Tue, 8 Dec, arriving in Honolulu International.Inbound indirect flight with Southwest Airlines, departs from Honolulu International on Fri, 11 Dec, arriving in Chicago Midway.Price includes taxes and charges.From $637, select.
      Honolulu.$694 per passenger.Departing Tue, 20 Oct, returning Fri, 23 Oct.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Tue, 20 Oct, arriving in Honolulu International.Inbound indirect flight with Southwest Airlines, departs from Honolulu International on Fri, 23 Oct, arriving in Chicago Midway.Price includes taxes and charges.From $694, select.
      Honolulu.$694 per passenger.Departing Fri, 6 Nov, returning Sun, 8 Nov.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Fri, 6 Nov, arriving in Honolulu International.Inbound indirect flight with Southwest Airlines, departs from Honolulu International on Sun, 8 Nov, arriving in Chicago Midway.Price includes taxes and charges.From $694, select.
      Honolulu.$730 per passenger.Departing Fri, 23 Oct, returning Tue, 3 Nov.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Fri, 23 Oct, arriving in Honolulu International.Inbound indirect flight with Southwest Airlines, departs from Honolulu International on Tue, 3 Nov, arriving in Chicago Midway.Price includes taxes and charges.From $730, select.
      Honolulu.$737 per passenger.Departing Mon, 14 Sep, returning Mon, 21 Sep.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Mon, 14 Sep, arriving in Honolulu International.Inbound indirect flight with Southwest Airlines, departs from Honolulu International on Mon, 21 Sep, arriving in Chicago Midway.Price includes taxes and charges.From $737, select.
      Honolulu.$739 per passenger.Departing Tue, 9 Feb, returning Wed, 17 Feb.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Tue, 9 Feb, arriving in Honolulu International.Inbound indirect flight with Southwest Airlines, departs from Honolulu International on Wed, 17 Feb, arriving in Chicago Midway.Price includes taxes and charges.From $739, select.
      Honolulu.$780 per passenger.Departing Wed, 25 Nov, returning Wed, 2 Dec.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Wed, 25 Nov, arriving in Honolulu International.Inbound indirect flight with Southwest Airlines, departs from Honolulu International on Wed, 2 Dec, arriving in Chicago Midway.Price includes taxes and charges.From $780, select.
      Honolulu.$793 per passenger.Departing Tue, 29 Sep, returning Tue, 6 Oct.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Tue, 29 Sep, arriving in Honolulu International.Inbound indirect flight with Southwest Airlines, departs from Honolulu International on Tue, 6 Oct, arriving in Chicago Midway.Price includes taxes and charges.From $793, select.
      Honolulu.$813 per passenger.Departing Sat, 12 Dec, returning Fri, 15 Jan.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Sat, 12 Dec, arriving in Honolulu International.Inbound indirect flight with Southwest Airlines, departs from Honolulu International on Fri, 15 Jan, arriving in Chicago Midway.Price includes taxes and charges.From $813, select.
      Honolulu.$830 per passenger.Departing Tue, 23 Feb, returning Tue, 2 Mar.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Tue, 23 Feb, arriving in Honolulu International.Inbound indirect flight with Southwest Airlines, departs from Honolulu International on Tue, 2 Mar, arriving in Chicago Midway.Price includes taxes and charges.From $830, select.
      Honolulu.$830 per passenger.Departing Mon, 25 Jan, returning Fri, 29 Jan.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Mon, 25 Jan, arriving in Honolulu International.Inbound indirect flight with Southwest Airlines, departs from Honolulu International on Fri, 29 Jan, arriving in Chicago Midway.Price includes taxes and charges.From $830, select.
      Honolulu.$903 per passenger.Departing Sat, 29 Aug, returning Sun, 13 Sep.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Sat, 29 Aug, arriving in Honolulu International.Inbound indirect flight with Southwest Airlines, departs from Honolulu International on Sun, 13 Sep, arriving in Chicago Midway.Price includes taxes and charges.From $903, select.
      Honolulu.$909 per passenger.Departing Fri, 29 Jan, returning Mon, 8 Feb.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Fri, 29 Jan, arriving in Honolulu International.Inbound indirect flight with Southwest Airlines, departs from Honolulu International on Mon, 8 Feb, arriving in Chicago Midway.Price includes taxes and charges.From $909, select.
      Honolulu.$925 per passenger.Departing Mon, 22 Mar, returning Thu, 25 Mar.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Mon, 22 Mar, arriving in Honolulu International.Inbound indirect flight with Delta, departs from Honolulu International on Thu, 25 Mar, arriving in Chicago Midway.Price includes taxes and charges.From $925, select.
      Honolulu.$999 per passenger.Departing Wed, 21 Apr, returning Wed, 28 Apr.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Wed, 21 Apr, arriving in Honolulu International.Inbound indirect flight with Delta, departs from Honolulu International on Wed, 28 Apr, arriving in Chicago Midway.Price includes taxes and charges.From $999, select.

      Find the cheapest month to fly from Chicago Midway to Honolulu International

      We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago Midway to Honolulu International flights are currently cheapest in December.
      Aug
      from $1,054
      Sep
      from $737
      Oct
      from $694
      Nov
      from $694
      Dec
      from $637
      Jan
      from $830
      Feb
      from $739
      Mar
      from $925
      Apr
      from $999
      May
      from $1,031
      Jun
      from $1,368
      Jul
      Find prices

      Chicago Midway to Honolulu International: Alternative routes

      Compare routes from Chicago Midway to Honolulu below. You may find an airport to fly into that's cheaper, faster, or easier than Honolulu International.

      Honolulu International

      7km from central Honolulu
      ClosestCheapest
      from $612
      Search flights

      Hoolehua

      81km from central Honolulu
      from $2,363
      Search flights

      Chicago to Honolulu: Flight information

      The things to know before you go.
      Cheapest flight found$612
      Cheapest month to flyNovember

      Finding cheap flights from Chicago Midway to Honolulu International: Frequently asked questions

      The best price we found for a return flight from Chicago Midway to Honolulu International is $612. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
      Currently, there are no airlines that fly direct from Chicago Midway to Honolulu International. But we found flights with one or more stops from $612.
      As of August 2026, there are no flights flying from Chicago Midway to Honolulu International.
      The cheapest month to fly from Chicago Midway to Honolulu International is usually November.
      After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Chicago Midway Airport to Honolulu International Airport on Tuesday, 17 November 2026.
      No airlines currently offer direct flights between Chicago Midway Airport and Honolulu International Airport. Most routes have one or more stops.
      We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Honolulu International but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.

      We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Honolulu is around 40 days in advance, so don’t leave your flight to the last minute.

      Currently, Southwest Airlines offers the cheapest flight tickets to Honolulu International.

      Travelling from Chicago Midway Airport (MDW) to Honolulu International Airport (HNL): what you need to know

      • Honolulu is four hours behind Chicago and observes the UTC-10 timezone.

      • To ensure you catch your MDW to HNL flight, leave plenty of time to navigate the airport and find your gate. Arriving two hours ahead of international departures and an hour before domestic flights is the general rule.

      • Travelling during a peak month like July? Public holidays and other high seasons can result in longer queues at check-in and security. Be extra cautious and arrive up to four hours ahead of an international flight and two hours before domestic departures.

      • If you'd like to explore another city along the way, just deselect 'Direct flights only' when searching for your ticket from Chicago Midway Airport to Honolulu International Airport. These are the top stopovers between MDW and HNL:

        • Los Angeles International Airport

        • Phoenix Sky Harbour Airport

        • Minneapolis St Paul Airport

      How to find the cheapest flights from Chicago Midway Airport (MDW) to Honolulu International Airport (HNL)

      • The cheapest price we've found for a one-way Chicago Midway Airport to Honolulu International Airport flight is $347. A return plane ticket is currently $612. Depending on the availability and when you book, these fares may change.

      • Don't leave everything to the last moment. You're more likely to get cheap tickets from MDW to HNL if you book early. Airlines often offer some amazing early bird discounts.

      • If you can be flexible with your trip dates, use the 'Whole month' search function. It'll find the cheapest price in every month when searching for a flight from Chicago Midway Airport to Honolulu International Airport.

      • Cut down on the time spent looking for cheap flights from MDW to HNL by setting up a Price Alert. You'll get an email or push notification on the app when a new discounted fare appears.

      • Select your preferred departure and arrival times, airlines and number of stops with the filters. Or sort your results by 'Cheapest' to get the best deals on flights from Chicago Midway Airport to Honolulu International Airport.

      Handy information about Chicago Midway Airport (MDW)

      • MDW is located at 5700 South Cicero.

      • When it comes to Chicago Midway Airport's on-time performance, 76% of flights arrive within the scheduled timeframe.

      • To get to Chicago Midway Airport from central Chicago, it'll take about 25 minutes by car. Of course, this depends on traffic conditions. It's approximately 16 kilometres from the airport to the city centre.

      • You can expect a journey time of about 30 minutes when using public transport.

      • Get your travels off to a stress-free start by staying near MDW. Whether you have an early flight from Chicago Midway Airport to Honolulu International Airport or just don't like being rushed, these stays have you covered:

      Arriving at Honolulu International Airport (HNL)

      When to fly to Honolulu International Airport (HNL)

      • It's time to pick your trip dates for your flight from Chicago Midway Airport to Honolulu International Airport. July is the busiest month to head to Honolulu. If you like a more low-key vibe, go in March.

      • The warmest month in Honolulu is September, with the temperature ranging between 23ºC (73ºF) and 29ºC (84ºF). Lock in your flights from Chicago Midway Airport to Honolulu International Airport in this month if this is the kind of weather you like.

      • Search for cheap tickets from MDW to HNL in February if you like travelling in cooler conditions. Temperatures are at their lowest around then, ranging between 18ºC (64ºF) and 25ºC (77ºF) on average.

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      Prices shown on this page are estimated lowest prices only. Found in the last 12 days.