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461 € Cheap Flights from Honolulu International to Chicago Midway

Compare Honolulu International to Chicago Midway flight deals

Find the cheapest month or even day of the year to fly to Chicago Midway

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Flight deals from Honolulu International to Chicago Midway

Looking for a cheap last-minute deal or the best return flight from Honolulu International Airport to Chicago Midway Airport? If you want to travel next month, return fares start from 489 €. Find the lowest prices on one-way and return tickets right here.
Chicago.461 € per passenger.Departing Thu, 27 Aug, returning Wed, 9 Sep.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Honolulu International on Thu, 27 Aug, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Wed, 9 Sep, arriving in Honolulu International.Price includes taxes and charges.From 461 €, select.
Chicago.465 € per passenger.Departing Tue, 1 Sep, returning Tue, 15 Sep.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Honolulu International on Tue, 1 Sep, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Tue, 15 Sep, arriving in Honolulu International.Price includes taxes and charges.From 465 €, select.
Chicago.484 € per passenger.Departing Tue, 3 Nov, returning Tue, 10 Nov.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Honolulu International on Tue, 3 Nov, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Tue, 10 Nov, arriving in Honolulu International.Price includes taxes and charges.From 484 €, select.
Chicago.489 € per passenger.Departing Wed, 26 Aug, returning Sun, 30 Aug.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Honolulu International on Wed, 26 Aug, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Sun, 30 Aug, arriving in Honolulu International.Price includes taxes and charges.From 489 €, select.
Chicago.502 € per passenger.Departing Wed, 9 Dec, returning Mon, 14 Dec.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Honolulu International on Wed, 9 Dec, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Mon, 14 Dec, arriving in Honolulu International.Price includes taxes and charges.From 502 €, select.
Chicago.509 € per passenger.Departing Thu, 1 Oct, returning Thu, 12 Nov.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Honolulu International on Thu, 1 Oct, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Thu, 12 Nov, arriving in Honolulu International.Price includes taxes and charges.From 509 €, select.
Chicago.512 € per passenger.Departing Thu, 15 Oct, returning Thu, 22 Oct.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Honolulu International on Thu, 15 Oct, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Thu, 22 Oct, arriving in Honolulu International.Price includes taxes and charges.From 512 €, select.
Chicago.513 € per passenger.Departing Wed, 3 Feb, returning Fri, 19 Feb.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Honolulu International on Wed, 3 Feb, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Fri, 19 Feb, arriving in Honolulu International.Price includes taxes and charges.From 513 €, select.
Chicago.593 € per passenger.Departing Tue, 22 Dec, returning Tue, 5 Jan.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Honolulu International on Tue, 22 Dec, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Tue, 5 Jan, arriving in Honolulu International.Price includes taxes and charges.From 593 €, select.
Chicago.618 € per passenger.Departing Mon, 28 Sep, returning Fri, 2 Oct.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Honolulu International on Mon, 28 Sep, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Fri, 2 Oct, arriving in Honolulu International.Price includes taxes and charges.From 618 €, select.
Chicago.693 € per passenger.Departing Thu, 4 Mar, returning Sat, 27 Mar.Return flight with Delta.Outbound indirect flight with Delta, departs from Honolulu International on Thu, 4 Mar, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Sat, 27 Mar, arriving in Honolulu International.Price includes taxes and charges.From 693 €, select.
Chicago.761 € per passenger.Departing Thu, 30 Jul, returning Sun, 2 Aug.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Honolulu International on Thu, 30 Jul, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Sun, 2 Aug, arriving in Honolulu International.Price includes taxes and charges.From 761 €, select.
Chicago.783 € per passenger.Departing Fri, 26 Mar, returning Fri, 2 Apr.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Honolulu International on Fri, 26 Mar, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Fri, 2 Apr, arriving in Honolulu International.Price includes taxes and charges.From 783 €, select.
Chicago.1.016 € per passenger.Departing Sun, 3 Jan, returning Sun, 10 Jan.Return flight with Delta.Outbound indirect flight with Delta, departs from Honolulu International on Sun, 3 Jan, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Sun, 10 Jan, arriving in Honolulu International.Price includes taxes and charges.From 1.016 €, select.
Chicago.1.393 € per passenger.Departing Thu, 13 May, returning Tue, 18 May.Return flight with Delta.Outbound indirect flight with Delta, departs from Honolulu International on Thu, 13 May, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Tue, 18 May, arriving in Honolulu International.Price includes taxes and charges.From 1.393 €, select.

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

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Honolulu International to Chicago Midway flights are currently cheapest in September.
Jul
Find prices
Aug
from 489 €
Sep
from 465 €
Oct
from 512 €
Nov
from 484 €
Dec
from 502 €
Jan
from 1.016 €
Feb
from 513 €
Mar
from 693 €
Apr
Find prices
May
from 1.393 €
Jun
Find prices

Honolulu International to Chicago Midway: Alternative routes

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

Chicago Midway

14km from central Chicago
ClosestCheapest
from 461 €
Search flights

Chicago O'Hare International

25km from central Chicago
Cheapest
from 461 €
Search flights

Chicago Rockford

127km from central Chicago
from 952 €
Search flights

Honolulu to Chicago: Flight information

The things to know before you go.
Cheapest flight found461 €
Cheapest month to flyAugust

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

The best price we found for a return flight from Honolulu International to Chicago Midway is 461 €. 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 Honolulu International to Chicago Midway. But we found flights with one or more stops from 461 €.
As of July 2026, there are no flights flying from Honolulu International to Chicago Midway.
The cheapest month to fly from Honolulu International to Chicago Midway is usually August.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Honolulu International Airport to Chicago Midway Airport on Thursday, 27 August 2026.
No airlines currently offer direct flights between Honolulu International Airport and Chicago Midway 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 Chicago Midway 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 Chicago 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 Chicago Midway.

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

  • Chicago's timezone is UTC-6, which makes Chicago four hours ahead of Honolulu.

  • To ensure you get on your HNL to MDW flight, allow plenty of time to check in and drop off your luggage. Arriving two hours before international departures and an hour before domestic flights is the general travel rule.

  • Travelling during a peak time like July? Public holidays and other popular periods can lead to longer lines at security. Play it safe and arrive up to four hours before international flights and two hours before domestic departures.

  • Consider adding a stopover when booking your ticket from Honolulu International Airport to Chicago Midway Airport. Just uncheck 'Direct flights only' to break up your journey, or even explore someplace new along the way. Here are some options between HNL and MDW:

    • Denver International Airport

    • Los Angeles International Airport

    • Harry Reid International Airport

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

  • 190 € is the best price for a one-way Honolulu International Airport to Chicago Midway Airport flight. A return flight starts at 461 €. These prices can change depending on demand.

  • Don't wait until the last moment. You're more likely to get cheap tickets from HNL to MDW if you book ahead. Airlines often offer some excellent early bird deals.

  • The 'Whole month' search function shows you the cheapest flights from Honolulu International Airport to Chicago Midway Airport throughout the entire month. It's a good way to find a bargain if your plans aren't set in stone.

  • There's no need to check back in every day to find out if fares have dropped when you create a Price Alert. We'll notify you as soon as there's a better deal on cheap flights from HNL to MDW.

  • Discover the perfect flight for you by using the filters. To see the 'Fastest,' 'Best' or 'Cheapest' flights from Honolulu International Airport to Chicago Midway Airport, use the 'Sort by' function. You can also filter by arrival and departure times, airline, and journey duration.

Handy information about Honolulu International Airport (HNL)

  • You'll find HNL at 300 Rodgers Blvd., #12.

  • 82% of flights leaving Honolulu International Airport reach their destination as planned. Given its strong on-time performance, you're unlikely to be delayed when taking off from HNL.

  • Central Honolulu to Honolulu International Airport is approximately 10 kilometres. Depending on traffic, it'll take you about 20 minutes to get there if you're catching a taxi, ride-sharing or driving.

  • You can expect a trip time of around 45 minutes on public transport.

  • Need a convenient hotel close to HNL? If you've booked an early flight from Honolulu International Airport to Chicago Midway Airport, these accommodation options will put you moments from your departure gate:

Arriving at Chicago Midway Airport (MDW)

When to fly to Chicago Midway Airport (MDW)

  • The quietest month for a flight from Honolulu International Airport to Chicago Midway Airport is December, while July is the busiest. Pick the ideal time to visit Chicago based on whether you prefer a faster pace or a more relaxed vibe.

  • Book your flight from Honolulu International Airport to Chicago Midway Airport for July if you want to explore Chicago during its warmest month. Expect temperatures of between 16ºC (61ºF) and 28ºC (82ºF).

  • If you'd rather travel in cooler conditions, look for a cheap ticket from HNL to MDW in January. Average temperatures are between -12ºC (10ºF) and 3ºC (37ºF) then.

Explore more of the United States

  • Chicago has loads to offer, but there are so many other parts of the United States just waiting to be discovered. Around 451 kilometres south-east of Chicago, a visit to Columbus will keep you busy. Start with leading sights like Franklin Park Conservatory and Botanical Gardens, Whetstone Park / Park of Roses and Ohio Theatre.

  • Around 257 kilometres south-east of Chicago, Indianapolis is another essential stop in the United States. No visit is complete without checking out Lucas Oil Stadium, Eiteljorg Museum and The Children's Museum of Indianapolis.

Plan the rest of your trip from Honolulu to Chicago

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