Image Credits: Kasuga Huang, Creative Commons 3.0
Published July 30, 2024 by

Cheap Flights: Chicago to/from Kahului-Maui or Kona, Hawaii $319-$346 r/t [August-November] (No Thanksgiving) – Delta

[07/30/2024 @ 01:23 PM CT] Deal time-stamp.
[2024-09-01 08:38:00] This fare IS NO LONGER BEING MONITORED because the deal has expired, been removed, or became too old. If it goes back online we will send out another notification.

Deals are usually valid 24 to 72 hours after posting, but can expire at any time (see time-stamp).

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Delta has round-trip flights from Chicago (ORD) to Kahului or Kona, Hawaii (OGG, KOA) for $319-$346 with a connection. Flights August to November. Weekends available. Origin/Destination reversible. No Thanksgiving dates.

A Carry-on bag and also a personal item is allowed for free on Delta. You can avoid paying for seat selection by accepting the randomly assigned seat at the gate.

If you travel on Delta often, consider getting their credit card. Most of their cards allow for a free checked bag perk and a 15% discount on points redemptions.

There is currently a limited time offer for Delta’s co-branded credit card with a higher than normal welcome offer! (the card offer ends 10/29/2025) Visit our Delta credit card landing page for the current sign-up offer and more details (link).

You can usually save more money by booking your flight+hotel together as a package instead of separately.

Do a search on Tripadvisor to find guides, tours, restaurants, attractions, and cool things to do. It’s a good resource to use for planning your day-to-day itinerary while on vacation.

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  • Tips: The Chase Sapphire Preferred® Card allows for 1-to-1 point transfers to several airline loyalty programs. Booking with points is a good alternative to paying with cash when the price of airfare is high. Here is the current list of Chase Sapphire transfer partners: United, Southwest, jetBlue, British Airways, Iberia, Singapore Airlines, Emirates, Air France, KLM, Virgin Atlantic, Aer Lingus, and Air Canada.
  • Tips: Use Tripadvisor to create a Hotel “short list”. First, plug in your dates and destination. Then select “Sort by Traveler Ranked”. Finally, select the “Traveler Ranking” filter to show “only 4* and up”. Use this resulting “short list” of hotels to find the cheapest one with a high ranking.
  • Tips: Hotel rates for Weekend dates are usually higher than the rates for Sunday through Thursday. Tripadvisor has a color-coded date calendar, red when the average hotel price for that day is more expensive, green for less expensive. You can use this to get an overview of what dates in the month are at a discount.
  • Tips: Different booking websites will often have differing routes, prices, and availability. Before you finalize your purchase, do a quick check on BookingBuddy, Skyscanner, and Kayak to see if any other site or airline is offering a better deal.


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Ren P. Artemio

Ren P. Artemio

Ren is the Chief Director of Nap Times at Escape Houston, Escape ATX, Cheap DFW, and Escape Flights. He really likes researching airfare and the travel industry, especially when it means getting a cheap flight to anywhere (he's not picky).

Airfare Deals Delta Flights from Chicago / Milwaukee Kahului SkyTeam