$192 Find Cheap Flights from Maui to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Chicago departing on 1/12. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$417
Overall average: $590
Alaska Airlines
Tue 3/3Wed 3/4
OGG - ORD • 1 stop
Cheapest non-stop
$854
United Airlines
Fri 12/19Mon 12/29
OGG - ORD • Non-stop
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We hope you love your trip to Chicago!
Flight Deals
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Flight Deals

Cheap Flights from Maui to Chicago

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Maui to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Maui to Chicago

Tue, Mar 3 - Wed, Mar 4
Alaska Airlines Logo
2:10 pm - 5:04 amOGG-ORD
10h 54m1 stop
Alaska Airlines Logo
9:00 am - 10:48 pmORD-OGG
17h 48m1 stop
$417Alaska Airlines
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Tue, Mar 3 - Wed, Mar 4
Alaska Airlines Logo
8:46 am - 5:04 amOGG-ORD
16h 18m2 stops
Alaska Airlines Logo
9:00 am - 10:48 pmORD-OGG
17h 48m1 stop
$422Alaska Airlines
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Tue, Mar 3 - Wed, Mar 4
Alaska Airlines Logo
11:20 pm - 1:59 pmOGG-ORD
10h 39m1 stop
Alaska Airlines Logo
6:50 pm - 2:20 pmORD-OGG
23h 30m1 stop
$434Alaska Airlines
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Thu, Nov 20 - Tue, Dec 2
Multiple Airlines Logo
2:42 pm - 6:25 amOGG-ORD
35h 43m2 stops
Multiple Airlines Logo
8:18 pm - 12:19 pmORD-OGG
20h 01m1 stop
$450Multiple Airlines
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Wed, Dec 17 - Tue, Dec 30
Alaska Airlines Logo
11:59 pm - 2:37 pmOGG-ORD
10h 38m1 stop
Alaska Airlines Logo
8:58 pm - 9:37 pmORD-OGG
28h 39m1 stop
$453Alaska Airlines
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Thu, Dec 18 - Tue, Dec 30
Delta Logo
5:10 pm - 9:54 amOGG-MDW
12h 44m1 stop
Delta Logo
6:00 am - 3:24 pmMDW-OGG
13h 24m1 stop
$461Delta
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Wed, Nov 12 - Sun, Nov 16
Multiple Airlines Logo
3:52 pm - 7:28 amOGG-ORD
11h 36m1 stop
Multiple Airlines Logo
10:43 pm - 1:40 pmORD-OGG
42h 57m2 stops
$501Multiple Airlines
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Sat, Dec 20 - Tue, Dec 30
Delta Logo
5:05 pm - 9:05 amOGG-MDW
12h 00m1 stop
Delta Logo
6:00 am - 3:24 pmMDW-OGG
13h 24m1 stop
$563Delta
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Thu, Nov 20 - Tue, Dec 2
Southwest Logo
9:25 pm - 3:25 pmOGG-ORD
14h 00m2 stops
Southwest Logo
7:15 am - 4:35 pmORD-OGG
13h 20m2 stops
$669Southwest
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Fri, Dec 19 - Sun, Dec 28
Southwest Logo
10:00 am - 5:05 amOGG-MDW
15h 05m2 stops
Southwest Logo
5:40 am - 4:35 pmMDW-OGG
14h 55m2 stops
$1,004Southwest
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Useful Info

Good to know

Low seasonJanuary
Cheapest flight$192
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly with an average 1% increase in price.
Flight from Kahului to Chicago O'Hare Airport

FAQs for booking flights from Maui to Chicago

  • How does KAYAK find such low prices on flights from Maui to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Maui to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Maui to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Maui is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Maui to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Maui with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Maui to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Maui up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Saint Joseph
Hammond
Portage
Lansing
Valparaiso
Chesterton
Schererville
Munster
Porter
Monticello
Saint John
Griffith

Everything you need to know for your flight to Chicago

Cabin class types available on flights to Maui

Cabin classes available on flights to Chicago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.
First Class flights to Chicagofrom $248
Business Class flights to Chicagofrom $190
Prem Econ Class flights to Chicagofrom $78
Economy Class flights to Chicagofrom $24

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