$217 Find Cheap Flights from Maui to Chicago - Compare and Save

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 8/20. 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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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

Thu, Sep 24 - Mon, Sep 28
Alaska Airlines Logo
10:40 pm - 7:21 pm
OGG
-
ORD
15h 41m
1 stop
Alaska Airlines Logo
2:18 pm - 9:37 pm
ORD
-
OGG
12h 19m
1 stop
$520Alaska Airlines
Thu, Sep 24 - Mon, Sep 28
Multiple Airlines Logo
10:40 pm - 7:21 pm
OGG
-
ORD
15h 41m
1 stop
Multiple Airlines Logo
7:20 am - 5:24 pm
ORD
-
OGG
15h 04m
2 stops
$525Multiple Airlines
Thu, Sep 24 - Mon, Sep 28
Alaska Airlines Logo
10:40 pm - 11:59 pm
OGG
-
ORD
20h 19m
1 stop
Alaska Airlines Logo
7:20 am - 9:37 pm
ORD
-
OGG
19h 17m
1 stop
$529Alaska Airlines
Thu, Sep 24 - Mon, Sep 28
Multiple Airlines Logo
6:00 am - 11:59 pm
OGG
-
ORD
12h 59m
2 stops
Multiple Airlines Logo
7:20 am - 5:24 pm
ORD
-
OGG
15h 04m
2 stops
$543Multiple Airlines
Mon, Oct 12 - Mon, Oct 19
Multiple Airlines Logo
2:49 pm - 6:20 pm
OGG
-
ORD
22h 31m
2 stops
Multiple Airlines Logo
2:21 pm - 9:59 pm
ORD
-
OGG
12h 38m
1 stop
$546Multiple Airlines
Tue, Oct 6 - Tue, Oct 20
Multiple Airlines Logo
10:59 pm - 11:59 pm
OGG
-
ORD
20h 00m
1 stop
Multiple Airlines Logo
2:21 pm - 12:05 pm
ORD
-
OGG
26h 44m
2 stops
$550Multiple Airlines
Thu, Oct 15 - Sun, Oct 25
Delta Logo
8:12 pm - 12:25 pm
OGG
-
ORD
11h 13m
1 stop
Delta Logo
7:30 am - 2:04 pm
ORD
-
OGG
11h 34m
1 stop
$554Delta
Mon, Oct 19 - Mon, Oct 26
Delta Logo
12:45 pm - 1:47 pm
OGG
-
ORD
20h 02m
1 stop
Delta Logo
7:30 am - 2:04 pm
ORD
-
OGG
11h 34m
1 stop
$566Delta
Mon, Jul 20 - Thu, Jul 23
Southwest Logo
10:50 am - 5:45 am
OGG
-
MDW
13h 55m
1 stop
Southwest Logo
6:30 am - 12:35 pm
MDW
-
OGG
11h 05m
1 stop
$750Southwest
Tue, Jul 21 - Fri, Jul 31
Southwest Logo
8:55 pm - 12:25 pm
OGG
-
MDW
10h 30m
1 stop
Southwest Logo
5:45 am - 2:50 pm
MDW
-
OGG
14h 05m
2 stops
$756Southwest
Useful Info

Good to know

Cheapest flight$217
Flight from Kahului to Chicago Midway 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
Schererville
Munster
Chesterton
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 $323
Business Class flights to Chicagofrom $312
Premium Economy Class flights to Chicagofrom $240
Economy Class flights to Chicagofrom $56