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Cheap flights from Chicago to Maui from $202

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Maui departing on 1/5. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Chicago to Maui

Cheap round-trip flights

These are some of the best round-trip flight deals from Chicago to Maui that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Chicago to Maui.

Cheap last minute flights

Planning a quick getaway from Chicago to Maui? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Maui, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Chicago to Maui

Find recent round-trip train or bus tickets from Chicago to Maui.

All round-trip flight deals to Maui

The cheapest plane tickets to Maui found on KAYAK recently.
6:00 am - 5:39 pmMDW-OGG
15h 39m1 stop
4:45 pm - 10:12 amOGG-MDW
13h 27m1 stop
$404Delta
Find Deal
Mon, Jan 20 - Thu, Jan 30
5:45 am - 5:39 pmORD-OGG
15h 54m1 stop
9:19 pm - 1:15 pmOGG-ORD
11h 56m1 stop
$404Delta
Find Deal
Mon, Jan 20 - Wed, Jan 29
7:45 am - 5:28 pmORD-OGG
13h 43m1 stop
7:49 pm - 5:59 pmOGG-ORD
18h 10m2 stops
$409Alaska Airlines
Find Deal
Mon, Jan 13 - Fri, Jan 17
7:45 am - 6:00 pmORD-OGG
14h 15m2 stops
8:30 pm - 5:59 pmOGG-ORD
17h 29m2 stops
$414Alaska Airlines
Find Deal
Mon, Jan 13 - Wed, Jan 22
12:45 pm - 8:54 pmORD-OGG
12h 09m1 stop
2:20 pm - 5:53 amOGG-ORD
11h 33m1 stop
$433United Airlines
Find Deal
Thu, Feb 6 - Thu, Feb 13
6:30 am - 3:24 pmORD-OGG
12h 54m1 stop
2:43 pm - 5:05 amOGG-ORD
10h 22m1 stop
$434American Airlines
Find Deal
Tue, Jan 21 - Sun, Feb 9
7:00 am - 3:46 pmORD-OGG
12h 46m1 stop
2:43 pm - 5:05 amOGG-ORD
10h 22m1 stop
$443American Airlines
Find Deal
Mon, Jan 13 - Fri, Jan 17
8:45 am - 4:31 pmORD-OGG
11h 46m1 stop
9:00 pm - 11:20 amOGG-ORD
10h 20m1 stop
$463United Airlines
Find Deal
Thu, Jan 9 - Sun, Jan 12
7:30 am - 4:30 pmMDW-OGG
14h 00m2 stops
8:25 pm - 1:00 pmOGG-MDW
11h 35m1 stop
$553Southwest
Find Deal
Tue, Apr 22 - Tue, May 6
6:00 am - 12:25 pmMDW-OGG
11h 25m1 stop
8:25 pm - 1:00 pmOGG-MDW
11h 35m1 stop
$575Southwest
Find Deal
Tue, Apr 22 - Tue, May 6
6:00 am - 5:46 pmMDW-OGG
15h 46m1 stop
$202Delta
Find Deal
Sun, Jan 5
7:05 am - 5:46 pmORD-OGG
14h 41m1 stop
$202Delta
Find Deal
Sun, Jan 5
4:05 pm - 11:15 amORD-OGG
23h 10m1 stop
$208Alaska Airlines
Find Deal
Sat, Mar 1
7:00 pm - 2:35 pmORD-OGG
23h 35m2 stops
$227Alaska Airlines
Find Deal
Sat, Mar 1
6:30 am - 3:24 pmORD-OGG
12h 54m1 stop
$232American Airlines
Find Deal
Fri, Jan 31
8:00 am - 4:10 pmMDW-OGG
12h 10m1 stop
$292Southwest
Find Deal
Tue, Nov 26
5:10 am - 4:20 pmMDW-OGG
15h 10m1 stop
$346Southwest
Find Deal
Mon, Feb 17
2:25 pm - 1:00 pmORD-OGG
26h 35m2 stops
$446United Airlines
Find Deal
Thu, Dec 5
2:30 pm - 12:49 pmORD-OGG
26h 19m2 stops
$510United Airlines
Find Deal
Tue, Dec 24
6:00 am - 1:32 pmORD-OGG
12h 32m1 stop
$1,225American Airlines
Find Deal
Wed, May 7
1:15 pm - 8:31 pmORD-OGG
11h 16m1 stop
9:00 pm - 1:18 pmOGG-ORD
12h 18m1 stop
$433United Airlines
Find Deal
Fri, Nov 22 - Fri, Jan 17
12:45 pm - 8:31 pmORD-OGG
11h 46m1 stop
9:00 pm - 11:20 amOGG-ORD
10h 20m1 stop
$487United Airlines
Find Deal
Fri, Nov 22 - Sat, Jan 18
1:15 pm - 8:31 pmORD-OGG
11h 16m1 stop
2:05 pm - 10:14 amOGG-ORD
16h 09m2 stops
$578United Airlines
Find Deal
Fri, Nov 22 - Fri, Jan 17
6:00 am - 9:52 pmORD-OGG
19h 52m1 stop
1:10 pm - 4:53 pmOGG-ORD
23h 43m1 stop
$796Alaska Airlines
Find Deal
Sun, Nov 24 - Wed, Nov 27
6:00 am - 9:00 pmORD-OGG
19h 00m2 stops
9:19 pm - 4:13 pmOGG-ORD
14h 54m2 stops
$841Delta
Find Deal
Fri, Nov 22 - Fri, Jan 17
8:00 am - 9:52 pmORD-OGG
17h 52m1 stop
5:25 pm - 12:16 pmOGG-ORD
14h 51m1 stop
$952Alaska Airlines
Find Deal
Sat, Nov 23 - Fri, Nov 29
5:30 am - 1:35 pmMDW-OGG
12h 05m1 stop
8:00 am - 10:00 pmOGG-MDW
10h 00m1 stop
$992Southwest
Find Deal
Fri, Nov 22 - Fri, Nov 29
5:30 am - 1:35 pmMDW-OGG
12h 05m1 stop
9:00 am - 8:55 amOGG-MDW
19h 55m2 stops
$997Southwest
Find Deal
Fri, Nov 22 - Fri, Nov 29
6:00 am - 6:46 pmMDW-OGG
16h 46m2 stops
3:40 pm - 10:37 amOGG-MDW
14h 57m2 stops
$1,027Delta
Find Deal
Sun, Nov 24 - Wed, Nov 27
5:00 am - 3:20 pmORD-OGG
14h 20m2 stops
10:01 pm - 12:16 pmOGG-ORD
10h 15m1 stop
$1,710American Airlines
Find Deal
Sat, Nov 23 - Sat, Nov 30
9:30 am - 3:00 pmORD-OGG
9h 30mnonstop
6:15 pm - 6:06 amOGG-ORD
7h 51mnonstop
$873United Airlines
Find Deal
Thu, Feb 13 - Tue, Feb 18
9:30 am - 2:46 pmORD-OGG
9h 16mnonstop
6:15 pm - 6:13 amOGG-ORD
7h 58mnonstop
$883United Airlines
Find Deal
Wed, Jan 1 - Fri, Jan 31
9:30 am - 2:46 pmORD-OGG
9h 16mnonstop
6:15 pm - 6:13 amOGG-ORD
7h 58mnonstop
$893United Airlines
Find Deal
Fri, Jan 10 - Sun, Jan 12
9:30 am - 2:46 pmORD-OGG
9h 16mnonstop
6:15 pm - 6:06 amOGG-ORD
7h 51mnonstop
$926United Airlines
Find Deal
Sun, Feb 2 - Sat, Feb 15
9:30 am - 2:00 pmORD-OGG
9h 30mnonstop
5:15 pm - 6:06 amOGG-ORD
7h 51mnonstop
$933United Airlines
Find Deal
Sun, Mar 9 - Sun, Mar 16
9:20 am - 1:41 pmORD-OGG
9h 21mnonstop
5:10 pm - 6:02 amOGG-ORD
7h 52mnonstop
$963United Airlines
Find Deal
Sat, May 3 - Sat, May 10
9:30 am - 2:46 pmORD-OGG
9h 16mnonstop
6:15 pm - 6:13 amOGG-ORD
7h 58mnonstop
$983United Airlines
Find Deal
Mon, Jan 13 - Fri, Jan 17
9:30 am - 3:00 pmORD-OGG
9h 30mnonstop
6:15 pm - 6:06 amOGG-ORD
7h 51mnonstop
$1,013United Airlines
Find Deal
Thu, Feb 13 - Thu, Feb 20
9:30 am - 2:46 pmORD-OGG
9h 16mnonstop
6:15 pm - 6:13 amOGG-ORD
7h 58mnonstop
$1,023United Airlines
Find Deal
Sat, Jan 4 - Mon, Jan 13
9:30 am - 2:46 pmORD-OGG
9h 16mnonstop
6:15 pm - 6:13 amOGG-ORD
7h 58mnonstop
$1,033United Airlines
Find Deal
Fri, Jan 10 - Fri, Jan 17

Delta flights from Chicago to Maui

Our best Delta deals on Chicago to Maui flight tickets
Delta
Jan 20
MDW6:00 amChicago Midway
15h 39m
1 stop
OGG5:39 pmKahului
Jan 30
OGG4:45 pmKahului
13h 27m
1 stop
MDW10:12 amChicago Midway
Delta
Jan 20
MDW6:00 amChicago Midway
15h 39m
1 stop
OGG5:39 pmKahului
Jan 30
OGG4:45 pmKahului
16h 01m
2 stops
MDW12:46 pmChicago Midway
Delta
Jan 13
ORD7:05 amChicago O'Hare Intl
14h 34m
1 stop
OGG5:39 pmKahului
Jan 27
OGG4:45 pmKahului
16h 10m
2 stops
ORD12:55 pmChicago O'Hare Intl

Alaska Airlines flights from Chicago to Maui

Our best Alaska Airlines deals on Chicago to Maui flight tickets
Alaska Airlines
Jan 13
ORD7:45 amChicago O'Hare Intl
13h 43m
1 stop
OGG5:28 pmKahului
Jan 17
OGG7:49 pmKahului
18h 10m
2 stops
ORD5:59 pmChicago O'Hare Intl
Alaska Airlines
Jan 13
ORD7:45 amChicago O'Hare Intl
14h 15m
2 stops
OGG6:00 pmKahului
Jan 22
OGG8:30 pmKahului
17h 29m
2 stops
ORD5:59 pmChicago O'Hare Intl
Alaska Airlines
Jan 31
ORD6:55 pmChicago O'Hare Intl
20h 54m
1 stop
OGG11:49 amKahului
Feb 14
OGG3:35 pmKahului
17h 29m
1 stop
ORD1:04 pmChicago O'Hare Intl

See travel insights to Maui from

How to get the cheapest flight ticket from Chicago to Maui

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest day to depart on your flight to Maui?

On average, the least expensive day to fly to Maui from Chicago is on a Tuesday. momondo users have found tickets for Tuesday departures for as low as $609. However, this price may fluctuate depending on the airline, the season, and holidays. The most expensive day to fly to Maui is Saturday, with ticket prices averaging around $842.

What is the cheapest Chicago to Maui flight route?

Fly from Chicago O'Hare Intl to Kahului for the best Chicago - Maui flight prices

What cabin class options are available on Chicago to Maui flights?

There are 4 cabin classes available to choose from on Chicago to Maui flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Chicago to Maui flights?

You could potentially save up to 64% on your flight if you consider stops on a Chicago to Maui flight.

Cheap Chicago to Maui flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Maui

Best Price Found

$202

Fastest flight time

9h 16m

Direct flights

Every day

Airports in Maui

1 airport
The best one-way flight to Maui from Chicago in the past 72 hours is $202. The best round-trip flight deal from Chicago to Maui found on momondo in the last 72 hours is $404.
The fastest flight from Chicago to Maui takes 9h 16m
Direct flights go from Chicago to Maui every day.
There is 1 airport near Maui: Kahului (OGG)

  • When did momondo last update prices for flights from Chicago to Maui?

    Prices for flights from Chicago to Maui were last updated today.

  • How many operators does momondo search for flights from Chicago to Maui?

  • How old do you have to be to fly from Chicago to Maui?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago to Maui.

  • What documentation or ID do you need to fly to Maui?

    The travel and health documents you'll need for your trip to Maui may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Maui. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Chicago to Maui?


Best airlines flying from Chicago to Maui

Compare and see reviews for airlines that fly from Chicago to Maui with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $341Free CancellationRating
8.0
8,755 reviews
Search Delta flights
American AirlinesPriceFrom $350Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
Alaska AirlinesPriceFrom $410Free CancellationRating
8.0
9,464 reviews
Search Alaska Airlines flights
SouthwestPriceFrom $437Free CancellationRating
8.1
5,005 reviews
Search Southwest flights
United AirlinesPriceFrom $470Free CancellationRating
7.4
9,172 reviews
Search United Airlines flights

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Maui?

It is quick and easy to find Chicago to Maui flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Maui that suits you.

Can I find flights from Chicago to Maui with flexible booking policies on momondo?

Flights from Chicago to Maui with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Chicago to Maui?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Chicago to Maui.

I’m not ready to book a flight from Chicago to Maui right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Maui from Chicago. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.


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