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$202+ Cheap flights from Chicago (CHI) to Maui

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/22. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OGG
dic. 28 — ene. 41
sáb. 12/28
sáb. 1/4
1 adult, Economy
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Cheap flight deals from Chicago to Maui

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Maui (zzFUK). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated diciembre 23, 2024.

Round-trip from

$414
(United Airlines)

One-way from

$202
(Southwest)
From Chicago (CHI) to Maui
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One-way flight from Chicago (CHI) to Maui
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Find flight deals from Chicago to Maui

Cheapest flights from Chicago to Maui
Explore the most affordable flight options available from Chicago to Maui. Find the lowest fares from popular airlines and budget airlines, with prices last updated on diciembre 23, 2024.

This United deal was found by Cheapflights users on 12/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/306:15 amORD - OGG
2 stops18h 34mUnited Airlines
jue. 1/92:05 pmOGG - ORD
1 stop11h 49mUnited Airlines
Deal found 12/23$792
This American Airlines deal was found by Cheapflights users on 12/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/308:25 pmORD - OGG
1 stop21h 05mAmerican Airlines
jue. 1/97:05 pmOGG - ORD
1 stop10h 21mAmerican Airlines
Deal found 12/23$816
This Alaska Airlines deal was found by Cheapflights users on 12/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/236:56 pmORD - OGG
2 stops23h 48mAlaska Airlines
sáb. 12/282:45 pmOGG - ORD
1 stop10h 45mAlaska Airlines
Deal found 12/22$854
This Delta deal was found by Cheapflights users on 12/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/256:00 amORD - OGG
1 stop16h 22mDelta
mar. 12/3110:15 pmOGG - ORD
1 stop11h 00mDelta
Deal found 12/22$1,172
This Southwest deal was found by Cheapflights users on 12/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 12/285:35 amMDW - OGG
1 stop12h 00mSouthwest
mié. 1/19:00 amOGG - MDW
2 stops20h 15mSouthwest
Deal found 12/22$1,332
This Southwest deal was found by Cheapflights users on 12/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/256:15 amORD - OGG
1 stop13h 55mSouthwest
mié. 1/16:00 amOGG - ORD
2 stops13h 05mSouthwest
Deal found 12/22$1,332
This Delta deal was found by Cheapflights users on 12/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/259:30 amMDW - OGG
2 stops16h 19mDelta
mar. 12/311:21 pmOGG - MDW
2 stops17h 47mDelta
Deal found 12/22$1,452
This United Airlines deal was found by Cheapflights users on 12/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 12/299:30 amORD - OGG
Nonstop9h 16mMultiple Airlines
dom. 1/53:10 pmOGG - ORD
1 stop11h 00mMultiple Airlines
Deal found 12/22$1,684
This Mytrip deal was found by Cheapflights users on 12/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/279:35 pmORD - JHM
3 stops44h 10mMultiple Airlines
jue. 1/92:05 pmJHM - ORD
2 stops27h 47mMultiple Airlines
Deal found 12/22$1,825

Find flights from Chicago to Maui within your budget

Customize your flight search to find flights from Chicago to Maui that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated diciembre 23, 2024.

Fly from

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Fly to

Any airport

Route

Depart

Return

Price

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

mié. 1/22

10:35 am-8:54 pm

2 stops14h 19m

Kahului

mar. 1/28

11:31 pm-4:31 pm

2 stops13h 00m

$414

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

mié. 2/5

1:39 pm-10:45 am

2 stops25h 06m

Kahului

mié. 2/12

6:00 am-5:40 am

2 stops19h 40m

$419

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

vie. 2/7

6:55 pm-11:49 am

1 stop20h 54m

Kahului

jue. 2/13

3:20 pm-5:53 am

1 stop10h 33m

$422

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

lun. 1/27

6:00 am-5:39 pm

1 stop15h 39m

Kahului

lun. 2/3

5:30 pm-10:12 am

1 stop12h 42m

$425

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

mar. 1/21

7:15 am-7:55 pm

1 stop16h 40m

Kahului

dom. 2/9

8:55 pm-12:40 pm

1 stop11h 45m

$425

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

mié. 2/26

6:41 am-3:30 pm

1 stop12h 49m

Kahului

dom. 3/2

2:55 pm-6:19 am

1 stop11h 24m

$446

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

mié. 1/22

7:20 am-4:20 pm

1 stop13h 00m

Kahului

mar. 1/28

9:35 am-11:20 pm

1 stop9h 45m

$474

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

lun. 1/27

7:15 am-8:54 pm

2 stops17h 39m

Kahului

lun. 2/3

2:50 pm-4:20 pm

3 stops21h 30m

$517

ChicagoHana

ORD - HNM

ORDHNM

Chicago O'Hare Intl

mié. 1/22

2:07 pm-8:38 am

3 stops22h 31m

Hana

mar. 1/28

9:00 am-1:07 pm

2 stops24h 07m

$660

ChicagoKapalua

ORD - JHM

ORDJHM

Chicago O'Hare Intl

mié. 1/22

5:28 pm-1:45 pm

3 stops24h 17m

Kapalua West Maui

mar. 1/28

2:05 pm-5:59 pm

2 stops23h 54m

$940

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/21

Showing 1-10 of 21 results
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Best time to book a flight from Chicago to Maui

Have a flexible travel schedule? Discover the best time to fly to Maui from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Travel insights for flights from Chicago to Maui

Get recent, data-driven insights about flights from Chicago to Maui including ideal travel times, pricing trends, and more.

What is the cheapest month to book a flight from Chicago to Maui?

Currently, November is the cheapest month in which you can book a flight from Chicago to Maui (average of $391). Flying from Chicago to Maui in June is currently the most expensive (average of $576). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to FUK?

Find hourly flight availability from Chicago to Maui. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated diciembre 23, 2024.

When flying from Chicago to Maui, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Weekly flight availability from Chicago to Maui

Explore weekly flight availability from Chicago to Maui. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated diciembre 23, 2024.

The most flights from CHI to zzFUK are scheduled on a Monday (1 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (1 on average).

Rainfall in Maui by month

Plan your trip to Maui by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Maui ranges from 0.1 - 3.8 inches per month. January is typically the wettest month, when rainfall can reach 3.8 in. June is typically the driest time to visit Maui when rainfall is around 0.1 in.

Temperature in Maui by month

Plan your trip to Maui by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Maui, use this chart to help with planning. For those seeking warmer temperatures, August is the ideal time of year to visit, when temperatures reach an average of 80.6 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 71.6 F).

Reviews of airlines servicing Maui

Get insights into the airlines that provide service to Maui. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Maui. Reviews last updated diciembre 23, 2024.
Get a feel of what it's like to fly with United Airlines, American Airlines and Alaska Airlines from Chicago to Maui by reading reviews from past customers. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,780 reviews

Overall

8.1

Comfort

8.1

Crew

8.7

Food

7.2

Entertainment

7.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,780 reviews
Southwest
8.1
Very good
4,780 reviews

Overall

8.1

Comfort

8.1

Crew

8.7

Food

7.2

Entertainment

7.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Alaska Airlines
8.0
Very good
9,549 reviews
Southwest
8.1
Very good
4,780 reviews

Overall

8.1

Comfort

8.1

Crew

8.7

Food

7.2

Entertainment

7.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,588 reviews
Southwest
8.1
Very good
4,780 reviews

Overall

8.1

Comfort

8.1

Crew

8.7

Food

7.2

Entertainment

7.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

United Airlines
7.4
Good
9,020 reviews
Southwest
8.1
Very good
4,780 reviews

Overall

8.1

Comfort

8.1

Crew

8.7

Food

7.2

Entertainment

7.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,780 reviews

Overall

8.1

Comfort

8.1

Crew

8.7

Food

7.2

Entertainment

7.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Maui. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What are the cheapest airlines to fly from Chicago to Maui one-way?

    For one-way options, check prices for Southwest. According to our data, you can fly for as low as $202. Users have also found prices from $202 and $223 on Alaska Airlines and Delta, respectively.

  • What are the most popular routes from Chicago to Maui?

    Most travelers choose Chicago O'Hare Intl - Kahului, Chicago Midway - Kahului or Chicago O'Hare Intl - Kapalua West Maui when deciding on the best route from Chicago to Maui.

  • What are the cheapest flights from Chicago to Maui?

    Looking at all options, your cheapest flight can be booked for $385. While the most popular route (Chicago O'Hare Intl - Kahului) can be booked for $404 on average our data indicates $871 when flying from Chicago to Maui.

  • Can I find deals for flights from Chicago to Maui that include hotel bookings?

    Yes. In addition to deals on Chicago to Maui flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Maui?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Maui.

  • Can I find deals for business class flights from Chicago to Maui?

    Yes. Cheapflights offers flight deals from Chicago to Maui by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Maui?

    Currently, November is the cheapest month in which you can book a flight from Chicago to Maui (average of $391). Flying from Chicago to Maui in June is currently the most expensive (average of $576). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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Alternative routes for Chicago to Maui

See prices for flight routes from nearby airports that may be better suited for you.
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Top 5 airlines flying from Chicago to Maui

Discover the top 5 airlines that operate flights from Chicago to Maui. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated diciembre 23, 2024.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$341Average$521FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$349Average$691FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$419Average$610FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$463Average$804FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$464Average$962FlexibilityNo cancel feeOn-time69%
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