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$171+ Cheap flights from Maui to Chicago (CHI)

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 12/10. Fares are subject to change and may not be available on all flights or dates of travel.
OGG — CHI
Nov 18 — Nov 251
1 adult
Mon 11/18
Mon 11/25
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Cheap flight deals from Maui to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Maui (zzFUK) to Chicago (CHI). 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 November 13, 2024.

Find flight deals from Maui to Chicago

Cheapest flights from Maui to Chicago
Explore the most affordable flight options available from Maui to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 13, 2024.

This United Airlines deal was found by Cheapflights users on 11/11. 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.
Tue 11/122:20 pmOGG - ORD
1 stop10h 44mUnited Airlines
Sat 11/1612:45 pmORD - OGG
1 stop12h 06mUnited Airlines
Deal found 11/11$441
This Delta deal was found by Cheapflights users on 11/11. 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.
Tue 11/129:12 pmOGG - ORD
2 stops15h 57mDelta
Fri 11/156:05 amORD - OGG
1 stop16h 05mDelta
Deal found 11/11$547
This American Airlines deal was found by Cheapflights users on 11/12. 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.
Fri 12/276:57 pmOGG - ORD
1 stop10h 28mAmerican Airlines
Thu 1/28:25 pmORD - OGG
1 stop21h 05mAmerican Airlines
Deal found 11/12$575
This Southwest deal was found by Cheapflights users on 11/11. 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.
Tue 11/128:00 amOGG - MDW
1 stop10h 00mSouthwest
Sat 11/168:10 amMDW - OGG
1 stop12h 00mSouthwest
Deal found 11/11$579
This Alaska Airlines deal was found by Cheapflights users on 11/12. 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.
Mon 11/1810:50 pmOGG - ORD
1 stop33h 19mAlaska Airlines
Thu 12/55:34 pmORD - OGG
1 stop33h 06mAlaska Airlines
Deal found 11/12$583
This Southwest deal was found by Cheapflights users on 11/12. 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.
Fri 12/2712:00 pmOGG - ORD
2 stops17h 20mSouthwest
Thu 1/26:15 amORD - OGG
1 stop13h 55mSouthwest
Deal found 11/12$619
This Delta deal was found by Cheapflights users on 11/11. 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.
Tue 11/129:12 pmOGG - MDW
2 stops15h 50mDelta
Fri 11/156:00 amMDW - OGG
2 stops19h 00mDelta
Deal found 11/11$635

Find flights from Maui to Chicago within your budget

Customize your flight search to find flights from Maui to Chicago 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 2,744,491 searches. Data last updated November 13, 2024.

Fly from

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Fly to

Any airport

Route

Depart

Return

Price

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Tue 2/4

10:31 pm-2:03 pm

1 stop11h 32m

Chicago O'Hare Intl

Sat 2/8

6:55 pm-10:57 pm

1 stop32h 02m

$404

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Sun 2/2

9:19 pm-1:15 pm

1 stop11h 56m

Chicago O'Hare Intl

Tue 2/4

6:15 am-7:54 pm

2 stops17h 39m

$473

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Mon 2/3

9:35 am-11:20 pm

1 stop9h 45m

Chicago Midway

Fri 2/7

5:30 am-4:20 pm

1 stop14h 50m

$521

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Mon 2/3

4:45 pm-10:12 am

1 stop13h 27m

Chicago Midway

Mon 2/10

6:00 am-5:39 pm

1 stop15h 39m

$533

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Fri 12/27

6:57 pm-9:25 am

1 stop10h 28m

Chicago O'Hare Intl

Thu 1/2

8:25 pm-1:30 pm

1 stop21h 05m

$575

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Tue 2/4

9:00 pm-1:18 pm

1 stop12h 18m

Chicago O'Hare Intl

Fri 2/7

7:10 am-8:49 pm

2 stops17h 39m

$583

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Fri 12/27

12:00 pm-9:20 am

2 stops17h 20m

Chicago O'Hare Intl

Thu 1/2

6:15 am-4:10 pm

1 stop13h 55m

$619

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Tue 12/10

2:49 pm-6:11 am

1 stop11h 22m

$171

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Tue 12/10

9:12 pm-4:58 pm

2 stops15h 46m

$176

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Tue 12/10

10:15 pm-11:47 pm

1 stop21h 32m

$202

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/13

Showing 1-10 of 16 results
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Best time to book a flight from Maui to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Maui 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 Maui to Chicago

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

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

Currently, September is the cheapest month in which you can book a flight from Maui to Chicago (average of $232). Flying from Maui to Chicago in June is currently the most expensive (average of $308). 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 FUK to CHI?

Find hourly flight availability from Maui to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 13, 2024.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Maui to Chicago as you normally would.

Rainfall in Chicago by month

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

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

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

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated November 13, 2024.
Get a feel of what it's like to fly with Alaska Airlines, Delta and United Airlines from Maui to Chicago 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
5,048 reviews

Overall

8.1

Crew

8.7

Food

7.2

Comfort

8.1

Entertainment

7.7

Boarding

8.3

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Southwest
8.1
Very good
5,048 reviews
Southwest
8.1
Very good
5,048 reviews

Overall

8.1

Crew

8.7

Food

7.2

Comfort

8.1

Entertainment

7.7

Boarding

8.3

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Alaska Airlines
8.0
Very good
9,434 reviews
Southwest
8.1
Very good
5,048 reviews

Overall

8.1

Crew

8.7

Food

7.2

Comfort

8.1

Entertainment

7.7

Boarding

8.3

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Delta
8.0
Very good
8,789 reviews
Southwest
8.1
Very good
5,048 reviews

Overall

8.1

Crew

8.7

Food

7.2

Comfort

8.1

Entertainment

7.7

Boarding

8.3

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

United Airlines
7.4
Good
9,189 reviews
Southwest
8.1
Very good
5,048 reviews

Overall

8.1

Crew

8.7

Food

7.2

Comfort

8.1

Entertainment

7.7

Boarding

8.3

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

WestJet
7.3
Good
2,803 reviews
Southwest
8.1
Very good
5,048 reviews

Overall

8.1

Crew

8.7

Food

7.2

Comfort

8.1

Entertainment

7.7

Boarding

8.3

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Related info for your journey

Find useful and relevant information for your journey from Maui to Chicago. 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 Maui to Chicago one-way?

    For one-way options, check prices for American Airlines. According to our data, you can fly for as low as $171. Users have also found prices from $176 and $202 on Delta and Alaska Airlines, respectively.

  • What are the cheapest flights from Maui to Chicago?

    The cheapest flight price from Maui to Chicago is $245. On average you can expect to pay $1,487. The most popular route, (Kahului - Chicago Midway), can usually be booked for $521.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Maui to Chicago 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 Maui to Chicago?

    Currently, September is the cheapest month in which you can book a flight from Maui to Chicago (average of $232). Flying from Maui to Chicago in June is currently the most expensive (average of $308). 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.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

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Top 4 airlines flying from Maui to Chicago

Discover the top 4 airlines that operate flights from Maui to Chicago. 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 2,744,491 searches. Data last updated November 13, 2024.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$312Average$535FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$349Average$640FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$485Average$732FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$495Average$791FlexibilityNo cancel feeOn-time75%
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