Cheap flights from Maui to Chicago (OGG - CHI)

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The best prices from Maui to Chicago are usually found in January or August, booked 60 days in advance, depart on a Friday or Tuesday and return on a Tuesday

How to find the cheapest flight from
Maui (OGG) to Chicago (CHI)

All the information you need to plan the best OGG to CHI flight in 2021: compare Maui to Chicago flight prices with the expected peak season, weather and rainfall in Chicago.
OGG - CHI
Price
$526 - $959
CHI
Temperature
33.8 - 84.2 °F
CHI
Rainfall
0.7 - 4.3 inches

Popular in

March

High demand for flights, 34% potential price rise

Cheapest in

January

Best time to find cheap flights, 16% potential price drop

Round-trip from

$526

From Maui to Chicago

One-way from

$228

One-way flight from Maui to Chicago

Flight route prices based on searches on Cheapflights within the last 3 days, monthly prices based on aggregated historical data.
What is the cheapest day to fly round-trip from Maui to Chicago?

Flights from Maui to Chicago are found to be more expensive on Friday. This shouldn't discourage you from searching as you can still find great deals by being flexible with your options. Use our search form to find deals on tickets to Chicago.

How far in advance should I book a flight from Maui to Chicago?

To save on the cost of your flight from Maui to Chicago, book at least 20 days before your planned departure. Booking around this time can save you about 10% on the cost of this flight compared to booking a flight leaving this week. We have found prices from $137 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as $157.

What is the cheapest month to fly from Maui to Chicago?

The best pricing can be found in the month of April. Prices to Chicago from Maui average $135. You can even find prices in April for less than $135, as users have found deals to Chicago from as low as $33. The month of December appears to be one of the more expensive times to travel to Chicago from Maui. Flying in the targeted month can save you up to 49%.

When is the cheapest time to fly from Maui to Chicago (OGG - CHI)?

When flying from Maui to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight in the morning, which can drop the price by up to 60% versus a flight in the afternoon.

Cheap flights from Maui to Chicago in May, June 2021

The best prices found for OGG to CHI flights for May, June
21 Jun - 4 Jul
$577pp
OGG
Kahului
United Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
 
1 STOP
OGG
Kahului
21 Jun - 3 Jul
$583pp
OGG
Kahului
United Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
   
2 STOPS
OGG
Kahului
17 Jun - 4 Jul
$583pp
OGG
Kahului
Delta
   
2 STOPS
MDW
Chicago Midway
MDW
Chicago Midway
Delta
   
2 STOPS
OGG
Kahului

Maui to Chicago 2021 flight deals

Cheap flights to Chicago from Maui found for this year
28 Jul - 11 Aug
$501pp
OGG
Kahului
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
OGG
Kahului
28 Jul - 11 Aug
$509pp
OGG
Kahului
Multiple Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
OGG
Kahului
21 Jul - 27 Jul
$510pp
OGG
Kahului
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
   
2 STOPS
OGG
Kahului

Non-stop flights to Chicago from Maui

Save time with Maui to Chicago direct flight deals
27 Jul - 9 Aug
$851pp
OGG
Kahului
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
OGG
Kahului
17 Jun - 5 Jul
$856pp
OGG
Kahului
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
OGG
Kahului
14 Jun - 21 Jun
$861pp
OGG
Kahului
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
OGG
Kahului

One-way flights to Chicago from Maui

The cheapest one-way flights from Maui to Chicago
5:28 pm - 2:15 pm
Delta
2 Stops
15h 47m
OGG - ORD
Delta
$228
Delta
6:10 pm - 7:59 pm
Alaska Airlines
1 Stop
20h 49m
OGG - ORD
Alaska Airlines
2:57 pm - 12:03 pm
Multiple Airlines
2 Stops
16h 06m
OGG - ORD
Multiple Airlines
$263
Gotogate

Related info for your journey

Useful info, stats and facts about <span class="emphasized">Maui</span> to <span class="emphasized">Chicago</span> flights.

Flight FAQs

From Maui to Chicago

Are flight prices decreasing from Kahului to Chicago due to COVID-19 (coronavirus)?

At this time, Cheapflights has noticed price decreases for many domestic flights due to COVID-19. Travel is not necessarily recommended at this time, and flights may be prone to cancellation: please check with local authorities in both Kahului and Chicago for travel alerts, and be sure to review the airline's cancellation policy and travel advisories before booking. For more information, please view our post on what to know about COVID-19 (coronavirus) and travel.

What safety measures are being taken by airlines flying from Kahului to Chicago to control the spread of COVID-19?

Airlines globally have implemented additional safety measures to accommodate you. Alaska Airlines is one of them. Airline carriers are regularly disinfecting and sanitizing their aircraft. Masks are provided and are mandatory while on board. Pre-flight testing for symptoms and antibodies, alongside socially distanced seating (for a limited time) will work towards keeping travelers safer while flying from Kahului to Chicago. Policies will vary by airline.

Which airlines flying from Kahului to Chicago have flexible cancellations due to COVID-19?

American Airlines, United Airlines, and Delta are some of the carriers that may have flexible cancellation policies. You can use our site to filter for other airlines that may also have this kind of flexibility.

What airport do you fly from for flights from Kahului to Chicago?

Located just 2.7 mi from the city center, Kahului is the airport most travelers will use when flying to Chicago from Kahului. Booking flights from Kahului (OGG) to Chicago should be relatively easy as there is 1 daily outbound flight to Chicago from 4 different airlines.

Can I find flights from Maui to Chicago for under $500 on Cheapflights?

Yes, there are multiple flights from Maui to Chicago for under $500. The cheapest flight booked recently is on Multiple Airlines for just $495, but on average you can expect to pay $545.

Are there nonstop flights from Maui to Chicago for under $900 on Cheapflights?

Cheapflights has at least 20 direct flights from Maui to Chicago under $900. A good price for a nonstop flight from Maui to Chicago is less than $962.

Is Kahului weather warmer or cooler than Chicago?

Expect the weather to be around 88 °F on average in July. As the temperature peaks, try to get your plans done early, as flight price and availability will have an impact on your travels. The climate in Chicago is generally colder than in Kahului.

How long is the flight from Maui to Chicago?

A quick flight from Maui to Chicago can take about 7h 50m. United Airlines provides one of the quickest options available for as low as $805. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

What are the cheapest airlines flying from Maui to Chicago round-trip?

Flying on Alaska Airlines is currently your cheapest option to Chicago, with prices starting at $523. Additional round-trip tickets that might be worth considering are offered by Delta and American Airlines, with the lowest prices starting at $545 and $560, respectively. Alaska Airlines is 16% cheaper than the average price of flights available within the next 90 days to this destination.

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

For one-way options, check prices for Alaska Airlines. According to our data, you can fly for as low as $223. Users have also found prices from $225 and $259 on Alaska Airlines and Delta, respectively.

Destination information for Chicago

Things to know before you go - useful duration and weather info for your trip from Maui to Chicago.
Average temperature for May in Chicago
71.6 °F
Avg rainfall for May in Chicago
4.3 ″

Airports servicing Kahului

Airports servicing Chicago

Chicago Midway (MDW)
Rockford (RFD)

Top 4 airlines flying from Maui to Chicago

The chart below displays the airlines Cheapflights users traveling from Maui to Chicago choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
Airline Cheapest Average Flexibility On-time COVID-19 safety
Delta
$301 $564 No cancel fee N/A
American Airlines
$274 $573 No cancel fee 71%
Alaska Airlines
$361 $598 No cancel fee 75%
United Airlines
$304 $690 No cancel fee 69%

Hourly flight availability from Maui to Chicago

See what time of day planes typically take off from Maui towards Chicago.
Afternoon Noon to 6 PM 100% of OGG to CHI departures
Early morning Midnight to 6 AM 0% of OGG to CHI departures
Morning 6 AM to noon 0% of OGG to CHI departures
Evening 6 PM to midnight 0% of OGG to CHI departures
Midnight
6 AM
Noon
6 PM
Weekly flight availability
from Maui to Chicago
See how many times per day planes take to the skies headed from Maui to Chicago.
Sunday
2 daily flights
Monday
2 daily flights
Tuesday
0 flights
Wednesday
0 flights
Thursday
2 daily flights
Friday
2 daily flights
Saturday
2 daily flights
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