Cheap flights from Chicago to Maui from $252
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 6/7. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
Discover deals from 900+ travel sites with momondo.
Save money when you book flights with momondo
Big names and deals
Big names and deals
Search 100s of travel sites to compare prices.Filter for what you want
Filter for what you want
Free Wi-Fi? Stopover? Instantly customize your results.Trusted and free
Trusted and free
We’re completely free to use - no hidden charges or fees.Price Alerts
Price Alerts
Not ready to book? to track prices.Find the cheapest flights from Chicago to Maui
Cheap round-trip flights
Cheap one-way flights
Cheap last minute flights
Cheap direct flights
Hawaiian Airlines flights from Chicago to Maui
Our best Hawaiian Airlines deals on Chicago to Maui flight tickets
Alaska Airlines flights from Chicago to Maui
Our best Alaska Airlines deals on Chicago to Maui flight tickets
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 month to fly to Maui?
The month of September is, on average, the cheapest month to fly to Maui from Chicago, with most prices found around $443. If you are unable to visit Maui during the month of September, then departing from Chicago during the month November is also very affordable. Most momondo users find prices during this month for around $497.
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 Monday. momondo users have found tickets for Monday departures for as low as $1,074. However, this price may fluctuate depending on the airline, the season, and holidays. The most expensive day to fly to Maui is Wednesday, with ticket prices averaging around $1,327.
What is the cheapest time of day to depart on your flight to Maui?
Flying to Maui from Chicago in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $531 when looking at flights departing in the afternoon. Flights to Maui are more costly in the morning, with an average ticket price of $1,144. Departure times in the morning fall within the peak daily travel times, which is why tickets can be more expensive.
What is the cheapest Chicago to Maui flight route?
Fly from Chicago O'Hare Intl to Kahului for the best Chicago - Maui flight prices
How far in advance should I book a flight to Maui?
You are more likely to see cheaper flights to Maui from Chicago when booking 6 weeks ahead of your departure date. In general, you can expect to find flights to Maui for around $748 when searching 6 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Maui from Chicago for as low as $551 on momondo.
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.
What is the cheapest airline that flies from Chicago to Maui?
Alaska Airlines, Southwest, and Delta are the most popular carriers operating from Chicago to Maui
What airlines fly to Maui?
United Airlines, American Airlines and Alaska Airlines are the top three most popular airlines that fly to Maui from Chicago according to our data. United Airlines is the first choice among our users, with 42% of people opting to fly with this airline when traveling to Maui. Keep in mind that there are 6 different airlines that fly to Maui on a routine basis, so you have a few additional options to choose from.
Cheap Chicago to Maui flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Chicago to Maui
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?
There are 6 operators available for flights from Chicago to Maui as of April 2025.
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?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Chicago to Maui is Airbus A321neo (14.04% of total bookings). The next most popular plane models are Boeing 737-800 (13.90%), Airbus A320neo (13.44%), and Boeing 737-900 (7.40%).
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 | ||
|---|---|---|---|---|---|
| PriceFrom $341 | Free Cancellation | Rating 8.0 7,920 reviews | |||
| PriceFrom $349 | Free Cancellation | Rating 7.2 10,000 reviews | |||
| PriceFrom $419 | Free Cancellation | Rating 8.0 9,918 reviews | |||
| PriceFrom $448 | Free Cancellation | Rating 7.9 2,393 reviews | |||
| PriceFrom $476 | Free Cancellation | Rating 7.4 8,685 reviews | |||
| PriceFrom $479 | Free Cancellation | Rating 8.0 4,287 reviews |
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.