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Lowest round trip fares by airline from Chicago and Maui

Cheapest prices ($183 One Way, $369 Round Trip) found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Great Deals On Cheap Hotels in Maui

Maui Seaside Hotel

Maui Seaside Hotel

3 out of 5
100 W Kaahumanu Ave, Kahului, HI
The price is $339 per night from Mar 29 to Mar 30
$339
per night
Mar 29 - Mar 30
Stay at this beach hotel in Kahului. Enjoy free WiFi, a beach locale, and onsite parking. Our guests praise the pool and the restaurant in our reviews. Popular ...
8.4/10 Very Good! (1,135 reviews)
"Close to airport and a few restaurants."

Reviewed on Mar 21, 2024

Maui Seaside Hotel
Maui Beach Hotel

Maui Beach Hotel

3 out of 5
170 W Kaahumanu Avenue, Kahului, HI
The price is $249 per night from Apr 21 to Apr 22
$249
per night
Apr 21 - Apr 22
Stay at this beach hotel in Kahului. Enjoy breakfast, WiFi, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. ...
7/10 Good! (1,005 reviews)
"Great location, easy parking. nice room"

Reviewed on Mar 24, 2024

Maui Beach Hotel
Days Inn by Wyndham Maui Oceanfront

Days Inn by Wyndham Maui Oceanfront

2.5 out of 5
2980 S Kihei Road, Kihei, HI
The price is $281 per night from Apr 9 to Apr 10
$281
per night
Apr 9 - Apr 10
Stay at this beach hotel in Kihei. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8/10 Very Good! (1,011 reviews)
"Nice No pool and access to the beach not to safe"

Reviewed on Mar 26, 2024

Days Inn by Wyndham Maui Oceanfront
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Fly From Chicago to Maui

Origin
Chicago
Destination
Maui
Number of Daily Flights
1
Earliest Flight Departure Date
Apr 4
Latest Flight Departure Date
Apr 4
Popular Airlines
United Airlines

Cheap flights from Chicago to Maui (Island of Maui)

Chicago O’Hare International Airport (ORD) is the main hub of the windy city. Located off I-90 and I-94, you can reach ORD via taxi, Pace bus, the CTA “L” train, the Metra North Central line, or even by riding your bike.

From ORD you will have an eight-and-a-half flight to Kahului Airport (OGG). Upon arrival in Hawaii, rent a car to get around or arrange for shuttle transportation to and from the airport. There are also taxi and private car services available.

Attractions and tips

Maui offers many activities for its visitors, including the Haleakala National Park, where you can hike through sub-tropical rainforests to volcanos.

Beach goers should check out the popular Wailea, Kanaha and Baldwin beaches. The former Hawaiian capital of Lahaina is now a National Historic Landmark and a great place to observe Hawaiian history.

Hotels and condominiums are located on the western and southern parts of the island. If you want fun without crowds, you want to visit Maui in the spring or fall. If you like to surf, you want to visit in the winter, but understand the crowds will be formidable. No matter when you book your Maui trip, expect warm weather, with temperatures rarely dipping below 65 degrees.

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.