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Lowest round trip fares by airline from Chicago and Maui

Cheapest prices ($245 One Way, $466 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
2.5 out of 5.0
3.7 out of 5 (82 reviews)

Situated near the airport, this hotel is within 1 mi (2 km) of Ho'aloha Park and Maui Arts and Cultural Center. Kahului Bay is 1.3 mi (2.1 km) away.

Clean and very convenient. Nice staff and it was close to the beach
Maui Beach Hotel
2.5 out of 5.0
3.5 out of 5 (46 reviews)

Located in the heart of Kahului, this beach hotel is within a 15-minute walk of Queen Ka’ahumanu Center and Maui Arts and Cultural Center. Maui Nui Botanical ...

Total lack of atmosphere at the bar which closes way to early.
Days Inn by Wyndham Maui Oceanfront
2.5 out of 5.0
4.0 out of 5 (7 reviews)

Nestled on the beach, this Kihei hotel is within a 15-minute walk of Keawakapu Beach, Wailea Beach, and Kamaole Beach Park 3. Mokapu Beach and Kamaole Beach ...

Liked everything. Good thing for the extra parking, the locals like that beach area.

Fly From Chicago to Maui

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Cheap flights from Chicago to Maui

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.