Cheap flights from Chicago (CHI) to Maui (OGG)

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Lowest round trip fares by airline from Chicago and Maui

Cheapest prices ($307 One Way, $528 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, 96732
The price is $263 per night from May 30 to May 31
Stay at this 3-star business-friendly hotel in Kahului. Enjoy free WiFi, a free airport shuttle, and onsite parking. Our guests praise the helpful staff and ...
4.6/5 Wonderful! (18 reviews)
"Very clean and maintained. Friendly staff and helpful"

Reviewed on May 16, 2022

Maui Seaside Hotel
Maui Beach Hotel

Maui Beach Hotel

2.5 out of 5
170 Kaahumanu Avenue, Kahului, HI, 96732
The price is $269 per night from May 30 to May 31
Stay at this beach hotel in Kahului. Enjoy free WiFi, a 24-hour fitness center, and onsite parking. Our guests praise the breakfast and the helpful staff in ...
3.4/5 (8 reviews)
"The pictures of this hotel are very deceiving. We picked this hotel based on the rating and pictures. We only needed one night as we reserved our resort from Saturday to Saturday. So we wanted something close to airport since we got in late Friday night. The lobby has been recently updated and the ..."

Reviewed on Apr 24, 2022

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, 96753
The price is $319 per night from May 23 to May 24
Stay at this beach hotel in Kihei. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the restaurant and the clean rooms in our reviews. Popular ...
4.3/5 Excellent! (4 reviews)
"Liked everything. Good thing for the extra parking, the locals like that beach area."

Reviewed on Jun 19, 2019

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 May 27
Latest Flight Departure Date May 27
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.