Important: This destination may have COVID-19 travel restrictions in place, including specific restrictions for lodging. Check any national, local, and health advisories for this destination before you book.

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

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Lowest round trip fares by airline from Chicago and Maui

Cheapest prices ($241 One Way, $479 Round Trip) found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Tue, Oct 5
ORD
Chicago
OGG
Kahului
$241
Bargain Flight
Tue, Oct 19
ORD
Chicago
OGG
Kahului
$243
Alaska Airlines
Wed, Oct 6
ORD
Chicago
OGG
Kahului
$259
United
Tue, Sep 28
ORD
Chicago
OGG
Kahului
$259
American Airlines
Thu, Sep 16
ORD
Chicago
OGG
Kahului
$274
Delta
Tue, Nov 2 - Tue, Nov 9
ORD
Chicago
OGG
Kahului
$479
Bargain Flight
Wed, Sep 29 - Mon, Oct 4
ORD
Chicago
OGG
Kahului
$518
United
Tue, Sep 28 - Tue, Oct 5
ORD
Chicago
OGG
Kahului
$518
American Airlines
Sun, Sep 5 - Thu, Sep 9
ORD
Chicago
OGG
Kahului
$621
Delta
Fri, Aug 20 - Wed, Aug 25
MDW
Chicago
OGG
Kahului
$677
Delta

Great Deals On Cheap Hotels in Maui

Maui Seaside Hotel

Maui Seaside Hotel

2.5 out of 5
100 W Kaahumanu Ave, Kahului, HI
The price is $242 per night from Jun 1 to Jun 1
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.
4.5/5Wonderful! (19 reviews)
"Clean and very convenient. Nice staff and it was close to the beach"

Reviewed on Mar 2, 2020

Maui Seaside Hotel
Maui Beach Hotel

Maui Beach Hotel

2.5 out of 5
170 Kaahumanu Avenue, Kahului, HI
The price is $209 per night from May 17 to May 17
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 ...
3.8/5Good! (9 reviews)
"The toilet and sheets were clean. That is the only positive can say about this $200 after fees hotel. Unidentifiable stains on carpet and curtains. Outdated and unkept."

Reviewed on Mar 12, 2021

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 $239 per night from May 12 to May 12
Nestled on the beach, this Kihei hotel is within a 10-minute walk of Keawakapu Beach and Kamaole Beach Park 3. Wailea Beach is 0.7 mi (1.1 km) away.
4/5Very Good! (6 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
Earliest Flight Departure Date
Latest Flight Departure Date
Popular 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.