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Lowest round trip fares by airline from Chicago and Maui

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

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.

Packages from Chicago to Maui

Maui vacations with economy flights

Hotels in Maui

See all 6,363 Properties in Maui
Maui Seaside Hotel

Maui Seaside Hotel

100 W Kaahumanu Ave, Kahului, HI
    2.5 out of 5.0
     
     
    3.6 out of 5 (75 reviews)

    Situated near the airport, this hotel is within 1 mi (2 km) of Ho'aloha Park and Maui Arts and Cultural Center. Maui Nui Botanical Gardens is 1.3 mi (2 km) ...

    Maui Seaside Hotel$144

    Maui Seaside Hotel$144
    Honua Kai Resort & Spa

    Honua Kai Resort & Spa

    130 Kai Malina Parkway, Lahaina, HI
      4.0 out of 5.0
       
       
      4.4 out of 5 (29 reviews)

      Located in Lahaina, this beachfront condo resort is in the historical district and within 3 mi (5 km) of Kahekili Beach, Whalers Village, and Kaanapali Beach. ...

      Honua Kai Resort & Spa$359

      Honua Kai Resort & Spa$359
      The Westin Maui Resort & Spa, Ka'anapali

      The Westin Maui Resort & Spa, Ka'anapali

      2365 Kaanapali Pkwy, Lahaina, HI
        4.0 out of 5.0
         
         
        4.1 out of 5 (88 reviews)

        Located in Lahaina, this beachfront resort is next to a golf course, just steps from Whalers Village and Kaanapali Beach. Black Rock is 0.9 mi (1.4 km) away. ...

        The Westin Maui Resort & Spa, Ka'anapali$279

        The Westin Maui Resort & Spa, Ka'anapali$279
        Grand Wailea Maui, A Waldorf Astoria Resort

        Grand Wailea Maui, A Waldorf Astoria Resort

        3850 Wailea Alanui Drive, Kihei, HI
          4.5 out of 5.0
           
           
          4.7 out of 5 (12 reviews)

          Located in Wailea, this beachfront resort is next to a golf course and within 2 mi (3 km) of Shops at Wailea, Wailea Beach, and Keawakapu Beach. Kamaole Beach ...

          Grand Wailea Maui, A Waldorf Astoria Resort$359

          Grand Wailea Maui, A Waldorf Astoria Resort$359
          Maui Coast Hotel

          Maui Coast Hotel

          2259 S Kihei Rd, Kihei, HI
            3.5 out of 5.0
             
             
            4.3 out of 5 (65 reviews)

            Situated in Kihei, this golf hotel is within a 15-minute walk of Kamaole Beach Park and Kamaole Beach Park 3. Wailea Beach and Keawakapu Beach are also within ...

            Maui Coast Hotel$259

            Maui Coast Hotel$259
            Kaanapali Beach Hotel

            Kaanapali Beach Hotel

            2525 Kaanapali Parkway, Lahaina, HI
              3.0 out of 5.0
               
               
              4.3 out of 5 (7 reviews)

              Located in Lahaina, this beachfront hotel is next to a golf course and within a 10-minute walk of Kaanapali Beach and Whalers Village. Black Rock is 0.7 mi (1.1 ...

              Kaanapali Beach Hotel$218

              Kaanapali Beach Hotel$218
              Aston Kaanapali Shores

              Aston Kaanapali Shores

              3445 Lower Honoapiilani Hwy, Lahaina, HI
                3.5 out of 5.0
                 
                 
                3.9 out of 5 (73 reviews)

                Located in Lahaina, this beachfront condo resort is in the historical district and within 3 mi (5 km) of Kahekili Beach, Whalers Village, and Kaanapali Beach. ...

                Aston Kaanapali Shores$235

                Aston Kaanapali Shores$235
                Hyatt Regency Maui Resort & Spa

                Hyatt Regency Maui Resort & Spa

                200 Nohea Kai Dr, Lahaina, HI
                  4.0 out of 5.0
                   
                   
                  4.4 out of 5 (49 reviews)

                  Nestled on the beach, this Lahaina resort is within a 15-minute walk of Kaanapali Beach and Whalers Village. Black Rock and Maui Theater are also within 3 mi ...

                  Hyatt Regency Maui Resort & Spa$339

                  Hyatt Regency Maui Resort & Spa$339
                  Maui Beach Hotel

                  Maui Beach Hotel

                  170 Kaahumanu Avenue, Kahului, HI
                    2.5 out of 5.0
                     
                     
                    3.4 out of 5 (45 reviews)

                    Located in Kahului, this beachfront hotel is in the city center and within a 15-minute walk of Ho'aloha Park and Maui Arts and Cultural Center. Maui Nui Botanical ...

                    Maui Beach Hotel$129

                    Maui Beach Hotel$129
                    Andaz Maui at Wailea Resort - a concept by Hyatt

                    Andaz Maui at Wailea Resort - a concept by Hyatt

                    3550 Wailea Alanui Dr, Kihei, HI
                      4.5 out of 5.0
                       
                       
                      5.0 out of 5 (2 reviews)

                      Located in Wailea, this beachfront resort is next to a golf course and within 1 mi (2 km) of Shops at Wailea and Keawakapu Beach. Wailea Beach and Kamaole Beach ...

                      Andaz Maui at Wailea Resort - a concept by Hyatt$459

                      Andaz Maui at Wailea Resort - a concept by Hyatt$459
                      Map

                      *Savings based on all holiday package bookings with Flight + Hotel on CheapTickets.com from January through December 2017, as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages. For Free Flight or 100% Off Flight deals, package savings is greater than or equal to the current cost of one component, when both are priced separately.

                      *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.