Skip to content
LarkTours

Routes · Americas

Chicago to Hawaii: Honolulu, Maui and the Big Island

Chicago → Honolulu → Maui → Big Island

Diamond Head, Hawaii
"Diamond_Head_Hawaii_From_Round_Top_Rd.JPG" by mar1865, CC BY-SA 3.0, via Wikimedia Commons· licence
2022 Views from Diamond Head 02 (Honolulu)
Photo: Farragutful, CC BY-SA 4.0, via Wikimedia Commons

Hawaii islands Best season (general guide): Apr–May, Sep–Oct

The Hawaiian islands each have a distinct character, and hopping between three of them shows the range from city beaches to volcanic landscapes. This route begins on Oahu in Honolulu, continues to Maui and ends on the Big Island. From Chicago you'll fly to Honolulu; short inter-island flights do the rest.

On Oahu, you can combine Waikiki's beach with the hike up Diamond Head and a visit to the Pearl Harbor National Memorial. The north shore is known for big winter surf. Maui's highlights take time: the winding Road to Hana passes waterfalls and rainforest, and sunrise from the summit of Haleakalā requires a reservation. The Big Island has black-sand beaches, coffee farms on the Kona side and, in Hawaiʻi Volcanoes National Park, craters and lava fields around Kīlauea. The park's eruption viewing areas depend on current activity.

The islands are warm all year. Late April to May and late September to October tend to be quieter and are often recommended as good months. Kīlauea erupts from time to time, and the park can close trails for safety, so check the USGS and NPS updates before your trip.

Plan time for driving: distances on Maui and the Big Island are longer than they look on a map. Respect closures and reef-safe guidance.

How to pace it: three nights on each island means one day for the main sight, one for something slower and one in reserve. On Maui, the drive to Hana and the trip to Haleakalā each take most of a day, so don't schedule them back to back. On the Big Island, base yourself near the national park for a night or two if you want to see it in the evening. Inter-island flights are short, but airport time adds up, so travel in the morning.

Suggested outline

  1. Chicago

    Start

  2. Honolulu

    By air · 3 nights suggested

    On Oahu. Waikiki beach, Diamond Head crater and Pearl Harbor's memorials.

  3. Maui

    By air · 3 nights suggested

    Reached by a short inter-island flight. The Road to Hana and the summit of Haleakalā are the classic outings.

    Haleakalā
    "Haleakala_crater_(1).jpg" by Navin75, CC BY-SA 2.0, via Wikimedia Commons· licence

  4. Big Island

    By air · 3 nights suggested

    Hawaii Island, the largest in the chain. Hawaiʻi Volcanoes National Park protects Kīlauea, one of the world's most active volcanoes.

    Hawaiʻi Volcanoes National Park
    "Pāhoehoe_and_Aa_flows_at_Hawaii.jpg" by Brocken Inaglory, CC BY-SA 3.0, via Wikimedia Commons· licence

Day by day

  1. Day 1 · Honolulu — Arrive; Waikiki· Chicago → Honolulu (by air) — long-haul; may arrive the next calendar day
  2. Day 2 · Honolulu — Diamond Head hike
  3. Day 3 · Honolulu — Pearl Harbor National Memorial
  4. Day 4 · Maui — Fly to Maui· Honolulu → Maui (by air)
  5. Day 5 · Maui — Road to Hana
  6. Day 6 · Maui — Haleakalā sunrise (reservation)
  7. Day 7 · Big Island — Fly to Kona· Maui → Big Island (by air)
  8. Day 8 · Big Island — Hawaiʻi Volcanoes National Park (check closures)
  9. Day 9 · Big Island — Coffee farms or black-sand beach
  10. Day 10 · Big Island — Travel home from Big Island· Big Island → Chicago (by air)

A suggested pace only; expedition days are set by the operator.

Flights, leg by leg

Each button opens a live, dated search. We don't show stored fares here: check today's price on the booking site.

Showing dates about a month ahead — change them when you search.

Honolulu

More about Honolulu →

Plan the trip: Honolulu

These links go to partner sites. We may earn a commission if you buy through them, at no extra cost to you. Prices and terms are set by the partner.

Maui

Nearest airport: Kahului Search fares · Kahului ↗

Big Island

Nearest airport: Kailua-Kona Search fares · Kailua-Kona ↗

Partner links may earn LarkTours a commission at no extra cost to you. Prices, availability and terms are set by each partner.