Southwest® flights from Chicago-Midway to Honolulu, Oahu, Hawaii from $285

How to Find Cheap Flights from Chicago (MDW) to Honolulu (HNL)

A few simple strategies can help you find cheap flights from Chicago to Honolulu. Keep these tips top of mind:

• Use the Low Fare Calendar: If you can flex your travel dates, the Southwest Low Fare Calendar is your new best friend for finding more affordable flights to Hawaii from Chicago.
• Book early: As with many long-haul routes, pricing for Chicago to Honolulu flights can change quickly based on seasonal demand, so book sooner rather than later.
• Travel in the shoulder seasons: Avoid peak holiday periods by planning your trip during the spring or fall.
• Set alerts: Subscribe to Southwest alerts to get the drop on all our best promotions and flight offers.

Island Hopping from Honolulu (HNL)

As the largest city in Hawaii, Honolulu is the perfect central hub for exploring the rest of the Hawaiian islands. Frequent inter-island flights connect Oahu to Maui, Kauai, and the Big Island, so your flight to Hawaii from Chicago can be the jump-off for a multi-island adventure.

Flying is the primary and most efficient way to travel between the islands, so many travelers use Honolulu as their starting point before continuing their tropical adventure. If you’re a Hawaii resident, learn about our Ohana Rewards program and start earning the bonuses that we offer for our Hawaii family.

Getting From HNL to Wakikki, downtown Honolulu and Nearby Areas

Oahu is relatively easy to get around compared to other Hawaiian islands, and you’ll have several transportation options available once your flight from Chicago to Honolulu lands:

• Rental cars: For maximum flexibility, reserve a rental car in advance, then pick it up at HNL. This is especially key if you plan to explore areas beyond Waikiki, like the North Shore or Ko Olina.
• Rideshares and taxis: Follow signs to the designated pickup areas outside baggage claim for Uber, Lyft, or taxis; Waikiki is typically a 20–30 minute ride, depending on traffic.
• Hotel shuttles: Some Waikiki hotels offer pre-arranged or scheduled airport transfers, so it’s worth checking ahead of time and reserving a spot if needed.
• Public transit (TheBus): Honolulu’s public bus system, TheBus, is the most affordable option, with routes connecting the airport to Waikiki and other parts of Honolulu. Be aware that there might be luggage size limits and you may need to transfer depending on your destination.

What’s the Best Time to Travel from Chicago to Honolulu?

• Winter: Trading Midwest snow for island sunshine is always a great idea, and winter is also prime whale-watching season. However, crowds tend to be larger because everyone else has the same good idea as you.
• Spring and fall: If you’re looking for fewer crowds and better deals on airfare from Chicago to Honolulu, the so-called “shoulder seasons” are your best bet. You’ll find great deals and still enjoy that beautiful Hawaiian weather.
• Summer: It’s a busy season with school out and families on vacation, but it’s a great time for a classic summer trip.
• Anytime: Let’s be real, there’s no bad time to visit Honolulu. Its warm, tropical climate makes it a perfect year-round destination.

What to Do in Honolulu After You Land

• Waikiki Beach: Catch some waves, take a surfing lesson, or just relax on the world-famous white sand.
• Diamond Head State Monument: Hike to the top of this iconic volcanic crater for sweeping panoramic views of the coastline.
• Pearl Harbor National Memorial: Pay your respects and learn about a pivotal moment in American history.
• Hanauma Bay: Grab some snorkeling gear and explore this protected marine sanctuary, where you can swim alongside colorful fish and sea turtles.