Chicago to Honolulu Starting at $342 for Travel in February and March!
As you know…. Especially right now…. Winter in the Midwest can be a grind, so seeing flights from Chicago to Honolulu starting at $342 round trip definitely grabbed my attention. This route is normally $550+, so this is a rare chance to trade snow boots for sandals and squeeze in a serious winter warm-up at a deep discount. Availability is limited to February and March, which is prime timing for escaping cold temps without peak summer crowds.
Why people love Honolulu:
• Perfect mix of beach + city – world-class beaches like Waikiki paired with great dining, shopping, and nightlife
• Unreal scenery – Diamond Head, lush hikes, waterfalls, and turquoise water everywhere you look
• Easy island access – simple day trips to the North Shore, Pearl Harbor, or snorkeling at Hanauma Bay
• Year-round sunshine – even “winter” in Hawaii feels pretty close to perfect
If you’ve been dreaming about Hawaii but waiting for prices to come back down, this is one of the better Chicago-to-Hawaii deals I’ve seen in a while. Perfect excuse to break up winter and come back recharged 🌺✈️
The Flights
Super solid breakdown of the deal value here. That $517 cheaper than usual stat really puts it into perspective and I've been burned befor by waiting on Hawaii fares only to see them spike. The Feb-March window being ideal for dodging summer crowds is lowkey the best part since my last trip to Oahu in off-peak season made all the differnce.