Cheap flights from Chicago to Honolulu
The cheapest round trip from Chicago to Honolulu that travelers found recently is $501 with a carry-on: a $501 fare on United, which usually includes a carry-on. It leaves Mon, Dec 7 and comes back Mon, Dec 14.
Live prices for Mon, Dec 7 to Mon, Dec 14
Cheapest trips travelers found recently
| Leave | Return | Airline | Airports | Stops | Fare | Carry-on (est.) | Total | Live prices |
|---|---|---|---|---|---|---|---|---|
| Mon, Dec 7 | Mon, Dec 14 | United | ORD → HNL | 2 stops | $501 | Included | $501 | Live price |
| Mon, Jan 11 | Mon, Jan 25 | Alaska Airlines | ORD → HNL | 1 stop | $514 | Included | $514 | Live price |
| Wed, Mar 3 | Wed, Mar 10 | American Airlines | ORD → HNL | Nonstop | $560 | Included | $560 | Live price |
| Sun, Nov 15 | Sun, Nov 22 | Southwest | MDW → HNL | 1 stop | $567 | Included | $567 | Live price |
| Sat, Oct 31 | Sun, Nov 8 | Alaska Airlines | ORD → HNL | 1 stop | $632 | Included | $632 | Live price |
| Sun, Jan 17 | Sun, Jan 24 | Southwest | MDW → HNL | 1 stop | $645 | Included | $645 | Live price |
| Sat, Jan 16 | Sat, Jan 23 | American Airlines | ORD → HNL | 1 stop | $662 | Included | $662 | Live price |
| Sat, Nov 14 | Thu, Nov 26 | Alaska Airlines | ORD → HNL | 1 stop | $664 | Included | $664 | Live price |
| Sat, Feb 20 | Sat, Feb 27 | Alaska Airlines | ORD → HNL | 1 stop | $666 | Included | $666 | Live price |
| Sat, Apr 10 | Sat, Apr 17 | Southwest | MDW → HNL | 1 stop | $683 | Included | $683 | Live price |
Round-trip prices per person, from real fares travelers found in the last few days. Carry-on fees are our estimate for each airline, both ways. Prices change fast: check the live price before you book.
Cheapest month to fly
| Month | Cheapest trip | From | Live prices |
|---|---|---|---|
| October 2026 | Sat, Oct 31 to Sun, Nov 8, 8 nights | $632 | Live price |
| November 2026 | Sun, Nov 15 to Sun, Nov 22, 7 nights | $567 | Live price |
| December 2026 | Mon, Dec 7 to Mon, Dec 14, 7 nights | $501 | Live price |
| January 2027 | Mon, Jan 11 to Mon, Jan 25, 14 nights | $514 | Live price |
| February 2027 | Sat, Feb 20 to Sat, Feb 27, 7 nights | $666 | Live price |
| March 2027 | Wed, Mar 3 to Wed, Mar 10, 7 nights | $560 | Live price |
Bag fees on this route
What the airlines flying Chicago to Honolulu usually charge for one bag each way. Budget airlines often sell the cheapest fares and charge the most for bags, so compare the total, not the fare.
| Airline | Carry-on, each way | Checked bag, each way |
|---|---|---|
| Alaska Airlines | Included | $40 |
| American Airlines | Included | $40 |
| Southwest | Included | $35 |
| United | Included | $40 |
Our estimates: fees depend on the fare type and when you pay. Check the airline's own price when you book.
How these prices work
These are real round-trip fares that travelers found on Aviasales recently, not a live search, so they can change or sell out. Dipt adds an estimate of each airline's carry-on fee, so a cheap fare with expensive bags doesn't look cheaper than it is. "Live price" opens Dipt's live flight search for those dates, where you book with the airline or travel site you pick. Dipt may earn a commission when you book, at no extra cost to you (how Dipt makes money).
Not sure where to go? Tell Dipt your budget and vibe and it finds the trip.
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