Chicago to Hawaii flight deals
Compare flights from Chicago to Hawaii across upcoming months. Explore the dated fares below, or search your own trip.
Browse months: November 2026 · December 2026
Compare destinations for the same trip
Nov 10–17, 2026 · 1 adult · Economy · Round trip
- MDW → Oahu / Honolulu (HNL): $471 Axel vs $496 airline · Save $25. Check HNL prices
- ORD → Oahu / Honolulu (HNL): $483 Axel vs $510 airline · Save $27. Check HNL prices
- ORD → Maui / Kahului (OGG): $534 Axel vs $562 airline · Save $28. Check OGG prices
- MDW → Maui / Kahului (OGG): $539 Axel vs $570 airline · Save $31. Check OGG prices
Flights from Chicago · Chicago to United States flight deals
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Oahu / Honolulu (HNL) · Maui / Kahului (OGG)
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Fares observed September 28, 2026. USD for the travelers shown. Search a trip for current prices.
November 2026
1 adult · Economy · Round-trip totals
| From | Destination | Travel dates | Flights (out / return) | Axel | Airline fare | Search |
|---|---|---|---|---|---|---|
| MDW | Oahu / Honolulu (HNL) | Nov 10–17, 2026 · 7 days | 2 stops / 1 stop · 13h 15m / 10h 40m | $471 · Save $25 | $496 | Check Axel prices |
| ORD | Oahu / Honolulu (HNL) | Nov 10–17, 2026 · 7 days | 1 stop / 1 stop · 22h 56m / 22h 0m | $483 · Save $27 | $510 | Check Axel prices |
| ORD | Oahu / Honolulu (HNL) | Nov 10–17, 2026 · 7 days | 1 stop / Nonstop · 22h 56m / 8h 6m | $512 · Save $27 | $539 | Check Axel prices |
| ORD | Maui / Kahului (OGG) | Nov 10–17, 2026 · 7 days | 2 stops / 1 stop · 17h 22m / 12h 59m | $534 · Save $28 | $562 | Check Axel prices |
| ORD | Maui / Kahului (OGG) | Nov 10–17, 2026 · 7 days | 2 stops / 1 stop · 17h 22m / 10h 0m | $536 · Save $30 | $566 | Check Axel prices |
| MDW | Maui / Kahului (OGG) | Nov 10–17, 2026 · 7 days | 1 stop / 1 stop · 11h 35m / 10h 0m | $539 · Save $31 | $570 | Check Axel prices |
| MDW | Oahu / Honolulu (HNL) | Nov 17–24, 2026 · 7 days | 2 stops / 2 stops · 13h 15m / 12h 25m | $513 · Save $28 | $541 | Check Axel prices |
| MDW | Oahu / Honolulu (HNL) | Nov 17–24, 2026 · 7 days | 2 stops / 1 stop · 13h 15m / 10h 15m | $556 · Save $30 | $586 | Check Axel prices |
| ORD | Oahu / Honolulu (HNL) | Nov 17–24, 2026 · 7 days | 1 stop / Nonstop · 14h 31m / 8h 6m | $513 · Save $27 | $540 | Check Axel prices |
| ORD | Maui / Kahului (OGG) | Nov 17–24, 2026 · 7 days | 2 stops / 1 stop · 17h 22m / 12h 59m | $534 · Save $28 | $562 | Check Axel prices |
| ORD | Maui / Kahului (OGG) | Nov 17–24, 2026 · 7 days | 2 stops / 1 stop · 17h 22m / 10h 0m | $628 · Save $33 | $661 | Check Axel prices |
| MDW | Maui / Kahului (OGG) | Nov 17–24, 2026 · 7 days | 2 stops / 2 stops · 13h 0m / 15h 35m | $504 · Save $27 | $531 | Check Axel prices |
| MDW | Maui / Kahului (OGG) | Nov 17–24, 2026 · 7 days | 2 stops / 1 stop · 13h 0m / 10h 35m | $639 · Save $35 | $674 | Check Axel prices |
December 2026
1 adult · Economy · Round-trip totals
| From | Destination | Travel dates | Flights (out / return) | Axel | Airline fare | Search |
|---|---|---|---|---|---|---|
| MDW | Oahu / Honolulu (HNL) | Dec 1–8, 2026 · 7 days | 2 stops / 1 stop · 17h 10m / 10h 40m | $576 · Save $31 | $607 | Check Axel prices |
| ORD | Oahu / Honolulu (HNL) | Dec 1–8, 2026 · 7 days | Nonstop / 1 stop · 9h 12m / 10h 54m | $547 · Save $30 | $577 | Check Axel prices |
| ORD | Oahu / Honolulu (HNL) | Dec 1–8, 2026 · 7 days | Nonstop / Nonstop · 9h 12m / 8h 6m | $588 · Save $32 | $620 | Check Axel prices |
| MDW | Maui / Kahului (OGG) | Dec 1–8, 2026 · 7 days | 2 stops / 1 stop · 14h 50m / 10h 0m | $546 · Save $30 | $576 | Check Axel prices |
| ORD | Maui / Kahului (OGG) | Dec 1–8, 2026 · 7 days | 1 stop / 1 stop · 11h 52m / 10h 15m | $556 · Save $30 | $586 | Check Axel prices |
| MDW | Oahu / Honolulu (HNL) | Dec 8–15, 2026 · 7 days | 1 stop / 1 stop · 13h 45m / 10h 40m | $588 · Save $32 | $620 | Check Axel prices |
| ORD | Oahu / Honolulu (HNL) | Dec 8–15, 2026 · 7 days | Nonstop / 1 stop · 9h 12m / 10h 59m | $547 · Save $30 | $577 | Check Axel prices |
| ORD | Oahu / Honolulu (HNL) | Dec 8–15, 2026 · 7 days | Nonstop / Nonstop · 9h 12m / 8h 6m | $703 · Save $39 | $742 | Check Axel prices |
| MDW | Maui / Kahului (OGG) | Dec 8–15, 2026 · 7 days | 1 stop / 1 stop · 11h 20m / 14h 5m | $539 · Save $31 | $570 | Check Axel prices |
| MDW | Maui / Kahului (OGG) | Dec 8–15, 2026 · 7 days | 1 stop / 1 stop · 11h 20m / 10h 0m | $609 · Save $33 | $642 | Check Axel prices |
| ORD | Maui / Kahului (OGG) | Dec 8–15, 2026 · 7 days | 1 stop / 1 stop · 11h 18m / 10h 15m | $556 · Save $30 | $586 | Check Axel prices |
The prices shown are what a free account pays, and most travelers book that way. Membership is optional and takes the same flights lower. Live search shows the same free-account price.
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- This page: Chicago to Hawaii flight deals. Chicago to Hawaii flight deals. Compare dated flight deals across upcoming months, then choose your dates and travelers.
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