$187 Cheap flight deals from Chicago (CHI) to Upcountry Maui (OGG)
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This Weekend's Flight Deals from Chicago to Upcountry Maui
This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
Airfares from $187 One Way, $372 Round Trip from Chicago to Upcountry Maui
Prices starting at $372 for return flights and $187 for one-way flights to Upcountry Maui were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
Upcountry Maui economy flight packages
Maui Beach Vacation Club
Sep 8 - Sep 15
Chicago (CHI) to Kahului (OGG)
Reviewed on Jul 30, 2025
Upcountry Maui packages with premium economy flights
The Westin Maui Resort & Spa, Ka'anapali
Sep 10 - Sep 17
Chicago (ORD) to Kahului (OGG)
Reviewed on May 30, 2025
The Ritz-Carlton Maui, Kapalua
Sep 10 - Sep 17
Chicago (ORD) to Kahului (OGG)
Reviewed on Jul 5, 2025
Residence Inn by Marriott Maui Wailea
Sep 10 - Sep 17
Chicago (ORD) to Kahului (OGG)
Reviewed on Jan 31, 2023
More About Flying To Upcountry Maui from Chicago
Route Information for Flights from Chicago to Upcountry Maui
Origin Airport IATA Code | CHI |
|---|---|
Destination Airport IATA Code | OGG |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Chicago to Upcountry Maui
Planning a trip is rarely straight forward, especially when searching for cheap deals. At Orbitz.com, we make it easier than anywhere else by providing you with guaranteed low prices. So if you are looking for Chicago to Upcountry Maui flights at low cost, you will not be disappointed.
Cruising for a bargain deal
Regardless of your destination, we always provide you fantastic bargains for your trip, and that includes on hotels and even cruises. We offer budget air fares on flights from Chicago to Upcountry Maui so you can reach your destination with more money in your pocket to spend.
Cheap Chicago to Upcountry Maui flights that lead to rewards
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Quality combinations
If you require budget Chicago to Upcountry Maui flights and a bargain hotel to go with it, Orbitz will wow you with the great combinations we can offer. The quality is always high and always a superb value.
Even last minute bookings on our apps
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Upcountry Maui Airports
Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.
Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.
Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.