$188 Cheap flight deals from Chicago (CHI) to Koloa (LIH)

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Airfares from $188 One Way, $410 Round Trip from Chicago to Koloa

Prices starting at $410 for return flights and $188 for one-way flights to Koloa were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Mon, Mar 9 - Wed, Mar 18
ORD
Chicago
LIH
Kauai
$410 Roundtrip, found 10 hours ago
$410
Roundtrip
found 10 hours ago
Select Alaska Airlines flight, departing Mon, Mar 9 from Chicago to Kauai, returning Wed, Mar 18, priced at $410 found 10 hours ago
Mon, Mar 9 - Wed, Mar 18
ORD
Chicago
LIH
Kauai
$416 Roundtrip, found 10 hours ago
$416
Roundtrip
found 10 hours ago
Select Alaska Airlines flight, departing Mon, Mar 9 from Chicago to Kauai, returning Wed, Mar 18, priced at $416 found 10 hours ago
Wed, Apr 15 - Wed, Apr 22
ORD
Chicago
LIH
Kauai
$421 Roundtrip, just found
$421
Roundtrip
just found
Select Alaska Airlines flight, departing Wed, Apr 15 from Chicago to Kauai, returning Wed, Apr 22, priced at $421 just found
Sat, Dec 5 - Wed, Dec 9
ORD
Chicago
LIH
Kauai
$424 Roundtrip, found 2 days ago
$424
Roundtrip
found 2 days ago
Select Alaska Airlines flight, departing Sat, Dec 5 from Chicago to Kauai, returning Wed, Dec 9, priced at $424 found 2 days ago
Mon, Jan 4 - Sun, Jan 10
ORD
Chicago
LIH
Kauai
$424 Roundtrip, found 7 hours ago
$424
Roundtrip
found 7 hours ago
Select American Airlines flight, departing Mon, Jan 4 from Chicago to Kauai, returning Sun, Jan 10, priced at $424 found 7 hours ago

Koloa economy flight packages

Price found within the past 48 hours. Click for updated prices.
Waipouli Beach Resorts & Spa Kauai by OUTRIGGER
4.0-star property

Waipouli Beach Resorts & Spa Kauai by OUTRIGGER

8.8/10 Excellent! (1,002 reviews)

Mar 24 - Mar 31

7 night stay

Chicago (CHI) to Lihue (LIH)

Delta • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $2,703, price is now $1,625 per person
$1,625
per person
found 1 day ago
We will liked the condo and how it was layed out and it was convenient to the pool/ocean/parking/etc. I wish there would have been more conveniences in the condo itself (examples: hair dryer, pool toys, cooler, more pans & accessories in the kitchen). We had a great time and loved how quiet and safe it was!

Reviewed on Jan 5, 2026

Ko'a Kea Resort on Po'ipu Beach
4.5-star property

Ko'a Kea Resort on Po'ipu Beach

9.4/10 Exceptional! (1,001 reviews)

Mar 24 - Mar 31

7 night stay

Chicago (CHI) to Lihue (LIH)

Delta • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $4,317, price is now $3,027 per person
$3,027
per person
found 1 day ago
Another place cancelled our reservation and this hotel was kind enough to let five of us stayed in one room that sleeps 3 people. Staff members were very nice and accomodating.

Reviewed on Jan 8, 2026

1 Hotel Hanalei Bay
5.0-star property

1 Hotel Hanalei Bay

9.2/10 Wonderful! (275 reviews)

Mar 24 - Mar 31

7 night stay

Chicago (CHI) to Lihue (LIH)

Delta • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $7,044, price is now $5,048 per person
$5,048
per person
found 1 day ago
Views were gorgeous and property is well maintained. The staff was extremely nice.

Reviewed on Jun 29, 2025

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More About Flying To Koloa from Chicago

Route Information for Flights from Chicago to Koloa

Origin Airport IATA Code
CHI
Destination Airport IATA Code
LIH
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Chicago to Koloa

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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.