A cityscape with a prominent mountain in the background and dense greenery in the foreground.

Flights from Chicago Midway Airport (MDW) to Daniel K. Inouye Intl. Airport (HNL)
Flights to Honolulu
Hawaii
United States of America
Flights
Expedia.co.jp

Popular airlines from Chicago Midway Airport (MDW) to Daniel K. Inouye Intl. Airport (HNL)

Southwest Airlines
Delta

Be in the know
Get alerts if flight prices drop or rise*
Book smarter
Save up to 40% on select hotels after you book a flight*
Earn twice
Earn your airline miles on top of our rewards
Sign in

Cheap Flights from Chicago to Oahu (MDW-HNL)

Prices were available within the past 7 days and start at ￥49,560 for one-way flights and ￥95,660 for roundtrip, for the period specified. Prices and availability are subject to change.

All deals

One way

Roundtrip

Sun, Nov 1 - Wed, Nov 4

MDW

Chicago

HNL

Oahu

￥95,660

Roundtrip

Found 5 days ago

Select Southwest Airlines flight, departing Sun, Nov 1 from Chicago to Oahu, returning Wed, Nov 4, priced at ￥95,660 Found 5 days ago

Sun, Nov 1 - Wed, Nov 4

MDW

Chicago

HNL

Oahu

￥96,500

Roundtrip

Found 5 days ago

Select Southwest Airlines flight, departing Sun, Nov 1 from Chicago to Oahu, returning Wed, Nov 4, priced at ￥96,500 Found 5 days ago

Tue, Nov 3 - Sat, Nov 7

MDW

Chicago

HNL

Oahu

￥102,630

Roundtrip

Found 18 hours ago

Select Southwest Airlines flight, departing Tue, Nov 3 from Chicago to Oahu, returning Sat, Nov 7, priced at ￥102,630 Found 18 hours ago

Tue, Nov 3 - Sat, Nov 7

MDW

Chicago

HNL

Oahu

￥105,920

Roundtrip

Found 18 hours ago

Select Delta flight, departing Tue, Nov 3 from Chicago to Oahu, returning Sat, Nov 7, priced at ￥105,920 Found 18 hours ago

Tue, Nov 3 - Sat, Nov 7

MDW

Chicago

HNL

Oahu

￥106,030

Roundtrip

Found 18 hours ago

Select Delta flight, departing Tue, Nov 3 from Chicago to Oahu, returning Sat, Nov 7, priced at ￥106,030 Found 18 hours ago

Fri, Jan 8 - Fri, Jan 15

MDW

Chicago

HNL

Oahu

￥106,140

Roundtrip

Found 3 days ago

Select Southwest Airlines flight, departing Fri, Jan 8 from Chicago to Oahu, returning Fri, Jan 15, priced at ￥106,140 Found 3 days ago

Sun, Nov 1 - Wed, Nov 4

MDW

Chicago

HNL

Oahu

￥108,570

Roundtrip

Found 5 days ago

Select Southwest Airlines flight, departing Sun, Nov 1 from Chicago to Oahu, returning Wed, Nov 4, priced at ￥108,570 Found 5 days ago

Sat, Nov 14 - Sat, Nov 21

MDW

Chicago

HNL

Oahu

￥108,680

Roundtrip

Found 6 days ago

Select Delta flight, departing Sat, Nov 14 from Chicago to Oahu, returning Sat, Nov 21, priced at ￥108,680 Found 6 days ago

Sun, Nov 1 - Wed, Nov 4

MDW

Chicago

HNL

Oahu

￥109,410

Roundtrip

Found 5 days ago

Select Southwest Airlines flight, departing Sun, Nov 1 from Chicago to Oahu, returning Wed, Nov 4, priced at ￥109,410 Found 5 days ago

Sun, Nov 1 - Wed, Nov 4

MDW

Chicago

HNL

Oahu

￥110,120

Roundtrip

Found 5 days ago

Select Southwest Airlines flight, departing Sun, Nov 1 from Chicago to Oahu, returning Wed, Nov 4, priced at ￥110,120 Found 5 days ago

Find the cheapest month to fly from Chicago (MDW) to Oahu (HNL)

November is typically the cheapest month to fly

From ￥36,368 - ￥161,021 per traveler.

Travel information

Origin airport	Chicago Midway Airport
Destination airport	Daniel K. Inouye Intl. Airport
Distance	6,832 km away
Airlines serving	Southwest Airlines, Delta
Popular airline	Southwest Airlines
Roundtrip price	￥95,660

Explore a world of travel with Expedia

Lodging
Flights
Cars
Vacation Rentals

Hotels with Early Check-in in Downtown Honolulu
Standard Link for Hotels with Early Check-in in Downtown Honolulu
Naval Station Pearl Harbor Hotels
Standard Link for Naval Station Pearl Harbor Hotels
Capsule Hotels in Honolulu County
Standard Link for Capsule Hotels in Honolulu County
Aparthotels in Honolulu
Standard Link for Aparthotels in Honolulu
B&B in Aiea
Standard Link for B&B in Aiea
Hotels with smoking rooms in Honolulu
Standard Link for Hotels with smoking rooms in Honolulu
Historic Hotels in Western Honolulu
Standard Link for Historic Hotels in Western Honolulu
Apartments in Hickam Field
Standard Link for Apartments in Hickam Field
Resorts & Hotels with Spas in Ford Island
Standard Link for Resorts & Hotels with Spas in Ford Island
Adults Only Resorts & in Western Honolulu
Standard Link for Adults Only Resorts & in Western Honolulu
All-Inclusive Hotel Hotels in Aiea
Standard Link for All-Inclusive Hotel Hotels in Aiea
Luxury Hotels in Ford Island
Standard Link for Luxury Hotels in Ford Island
Hotels near Daniel K. Inouye Intl.
Standard Link for Hotels near Daniel K. Inouye Intl.
Capsule Hotels in Joint Base Pearl Harbor-Hickam
Standard Link for Capsule Hotels in Joint Base Pearl Harbor-Hickam
Hotels near Aloha Tower Marketplace
Standard Link for Hotels near Aloha Tower Marketplace
Boutique Hotels in Western Honolulu
Standard Link for Boutique Hotels in Western Honolulu
Luxury Hotels in Joint Base Pearl Harbor-Hickam
Standard Link for Luxury Hotels in Joint Base Pearl Harbor-Hickam
Resorts in Joint Base Pearl Harbor-Hickam
Standard Link for Resorts in Joint Base Pearl Harbor-Hickam
B&B in Joint Base Pearl Harbor-Hickam
Standard Link for B&B in Joint Base Pearl Harbor-Hickam
Gay friendly Hotels in Western Honolulu
Standard Link for Gay friendly Hotels in Western Honolulu
Moanalua Hotels
Standard Link for Moanalua Hotels
Hotels with a Lazy River in Western Honolulu
Standard Link for Hotels with a Lazy River in Western Honolulu
Family Hotels in Honolulu
Standard Link for Family Hotels in Honolulu
Luxury Hotels in Naval Station Pearl Harbor
Standard Link for Luxury Hotels in Naval Station Pearl Harbor
Resorts & Hotels with Spas in Honolulu
Standard Link for Resorts & Hotels with Spas in Honolulu
Resorts in Camp H M Smith
Standard Link for Resorts in Camp H M Smith
Downtown Honolulu Hotels
Standard Link for Downtown Honolulu Hotels
Historic Hotels in Honolulu
Standard Link for Historic Hotels in Honolulu
Cabin Rentals in Joint Base Pearl Harbor-Hickam
Standard Link for Cabin Rentals in Joint Base Pearl Harbor-Hickam
Apartments in Honolulu County
Standard Link for Apartments in Honolulu County
Cheap Hotels in Naval Station Pearl Harbor
Standard Link for Cheap Hotels in Naval Station Pearl Harbor
Hotels near Pearlridge
Standard Link for Hotels near Pearlridge
Luxury Hotels in Moanalua
Standard Link for Luxury Hotels in Moanalua
Waterpark Hotels in Honolulu
Standard Link for Waterpark Hotels in Honolulu
Gay friendly Hotels in Honolulu
Standard Link for Gay friendly Hotels in Honolulu
Apartments in Camp H M Smith
Standard Link for Apartments in Camp H M Smith
Resorts & Hotels with Spas in Kalihi
Standard Link for Resorts & Hotels with Spas in Kalihi
Honolulu Hotels
Standard Link for Honolulu Hotels
Town Houses in Naval Station Pearl Harbor
Standard Link for Town Houses in Naval Station Pearl Harbor
Cheap Hotels in Joint Base Pearl Harbor-Hickam
Standard Link for Cheap Hotels in Joint Base Pearl Harbor-Hickam
Hotels with Early Check-in in Western Honolulu
Standard Link for Hotels with Early Check-in in Western Honolulu
Hostels in Honolulu
Standard Link for Hostels in Honolulu
Resorts in Honolulu County
Standard Link for Resorts in Honolulu County
Boutique Hotels in Honolulu
Standard Link for Boutique Hotels in Honolulu
Family Hotels in Western Honolulu
Standard Link for Family Hotels in Western Honolulu
Cheap Hotels in Ford Island
Standard Link for Cheap Hotels in Ford Island
Hotels with a Pool in Honolulu County
Standard Link for Hotels with a Pool in Honolulu County
All-Inclusive Hotel Hotels in Downtown Honolulu
Standard Link for All-Inclusive Hotel Hotels in Downtown Honolulu
Riads in Honolulu
Standard Link for Riads in Honolulu
Luxury Hotels in Honolulu County
Standard Link for Luxury Hotels in Honolulu County
Cheap Hotels in Honolulu County
Standard Link for Cheap Hotels in Honolulu County
Hotels near Pacific Aviation Museum Pearl Harbor
Standard Link for Hotels near Pacific Aviation Museum Pearl Harbor
Hotels near Aloha Stadium
Standard Link for Hotels near Aloha Stadium
Aiea Hotels
Standard Link for Aiea Hotels
Hotels near Honolulu Harbor
Standard Link for Hotels near Honolulu Harbor
Adventure Hotels in Liliha - Kapalama
Standard Link for Adventure Hotels in Liliha - Kapalama
Shopping Hotels in Downtown Honolulu
Standard Link for Shopping Hotels in Downtown Honolulu
Apartments in Naval Station Pearl Harbor
Standard Link for Apartments in Naval Station Pearl Harbor
5 Star Hotels in Honolulu
Standard Link for 5 Star Hotels in Honolulu
Apartments in Joint Base Pearl Harbor-Hickam
Standard Link for Apartments in Joint Base Pearl Harbor-Hickam
Hotels with Waterslides in Honolulu
Standard Link for Hotels with Waterslides in Honolulu
Ski Hotels in Kalihi
Standard Link for Ski Hotels in Kalihi
All-Inclusive Hotel Hotels in Honolulu
Standard Link for All-Inclusive Hotel Hotels in Honolulu
Joint Base Pearl Harbor-Hickam Hotels
Standard Link for Joint Base Pearl Harbor-Hickam Hotels
B&B in Camp H M Smith
Standard Link for B&B in Camp H M Smith
All-Inclusive Hotel Hotels in Kalihi
Standard Link for All-Inclusive Hotel Hotels in Kalihi
Hotels near Hawaii Children's Discovery Center
Standard Link for Hotels near Hawaii Children's Discovery Center
Business Hotels in Honolulu
Standard Link for Business Hotels in Honolulu
Family Hotels in Pearl City
Standard Link for Family Hotels in Pearl City
Hotels near Pearl Harbor Visitor Center
Standard Link for Hotels near Pearl Harbor Visitor Center
Cottages in Joint Base Pearl Harbor-Hickam
Standard Link for Cottages in Joint Base Pearl Harbor-Hickam
Holiday Park Resorts in Joint Base Pearl Harbor-Hickam
Standard Link for Holiday Park Resorts in Joint Base Pearl Harbor-Hickam
Aparthotels in Joint Base Pearl Harbor-Hickam
Standard Link for Aparthotels in Joint Base Pearl Harbor-Hickam
Hotels near Moanalua Gardens
Standard Link for Hotels near Moanalua Gardens
Hostels in Joint Base Pearl Harbor-Hickam
Standard Link for Hostels in Joint Base Pearl Harbor-Hickam
Pet-Friendly Hotels in Honolulu
Standard Link for Pet-Friendly Hotels in Honolulu
Apartments in Sand Island
Standard Link for Apartments in Sand Island
Cabin Rentals in Naval Station Pearl Harbor
Standard Link for Cabin Rentals in Naval Station Pearl Harbor
Farmstay in Joint Base Pearl Harbor-Hickam
Standard Link for Farmstay in Joint Base Pearl Harbor-Hickam
Hickam Field Hotels
Standard Link for Hickam Field Hotels
Chinatown Hotels
Standard Link for Chinatown Hotels
Resorts & Hotels with Spas in Downtown Honolulu
Standard Link for Resorts & Hotels with Spas in Downtown Honolulu
Cheap Hotels in Western Honolulu
Standard Link for Cheap Hotels in Western Honolulu
Hotels near Honolulu Hale
Standard Link for Hotels near Honolulu Hale
Hotels near Keʻehi Lagoon Beach Park
Standard Link for Hotels near Keʻehi Lagoon Beach Park
Beach Hotels in Honolulu County
Standard Link for Beach Hotels in Honolulu County
Lodges in Honolulu
Standard Link for Lodges in Honolulu
Adventure Hotels in Downtown Honolulu
Standard Link for Adventure Hotels in Downtown Honolulu
Condo Resorts in Honolulu County
Standard Link for Condo Resorts in Honolulu County

Flights from Tokyo (TYO) to Honolulu (HNL)
Standard Link for Flights from Tokyo (TYO) to Honolulu (HNL)
Flights from Tokyo (NRT) to Honolulu (HNL)
Standard Link for Flights from Tokyo (NRT) to Honolulu (HNL)
Flights to Daniel K. Inouye Intl.
Standard Link for Flights to Daniel K. Inouye Intl.
Flights from Los Angeles (LAX) to Honolulu (HNL)
Standard Link for Flights from Los Angeles (LAX) to Honolulu (HNL)

Rental cars Daniel K. Inouye Intl. airport
Standard Link for Rental cars Daniel K. Inouye Intl. airport
Hertz Rental Cars in Honolulu
Standard Link for Hertz Rental Cars in Honolulu
Dollar Rent A Car Rental Cars in Honolulu
Standard Link for Dollar Rent A Car Rental Cars in Honolulu
Car rental Joint Base Pearl Harbor-Hickam
Standard Link for Car rental Joint Base Pearl Harbor-Hickam
Enterprise Rental Cars in Daniel K. Inouye Intl.
Standard Link for Enterprise Rental Cars in Daniel K. Inouye Intl.

Joint Base Pearl Harbor-Hickam Vacation Rentals
Standard Link for Joint Base Pearl Harbor-Hickam Vacation Rentals

*Available to One Key members.

￥49,560 Cheap Flights from Chicago (MDW) to Honolulu (HNL)

Popular airlines from Chicago Midway Airport (MDW) to Daniel K. Inouye Intl. Airport (HNL)

Be in the know

Book smarter

Earn twice

Cheap Flights from Chicago to Oahu (MDW-HNL)

Find the cheapest month to fly from Chicago (MDW) to Oahu (HNL)

November is typically the cheapest month to flyNovember is typically the cheapest month to fly

Travel information

Explore a world of travel with Expedia

November is typically the cheapest month to fly