App
Customer Support
CAD
Find Bookings
Trip.com
>
Cheap Flights
>
United States
>
Hawaiian Airlines
>
Hawaiian Airlines Flights to Chicago (CHI)
Worldwide Coverage
Worldwide Coverage
Flights to over 5,000 cities
One-stop Service Guarantee
One-stop Service Guarantee
Price guaranteed upon confirmed payment, booking guaranteed once tickets issued
Secure Payment
Secure Payment
Convenient & reliable booking and payment system
HA

Hawaiian Airlines Flights to Chicago

  • One way
  • Round-trip
      • HNL07:55
        17h 10m
        1 stop
        ORD05:05
        Hawaiian Airlines|Honolulu - Chicago|Sat, Jan 25
        CAD 251CAD 3,576
        93% OFF
        93% OFF
        CAD 3,576CAD 251

        Choose Hawaiian Airlines flights from Honolulu to Chicago. The one-way connecting flight with Hawaiian Airlines departs from Daniel K. Inouye International Airport on Sat, Jan 25, arriving at O'Hare International Airport. One-way Prices start from CAD 251 including taxes and charges.

      • ANC11:15
        9h 44m
        1 stop
        ORD23:59
        Hawaiian Airlines|Anchorage - Chicago|Fri, Jan 31
        CAD 289CAD 3,576
        92% OFF
        92% OFF
        CAD 3,576CAD 289

        Choose Hawaiian Airlines flights from Anchorage to Chicago. The one-way connecting flight with Hawaiian Airlines departs from Ted Stevens Anchorage International Airport on Fri, Jan 31, arriving at O'Hare International Airport. One-way Prices start from CAD 289 including taxes and charges.

      • OGG13:10
        18h 59m
        1 stop
        ORD12:09
        Hawaiian Airlines|Kahului - Chicago|Mon, Jan 27
        CAD 330CAD 3,576
        91% OFF
        91% OFF
        CAD 3,576CAD 330

        Choose Hawaiian Airlines flights from Kahului to Chicago. The one-way connecting flight with Hawaiian Airlines departs from Kahului Airport on Mon, Jan 27, arriving at O'Hare International Airport. One-way Prices start from CAD 330 including taxes and charges.

      • KOA16:25
        19h 34m
        1 stop
        ORD15:59
        Hawaiian Airlines|Kailua-Kona - Chicago|Mon, Feb 3
        CAD 344
        CAD 344

        Choose Hawaiian Airlines flights from Kailua-Kona to Chicago. The one-way connecting flight with Hawaiian Airlines departs from Kona International Airport on Mon, Feb 3, arriving at O'Hare International Airport. One-way Prices start from CAD 344 including taxes and charges.

      • LIH14:50
        17h 6m
        1 stop
        ORD11:56
        Hawaiian Airlines|Kauai - Chicago|Fri, Feb 14
        CAD 399
        CAD 399

        Choose Hawaiian Airlines flights from Kauai to Chicago. The one-way connecting flight with Hawaiian Airlines departs from Lihue Airport on Fri, Feb 14, arriving at O'Hare International Airport. One-way Prices start from CAD 399 including taxes and charges.

      • NRT19:55
        25h 21m
        1 stop
        ORD06:16
        Hawaiian Airlines|Tokyo - Chicago|Tue, Feb 4
        CAD 1,280
        CAD 1,280

        Choose Hawaiian Airlines flights from Tokyo to Chicago. The one-way connecting flight with Hawaiian Airlines departs from Narita International Airport on Tue, Feb 4, arriving at O'Hare International Airport. One-way Prices start from CAD 1,280 including taxes and charges.

      • OAK08:20
        19h 56m
        1 stop
        ORD06:16
        Hawaiian Airlines|Oakland - Chicago|Mon, Jan 20
        CAD 1,310
        CAD 1,310

        Choose Hawaiian Airlines flights from Oakland to Chicago. The one-way connecting flight with Hawaiian Airlines departs from Oakland International Airport on Mon, Jan 20, arriving at O'Hare International Airport. One-way Prices start from CAD 1,310 including taxes and charges.

      • SJC07:00
        21h 16m
        1 stop
        ORD06:16
        Hawaiian Airlines|San Jose - Chicago|Tue, Jan 21
        CAD 1,339
        CAD 1,339

        Choose Hawaiian Airlines flights from San Jose to Chicago. The one-way connecting flight with Hawaiian Airlines departs from SJ International Airport on Tue, Jan 21, arriving at O'Hare International Airport. One-way Prices start from CAD 1,339 including taxes and charges.

      • LGB08:55
        19h 18m
        1 stop
        ORD06:13
        Hawaiian Airlines|Long Beach - Chicago|Sun, Feb 9
        CAD 1,460
        CAD 1,460

        Choose Hawaiian Airlines flights from Long Beach to Chicago. The one-way connecting flight with Hawaiian Airlines departs from Long Beach Municipal Airport on Sun, Feb 9, arriving at O'Hare International Airport. One-way Prices start from CAD 1,460 including taxes and charges.

      • SYD21:40
        25h 36m
        1 stop
        ORD06:16
        Hawaiian Airlines|Sydney - Chicago|Fri, Jan 31
        CAD 1,625
        CAD 1,625

        Choose Hawaiian Airlines flights from Sydney to Chicago. The one-way connecting flight with Hawaiian Airlines departs from Kingsford Smith Airport on Fri, Jan 31, arriving at O'Hare International Airport. One-way Prices start from CAD 1,625 including taxes and charges.

      • SHA01:00 pm
        3h 5m
        Nonstop
        CHI02:00 pm
        Hawaiian Airlines|Shanghai - Chicago|Fri, Jan 17
        Find More Flights
        Find More Flights

Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

When is the cheapest time to fly to Chicago with Hawaiian Airlines?

Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.

There are 3 airports in Chicago. Find the most suitable Hawaiian Airlines flights to Chicago.

  • 24.74 km from central ChicagoCheapest
    O'Hare International Airport
    Tickets From
    CAD 251
  • 12.76 km from central ChicagoClosest
    Midway International Airport
    Tickets From
    CAD 270
  • 139.04 km from central Chicago
    Chicago Rockford International Airport
    Tickets From
    CAD 675

About Hawaiian Airlines

Airline Name
Hawaiian Airlines
Airline Code
HA
Airline Type
Full Service Carrier (FSC)
Popular Countries Hawaiian Airlines Flies to:
Australia, United States and Japan
Popular Hawaiian Airlines Arrival Cities
Popular Hawaiian Airlines Departure Cities
Based on Trip.com Historical Data

Hawaiian Airlines Flights to Chicago - FAQ

  • Does Hawaiian Airlines have baggage allowance?

    0-1 pieces of luggage are usually permitted for each economy class passenger traveling with Hawaiian Airlines (HA). This information can vary depending on your flight, so be sure to check your itinerary.

  • How long is the flights to Chicago?

    • Approx. 1 hour 53 minutes to fly from Toronto to Chicago.
    • Approx. 3 hours 50 minutes to fly from Calgary to Chicago.
    • Approx. 4 hours 37 minutes to fly from Montreal to Chicago.
    • Approx. 5 hours 32 minutes to fly from Vancouver to Chicago.

  • How to get cheapest flights to Chicago?

    You can book cheaper flights in the following ways:
    • Search for tickets to a city or airport near Chicago.
    • Look up different airlines that have flights to Chicago.
    • Browse different departure dates from the same month.
    • Filter for different departure times from the same day.
    • Check for discount information on various social media sites.
    • Explore deals and discounts on airline websites.

  • What is the most popular month to visit Chicago?

    Understanding peak and off travel seasons to Chicago can help you arrange your travel plans accordingly. The most popular month to visit Chicago is February. The average price of flight tickets to Chicago in February is CAD 324.

  • When are flight to Chicago cheapest?

    Flight tickets to Chicago are the cheapest in March compared to other months, the average price is CAD 363.

  • What are the major airports in Chicago?

  • What is the transportation method from the main airport to downtown in Chicago?

    • The distance from O'Hare International Airport to downtown is about 25km, by taxi about 40 minutes.
    • The distance from Midway International Airport to downtown is about 14km, by taxi about 30 minutes.

Contact Us

About

Other Services

Payment Methods
Our Partners
Copyright © 2025 Trip.com Travel Singapore Pte. Ltd. All rights reserved
Site Operator: Trip.com Travel Singapore Pte. Ltd.