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Whitefish

$121+ Cheap flights from Chicago (CHI) to Whitefish, MT

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/12. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — FCA
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Whitefish are usually found in May or November, booked 59 days in advance, depart on a Monday or Wednesday and return on a Friday

Cheap flight deals from Chicago to Whitefish

Keep the following information in mind while searching for Chicago to Whitefish flight deals. Data was last updated September 11, 2025.

Round-trip from

$266
(Hawaiian Airlines)

One-way from

$121
(Kiwi.com)

Popular in

March

Cheapest in

May

Average price

$389
From Chicago (CHI) to Whitefish
Search Deals
One-way flight from Chicago (CHI) to Whitefish
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Highest demand for flights based on searches. 14% potential increase in price ($75 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Chicago to Whitefish

Cheapest flights from Chicago to Whitefish
Explore the most affordable flight options available from Chicago to Whitefish. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 11, 2025.

This Hawaiian Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/123:25 pmORD - FCA
1 stop9h 32mHawaiian Airlines
Wed 11/192:07 pmFCA - ORD
1 stop9h 17mHawaiian Airlines
Deal found 9/10$266
This American Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/289:55 amORD - FCA
Nonstop3h 48mAmerican Airlines
Sat 11/11:08 pmFCA - ORD
Nonstop3h 36mAmerican Airlines
Deal found 9/10$269
This American Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/269:55 amORD - FCA
Nonstop3h 48mAmerican Airlines
Fri 10/311:14 pmFCA - ORD
Nonstop3h 36mAmerican Airlines
Deal found 9/10$271
This United Airlines deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/238:45 amORD - FCA
Nonstop3h 50mUnited Airlines
Tue 10/282:38 pmFCA - ORD
1 stop8h 21mUnited Airlines
Deal found 9/11$279
This Hawaiian Airlines deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/147:00 amORD - FCA
1 stop7h 27mHawaiian Airlines
Mon 11/172:07 pmFCA - ORD
1 stop9h 17mHawaiian Airlines
Deal found 9/11$288
This United Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/61:51 pmORD - FCA
1 stop8h 55mUnited Airlines
Sat 12/132:37 pmFCA - ORD
1 stop8h 22mUnited Airlines
Deal found 9/10$289
This Delta deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/288:57 amORD - FCA
1 stop6h 32mDelta
Sat 11/15:20 amFCA - ORD
2 stops10h 30mDelta
Deal found 9/11$294
This American Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/276:00 amORD - FCA
1 stop9h 23mAmerican Airlines
Thu 10/25:23 pmFCA - ORD
Nonstop3h 22mAmerican Airlines
Deal found 9/10$299
This Alaska Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1210:00 amORD - FCA
2 stops28h 27mAlaska Airlines
Wed 11/192:07 pmFCA - ORD
1 stop6h 33mAlaska Airlines
Deal found 9/10$300
This Alaska Airlines deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/147:00 amORD - FCA
1 stop7h 27mAlaska Airlines
Mon 11/171:06 pmFCA - ORD
2 stops16h 16mAlaska Airlines
Deal found 9/11$302
This Hawaiian Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/277:00 amORD - FCA
1 stop7h 30mHawaiian Airlines
Thu 10/24:22 pmFCA - ORD
1 stop6h 41mHawaiian Airlines
Deal found 9/10$308
This Delta deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/101:14 pmMDW - FCA
2 stops10h 50mDelta
Wed 12/175:00 amFCA - MDW
2 stops12h 00mDelta
Deal found 9/9$324

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Whitefish that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 11, 2025.
Use the filters below to find and compare flights from Chicago to Whitefish that are best for you.

Fly from

Chicago

Fly to

Whitefish

Route

Depart

Return

Price

ChicagoKalispell

MDW - FCA

MDWFCA

Chicago Midway

Wed 12/10

1:14 pm-11:04 pm

2 stops10h 50m

Kalispell Glacier Park

Wed 12/17

5:00 am-6:00 pm

2 stops12h 00m

$324

ChicagoKalispell

ORD - FCA

ORDFCA

Chicago O'Hare Intl

Fri 11/7

8:57 am-2:29 pm

1 stop6h 32m

Kalispell Glacier Park

Tue 11/11

5:05 am-12:38 pm

1 stop6h 33m

$330

ChicagoKalispell

ORD - FCA

ORDFCA

Chicago O'Hare Intl

Fri 11/7

8:57 am-2:29 pm

1 stop6h 32m

Kalispell Glacier Park

Mon 11/10

6:06 pm-8:41 am

2 stops13h 35m

$335

ChicagoKalispell

ORD - FCA

ORDFCA

Chicago O'Hare Intl

Fri 10/17

8:45 am-11:35 am

Nonstop3h 50m

Kalispell Glacier Park

Sun 10/19

12:41 pm-5:10 pm

Nonstop3h 29m

$349

ChicagoKalispell

ORD - FCA

ORDFCA

Chicago O'Hare Intl

Thu 10/16

8:45 am-11:35 am

Nonstop3h 50m

Kalispell Glacier Park

Sun 10/19

12:41 pm-5:10 pm

Nonstop3h 29m

$349

ChicagoKalispell

ORD - FCA

ORDFCA

Chicago O'Hare Intl

Tue 9/23

6:20 am-12:27 pm

1 stop7h 07m

Kalispell Glacier Park

Mon 9/29

4:22 pm-12:03 am

1 stop6h 41m

$378

ChicagoKalispell

ORD - FCA

ORDFCA

Chicago O'Hare Intl

Tue 9/23

4:47 pm-7:43 pm

Nonstop3h 56m

Kalispell Glacier Park

Sat 9/27

5:06 pm-11:59 pm

1 stop5h 53m

$399

ChicagoKalispell

MDW - FCA

MDWFCA

Chicago Midway

Wed 11/26

1:14 pm-11:00 pm

2 stops10h 46m

Kalispell Glacier Park

Mon 12/1

2:51 pm-9:54 am

2 stops18h 03m

$447

ChicagoKalispell

MDW - FCA

MDWFCA

Chicago Midway

Tue 10/28

9:20 am-2:29 pm

1 stop6h 09m

Kalispell Glacier Park

Sat 11/1

5:20 am-5:55 pm

2 stops11h 35m

$475

ChicagoKalispell

MDW - FCA

MDWFCA

Chicago Midway

Mon 10/6

9:20 am-2:29 pm

1 stop6h 09m

Kalispell Glacier Park

Sat 10/11

5:20 am-5:43 pm

2 stops11h 23m

$479

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

Showing 1-10 of 29 results
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Best time to book a flight from Chicago to Whitefish

Have a flexible travel schedule? Discover the best time to fly to Whitefish from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Whitefish

How far ahead should I book a flight from Chicago to Whitefish?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Whitefish. Price data was last updated on August 29, 2025.

Booking 59 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to Whitefish. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

What is the cheapest month to book a flight from Chicago to Whitefish?

Currently, October is the cheapest month in which you can book a flight from Chicago to Whitefish (average of $373). Flying from Chicago to Whitefish in July is currently the most expensive (average of $600). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to WF5?

Find hourly flight availability from Chicago to Whitefish. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 11, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago to Whitefish as you normally would.

What is the cheapest day to fly from Chicago to Whitefish?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Whitefish. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Chicago to Whitefish flight should consider departing on Monday at noon when fares are most often at their lowest. Wednesday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Chicago to Whitefish

Explore weekly flight availability from Chicago to Whitefish. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated September 11, 2025.

The most flights from CHI to WF5 are scheduled on a Monday (6 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (4 on average).

How much does it cost to fly round-trip from Chicago to Whitefish?

Reviews of airlines servicing Whitefish

Get insights into the airlines that provide service to Whitefish. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Whitefish. Reviews last updated September 11, 2025.
Peruse reviews from past customers who have flown with Alaska Airlines, Delta, and United Airlines from Chicago to Whitefish to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Overall

8.0

Entertainment

7.0

Crew

8.5

Comfort

7.8

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Overall

8.0

Entertainment

7.0

Crew

8.5

Comfort

7.8

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Delta
8.0
Very good
7,960 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Overall

8.0

Entertainment

7.0

Crew

8.5

Comfort

7.8

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
United Airlines
7.4
Good
8,937 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Overall

8.0

Entertainment

7.0

Crew

8.5

Comfort

7.8

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Overall

8.0

Entertainment

7.0

Crew

8.5

Comfort

7.8

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Whitefish. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Chicago to Whitefish?

    A quick flight from Chicago to Whitefish can take about 3h 50m. Delta provides one of the quickest options available for as low as $349. The distance from Chicago to Whitefish is about 1348 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Chicago to Whitefish one-way?

    The cheapest airlines for a one-way flight from Chicago to Whitefish are Alaska Airlines ($142), Hawaiian Airlines ($142), and Delta ($186).

  • What are the most reliable airlines from Chicago to Whitefish?

    The top 3 most reliable airlines when flying from Chicago to Whitefish are United Airlines (82%), SkyWest Airlines (82%) and Alaska Airlines (74%).

  • What are the cheapest flights from Chicago to Whitefish?

    On average you can expect to pay $388 for a flight from Chicago to Whitefish. The cheapest flight overall is $231 while the most popular route, (Chicago O'Hare Intl - Kalispell Glacier Park) is currently priced at $266.

  • Can I find deals for flights from Chicago to Whitefish that include hotel bookings?

    Yes. In addition to deals on Chicago to Whitefish flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Whitefish?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Whitefish.

  • Can I find deals for business class flights from Chicago to Whitefish?

    Yes. Cheapflights offers flight deals from Chicago to Whitefish by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Whitefish?

    Currently, October is the cheapest month in which you can book a flight from Chicago to Whitefish (average of $373). Flying from Chicago to Whitefish in July is currently the most expensive (average of $600). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for Chicago to Whitefish

See prices for flight routes from nearby airports that may be better suited for you.
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Top 4 airlines flying from Chicago to Whitefish

Discover the top 4 airlines that operate flights from Chicago to Whitefish. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$269Average$404FlexibilityNo cancel feeOn-time71%
DeltaCheapest$272Average$383FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$329Average$498FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$426Average$530FlexibilityNo cancel feeOn-time75%

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