HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Big Sky

$96+ Cheap flights from Chicago (CHI) to Big Sky, 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 9/9. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BZN
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Big Sky with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheapflights Tip: The best prices from Chicago to Big Sky are usually found in April or July, booked 58 days in advance, depart on a Tuesday or Wednesday and return on a Wednesday

Cheap flight deals from Chicago to Big Sky

Keep the following information in mind while searching for Chicago to Big Sky flight deals. Data was last updated July 31, 2025.

Round-trip from

$210
(Hawaiian Airlines)

One-way from

$96
(United Airlines)

Popular in

December

Cheapest in

April

Average price

$369
From Chicago (CHI) to Big Sky
Search Deals
One-way flight from Chicago (CHI) to Big Sky
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($47 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2025
Search Deals

Find flight deals from Chicago to Big Sky

Cheapest flights from Chicago to Big Sky
Explore the most affordable flight options available from Chicago to Big Sky. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 31, 2025.

This Hawaiian Airlines deal was found by Cheapflights users on 7/30. 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 9/68:00 amORD - BZN
1 stop7h 14mHawaiian Airlines
Fri 9/1211:26 amBZN - ORD
1 stop9h 41mHawaiian Airlines
Deal found 7/30$210
This American Airlines deal was found by Cheapflights users on 7/29. 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.
Fri 9/51:20 pmORD - BZN
1 stop6h 57mAmerican Airlines
Thu 9/1112:44 pmBZN - ORD
1 stop9h 55mAmerican Airlines
Deal found 7/29$211
This Southwest deal was found by Cheapflights users on 7/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/147:00 pmMDW - BZN
1 stop5h 25mSouthwest
Thu 10/168:00 pmBZN - MDW
1 stop8h 15mSouthwest
Deal found 7/30$211
This United Airlines deal was found by Cheapflights users on 7/30. 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.
Wed 8/277:15 amORD - BZN
1 stop7h 16mUnited Airlines
Wed 9/34:20 pmBZN - ORD
1 stop6h 39mUnited Airlines
Deal found 7/30$216
This Mytrip deal was found by Cheapflights users on 7/31. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/148:12 pmORD - BZN
2 stops16h 30mMultiple Airlines
Fri 8/225:48 pmBZN - ORD
2 stops24h 19mMultiple Airlines
Deal found 7/31$224
This Alaska Airlines deal was found by Cheapflights users on 7/31. 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.
Mon 9/156:20 amORD - BZN
1 stop8h 54mAlaska Airlines
Fri 9/263:08 pmBZN - ORD
1 stop7h 55mAlaska Airlines
Deal found 7/31$228
This Delta deal was found by Cheapflights users on 7/30. 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.
Sat 8/165:30 pmORD - BZN
1 stop6h 59mDelta
Sat 9/66:05 amBZN - ORD
1 stop4h 59mDelta
Deal found 7/30$237
This Delta deal was found by Cheapflights users on 7/30. 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 8/196:04 amMDW - BZN
1 stop8h 04mDelta
Sat 8/236:05 amBZN - MDW
1 stop5h 58mDelta
Deal found 7/30$237
This Southwest deal was found by Cheapflights users on 7/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/205:25 pmORD - BZN
1 stop6h 45mSouthwest
Fri 10/246:00 amBZN - ORD
1 stop7h 25mSouthwest
Deal found 7/29$240

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Big Sky 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 July 31, 2025.
Use the filters below to find and compare flights from Chicago to Big Sky that are best for you.

Fly from

Chicago

Fly to

Big Sky

Route

Depart

Return

Price

ChicagoBozeman

ORD - BZN

ORDBZN

Chicago O'Hare Intl

Sat 9/6

8:00 am-2:14 pm

1 stop7h 14m

Bozeman Gallatin Field

Fri 9/12

11:26 am-10:07 pm

1 stop9h 41m

$210

ChicagoBozeman

ORD - BZN

ORDBZN

Chicago O'Hare Intl

Fri 9/5

1:20 pm-7:17 pm

1 stop6h 57m

Bozeman Gallatin Field

Thu 9/11

12:44 pm-11:39 pm

1 stop9h 55m

$211

ChicagoBozeman

MDW - BZN

MDWBZN

Chicago Midway

Tue 10/14

7:00 pm-11:25 pm

1 stop5h 25m

Bozeman Gallatin Field

Thu 10/16

8:00 pm-5:15 am

1 stop8h 15m

$211

ChicagoBozeman

ORD - BZN

ORDBZN

Chicago O'Hare Intl

Wed 8/27

7:15 am-1:31 pm

1 stop7h 16m

Bozeman Gallatin Field

Wed 9/3

4:20 pm-11:59 pm

1 stop6h 39m

$216

ChicagoBozeman

ORD - BZN

ORDBZN

Chicago O'Hare Intl

Thu 8/14

8:12 pm-11:42 am

2 stops16h 30m

Bozeman Gallatin Field

Fri 8/22

5:48 pm-7:07 pm

2 stops24h 19m

$224

ChicagoBozeman

ORD - BZN

ORDBZN

Chicago O'Hare Intl

Mon 9/15

6:20 am-2:14 pm

1 stop8h 54m

Bozeman Gallatin Field

Fri 9/26

3:08 pm-12:03 am

1 stop7h 55m

$228

ChicagoBozeman

ORD - BZN

ORDBZN

Chicago O'Hare Intl

Sat 8/16

5:30 pm-11:29 pm

1 stop6h 59m

Bozeman Gallatin Field

Sat 8/23

6:05 am-12:04 pm

1 stop4h 59m

$237

ChicagoBozeman

MDW - BZN

MDWBZN

Chicago Midway

Tue 8/19

6:04 am-1:08 pm

1 stop8h 04m

Bozeman Gallatin Field

Sat 8/23

6:05 am-1:03 pm

1 stop5h 58m

$237

ChicagoBozeman

ORD - BZN

ORDBZN

Chicago O'Hare Intl

Mon 10/20

5:25 pm-11:10 pm

1 stop6h 45m

Bozeman Gallatin Field

Fri 10/24

6:00 am-2:25 pm

1 stop7h 25m

$240

ChicagoBozeman

ORD - BZN

ORDBZN

Chicago O'Hare Intl

Tue 9/9

4:37 pm-6:55 pm

Nonstop3h 18m

$96

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

Showing 1-10 of 18 results
1
2

Best time to book a flight from Chicago to Big Sky

Have a flexible travel schedule? Discover the best time to fly to Big Sky 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 Big Sky

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

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Big Sky. Price data was last updated on July 25, 2025.

Booking 58 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to Big Sky. 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 Big Sky?

Currently, October is the cheapest month in which you can book a flight from Chicago to Big Sky (average of $371). Flying from Chicago to Big Sky in May is currently the most expensive (average of $478). 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 BS1?

Find hourly flight availability from Chicago to Big Sky. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 31, 2025.

When flying from Chicago to Big Sky, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

What is the cheapest day to fly from Chicago to Big Sky?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Big Sky. Price data was last updated on July 27, 2025.

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

Weekly flight availability from Chicago to Big Sky

Explore weekly flight availability from Chicago to Big Sky. 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 July 31, 2025.

The most flights from CHI to BS1 are scheduled on a Thursday (10 on average). You will have fewer flight options on Sunday, 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 Big Sky?

Reviews of airlines servicing Big Sky

Get insights into the airlines that provide service to Big Sky. 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 Big Sky. Reviews last updated July 31, 2025.
See what other customers who have flown with Alaska Airlines, Southwest, and Delta from Chicago to Big Sky have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Overall

8.0

Boarding

8.1

Crew

8.5

Entertainment

7.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Overall

8.0

Boarding

8.1

Crew

8.5

Entertainment

7.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Southwest
8.0
Very good
4,246 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Overall

8.0

Boarding

8.1

Crew

8.5

Entertainment

7.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Delta
8.0
Very good
7,981 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Overall

8.0

Boarding

8.1

Crew

8.5

Entertainment

7.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Hawaiian Airlines
7.8
Good
2,611 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Overall

8.0

Boarding

8.1

Crew

8.5

Entertainment

7.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
United Airlines
7.4
Good
8,900 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Overall

8.0

Boarding

8.1

Crew

8.5

Entertainment

7.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.

Related info for your journey

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

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

    $96 is the cheapest one-way deal found within the past few days, from United Airlines. You may also be able to find cheap deals on Southwest and Alaska Airlines, with prices starting from $96 and $100, respectively.

  • What are the most reliable airlines from Chicago to Big Sky?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Chicago to Big Sky on time: SkyWest Airlines (87%), United Airlines (75%), American Airlines (68%).

  • What are the cheapest flights from Chicago to Big Sky?

    On average you can expect to pay $280 for a flight from Chicago to Big Sky. The cheapest flight overall is $129 while the most popular route, (Chicago O'Hare Intl - Bozeman Gallatin Field) is currently priced at $191.

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

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

  • How can I find direct flights from Chicago to Big Sky?

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

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

    Yes. Cheapflights offers flight deals from Chicago to Big Sky 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 Big Sky?

    Currently, October is the cheapest month in which you can book a flight from Chicago to Big Sky (average of $371). Flying from Chicago to Big Sky in May is currently the most expensive (average of $478). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chicago to Big Sky

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Kalispell flights
O'Hare Intl to Bozeman flights
Midway to Kalispell flights
Midway to Bozeman flights
O'Hare Intl to Missoula flights
St. Louis to Kalispell flights
St. Louis to Missoula flights
O'Hare Intl to Billings flights
St. Louis to Bozeman flights
Bloomington to Kalispell flights
Midway to Missoula flights
St. Louis to Billings flights
St. Louis to Great Falls flights
Midway to Billings flights
Peoria to Missoula flights
Peoria to Kalispell flights
Bloomington to Missoula flights
O'Hare Intl to West Yellowstone flights
O'Hare Intl to Helena flights
Peoria to Billings flights
O'Hare Intl to Great Falls flights
O'Hare Intl to Cody flights
St. Louis to Cody flights
Moline to Kalispell flights
O'Hare Intl to Butte flights
Midway to Great Falls flights
Moline to Missoula flights
St. Louis to Helena flights
Midway to Helena flights
Moline to Bozeman flights
St. Louis to Butte flights
Peoria to Bozeman flights
Bloomington to Bozeman flights
Bloomington to Great Falls flights
Peoria to Helena flights
Springfield to Missoula flights
Springfield to Bozeman flights
St. Louis to West Yellowstone flights
Midway to West Yellowstone flights
Dubuque to Kalispell flights
Dubuque to Bozeman flights
Midway to Cody flights
Champaign to Bozeman flights
Champaign to Billings flights
Bloomington to Helena flights
Moline to Billings flights

Top 5 airlines flying from Chicago to Big Sky

Discover the top 5 airlines that operate flights from Chicago to Big Sky. 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 July 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$210Average$454FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$211Average$385FlexibilityNo cancel feeOn-time71%
DeltaCheapest$236Average$340FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$269Average$583FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$291Average$504FlexibilityNo cancel feeOn-time75%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.