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Big Sky

$77+ 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 10/15. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BZN
oct. 15 — oct. 221
mié. 10/15
mié. 10/22
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Big Sky are usually found in September or August, booked 58 days in advance, depart on a Tuesday or Saturday 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 septiembre 15, 2025.

Round-trip from

$228
(Alaska Airlines)

One-way from

$77
(Southwest)

Popular in

December

Cheapest in

September

Average price

$316
From Chicago (CHI) to Big Sky
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One-way flight from Chicago (CHI) to Big Sky
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Highest demand for flights based on searches. 13% potential increase in price ($62 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($10 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 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 septiembre 15, 2025.

This Alaska Airlines deal was found by Cheapflights users on 9/13. 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.
vie. 10/313:25 pmORD - BZN
1 stop8h 14mAlaska Airlines
mié. 11/53:02 pmBZN - ORD
1 stop8h 22mAlaska Airlines
Deal found 9/13$228
This American Airlines deal was found by Cheapflights users on 9/12. 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.
mié. 10/111:56 amORD - BZN
Nonstop3h 18mAmerican Airlines
mié. 10/84:54 pmBZN - ORD
Nonstop3h 10mAmerican Airlines
Deal found 9/12$231
This Vliegwinkel deal was found by Cheapflights users on 9/14. 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 Vliegwinkel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 10/186:00 amORD - BZN
1 stop9h 10mHawaiian Airlines
vie. 10/243:04 pmBZN - ORD
1 stop7h 55mHawaiian Airlines
Deal found 9/14$234
This Delta deal was found by Cheapflights users on 9/12. 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.
sáb. 10/42:25 pmORD - BZN
1 stop8h 58mDelta
mar. 10/73:01 pmBZN - ORD
1 stop7h 49mDelta
Deal found 9/12$237
This Delta deal was found by Cheapflights users on 9/13. 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.
sáb. 10/117:10 pmMDW - BZN
1 stop5h 27mDelta
sáb. 10/186:00 amBZN - MDW
1 stop6h 08mDelta
Deal found 9/13$237
This Southwest deal was found by Cheapflights users on 9/12. 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.
vie. 10/246:25 pmMDW - BZN
1 stop6h 45mSouthwest
dom. 10/266:15 pmBZN - MDW
1 stop5h 20mSouthwest
Deal found 9/12$238
This Alaska Airlines deal was found by Cheapflights users on 9/12. 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.
dom. 10/126:00 amORD - BZN
1 stop9h 10mAlaska Airlines
dom. 10/197:34 pmBZN - ORD
1 stop9h 50mAlaska Airlines
Deal found 9/12$240
This Southwest deal was found by Cheapflights users on 9/12. 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.
jue. 11/136:25 pmMDW - BZN
2 stops6h 50mSouthwest
dom. 11/165:00 amBZN - MDW
1 stop5h 05mSouthwest
Deal found 9/12$241
This Delta deal was found by Cheapflights users on 9/12. 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.
mié. 11/121:09 pmORD - BZN
2 stops12h 01mDelta
sáb. 11/1511:40 amBZN - ORD
2 stops9h 13mDelta
Deal found 9/12$247
This Alaska Airlines deal was found by Cheapflights users on 9/14. 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.
jue. 10/166:00 amORD - BZN
1 stop9h 10mAlaska Airlines
dom. 10/197:34 pmBZN - ORD
1 stop9h 50mAlaska Airlines
Deal found 9/14$248
This United Airlines deal was found by Cheapflights users on 9/14. 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.
vie. 10/244:40 pmORD - BZN
Nonstop3h 18mUnited Airlines
mié. 10/2912:45 pmBZN - ORD
Nonstop2h 59mUnited Airlines
Deal found 9/14$249
This American Airlines deal was found by Cheapflights users on 9/14. 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.
vie. 10/1710:36 amORD - BZN
Nonstop3h 32mAmerican Airlines
jue. 10/234:54 pmBZN - ORD
Nonstop3h 10mAmerican Airlines
Deal found 9/14$250

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 septiembre 15, 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

MDW - BZN

MDWBZN

Chicago Midway

sáb. 10/11

7:10 pm-11:37 pm

1 stop5h 27m

Bozeman Gallatin Field

sáb. 10/18

6:00 am-1:08 pm

1 stop6h 08m

$237

ChicagoBozeman

MDW - BZN

MDWBZN

Chicago Midway

vie. 10/24

6:25 pm-12:10 am

1 stop6h 45m

Bozeman Gallatin Field

dom. 10/26

6:15 pm-12:35 am

1 stop5h 20m

$238

ChicagoBozeman

MDW - BZN

MDWBZN

Chicago Midway

jue. 11/13

6:25 pm-12:15 am

2 stops6h 50m

Bozeman Gallatin Field

dom. 11/16

5:00 am-11:05 am

1 stop5h 05m

$241

ChicagoBozeman

ORD - BZN

ORDBZN

Chicago O'Hare Intl

sáb. 10/11

1:25 pm-11:37 pm

2 stops11h 12m

Bozeman Gallatin Field

sáb. 10/18

6:00 am-11:28 am

1 stop4h 28m

$242

ChicagoBozeman

ORD - BZN

ORDBZN

Chicago O'Hare Intl

jue. 1/29

7:45 am-2:25 pm

1 stop7h 40m

Bozeman Gallatin Field

lun. 2/2

3:25 pm-11:59 pm

1 stop7h 34m

$248

ChicagoBozeman

ORD - BZN

ORDBZN

Chicago O'Hare Intl

dom. 10/12

6:00 am-2:10 pm

1 stop9h 10m

Bozeman Gallatin Field

dom. 10/19

7:34 pm-6:24 am

1 stop9h 50m

$249

ChicagoBozeman

ORD - BZN

ORDBZN

Chicago O'Hare Intl

vie. 10/24

4:40 pm-6:58 pm

Nonstop3h 18m

Bozeman Gallatin Field

dom. 10/26

8:00 am-12:12 pm

Nonstop3h 12m

$249

ChicagoBozeman

ORD - BZN

ORDBZN

Chicago O'Hare Intl

sáb. 10/4

4:40 pm-6:58 pm

Nonstop3h 18m

Bozeman Gallatin Field

mar. 10/7

4:30 pm-10:39 pm

1 stop5h 09m

$252

ChicagoBozeman

ORD - BZN

ORDBZN

Chicago O'Hare Intl

lun. 11/3

9:15 am-11:43 am

Nonstop3h 28m

Bozeman Gallatin Field

jue. 11/13

2:43 pm-11:59 pm

1 stop8h 16m

$259

ChicagoBozeman

ORD - BZN

ORDBZN

Chicago O'Hare Intl

jue. 2/5

7:45 am-2:25 pm

1 stop7h 40m

Bozeman Gallatin Field

mar. 2/10

3:25 pm-11:59 pm

1 stop7h 34m

$269

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/12

Showing 1-10 of 43 results
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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 September 12, 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 $476). 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 septiembre 15, 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 September 14, 2025.

Travelers seeking maximum savings on their Chicago to Big Sky flight should consider departing on Sunday at noon when fares are most often at their lowest. Monday evenings 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 septiembre 15, 2025.

The most flights from CHI to BS1 are scheduled on a Monday (9 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (7 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 septiembre 15, 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

Crew

8.5

Comfort

7.8

Food

7.1

Entertainment

7.0

Overall

8.0

Boarding

8.1

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

Crew

8.5

Comfort

7.8

Food

7.1

Entertainment

7.0

Overall

8.0

Boarding

8.1

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.
Southwest
8.0
Very good
4,242 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Comfort

7.8

Food

7.1

Entertainment

7.0

Overall

8.0

Boarding

8.1

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
7,954 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Comfort

7.8

Food

7.1

Entertainment

7.0

Overall

8.0

Boarding

8.1

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
8,929 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Comfort

7.8

Food

7.1

Entertainment

7.0

Overall

8.0

Boarding

8.1

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

Crew

8.5

Comfort

7.8

Food

7.1

Entertainment

7.0

Overall

8.0

Boarding

8.1

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 Big Sky. 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 Big Sky?

    A quick flight from Chicago to Big Sky can take about 5h 27m. Delta provides one of the quickest options available for as low as $237. Airlines will cover a distance of 1194 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    $77 is the cheapest one-way deal found within the past few days, from Southwest. You may also be able to find cheap deals on Hawaiian Airlines and Alaska Airlines, with prices starting from $114 and $114, 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 (82%), United Airlines (70%), American Airlines (64%).

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

    On average you can expect to pay $261 for a flight from Chicago to Big Sky. The cheapest flight overall is $114 while the most popular route, (Chicago O'Hare Intl - Bozeman Gallatin Field) is currently priced at $133.

  • 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 $476). 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 Big Sky

See prices for flight routes from nearby airports that may be better suited for you.
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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 septiembre 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$210Average$456FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$211Average$373FlexibilityNo cancel feeOn-time71%
DeltaCheapest$236Average$340FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$252Average$619FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$291Average$504FlexibilityNo cancel feeOn-time75%

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