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Big Sky

$95+ 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 3/17. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BZN
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
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 74 days in advance, depart on a Tuesday or Friday and return on a Thursday

Cheap 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 December 18, 2025.

This Southwest deal was found by Cheapflights users on 12/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/255:15 amMDW - BZN
1 stop7h 40mSouthwest
Mon 12/295:30 pmBZN - MDW
1 stop5h 10mSouthwest
Deal found 12/14$379
This American Airlines deal was found by Cheapflights users on 12/16. 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.
Thu 12/258:25 amORD - BZN
Nonstop3h 44mAmerican Airlines
Wed 12/311:34 pmBZN - ORD
Nonstop3h 20mAmerican Airlines
Deal found 12/16$384
This United Airlines deal was found by Cheapflights users on 12/16. 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 12/179:20 amORD - BZN
Nonstop3h 28mUnited Airlines
Wed 12/2412:42 pmBZN - ORD
Nonstop3h 09mUnited Airlines
Deal found 12/16$434
This United Airlines deal was found by Cheapflights users on 12/16. 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 12/259:06 amORD - BZN
Nonstop3h 33mUnited Airlines
Wed 12/314:14 pmBZN - ORD
Nonstop3h 11mUnited Airlines
Deal found 12/16$445
This Delta deal was found by Cheapflights users on 12/17. 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 12/202:15 pmORD - BZN
1 stop9h 16mDelta
Tue 12/233:20 pmBZN - ORD
1 stop7h 42mDelta
Deal found 12/17$454
This Southwest deal was found by Cheapflights users on 12/16. 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.
Wed 12/175:15 amMDW - BZN
1 stop7h 40mSouthwest
Wed 12/2412:40 pmBZN - MDW
1 stop6h 25mSouthwest
Deal found 12/16$454
This Delta deal was found by Cheapflights users on 12/15. 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 12/245:59 pmMDW - BZN
1 stop6h 47mDelta
Sun 12/2812:36 pmBZN - MDW
1 stop8h 46mDelta
Deal found 12/15$471
This Southwest deal was found by Cheapflights users on 12/15. 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 12/235:10 amMDW - BZN
1 stop7h 45mSouthwest
Sat 12/275:00 amBZN - MDW
2 stops10h 30mSouthwest
Deal found 12/15$477
This United Airlines deal was found by Cheapflights users on 12/17. 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 12/1812:45 pmORD - BZN
Nonstop3h 25mUnited Airlines
Tue 12/234:14 pmBZN - ORD
Nonstop3h 11mUnited Airlines
Deal found 12/17$489
This Alaska Airlines deal was found by Cheapflights users on 12/16. 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.
Tue 12/165:51 pmORD - BZN
1 stop18h 15mAlaska Airlines
Thu 12/1812:43 pmBZN - ORD
1 stop10h 16mAlaska Airlines
Deal found 12/16$490
This Southwest deal was found by Cheapflights users on 12/16. 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.
Thu 12/252:15 pmORD - BZN
2 stops9h 30mSouthwest
Wed 12/3110:45 amBZN - ORD
1 stop10h 50mSouthwest
Deal found 12/16$497
This Delta deal was found by Cheapflights users on 12/15. 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 12/166:00 amMDW - BZN
1 stop8h 26mDelta
Thu 12/186:00 amBZN - MDW
1 stop6h 10mDelta
Deal found 12/15$509

Find 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 December 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$189
(Southwest)

One-way from

$95
(Southwest)

Popular in

March

Cheapest in

September

Average price

$449
Provider with most accurate pricing for Chicago (CHI)-Bozeman Gallatin Field flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Bozeman Gallatin Field flights.
Search Deals
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. 11% potential increase in price ($49 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 December 2025
Search Deals

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 December 18, 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

Tue 3/24

2:03 pm-8:14 pm

1 stop7h 11m

Bozeman Gallatin Field

Wed 4/1

5:50 am-1:23 pm

1 stop6h 33m

$217

ChicagoBozeman

ORD - BZN

ORDBZN

Chicago O'Hare Intl

Sun 2/15

5:29 pm-11:56 pm

1 stop7h 27m

Bozeman Gallatin Field

Fri 2/20

7:00 am-4:33 pm

1 stop8h 33m

$228

ChicagoBozeman

ORD - BZN

ORDBZN

Chicago O'Hare Intl

Thu 1/29

3:35 pm-11:56 pm

1 stop9h 21m

Bozeman Gallatin Field

Wed 2/4

7:20 am-5:10 pm

1 stop8h 50m

$228

ChicagoBozeman

ORD - BZN

ORDBZN

Chicago O'Hare Intl

Thu 1/29

3:35 pm-11:56 pm

1 stop9h 21m

Bozeman Gallatin Field

Mon 2/2

3:03 pm-11:50 pm

1 stop7h 47m

$228

ChicagoBozeman

ORD - BZN

ORDBZN

Chicago O'Hare Intl

Wed 1/21

8:00 am-2:09 pm

1 stop7h 09m

Bozeman Gallatin Field

Sat 1/24

3:03 pm-11:50 pm

1 stop7h 47m

$228

ChicagoBozeman

ORD - BZN

ORDBZN

Chicago O'Hare Intl

Fri 4/17

9:10 am-11:33 am

Nonstop3h 23m

Bozeman Gallatin Field

Mon 4/20

12:30 pm-4:30 pm

Nonstop3h 00m

$229

ChicagoBozeman

ORD - BZN

ORDBZN

Chicago O'Hare Intl

Tue 1/13

2:36 pm-9:33 pm

1 stop7h 57m

Bozeman Gallatin Field

Sat 1/17

4:16 pm-11:59 pm

1 stop6h 43m

$249

ChicagoBozeman

ORD - BZN

ORDBZN

Chicago O'Hare Intl

Mon 1/19

5:30 am-1:29 pm

1 stop8h 59m

Bozeman Gallatin Field

Fri 1/23

2:00 pm-9:43 pm

1 stop6h 43m

$249

ChicagoBozeman

ORD - BZN

ORDBZN

Chicago O'Hare Intl

Sat 1/17

5:20 pm-11:17 pm

1 stop6h 57m

Bozeman Gallatin Field

Thu 1/22

3:00 pm-11:53 pm

1 stop7h 53m

$249

ChicagoBozeman

ORD - BZN

ORDBZN

Chicago O'Hare Intl

Wed 2/11

2:20 pm-10:27 pm

1 stop9h 07m

Bozeman Gallatin Field

Tue 2/17

3:05 pm-11:52 pm

1 stop7h 47m

$249

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

Showing 1-10 of 42 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 December 12, 2025.

Booking 74 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 $190). Flying from Chicago to Big Sky in March is currently the most expensive (average of $290). 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 December 18, 2025.

It’s typically best to fly out from Chicago to Big Sky at noon. Doing so could potentially save you 33% on the flight price compared to flying in the morning, which is usually more expensive.

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 December 13, 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 December 18, 2025.

The most flights from CHI to BS1 are scheduled on a Thursday (8 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (3 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 December 18, 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
11,479 reviews

Comfort

7.8

Overall

8.0

Food

7.1

Boarding

8.1

Crew

8.5

Entertainment

7.0

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
Alaska Airlines
8.0
Very good
11,479 reviews
Alaska Airlines
8.0
Very good
11,479 reviews

Comfort

7.8

Overall

8.0

Food

7.1

Boarding

8.1

Crew

8.5

Entertainment

7.0

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
Southwest
7.9
Good
4,250 reviews
Alaska Airlines
8.0
Very good
11,479 reviews

Comfort

7.8

Overall

8.0

Food

7.1

Boarding

8.1

Crew

8.5

Entertainment

7.0

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
Delta
7.9
Good
8,008 reviews
Alaska Airlines
8.0
Very good
11,479 reviews

Comfort

7.8

Overall

8.0

Food

7.1

Boarding

8.1

Crew

8.5

Entertainment

7.0

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
United Airlines
7.4
Good
9,092 reviews
Alaska Airlines
8.0
Very good
11,479 reviews

Comfort

7.8

Overall

8.0

Food

7.1

Boarding

8.1

Crew

8.5

Entertainment

7.0

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
American Airlines
7.2
Good
11,054 reviews
Alaska Airlines
8.0
Very good
11,479 reviews

Comfort

7.8

Overall

8.0

Food

7.1

Boarding

8.1

Crew

8.5

Entertainment

7.0

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.

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 3h 23m. Delta provides one of the quickest options available for as low as $229. Airlines will cover a distance of 1182 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?

    $105 is the cheapest one-way deal found within the past few days, from American Airlines. You may also be able to find cheap deals on Delta and United Airlines, with prices starting from $108 and $124, 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: United Airlines (77%), Lufthansa (70%), Alaska Airlines (55%).

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

    On average you can expect to pay $270 for a flight from Chicago to Big Sky. The cheapest flight overall is $135 while the most popular route, (Chicago O'Hare Intl - Bozeman Gallatin Field) is currently priced at $229.

  • 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 $190). Flying from Chicago to Big Sky in March is currently the most expensive (average of $290). 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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$152Average$448FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$211Average$349FlexibilityNo cancel feeOn-time71%
DeltaCheapest$236Average$308FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$248Average$554FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$291Average$504FlexibilityNo cancel feeOn-time75%

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