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Big Sky

$115+ 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 2/24. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BZN
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
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 Saturday 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 January 29, 2026.

This American Airlines deal was found by Cheapflights users on 1/27. 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 2/215:00 am
ORD
-
BZN
1 stop6h 43m
American Airlines
Fri 2/273:36 pm
BZN
-
ORD
1 stop7h 00m
American Airlines
Deal found 1/27$250
This Delta deal was found by Cheapflights users on 1/28. 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.
Sun 8/237:15 am
ORD
-
BZN
1 stop8h 31m
Delta
Sat 8/295:45 am
BZN
-
ORD
2 stops8h 13m
Delta
Deal found 1/28$254
This Delta deal was found by Cheapflights users on 1/27. 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 5/22:12 pm
MDW
-
BZN
2 stops8h 50m
Delta
Tue 5/52:53 pm
BZN
-
MDW
1 stop6h 35m
Delta
Deal found 1/27$254
This American Airlines deal was found by Cheapflights users on 1/28. 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 8/235:00 am
ORD
-
BZN
1 stop8h 59m
American Airlines
Sat 8/294:54 pm
BZN
-
ORD
Nonstop3h 09m
American Airlines
Deal found 1/28$259
This American Airlines deal was found by Cheapflights users on 1/27. 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 2/277:45 pm
ORD
-
BZN
Nonstop3h 29m
American Airlines
Mon 3/23:36 pm
BZN
-
ORD
1 stop7h 00m
American Airlines
Deal found 1/27$260
This Delta deal was found by Cheapflights users on 1/28. 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 2/181:49 pm
MDW
-
BZN
2 stops10h 26m
Delta
Wed 2/256:00 am
BZN
-
MDW
2 stops10h 37m
Delta
Deal found 1/28$260
This United Airlines deal was found by Cheapflights users on 1/26. 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 6/108:13 pm
ORD
-
BZN
Nonstop3h 27m
United Airlines
Mon 6/152:26 pm
BZN
-
ORD
1 stop7h 18m
United Airlines
Deal found 1/26$265
This United Airlines deal was found by Cheapflights users on 1/28. 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.
Fri 4/249:05 am
ORD
-
BZN
Nonstop3h 24m
United Airlines
Sun 4/2612:32 pm
BZN
-
ORD
Nonstop3h 10m
United Airlines
Deal found 1/28$266
This United Airlines deal was found by Cheapflights users on 1/28. 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 7/297:55 pm
ORD
-
BZN
Nonstop3h 23m
United Airlines
Mon 8/34:22 pm
BZN
-
ORD
1 stop6h 35m
United Airlines
Deal found 1/28$269
This American Airlines deal was found by Cheapflights users on 1/28. 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 10/111:45 am
ORD
-
BZN
Nonstop3h 16m
American Airlines
Sun 10/43:29 pm
BZN
-
ORD
Nonstop3h 16m
American Airlines
Deal found 1/28$270
This Southwest deal was found by Cheapflights users on 1/28. 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 3/46:10 am
MDW
-
BZN
1 stop9h 55m
Southwest
Fri 3/64:25 pm
BZN
-
MDW
1 stop5h 25m
Southwest
Deal found 1/28$270
This American Airlines deal was found by Cheapflights users on 1/27. 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.
Mon 3/27:09 pm
ORD
-
BZN
Nonstop3h 29m
American Airlines
Thu 3/51:28 pm
BZN
-
ORD
Nonstop3h 09m
American Airlines
Deal found 1/27$271

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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$250
(American Airlines)

One-way from

$115
(Alaska Airlines)

Popular in

March

Cheapest in

September

Average price

$327
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. 13% potential increase in price ($54 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
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 January 29, 2026.
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

Wed 2/18

2:20 pm-10:25 pm

1 stop9h 05m

Bozeman Gallatin Field

Wed 2/25

6:00 am-4:41 pm

2 stops9h 41m

$254

ChicagoBozeman

ORD - BZN

ORDBZN

Chicago O'Hare Intl

Tue 2/24

2:05 pm-11:15 pm

2 stops10h 10m

Bozeman Gallatin Field

Sat 2/28

6:00 am-11:45 am

1 stop4h 45m

$254

ChicagoBozeman

ORD - BZN

ORDBZN

Chicago O'Hare Intl

Sun 2/22

5:25 am-11:24 am

1 stop6h 59m

Bozeman Gallatin Field

Fri 2/27

6:00 am-4:41 pm

2 stops9h 41m

$254

ChicagoBozeman

MDW - BZN

MDWBZN

Chicago Midway

Wed 2/18

1:49 pm-11:15 pm

2 stops10h 26m

Bozeman Gallatin Field

Wed 2/25

6:00 am-1:05 pm

1 stop6h 05m

$254

ChicagoBozeman

ORD - BZN

ORDBZN

Chicago O'Hare Intl

Tue 5/12

2:20 pm-9:37 pm

1 stop8h 17m

Bozeman Gallatin Field

Sat 5/16

12:35 pm-4:45 pm

Nonstop3h 10m

$269

ChicagoBozeman

ORD - BZN

ORDBZN

Chicago O'Hare Intl

Wed 3/18

7:10 am-1:35 pm

1 stop7h 25m

Bozeman Gallatin Field

Sun 3/22

5:20 am-12:18 pm

1 stop5h 58m

$270

ChicagoBozeman

ORD - BZN

ORDBZN

Chicago O'Hare Intl

Fri 5/15

7:59 pm-11:53 pm

1 stop4h 54m

Bozeman Gallatin Field

Sun 5/17

5:45 am-12:21 pm

1 stop5h 36m

$270

ChicagoBozeman

MDW - BZN

MDWBZN

Chicago Midway

Sat 2/28

3:15 pm-10:50 pm

1 stop8h 35m

Bozeman Gallatin Field

Tue 3/3

7:40 am-4:45 pm

2 stops8h 05m

$275

ChicagoBozeman

MDW - BZN

MDWBZN

Chicago Midway

Wed 4/15

1:23 pm-8:11 pm

2 stops7h 48m

Bozeman Gallatin Field

Tue 4/21

11:59 am-10:28 pm

2 stops9h 29m

$281

ChicagoBozeman

MDW - BZN

MDWBZN

Chicago Midway

Wed 6/10

6:20 am-12:50 pm

1 stop7h 30m

Bozeman Gallatin Field

Mon 6/15

1:50 pm-12:35 am

2 stops9h 45m

$295

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/28

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 January 23, 2026.

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 $289). 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 January 29, 2026.

It’s typically best to fly out from Chicago to Big Sky in the evening. Doing so could potentially save you 22% on the flight price compared to flying at noon, 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 January 24, 2026.

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. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

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 January 29, 2026.
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
11,807 reviews

Comfort

7.8

Entertainment

7.0

Food

7.1

Boarding

8.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
Alaska Airlines
8.0
Very good
11,807 reviews
Alaska Airlines
8.0
Very good
11,807 reviews

Comfort

7.8

Entertainment

7.0

Food

7.1

Boarding

8.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
Southwest
8.0
Very good
4,267 reviews
Alaska Airlines
8.0
Very good
11,807 reviews

Comfort

7.8

Entertainment

7.0

Food

7.1

Boarding

8.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
Delta
7.9
Good
8,128 reviews
Alaska Airlines
8.0
Very good
11,807 reviews

Comfort

7.8

Entertainment

7.0

Food

7.1

Boarding

8.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
United Airlines
7.4
Good
9,215 reviews
Alaska Airlines
8.0
Very good
11,807 reviews

Comfort

7.8

Entertainment

7.0

Food

7.1

Boarding

8.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
American Airlines
7.2
Good
11,205 reviews
Alaska Airlines
8.0
Very good
11,807 reviews

Comfort

7.8

Entertainment

7.0

Food

7.1

Boarding

8.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading

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 8h 17m. Delta provides one of the quickest options available for as low as $269. 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 $129, 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 (100%), Qatar Airways (100%), American Airlines (83%).

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

    On average you can expect to pay $259 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 $289). 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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$152Average$405FlexibilityNo cancel feeOn-time63%
DeltaCheapest$169Average$308FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$211Average$341FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$245Average$552FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$291Average$504FlexibilityNo cancel feeOn-time75%

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