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Big Sky

$102+ 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 4/22. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BZN
4月 22 — 4月 291
週三 4/22
週三 4/29
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Big Sky are usually found in September or January, booked 74 days in advance, depart on a Tuesday or Wednesday 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 3月 23, 2026.

This Southwest deal was found by Cheapflights users on 3/22. 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.
週二 5/54:50 pm
ORD
-
BZN
1 stop8h 25m
Southwest
週五 5/86:15 am
BZN
-
ORD
1 stop6h 40m
Southwest
Deal found 3/22$237
This Southwest deal was found by Cheapflights users on 3/23. 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.
週六 4/253:05 pm
ORD
-
BZN
1 stop7h 35m
Southwest
週六 5/27:30 am
BZN
-
ORD
2 stops13h 50m
Southwest
Deal found 3/23$247
This Southwest deal was found by Cheapflights users on 3/23. 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.
週六 4/256:00 am
MDW
-
BZN
1 stop5h 15m
Southwest
週六 5/27:30 am
BZN
-
MDW
2 stops8h 45m
Southwest
Deal found 3/23$247
This Southwest deal was found by Cheapflights users on 3/22. 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.
週一 5/46:15 pm
ORD
-
BZN
1 stop5h 45m
Southwest
週五 5/86:15 am
BZN
-
ORD
1 stop6h 40m
Southwest
Deal found 3/22$256
This Expedia deal was found by Cheapflights users on 3/20. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週四 4/238:48 pm
ORD
-
BZN
1 stop14h 55m
Alaska Airlines
週一 4/277:59 pm
BZN
-
ORD
1 stop9h 41m
Alaska Airlines
Deal found 3/20$265
This Southwest deal was found by Cheapflights users on 3/23. 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.
週一 4/206:00 am
MDW
-
BZN
1 stop5h 15m
Southwest
週一 4/274:20 pm
BZN
-
MDW
1 stop6h 20m
Southwest
Deal found 3/23$271
This American Airlines deal was found by Cheapflights users on 3/20. 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.
週一 6/11:44 pm
ORD
-
BZN
Nonstop3h 18m
American Airlines
週二 6/24:57 pm
BZN
-
ORD
Nonstop3h 28m
American Airlines
Deal found 3/20$285
This Southwest deal was found by Cheapflights users on 3/22. 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.
週一 8/1710:50 am
MDW
-
BZN
Nonstop3h 05m
Southwest
週五 8/2112:20 pm
BZN
-
MDW
Nonstop2h 55m
Southwest
Deal found 3/22$285
This United Airlines deal was found by Cheapflights users on 3/23. 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.
週六 4/259:05 am
ORD
-
BZN
Nonstop3h 24m
United Airlines
週六 5/22:40 pm
BZN
-
ORD
1 stop7h 18m
United Airlines
Deal found 3/23$291
This Southwest deal was found by Cheapflights users on 3/22. 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.
週一 8/2410:50 am
MDW
-
BZN
Nonstop3h 05m
Southwest
週三 9/22:00 pm
BZN
-
MDW
1 stop4h 45m
Southwest
Deal found 3/22$291
This American Airlines deal was found by Cheapflights users on 3/20. 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.
週三 5/272:59 pm
ORD
-
BZN
1 stop6h 45m
American Airlines
週六 5/304:57 pm
BZN
-
ORD
Nonstop3h 28m
American Airlines
Deal found 3/20$295
This Southwest deal was found by Cheapflights users on 3/19. 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.
週三 6/106:40 pm
MDW
-
BZN
1 stop7h 05m
Southwest
週三 6/176:40 am
BZN
-
MDW
Nonstop2h 50m
Southwest
Deal found 3/19$295

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 3月 23, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$237
(Southwest)

One-way from

$102
(Southwest)

Popular in

March

Cheapest in

September

Average price

$379
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. 8% potential increase in price ($29 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 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 3月 23, 2026.
Use the filters below to find and compare flights from Chicago to Big Sky that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoBozeman

ORD - BZN

ORDBZN

Chicago O'Hare Intl

週六 4/25

9:05 am-11:29 am

Nonstop3h 24m

Bozeman Gallatin Field

週六 5/2

12:35 pm-4:45 pm

Nonstop3h 10m

$285

ChicagoBozeman

ORD - BZN

ORDBZN

Chicago O'Hare Intl

週六 6/13

8:10 pm-10:38 pm

Nonstop3h 28m

Bozeman Gallatin Field

週三 6/17

4:20 pm-8:35 pm

Nonstop3h 15m

$300

ChicagoBozeman

ORD - BZN

ORDBZN

Chicago O'Hare Intl

週四 5/28

5:00 am-9:37 am

1 stop5h 37m

Bozeman Gallatin Field

週日 5/31

4:29 pm-12:44 am

1 stop7h 15m

$305

ChicagoBozeman

ORD - BZN

ORDBZN

Chicago O'Hare Intl

週三 6/10

2:07 pm-12:23 am

2 stops11h 16m

Bozeman Gallatin Field

週一 6/15

6:00 am-11:31 am

1 stop4h 31m

$310

ChicagoBozeman

MDW - BZN

MDWBZN

Chicago Midway

週一 4/20

6:00 am-10:15 am

1 stop5h 15m

Bozeman Gallatin Field

週二 4/28

11:20 am-9:45 pm

2 stops9h 25m

$310

ChicagoBozeman

ORD - BZN

ORDBZN

Chicago O'Hare Intl

週日 8/23

6:00 am-12:29 pm

1 stop7h 29m

Bozeman Gallatin Field

週六 8/29

5:45 am-4:48 pm

2 stops10h 03m

$310

ChicagoBozeman

MDW - BZN

MDWBZN

Chicago Midway

週六 4/25

7:50 am-2:15 pm

2 stops7h 25m

Bozeman Gallatin Field

週六 5/2

2:55 pm-9:20 pm

1 stop5h 25m

$310

ChicagoBozeman

MDW - BZN

MDWBZN

Chicago Midway

週六 4/25

1:24 pm-8:11 pm

2 stops7h 47m

Bozeman Gallatin Field

週六 5/2

2:53 pm-10:28 pm

1 stop6h 35m

$313

ChicagoBozeman

MDW - BZN

MDWBZN

Chicago Midway

週三 6/10

6:40 pm-12:45 am

1 stop7h 05m

Bozeman Gallatin Field

週二 6/16

3:55 pm-10:25 pm

1 stop5h 30m

$331

ChicagoBozeman

ORD - BZN

ORDBZN

Chicago O'Hare Intl

週三 9/9

9:45 am-12:02 pm

Nonstop3h 17m

Bozeman Gallatin Field

週六 9/12

1:39 pm-5:55 pm

Nonstop3h 16m

$349

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/20

Showing 1-10 of 36 resultsSorted by cheapest first
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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 March 13, 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 December is currently the most expensive (average of $281). 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 3月 23, 2026.

It’s typically best to fly out from Chicago to Big Sky in the evening. Doing so could potentially save you 30% 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 March 23, 2026.

Travelers seeking maximum savings on their Chicago to Big Sky flight should consider departing on Wednesday evenings 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.

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 3月 23, 2026.

The most flights from CHI to BS1 are scheduled on a Monday (8 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (4 on average).

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 3月 23, 2026.
See what other customers who have flown with Southwest,Alaska Airlines, andDelta 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.
Southwest
8.0
Very good
4,324 reviews

Overall

8.0

Comfort

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,324 reviews
Southwest
8.0
Very good
4,324 reviews

Overall

8.0

Comfort

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Alaska Airlines
7.9
Good
12,098 reviews
Southwest
8.0
Very good
4,324 reviews

Overall

8.0

Comfort

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Delta
7.9
Good
8,319 reviews
Southwest
8.0
Very good
4,324 reviews

Overall

8.0

Comfort

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
United Airlines
7.4
Good
9,462 reviews
Southwest
8.0
Very good
4,324 reviews

Overall

8.0

Comfort

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
American Airlines
7.1
Good
11,488 reviews
Southwest
8.0
Very good
4,324 reviews

Overall

8.0

Comfort

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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 24m. United Airlines provides one of the quickest options available for as low as $285. 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 $122, 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 (72%), United Airlines (70%), Lufthansa (58%).

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

    On average you can expect to pay $541 for a flight from Chicago to Big Sky. The cheapest flight overall is $122 while the most popular route, (Chicago O'Hare Intl - Bozeman Gallatin Field) is currently priced at $203.

  • 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 December is currently the most expensive (average of $281). 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

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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 3月 23, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$169Average$267FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$210Average$420FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$211Average$335FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$230Average$539FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$291Average$475FlexibilityNo cancel feeOn-time75%

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