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Big Sky

$143+ 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 7/8. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BZN
Jun 5 — Jun 121
Fri 6/5
Fri 6/12
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Big Sky are usually found in January or September, booked 61 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 May 6, 2026.

This Alaska Airlines deal was found by Cheapflights users on 5/3. 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 9/293:52 pm
ORD
-
BZN
1 stop8h 07m
Alaska Airlines
Wed 9/303:40 pm
BZN
-
ORD
1 stop7h 01m
Alaska Airlines
Deal found 5/3$291
This American Airlines deal was found by Cheapflights users on 5/5. 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.
Wed 6/105:00 am
ORD
-
BZN
1 stop6h 57m
American Airlines
Sun 6/145:00 pm
BZN
-
ORD
Nonstop3h 20m
American Airlines
Deal found 5/5$295
This Southwest deal was found by Cheapflights users on 5/2. 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.
Fri 7/36:00 pm
MDW
-
BZN
1 stop6h 30m
Southwest
Fri 7/107:35 am
BZN
-
MDW
Nonstop2h 50m
Southwest
Deal found 5/2$295
This American Airlines deal was found by Cheapflights users on 5/4. 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 7/129:40 am
ORD
-
BZN
1 stop6h 43m
American Airlines
Sun 7/195:03 pm
BZN
-
ORD
Nonstop3h 27m
American Airlines
Deal found 5/4$296
This United Airlines deal was found by Cheapflights users on 5/2. 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.
Mon 6/158:15 pm
ORD
-
BZN
Nonstop3h 28m
United Airlines
Thu 6/188:00 am
BZN
-
ORD
Nonstop2h 59m
United Airlines
Deal found 5/2$300
This Southwest deal was found by Cheapflights users on 5/6. 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.
Sat 6/612:20 pm
MDW
-
BZN
2 stops10h 35m
Southwest
Mon 6/87:35 am
BZN
-
MDW
Nonstop2h 50m
Southwest
Deal found 5/6$300
This Southwest deal was found by Cheapflights users on 5/5. 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 8/1010:50 am
MDW
-
BZN
Nonstop3h 05m
Southwest
Thu 8/132:30 pm
BZN
-
MDW
1 stop13h 00m
Southwest
Deal found 5/5$301
This Delta deal was found by Cheapflights users on 5/5. 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 8/267:45 am
ORD
-
BZN
1 stop8h 24m
Delta
Sat 9/125:45 am
BZN
-
ORD
1 stop5h 36m
Delta
Deal found 5/5$304
This Delta deal was found by Cheapflights users on 5/6. 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.
Thu 6/117:37 pm
ORD
-
BZN
1 stop5h 46m
Delta
Mon 6/1512:13 pm
BZN
-
ORD
1 stop5h 45m
Delta
Deal found 5/6$305
This Delta deal was found by Cheapflights users on 5/6. 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 6/67:13 pm
MDW
-
BZN
1 stop5h 31m
Delta
Sat 6/1311:27 am
BZN
-
MDW
1 stop5h 27m
Delta
Deal found 5/6$305
This Delta deal was found by Cheapflights users on 5/5. 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 8/262:12 pm
ORD
-
BZN
2 stops10h 04m
Delta
Thu 9/103:40 pm
BZN
-
ORD
1 stop7h 07m
Delta
Deal found 5/5$309
This Delta deal was found by Cheapflights users on 5/6. 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.
Thu 6/117:37 pm
ORD
-
BZN
1 stop5h 46m
Delta
Tue 6/165:15 am
BZN
-
ORD
2 stops8h 50m
Delta
Deal found 5/6$310

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 May 6, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$291
(Alaska Airlines)

One-way from

$143
(American Airlines)

Popular in

March

Cheapest in

January

Average price

$365
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. 5% potential increase in price ($21 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 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 May 6, 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

Mon 6/15

5:00 am-9:37 am

1 stop5h 37m

Bozeman Gallatin Field

Thu 6/18

8:00 am-11:59 am

Nonstop2h 59m

$295

ChicagoBozeman

MDW - BZN

MDWBZN

Chicago Midway

Fri 7/3

6:00 pm-11:30 pm

1 stop6h 30m

Bozeman Gallatin Field

Fri 7/10

7:35 am-11:25 am

Nonstop2h 50m

$295

ChicagoBozeman

ORD - BZN

ORDBZN

Chicago O'Hare Intl

Mon 7/27

8:27 am-2:47 pm

1 stop7h 20m

Bozeman Gallatin Field

Sat 8/1

6:00 am-11:45 am

1 stop4h 45m

$305

ChicagoBozeman

ORD - BZN

ORDBZN

Chicago O'Hare Intl

Sat 6/27

5:00 pm-10:08 pm

1 stop6h 08m

Bozeman Gallatin Field

Fri 7/3

3:56 pm-11:39 pm

1 stop6h 43m

$305

ChicagoBozeman

ORD - BZN

ORDBZN

Chicago O'Hare Intl

Wed 6/10

7:37 pm-12:23 am

1 stop5h 46m

Bozeman Gallatin Field

Sat 6/13

11:27 am-5:27 pm

1 stop5h 00m

$305

ChicagoBozeman

ORD - BZN

ORDBZN

Chicago O'Hare Intl

Fri 7/3

3:55 pm-7:45 pm

1 stop4h 50m

Bozeman Gallatin Field

Fri 7/10

8:25 am-9:48 pm

2 stops12h 23m

$310

ChicagoBozeman

ORD - BZN

ORDBZN

Chicago O'Hare Intl

Fri 7/10

2:07 pm-11:52 pm

2 stops10h 45m

Bozeman Gallatin Field

Fri 7/17

5:15 am-11:59 am

1 stop5h 44m

$310

ChicagoBozeman

ORD - BZN

ORDBZN

Chicago O'Hare Intl

Sat 7/18

8:27 am-2:50 pm

1 stop7h 23m

Bozeman Gallatin Field

Fri 7/31

5:15 am-11:59 am

1 stop5h 44m

$332

ChicagoBozeman

ORD - BZN

ORDBZN

Chicago O'Hare Intl

Mon 6/1

5:41 pm-11:59 pm

2 stops7h 18m

Bozeman Gallatin Field

Mon 6/8

5:15 am-12:00 pm

1 stop5h 45m

$337

ChicagoBozeman

MDW - BZN

MDWBZN

Chicago Midway

Sat 6/13

9:54 am-5:20 pm

2 stops8h 26m

Bozeman Gallatin Field

Wed 6/17

6:00 am-1:09 pm

1 stop6h 09m

$337

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/4

Showing 1-10 of 35 resultsSorted by cheapest first
1
2
3
4

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

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 May 6, 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.

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 May 6, 2026.

The most flights from CHI to BS1 are scheduled on a Monday (4 on average). You will have fewer flight options on Friday, which is when the least amount of flights are scheduled (1 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 May 6, 2026.
See what other customers who have flown with Alaska Airlines,Southwest, 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.
Alaska Airlines
7.9
Good
12,332 reviews

Entertainment

7.0

Boarding

8.1

Food

7.1

Comfort

7.8

Crew

8.5

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Eugene,Mar 2026

MFR - SEA

Alaska Airlines is is always good. There where few choices of what to drink, and no food. No blankets, no pillows, and you h ats ok. I just had open heart surgery And i could have used something. But the flight and the crew where exelent. So all is well
Alaska Airlines
7.9
Good
12,332 reviews
Alaska Airlines
7.9
Good
12,332 reviews

Entertainment

7.0

Boarding

8.1

Food

7.1

Comfort

7.8

Crew

8.5

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Eugene,Mar 2026

MFR - SEA

Alaska Airlines is is always good. There where few choices of what to drink, and no food. No blankets, no pillows, and you h ats ok. I just had open heart surgery And i could have used something. But the flight and the crew where exelent. So all is well
Southwest
7.9
Good
4,305 reviews
Alaska Airlines
7.9
Good
12,332 reviews

Entertainment

7.0

Boarding

8.1

Food

7.1

Comfort

7.8

Crew

8.5

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Eugene,Mar 2026

MFR - SEA

Alaska Airlines is is always good. There where few choices of what to drink, and no food. No blankets, no pillows, and you h ats ok. I just had open heart surgery And i could have used something. But the flight and the crew where exelent. So all is well
Delta
7.9
Good
8,456 reviews
Alaska Airlines
7.9
Good
12,332 reviews

Entertainment

7.0

Boarding

8.1

Food

7.1

Comfort

7.8

Crew

8.5

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Eugene,Mar 2026

MFR - SEA

Alaska Airlines is is always good. There where few choices of what to drink, and no food. No blankets, no pillows, and you h ats ok. I just had open heart surgery And i could have used something. But the flight and the crew where exelent. So all is well
United Airlines
7.4
Good
9,684 reviews
Alaska Airlines
7.9
Good
12,332 reviews

Entertainment

7.0

Boarding

8.1

Food

7.1

Comfort

7.8

Crew

8.5

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Eugene,Mar 2026

MFR - SEA

Alaska Airlines is is always good. There where few choices of what to drink, and no food. No blankets, no pillows, and you h ats ok. I just had open heart surgery And i could have used something. But the flight and the crew where exelent. So all is well
American Airlines
7.1
Good
11,666 reviews
Alaska Airlines
7.9
Good
12,332 reviews

Entertainment

7.0

Boarding

8.1

Food

7.1

Comfort

7.8

Crew

8.5

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Eugene,Mar 2026

MFR - SEA

Alaska Airlines is is always good. There where few choices of what to drink, and no food. No blankets, no pillows, and you h ats ok. I just had open heart surgery And i could have used something. But the flight and the crew where exelent. So all is well

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 37m. United Airlines provides one of the quickest options available for as low as $295. 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?

    $108 is the cheapest one-way deal found within the past few days, from Delta. You may also be able to find cheap deals on American Airlines and United Airlines, with prices starting from $114 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: Lufthansa (73%), United Airlines (73%), SkyWest Airlines (67%).

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

    On average you can expect to pay $312 for a flight from Chicago to Big Sky. The cheapest flight overall is $142 while the most popular route, (Chicago O'Hare Intl - Bozeman Gallatin Field) is currently priced at $285.

  • 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.

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 May 6, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$210Average$415FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$211Average$346FlexibilityNo cancel feeOn-time71%
DeltaCheapest$216Average$278FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$229Average$534FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$243Average$401FlexibilityNo cancel feeOn-time75%

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