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$110+ Cheap flights from Montana to Chicago (CHI)

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 2/11. Fares are subject to change and may not be available on all flights or dates of travel.
BZN — CHI
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheap flight deals from Montana to Chicago

Keep the following information in mind while searching for Montana to Chicago flight deals. Data was last updated September 15, 2025.

Round-trip from

$228
(Alaska Airlines)

One-way from

$110
(Trip.com)

Popular in

November

Cheapest in

July

Average price

$302

Good round-trip deal

$253 or less

Good one-way deal

$196 or less
From Montana to Chicago (CHI)
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One-way flight from Montana to Chicago (CHI)
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Highest demand for flights based on searches. 17% potential increase in price ($81 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Montana to Chicago (CHI).
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Price to beat on a one-way flight from Montana to Chicago (CHI).
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Find flight deals from Montana to Chicago

Cheapest flights from Montana to Chicago
Explore the most affordable flight options available from Montana to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 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.
Thu 12/117:00 amBZN - ORD
1 stop8h 55mAlaska Airlines
Mon 12/156:00 amORD - BZN
1 stop9h 04mAlaska Airlines
Deal found 9/13$228
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.
Sat 10/2512:20 pmBIL - ORD
Nonstop2h 57mAmerican Airlines
Wed 10/299:40 amORD - BIL
Nonstop3h 10mAmerican Airlines
Deal found 9/14$229
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/211:58 amBIL - ORD
Nonstop3h 00mUnited Airlines
Sun 10/58:55 amORD - BIL
Nonstop3h 21mUnited Airlines
Deal found 9/13$244
This Hawaiian 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 Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3111:16 amBZN - ORD
1 stop9h 24mHawaiian Airlines
Sun 11/25:00 amORD - BZN
1 stop9h 08mHawaiian Airlines
Deal found 9/14$248
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/226:25 amBIL - MDW
1 stop5h 42mDelta
Mon 11/247:02 pmMDW - BIL
1 stop5h 17mDelta
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.
Sat 10/181:00 pmBZN - ORD
Nonstop3h 03mAmerican Airlines
Tue 10/211:49 pmORD - BZN
Nonstop3h 12mAmerican Airlines
Deal found 9/14$249
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1211:46 amBZN - ORD
1 stop9h 44mAlaska Airlines
Sun 12/146:00 amORD - BZN
1 stop9h 04mAlaska Airlines
Deal found 9/13$252
This Delta deal was found by Cheapflights users on 9/15. 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.
Sat 10/256:25 amBIL - ORD
1 stop4h 03mDelta
Wed 10/291:25 pmORD - BIL
2 stops10h 53mDelta
Deal found 9/15$254
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/112:45 pmBZN - ORD
Nonstop2h 59mUnited Airlines
Tue 11/48:47 amORD - BZN
1 stop5h 48mUnited Airlines
Deal found 9/13$259
This American Airlines deal was found by Cheapflights users on 9/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/412:19 pmBIL - ORD
Nonstop2h 54mAmerican Airlines
Sun 10/129:40 amORD - BIL
Nonstop3h 10mAmerican Airlines
Deal found 9/15$265
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/186:00 amBZN - MDW
1 stop6h 08mDelta
Tue 10/216:00 amMDW - BZN
1 stop8h 19mDelta
Deal found 9/14$269
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.
Sat 11/84:12 pmMSO - ORD
1 stop7h 12mAlaska Airlines
Wed 11/123:25 pmORD - MSO
1 stop9h 18mAlaska Airlines
Deal found 9/14$269

Cheapflights Fare Finder

 
Customize your flight search to find flights from Montana to Chicago 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 September 15, 2025.
Use the filters below to find and compare flights from Montana to Chicago that are best for you.

Fly from

Montana

Fly to

Chicago

Route

Depart

Return

Price

BozemanChicago

BZN - MDW

BZNMDW

Bozeman Gallatin Field

Thu 2/26

6:00 am-6:34 pm

2 stops11h 34m

Chicago Midway

Mon 3/2

6:45 pm-12:04 am

1 stop6h 19m

$242

BozemanChicago

BZN - ORD

BZNORD

Bozeman Gallatin Field

Fri 10/31

11:16 am-9:40 pm

1 stop9h 24m

Chicago O'Hare Intl

Sun 11/2

5:00 am-1:08 pm

1 stop9h 08m

$248

BozemanChicago

BZN - ORD

BZNORD

Bozeman Gallatin Field

Thu 12/11

7:00 am-4:55 pm

1 stop8h 55m

Chicago O'Hare Intl

Sun 12/14

6:00 am-2:04 pm

1 stop9h 04m

$248

BillingsChicago

BIL - MDW

BILMDW

Billings Logan Intl

Sat 11/22

6:25 am-1:07 pm

1 stop5h 42m

Chicago Midway

Mon 11/24

7:02 pm-11:19 pm

1 stop5h 17m

$249

BillingsChicago

BIL - ORD

BILORD

Billings Logan Intl

Sat 11/22

6:25 am-11:35 am

1 stop4h 10m

Chicago O'Hare Intl

Mon 11/24

2:30 pm-11:19 pm

2 stops9h 49m

$254

BillingsChicago

BIL - ORD

BILORD

Billings Logan Intl

Sat 10/25

5:25 am-1:56 pm

1 stop7h 31m

Chicago O'Hare Intl

Wed 10/29

1:25 pm-10:25 pm

2 stops10h 00m

$254

BozemanChicago

BZN - ORD

BZNORD

Bozeman Gallatin Field

Wed 2/18

7:00 am-11:00 am

Nonstop3h 00m

Chicago O'Hare Intl

Sat 2/21

6:46 am-2:39 pm

1 stop8h 53m

$259

MissoulaChicago

MSO - ORD

MSOORD

Missoula Johnson-Bell Field

Wed 1/21

1:05 pm-5:35 pm

Nonstop3h 30m

Chicago O'Hare Intl

Mon 1/26

3:22 pm-9:41 pm

1 stop7h 19m

$259

MissoulaChicago

MSO - ORD

MSOORD

Missoula Johnson-Bell Field

Wed 1/14

7:00 am-5:38 pm

1 stop9h 38m

Chicago O'Hare Intl

Sun 1/18

9:45 am-12:25 pm

Nonstop3h 40m

$259

BillingsChicago

BIL - ORD

BILORD

Billings Logan Intl

Sat 10/4

12:19 pm-4:13 pm

Nonstop2h 54m

Chicago O'Hare Intl

Sun 10/12

9:40 am-11:50 am

Nonstop3h 10m

$265

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/13

Showing 1-10 of 60 results
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Best time to book a flight from Montana to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Montana 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 Montana to Chicago

What is the cheapest month to book a flight from Montana to Chicago?

Currently, August is the cheapest month in which you can book a flight from Montana to Chicago (average of $245). Flying from Montana to Chicago in March is currently the most expensive (average of $321). 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 MT to CHI?

Find hourly flight availability from Montana to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 15, 2025.

When flying from Montana to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Weekly flight availability from Montana to Chicago

Explore weekly flight availability from Montana to Chicago. 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 September 15, 2025.

The most flights from USMT to CHI are scheduled on a Monday (12 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (8 on average).

How much does it cost to fly round-trip from Montana to Chicago?

Related info for your journey

Find useful and relevant information for your journey from Montana to Chicago. 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 Montana to Chicago?

    For as low as $248, Delta can have you in Chicago from Montana in 8h 55m. The distance between Montana and Chicago is about 1182 mi. This flight may include one or multiple stops.

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

    The cheapest airlines for a one-way flight from Montana to Chicago are Alaska Airlines ($114), Hawaiian Airlines ($114), and Southwest ($135).

  • What are the most popular routes from Montana to Chicago?

    When deciding which route to take from Montana to Chicago consider Missoula Johnson-Bell Field - Chicago O'Hare Intl, Bozeman Gallatin Field - Chicago O'Hare Intl or Billings Logan Intl - Chicago O'Hare Intl as they are the most popular.

  • What are the most reliable airlines from Montana to Chicago?

    No one likes to see their flight delayed. When booking a flight from Montana to Chicago consider choosing SkyWest Airlines (79%), United Airlines (74%) or Lufthansa (71%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Montana to Chicago?

    On average you can expect to pay $704 for a flight from Montana to Chicago. The cheapest flight overall is $120 while the most popular route, (Missoula Johnson-Bell Field - Chicago O'Hare Intl) is currently priced at $257.

  • Can I find deals for flights from Montana to Chicago that include hotel bookings?

    Yes. In addition to deals on Montana to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Montana to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Montana to Chicago.

  • Can I find deals for business class flights from Montana to Chicago?

    Yes. Cheapflights offers flight deals from Montana to Chicago 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 Montana to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Montana to Chicago (average of $245). Flying from Montana to Chicago in March is currently the most expensive (average of $321). 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

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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Top 5 airlines flying from Montana to Chicago

Discover the top 5 airlines that operate flights from Montana to Chicago. 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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$191Average$345FlexibilityNo cancel feeOn-time71%
DeltaCheapest$236Average$389FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$239Average$550FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$267Average$450FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$388Average$420FlexibilityNo cancel feeOn-time63%

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