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$93+ 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 10/24. Fares are subject to change and may not be available on all flights or dates of travel.
BZN — CHI
Aug 4 — Aug 111
Mon 8/4
Mon 8/11
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 July 30, 2025.

Round-trip from

$191
(American Airlines)

One-way from

$93
(Mytrip)

Popular in

November

Cheapest in

July

Average price

$309

Good round-trip deal

$297 or less

Good one-way deal

$191 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 ($84 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 July 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 July 30, 2025.

This American Airlines deal was found by Cheapflights users on 7/30. 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 9/1112:50 pmMSO - ORD
Nonstop3h 31mAmerican Airlines
Mon 9/158:36 pmORD - MSO
Nonstop3h 42mAmerican Airlines
Deal found 7/30$191
This American Airlines deal was found by Cheapflights users on 7/29. 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 9/123:04 pmBZN - ORD
Nonstop3h 17mAmerican Airlines
Mon 9/1511:54 amORD - BZN
Nonstop3h 18mAmerican Airlines
Deal found 7/29$191
This Kiwi.com deal was found by Cheapflights users on 7/30. 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.
Thu 9/114:14 pmMSO - ORD
1 stop6h 49mHawaiian Airlines
Wed 9/175:45 pmORD - MSO
1 stop7h 42mHawaiian Airlines
Deal found 7/30$199
This Southwest deal was found by Cheapflights users on 7/28. 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.
Fri 9/511:20 amBZN - MDW
Nonstop2h 55mSouthwest
Mon 9/85:40 pmMDW - BZN
1 stop6h 55mSouthwest
Deal found 7/28$201
This Hawaiian Airlines deal was found by Cheapflights users on 7/29. 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.
Tue 8/263:08 pmBZN - ORD
1 stop7h 51mHawaiian Airlines
Wed 9/176:20 amORD - BZN
1 stop8h 54mHawaiian Airlines
Deal found 7/29$205
This Southwest deal was found by Cheapflights users on 7/28. 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.
Fri 10/244:00 pmBZN - ORD
1 stop6h 05mSouthwest
Mon 10/275:25 pmORD - BZN
1 stop6h 45mSouthwest
Deal found 7/28$206
This Alaska Airlines deal was found by Cheapflights users on 7/30. 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 9/43:08 pmBZN - ORD
1 stop7h 55mAlaska Airlines
Mon 9/87:00 amORD - BZN
1 stop7h 14mAlaska Airlines
Deal found 7/30$210
This American Airlines deal was found by Cheapflights users on 7/29. 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 10/212:19 pmBIL - ORD
Nonstop2h 54mAmerican Airlines
Tue 10/79:40 amORD - BIL
Nonstop3h 10mAmerican Airlines
Deal found 7/29$210
This United Airlines deal was found by Cheapflights users on 7/30. 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 9/112:40 pmMSO - ORD
1 stop8h 19mUnited Airlines
Mon 9/152:53 pmORD - MSO
1 stop7h 29mUnited Airlines
Deal found 7/30$211
This American Airlines deal was found by Cheapflights users on 7/28. 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.
Tue 9/93:49 pmFCA - ORD
1 stop7h 10mAmerican Airlines
Tue 9/168:25 amORD - FCA
1 stop6h 58mAmerican Airlines
Deal found 7/28$211
This United Airlines deal was found by Cheapflights users on 7/28. 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 9/57:00 amBZN - ORD
1 stop5h 15mUnited Airlines
Mon 9/82:53 pmORD - BZN
1 stop7h 38mUnited Airlines
Deal found 7/28$211
This United Airlines deal was found by Cheapflights users on 7/30. 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 10/1812:41 pmFCA - ORD
Nonstop3h 29mUnited Airlines
Mon 10/208:45 amORD - FCA
Nonstop3h 50mUnited Airlines
Deal found 7/30$220

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 July 30, 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

MissoulaChicago

MSO - ORD

MSOORD

Missoula Johnson-Bell Field

Thu 9/11

12:50 pm-5:21 pm

Nonstop3h 31m

Chicago O'Hare Intl

Mon 9/15

8:36 pm-11:18 pm

Nonstop3h 42m

$191

BozemanChicago

BZN - ORD

BZNORD

Bozeman Gallatin Field

Fri 9/12

3:04 pm-7:21 pm

Nonstop3h 17m

Chicago O'Hare Intl

Mon 9/15

11:54 am-2:12 pm

Nonstop3h 18m

$191

MissoulaChicago

MSO - ORD

MSOORD

Missoula Johnson-Bell Field

Thu 9/11

4:14 pm-12:03 am

1 stop6h 49m

Chicago O'Hare Intl

Wed 9/17

5:45 pm-12:27 am

1 stop7h 42m

$199

BozemanChicago

BZN - MDW

BZNMDW

Bozeman Gallatin Field

Fri 9/5

11:20 am-3:15 pm

Nonstop2h 55m

Chicago Midway

Mon 9/8

5:40 pm-11:35 pm

1 stop6h 55m

$201

BozemanChicago

BZN - ORD

BZNORD

Bozeman Gallatin Field

Tue 8/26

3:08 pm-11:59 pm

1 stop7h 51m

Chicago O'Hare Intl

Wed 9/17

6:20 am-2:14 pm

1 stop8h 54m

$205

BozemanChicago

BZN - ORD

BZNORD

Bozeman Gallatin Field

Fri 10/24

4:00 pm-11:05 pm

1 stop6h 05m

Chicago O'Hare Intl

Mon 10/27

5:25 pm-11:10 pm

1 stop6h 45m

$206

BozemanChicago

BZN - ORD

BZNORD

Bozeman Gallatin Field

Thu 9/4

3:08 pm-12:03 am

1 stop7h 55m

Chicago O'Hare Intl

Mon 9/8

7:00 am-1:14 pm

1 stop7h 14m

$210

BillingsChicago

BIL - ORD

BILORD

Billings Logan Intl

Thu 10/2

12:19 pm-4:13 pm

Nonstop2h 54m

Chicago O'Hare Intl

Tue 10/7

9:40 am-11:50 am

Nonstop3h 10m

$210

MissoulaChicago

MSO - ORD

MSOORD

Missoula Johnson-Bell Field

Thu 9/11

2:40 pm-11:59 pm

1 stop8h 19m

Chicago O'Hare Intl

Mon 9/15

2:53 pm-9:22 pm

1 stop7h 29m

$211

BozemanChicago

BZN - ORD

BZNORD

Bozeman Gallatin Field

Fri 9/5

7:00 am-1:15 pm

1 stop5h 15m

Chicago O'Hare Intl

Mon 9/8

2:53 pm-9:31 pm

1 stop7h 38m

$211

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

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 July 30, 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 July 30, 2025.

The most flights from USMT to CHI are scheduled on a Tuesday (11 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (1 on average).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated July 30, 2025.
Read through reviews of airlines operating flights from Montana to Chicago, such as Alaska Airlines, Southwest, and Delta. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Crew

8.5

Comfort

7.8

Overall

8.0

Food

7.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Crew

8.5

Comfort

7.8

Overall

8.0

Food

7.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Southwest
8.0
Very good
4,241 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Crew

8.5

Comfort

7.8

Overall

8.0

Food

7.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Delta
8.0
Very good
7,980 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Crew

8.5

Comfort

7.8

Overall

8.0

Food

7.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Hawaiian Airlines
7.8
Good
2,611 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Crew

8.5

Comfort

7.8

Overall

8.0

Food

7.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
United Airlines
7.4
Good
8,896 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Crew

8.5

Comfort

7.8

Overall

8.0

Food

7.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.

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.

  • 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 Southwest ($96), United Airlines ($96), and Alaska Airlines ($100).

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

    When deciding which route to take from Montana to Chicago consider Bozeman Gallatin Field - Chicago O'Hare Intl, Missoula Johnson-Bell 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 (90%), United Airlines (89%) or Lufthansa (87%) 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 $1,399 for a flight from Montana to Chicago. The cheapest flight overall is $135 while the most popular route, (Bozeman Gallatin Field - Chicago O'Hare Intl) is currently priced at $191.

  • 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
Valparaiso
Chesterton

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Alternative routes for Montana to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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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 July 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$191Average$351FlexibilityNo cancel feeOn-time71%
DeltaCheapest$216Average$396FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$239Average$531FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$267Average$463FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$388Average$418FlexibilityNo cancel feeOn-time63%

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