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$143+ 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 8/19. Fares are subject to change and may not be available on all flights or dates of travel.
BZN — CHI
Jul 24 — Jul 311
Fri 7/24
Fri 7/31
1 adult, Economy
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Cheap 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 June 24, 2026.

This Delta deal was found by Cheapflights users on 6/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/125:20 am
BIL
-
ORD
1 stop5h 39m
Delta
Sat 8/154:45 pm
ORD
-
BIL
1 stop7h 08m
Delta
Deal found 6/23$271
This Delta deal was found by Cheapflights users on 6/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/225:20 am
BIL
-
ORD
1 stop5h 39m
Delta
Tue 8/2511:22 am
ORD
-
BIL
2 stops12h 03m
Delta
Deal found 6/22$276
This American Airlines deal was found by Cheapflights users on 6/24. 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 7/315:03 pm
BZN
-
ORD
Nonstop3h 27m
American Airlines
Sun 8/21:49 pm
ORD
-
BZN
Nonstop3h 24m
American Airlines
Deal found 6/24$283
This Southwest deal was found by Cheapflights users on 6/23. 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.
Fri 9/2512:20 pm
BZN
-
MDW
Nonstop2h 55m
Southwest
Sun 9/2710:25 am
MDW
-
BZN
Nonstop3h 10m
Southwest
Deal found 6/23$285
This American Airlines deal was found by Cheapflights users on 6/24. 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 7/295:03 pm
BZN
-
ORD
Nonstop3h 27m
American Airlines
Sun 8/21:49 pm
ORD
-
BZN
Nonstop3h 24m
American Airlines
Deal found 6/24$285
This United Airlines deal was found by Cheapflights users on 6/22. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/202:30 pm
BZN
-
ORD
1 stop7h 16m
United Airlines
Sun 8/231:01 pm
ORD
-
BZN
Nonstop3h 22m
United Airlines
Deal found 6/22$291
This United Airlines deal was found by Cheapflights users on 6/23. 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.
Thu 8/272:29 pm
BIL
-
ORD
1 stop7h 16m
United Airlines
Sat 8/298:40 am
ORD
-
BIL
Nonstop3h 22m
United Airlines
Deal found 6/23$292
This American Airlines deal was found by Cheapflights users on 6/23. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/35:03 pm
BZN
-
ORD
Nonstop3h 27m
American Airlines
Sat 8/85:00 am
ORD
-
BZN
1 stop7h 05m
American Airlines
Deal found 6/23$295
This Delta deal was found by Cheapflights users on 6/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/171:15 pm
GTF
-
ORD
1 stop7h 32m
Delta
Mon 9/2111:20 am
ORD
-
GTF
2 stops12h 22m
Delta
Deal found 6/19$298
This Southwest deal was found by Cheapflights users on 6/23. 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.
Sat 9/264:10 pm
BZN
-
MDW
1 stop12h 30m
Southwest
Mon 9/2810:50 am
MDW
-
BZN
Nonstop3h 05m
Southwest
Deal found 6/23$301
This Delta deal was found by Cheapflights users on 6/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/226:26 am
BIL
-
MDW
1 stop5h 44m
Delta
Tue 8/257:25 pm
MDW
-
BIL
1 stop5h 05m
Delta
Deal found 6/22$302
This Delta deal was found by Cheapflights users on 6/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/205:20 am
BIL
-
ORD
1 stop5h 39m
Delta
Tue 8/256:45 pm
ORD
-
BIL
1 stop5h 45m
Delta
Deal found 6/22$302

Find flight deals from Montana to Chicago

Keep the following information in mind while searching for Montana to Chicago flight deals. Data was last updated June 24, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$271
(Delta)

One-way from

$143
(Southwest)

Popular in

May

Cheapest in

September

Average price

$410

Good round-trip deal

$348 or less

Good one-way deal

$201 or less
Provider with most accurate pricing for Bozeman Gallatin Field-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Bozeman Gallatin Field-Chicago (CHI) flights.
Search Deals
From Montana to Chicago (CHI)
Search Deals
One-way flight from Montana to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 18% potential increase in price ($71 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2026
Search Deals
Price to beat on a round-trip flight from Montana to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Montana to Chicago (CHI).
Search Deals

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 June 24, 2026.
Use the filters below to find and compare flights from Montana to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

BillingsChicago

BIL - ORD

BILORD

Billings Logan Intl

Wed 8/12

5:20 am-11:59 am

1 stop5h 39m

Chicago O'Hare Intl

Sat 8/15

4:45 pm-10:53 pm

1 stop7h 08m

$271

BozemanChicago

BZN - ORD

BZNORD

Bozeman Gallatin Field

Thu 10/1

2:37 pm-10:46 pm

1 stop7h 09m

Chicago O'Hare Intl

Sun 10/4

4:45 pm-7:12 pm

Nonstop3h 27m

$291

BozemanChicago

BZN - ORD

BZNORD

Bozeman Gallatin Field

Wed 7/22

4:29 pm-12:44 am

1 stop7h 15m

Chicago O'Hare Intl

Wed 7/29

8:15 pm-10:43 pm

Nonstop3h 28m

$295

BozemanChicago

BZN - ORD

BZNORD

Bozeman Gallatin Field

Thu 8/20

2:30 pm-10:46 pm

1 stop7h 16m

Chicago O'Hare Intl

Sun 8/23

5:00 am-9:39 am

1 stop5h 39m

$300

BillingsChicago

BIL - ORD

BILORD

Billings Logan Intl

Wed 9/23

4:07 pm-11:59 pm

1 stop6h 52m

Chicago O'Hare Intl

Mon 9/28

5:00 am-9:46 am

1 stop5h 46m

$302

BozemanChicago

BZN - MDW

BZNMDW

Bozeman Gallatin Field

Thu 10/1

6:17 am-1:20 pm

1 stop6h 03m

Chicago Midway

Sun 10/4

6:05 am-1:09 pm

1 stop8h 04m

$305

BozemanChicago

BZN - ORD

BZNORD

Bozeman Gallatin Field

Thu 8/13

4:32 pm-11:59 pm

1 stop6h 27m

Chicago O'Hare Intl

Tue 8/18

5:00 am-9:39 am

1 stop5h 39m

$305

BozemanChicago

BZN - MDW

BZNMDW

Bozeman Gallatin Field

Sat 8/1

6:00 am-1:09 pm

1 stop6h 09m

Chicago Midway

Tue 8/4

12:46 pm-12:04 am

2 stops12h 18m

$310

BozemanChicago

BZN - MDW

BZNMDW

Bozeman Gallatin Field

Fri 11/6

2:00 pm-10:10 pm

1 stop7h 10m

Chicago Midway

Mon 11/9

9:55 am-5:55 pm

2 stops9h 00m

$310

BozemanChicago

BZN - ORD

BZNORD

Bozeman Gallatin Field

Tue 9/15

6:00 am-6:45 pm

2 stops11h 45m

Chicago O'Hare Intl

Fri 9/18

7:00 am-2:37 pm

1 stop8h 37m

$310

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/20

Showing 1-10 of 60 resultsSorted by cheapest first
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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, July is the cheapest month in which you can book a flight from Montana to Chicago (average of $129). Flying from Montana to Chicago in November is currently the most expensive (average of $249). 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 June 24, 2026.

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 June 24, 2026.

The most flights from USMT to CHI are scheduled on a Tuesday (13 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (3 on average).

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

How far ahead should I book a flight from Montana to Chicago?

The best time to book flights from Montana to Chicago is 76 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

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 $271, Delta can have you in Chicago from Montana in 5h 39m. The distance between Montana and Chicago is about 1057 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 American Airlines ($96), United Airlines ($124), and Delta ($215).

  • 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 Kalispell Glacier Park - 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 Emirates (79%), Lufthansa (78%) or American Airlines (77%) 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 $1,225 for a flight from Montana to Chicago. The cheapest flight overall is $142 while the most popular route, (Bozeman Gallatin Field - Chicago O'Hare Intl) is currently priced at $285.

  • 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, July is the cheapest month in which you can book a flight from Montana to Chicago (average of $129). Flying from Montana to Chicago in November is currently the most expensive (average of $249). 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
Benton Harbor
Lansing
Merrillville
Hammond
Porter

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Alternative routes for Montana to Chicago

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Top 4 airlines flying from Montana to Chicago

Discover the top 4 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 June 24, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$129Average$488FlexibilityNo cancel feeOn-timeN/A
Alaska AirlinesCheapest$166Average$467FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$191Average$362FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$229Average$447FlexibilityNo cancel feeOn-time69%

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