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$77+ Cheap flights from Midway (MDW) to Montana

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 11/11. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — BZN
Oct 14 — Oct 211
Tue 10/14
Tue 10/21
1 adult, Economy
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Cheap flight deals from Midway to Montana

Keep the following information in mind while searching for Midway to Montana flight deals. Data was last updated September 14, 2025.

Round-trip from

$237
(Delta)

One-way from

$77
(Southwest)

Popular in

December

Cheapest in

September

Average price

$316
From Chicago Midway to Montana
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One-way flight from Chicago Midway to Montana
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Highest demand for flights based on searches. 13% potential increase in price ($62 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Midway to Montana

Cheapest flights from Midway to Montana
Explore the most affordable flight options available from Midway to Montana. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 14, 2025.

This Delta deal was found by Cheapflights users on 9/12. 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 10/117:10 pmMDW - BZN
1 stop5h 27mDelta
Sat 10/186:00 amBZN - MDW
1 stop6h 08mDelta
Deal found 9/12$237
This Southwest deal was found by Cheapflights users on 9/12. 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 10/246:25 pmMDW - BZN
1 stop6h 45mSouthwest
Sun 10/266:15 pmBZN - MDW
1 stop5h 20mSouthwest
Deal found 9/12$238
This Southwest deal was found by Cheapflights users on 9/12. 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.
Thu 11/136:25 pmMDW - BZN
2 stops6h 50mSouthwest
Sun 11/165:00 amBZN - MDW
1 stop5h 05mSouthwest
Deal found 9/12$241
This Delta deal was found by Cheapflights users on 9/12. 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.
Tue 12/91:50 pmMDW - BZN
2 stops11h 27mDelta
Sun 12/146:00 amBZN - MDW
1 stop6h 08mDelta
Deal found 9/12$242
This Southwest deal was found by Cheapflights users on 9/12. 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.
Tue 10/75:30 pmMDW - BZN
2 stops6h 55mSouthwest
Fri 10/108:00 pmBZN - MDW
1 stop8h 15mSouthwest
Deal found 9/12$249
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/287:10 pmMDW - BIL
1 stop5h 08mDelta
Tue 11/46:25 amBIL - MDW
1 stop5h 43mDelta
Deal found 9/13$249
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.
Fri 10/247:10 pmMDW - BZN
1 stop5h 27mDelta
Sun 10/266:10 amBZN - MDW
1 stop5h 58mDelta
Deal found 9/14$269
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 10/183:00 pmMDW - MSO
1 stop8h 12mDelta
Sat 10/255:25 amMSO - MDW
2 stops11h 18mDelta
Deal found 9/14$274
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/245:00 pmMDW - BZN
2 stops8h 10mSouthwest
Wed 10/295:30 amBZN - MDW
2 stops6h 40mSouthwest
Deal found 9/14$279
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/76:25 pmMDW - BZN
2 stops6h 50mSouthwest
Sun 11/95:45 pmBZN - MDW
1 stop5h 20mSouthwest
Deal found 9/14$285
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/309:55 amMDW - BZN
Nonstop3h 10mSouthwest
Sat 10/410:25 amBZN - MDW
1 stop9h 20mSouthwest
Deal found 9/14$295
This Delta deal was found by Cheapflights users on 9/12. 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 11/261:14 pmMDW - BIL
2 stops11h 35mDelta
Tue 12/26:24 amBIL - MDW
1 stop5h 44mDelta
Deal found 9/12$299

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Montana 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 14, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Montana that are best for you.

Fly from

Midway

Fly to

Montana

Route

Depart

Return

Price

ChicagoBozeman

MDW - BZN

MDWBZN

Chicago Midway

Sat 10/11

7:10 pm-11:37 pm

1 stop5h 27m

Bozeman Gallatin Field

Sat 10/18

6:00 am-1:08 pm

1 stop6h 08m

$237

ChicagoBozeman

MDW - BZN

MDWBZN

Chicago Midway

Fri 10/24

6:25 pm-12:10 am

1 stop6h 45m

Bozeman Gallatin Field

Sun 10/26

6:15 pm-12:35 am

1 stop5h 20m

$238

ChicagoBozeman

MDW - BZN

MDWBZN

Chicago Midway

Thu 11/13

6:25 pm-12:15 am

2 stops6h 50m

Bozeman Gallatin Field

Sun 11/16

5:00 am-11:05 am

1 stop5h 05m

$241

ChicagoBozeman

MDW - BZN

MDWBZN

Chicago Midway

Tue 12/9

1:50 pm-12:17 am

2 stops11h 27m

Bozeman Gallatin Field

Sun 12/14

6:00 am-1:08 pm

1 stop6h 08m

$242

ChicagoBillings

MDW - BIL

MDWBIL

Chicago Midway

Tue 10/28

7:10 pm-11:18 pm

1 stop5h 08m

Billings Logan Intl

Tue 11/4

6:25 am-1:08 pm

1 stop5h 43m

$249

ChicagoBozeman

MDW - BZN

MDWBZN

Chicago Midway

Fri 10/24

7:10 pm-11:37 pm

1 stop5h 27m

Bozeman Gallatin Field

Sun 10/26

6:10 am-1:08 pm

1 stop5h 58m

$269

ChicagoBozeman

MDW - BZN

MDWBZN

Chicago Midway

Sat 10/18

1:11 pm-10:54 pm

2 stops10h 43m

Bozeman Gallatin Field

Fri 10/24

2:29 pm-10:14 pm

1 stop6h 45m

$274

ChicagoMissoula

MDW - MSO

MDWMSO

Chicago Midway

Sat 10/18

3:00 pm-10:12 pm

1 stop8h 12m

Missoula Johnson-Bell Field

Sat 10/25

5:25 am-5:43 pm

2 stops11h 18m

$274

ChicagoBozeman

MDW - BZN

MDWBZN

Chicago Midway

Fri 10/24

5:00 pm-12:10 am

2 stops8h 10m

Bozeman Gallatin Field

Wed 10/29

5:30 am-1:10 pm

2 stops6h 40m

$279

ChicagoMissoula

MDW - MSO

MDWMSO

Chicago Midway

Fri 2/6

1:00 pm-8:17 pm

2 stops8h 17m

Missoula Johnson-Bell Field

Mon 2/9

8:00 am-6:34 pm

2 stops9h 34m

$279

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/12

Showing 1-10 of 56 results
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Best time to book a flight from Midway to Montana

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

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

Currently, October is the cheapest month in which you can book a flight from Chicago Midway Airport to Montana (average of $371). Flying from Chicago Midway Airport to Montana in May is currently the most expensive (average of $477). 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 MDW to MT?

Find hourly flight availability from Midway to Montana. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 14, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago Midway Airport to Montana as you normally would.

Reviews of airlines servicing Montana

Get insights into the airlines that provide service to Montana. 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 Montana. Reviews last updated September 14, 2025.
Read reviews from past customers who have flown Southwest from Chicago Midway Airport to Montana. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,245 reviews

Overall

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,245 reviews
Southwest
8.0
Very good
4,245 reviews

Overall

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

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

    For as low as $237, Delta can have you in Montana from Chicago Midway Airport in 5h 27m. Airlines will cover a distance of 1194 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    Most travelers choose Chicago Midway - Bozeman Gallatin Field, Chicago Midway - Kalispell Glacier Park or Chicago Midway - Missoula Johnson-Bell Field when deciding on the best route from Chicago Midway Airport to Montana.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Midway to Montana 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 Midway Airport to Montana?

    Currently, October is the cheapest month in which you can book a flight from Chicago Midway Airport to Montana (average of $371). Flying from Chicago Midway Airport to Montana in May is currently the most expensive (average of $477). 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

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Alternative routes for Midway to Montana

See prices for flight routes from nearby airports that may be better suited for you.
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Midway to Seattle flights

Top airline flying from Midway to Montana

Discover the top airline that operate flights from Midway to Montana. 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 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$210Average$492FlexibilityNo cancel feeOn-time63%

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