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$95+ 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 3/25. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — BZN
Jan 16 — Jan 231
Fri 1/16
Fri 1/23
1 adult, Economy
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Cheap 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 December 17, 2025.

This Southwest deal was found by Cheapflights users on 12/14. 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.
Thu 12/255:15 amMDW - BZN
1 stop7h 40mSouthwest
Mon 12/295:30 pmBZN - MDW
1 stop5h 10mSouthwest
Deal found 12/14$379
This Southwest deal was found by Cheapflights users on 12/16. 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.
Wed 12/175:15 amMDW - BZN
1 stop7h 40mSouthwest
Wed 12/2412:40 pmBZN - MDW
1 stop6h 25mSouthwest
Deal found 12/16$454
This Delta deal was found by Cheapflights users on 12/15. 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.
Wed 12/245:59 pmMDW - BZN
1 stop6h 47mDelta
Sun 12/2812:36 pmBZN - MDW
1 stop8h 46mDelta
Deal found 12/15$471
This Southwest deal was found by Cheapflights users on 12/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/235:10 amMDW - BZN
1 stop7h 45mSouthwest
Sat 12/275:00 amBZN - MDW
2 stops10h 30mSouthwest
Deal found 12/15$477
This Delta deal was found by Cheapflights users on 12/15. 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.
Tue 12/166:00 amMDW - BZN
1 stop8h 26mDelta
Thu 12/186:00 amBZN - MDW
1 stop6h 10mDelta
Deal found 12/15$509
This Delta deal was found by Cheapflights users on 12/17. 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 12/1812:45 pmMDW - BZN
2 stops11h 52mDelta
Tue 12/2312:15 pmBZN - MDW
2 stops9h 07mDelta
Deal found 12/17$519
This Delta deal was found by Cheapflights users on 12/16. 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 12/1912:50 pmMDW - BIL
2 stops12h 33mDelta
Sat 12/2011:52 amBIL - MDW
2 stops9h 30mDelta
Deal found 12/16$724
This Delta deal was found by Cheapflights users on 12/15. 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.
Wed 12/179:59 amMDW - MSO
2 stops8h 37mDelta
Wed 12/248:10 amMSO - MDW
1 stop8h 09mDelta
Deal found 12/15$1,015
This Delta deal was found by Cheapflights users on 12/15. 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.
Tue 12/305:59 pmMDW - BIL
1 stop6h 20mDelta
Sat 1/36:25 amBIL - MDW
2 stops10h 01mDelta
Deal found 12/15$1,058
This Delta deal was found by Cheapflights users on 12/15. 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.
Tue 12/235:59 pmMDW - BIL
1 stop6h 20mDelta
Sat 12/276:25 amBIL - MDW
2 stops10h 01mDelta
Deal found 12/15$1,214
This Delta deal was found by Cheapflights users on 12/17. 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 12/259:50 amMDW - MSO
2 stops11h 50mDelta
Sat 1/38:10 amMSO - MDW
1 stop8h 09mDelta
Deal found 12/17$1,454
This Delta deal was found by Cheapflights users on 12/16. 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 12/315:59 pmMDW - BIL
1 stop6h 20mDelta
Sun 1/45:14 amBIL - MDW
2 stops11h 05mDelta
Deal found 12/16$1,465

Find flight deals from Midway to Montana

Keep the following information in mind while searching for Midway to Montana flight deals. Data was last updated December 17, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$189
(Southwest)

One-way from

$95
(Southwest)

Popular in

March

Cheapest in

September

Average price

$449
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 Midway to Montana
Search Deals
One-way flight from Chicago Midway to Montana
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($49 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 December 17, 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 1/10

6:45 am-1:29 pm

1 stop7h 44m

Bozeman Gallatin Field

Thu 1/15

2:39 pm-10:07 pm

1 stop6h 28m

$249

ChicagoBillings

MDW - BIL

MDWBIL

Chicago Midway

Wed 1/21

1:49 pm-7:24 pm

1 stop6h 35m

Billings Logan Intl

Tue 1/27

6:10 am-1:09 pm

1 stop5h 59m

$249

ChicagoBillings

MDW - BIL

MDWBIL

Chicago Midway

Fri 1/9

1:49 pm-7:25 pm

1 stop6h 36m

Billings Logan Intl

Mon 1/12

6:22 am-1:09 pm

1 stop5h 47m

$249

ChicagoBillings

MDW - BIL

MDWBIL

Chicago Midway

Fri 1/30

1:49 pm-7:24 pm

1 stop6h 35m

Billings Logan Intl

Fri 2/6

6:10 am-1:06 pm

1 stop5h 56m

$249

ChicagoBozeman

MDW - BZN

MDWBZN

Chicago Midway

Wed 1/21

1:49 pm-8:06 pm

1 stop7h 17m

Bozeman Gallatin Field

Tue 1/27

6:00 am-5:55 pm

2 stops10h 55m

$254

ChicagoBozeman

MDW - BZN

MDWBZN

Chicago Midway

Sat 3/14

6:20 pm-10:50 pm

1 stop5h 30m

Bozeman Gallatin Field

Tue 3/17

3:25 pm-9:15 pm

1 stop4h 50m

$265

ChicagoBozeman

MDW - BZN

MDWBZN

Chicago Midway

Thu 1/8

5:35 pm-10:15 pm

1 stop5h 40m

Bozeman Gallatin Field

Wed 1/14

3:50 pm-9:50 pm

1 stop5h 00m

$270

ChicagoBozeman

MDW - BZN

MDWBZN

Chicago Midway

Sat 1/31

5:35 am-1:25 pm

1 stop8h 50m

Bozeman Gallatin Field

Sat 2/7

10:35 am-7:45 pm

1 stop8h 10m

$270

ChicagoBozeman

MDW - BZN

MDWBZN

Chicago Midway

Thu 1/22

1:49 pm-8:06 pm

1 stop7h 17m

Bozeman Gallatin Field

Tue 1/27

6:00 am-1:09 pm

1 stop6h 09m

$270

ChicagoBillings

MDW - BIL

MDWBIL

Chicago Midway

Fri 1/23

1:49 pm-7:24 pm

1 stop6h 35m

Billings Logan Intl

Sun 1/25

6:10 am-1:09 pm

1 stop5h 59m

$274

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/15

Showing 1-10 of 58 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 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 December 17, 2025.

It’s optimal to fly from Chicago Midway Airport to Montana in the evening. By choosing this option you can save up to 11% on the cost of your flight, compared to a flight in the afternoon.

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 December 17, 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
7.9
Good
4,250 reviews

Entertainment

7.5

Food

7.0

Crew

8.6

Boarding

8.1

Overall

7.9

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
7.9
Good
4,250 reviews
Southwest
7.9
Good
4,250 reviews

Entertainment

7.5

Food

7.0

Crew

8.6

Boarding

8.1

Overall

7.9

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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 $265, Delta can have you in Montana from Chicago Midway Airport in 5h 30m. 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 - Missoula Johnson-Bell Field or Chicago Midway - Kalispell Glacier Park 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.

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 Love Field 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 December 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$210Average$492FlexibilityNo cancel feeOn-time63%

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