HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Montana

$105+ 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 1/26. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — BZN
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Midway to Montana with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 October 30, 2025.

This Southwest deal was found by Cheapflights users on 10/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/209:40 amMDW - BZN
1 stop6h 45mSouthwest
Thu 11/2712:25 pmBZN - MDW
1 stop5h 00mSouthwest
Deal found 10/29$209
This Southwest deal was found by Cheapflights users on 10/28. 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 12/126:35 pmMDW - BZN
1 stop6h 40mSouthwest
Mon 12/1510:45 amBZN - MDW
1 stop10h 25mSouthwest
Deal found 10/28$214
This Delta deal was found by Cheapflights users on 10/27. 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 12/57:02 pmMDW - BZN
1 stop5h 35mDelta
Mon 12/82:36 pmBZN - MDW
1 stop8h 11mDelta
Deal found 10/27$217
This Delta deal was found by Cheapflights users on 10/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/221:47 pmMDW - BZN
2 stops10h 12mDelta
Tue 11/256:04 amBZN - MDW
1 stop6h 03mDelta
Deal found 10/28$259
This Delta deal was found by Cheapflights users on 10/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/201:15 pmMDW - BZN
2 stops11h 55mDelta
Thu 11/2711:40 amBZN - MDW
2 stops11h 00mDelta
Deal found 10/28$264
This Southwest deal was found by Cheapflights users on 10/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/81:20 pmMDW - BZN
2 stops10h 25mSouthwest
Sun 12/145:00 amBZN - MDW
1 stop6h 35mSouthwest
Deal found 10/29$279
This Delta deal was found by Cheapflights users on 10/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/227:02 pmMDW - BZN
1 stop5h 32mDelta
Wed 11/262:35 pmBZN - MDW
1 stop8h 05mDelta
Deal found 10/28$288
This Southwest deal was found by Cheapflights users on 10/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/25:15 amMDW - BZN
1 stop7h 40mSouthwest
Mon 12/812:40 pmBZN - MDW
1 stop6h 25mSouthwest
Deal found 10/30$291
This Delta deal was found by Cheapflights users on 10/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/77:02 pmMDW - BIL
1 stop5h 46mDelta
Wed 12/106:25 amBIL - MDW
1 stop5h 45mDelta
Deal found 10/29$291
This Delta deal was found by Cheapflights users on 10/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/77:02 pmMDW - BIL
1 stop5h 46mDelta
Thu 12/1111:47 amBIL - MDW
2 stops11h 00mDelta
Deal found 10/29$330
This Delta deal was found by Cheapflights users on 10/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/261:15 pmMDW - MSO
2 stops12h 04mDelta
Wed 12/37:45 amMSO - MDW
2 stops9h 15mDelta
Deal found 10/28$341
This Delta deal was found by Cheapflights users on 10/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/67:02 pmMDW - BIL
1 stop5h 46mDelta
Thu 12/116:25 amBIL - MDW
2 stops10h 35mDelta
Deal found 10/29$370

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 October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$209
(Southwest)

One-way from

$105
(Southwest)

Popular in

December

Cheapest in

September

Average price

$383
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. 8% potential increase in price ($34 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 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 October 30, 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

Tue 1/13

5:35 pm-10:15 pm

1 stop5h 40m

Bozeman Gallatin Field

Sat 1/17

10:35 am-7:45 pm

1 stop8h 10m

$209

ChicagoBozeman

MDW - BZN

MDWBZN

Chicago Midway

Thu 11/20

5:15 am-11:55 am

1 stop7h 40m

Bozeman Gallatin Field

Thu 11/27

12:25 pm-6:25 pm

1 stop5h 00m

$209

ChicagoBozeman

MDW - BZN

MDWBZN

Chicago Midway

Fri 12/12

6:35 pm-12:15 am

1 stop6h 40m

Bozeman Gallatin Field

Mon 12/15

10:45 am-10:10 pm

1 stop10h 25m

$214

ChicagoBozeman

MDW - BZN

MDWBZN

Chicago Midway

Fri 12/5

6:00 pm-10:45 pm

1 stop5h 45m

Bozeman Gallatin Field

Mon 12/8

5:30 am-12:35 pm

2 stops6h 05m

$214

ChicagoBozeman

MDW - BZN

MDWBZN

Chicago Midway

Tue 1/13

6:45 am-1:29 pm

1 stop7h 44m

Bozeman Gallatin Field

Sun 1/18

2:39 pm-10:09 pm

1 stop6h 30m

$217

ChicagoBozeman

MDW - BZN

MDWBZN

Chicago Midway

Sat 11/22

7:02 pm-11:34 pm

1 stop5h 32m

Bozeman Gallatin Field

Mon 11/24

6:04 am-1:07 pm

1 stop6h 03m

$217

ChicagoBozeman

MDW - BZN

MDWBZN

Chicago Midway

Fri 12/5

7:02 pm-11:37 pm

1 stop5h 35m

Bozeman Gallatin Field

Mon 12/8

2:36 pm-11:47 pm

1 stop8h 11m

$217

ChicagoBillings

MDW - BIL

MDWBIL

Chicago Midway

Sun 12/7

7:02 pm-11:48 pm

1 stop5h 46m

Billings Logan Intl

Wed 12/10

6:25 am-1:10 pm

1 stop5h 45m

$291

ChicagoBillings

MDW - BIL

MDWBIL

Chicago Midway

Sun 12/7

7:02 pm-11:48 pm

1 stop5h 46m

Billings Logan Intl

Thu 12/11

11:47 am-11:47 pm

2 stops11h 00m

$330

ChicagoMissoula

MDW - MSO

MDWMSO

Chicago Midway

Wed 11/26

1:15 pm-12:19 am

2 stops12h 04m

Missoula Johnson-Bell Field

Wed 12/3

7:45 am-6:00 pm

2 stops9h 15m

$341

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

Showing 1-10 of 44 results
1
2
3
...
5

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 October 30, 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 October 30, 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
4,243 reviews

Comfort

8.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Boarding

8.1

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
4,243 reviews
Southwest
8.0
Very good
4,243 reviews

Comfort

8.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Boarding

8.1

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 $209, Southwest can have you in Montana from Chicago Midway Airport in 5h 40m. 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 - Billings Logan Intl 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Midway to Montana

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to John F Kennedy Intl flights
O'Hare Intl to Sky Harbor Intl flights
O'Hare Intl to Dallas/Fort Worth flights
O'Hare Intl to Las Vegas flights
O'Hare Intl to LaGuardia flights
O'Hare Intl to Newark flights
O'Hare Intl to Orlando flights
O'Hare Intl to Miami flights
O'Hare Intl to Fort Lauderdale flights
O'Hare Intl to Los Angeles flights
O'Hare Intl to Tampa flights
O'Hare Intl to Denver flights
O'Hare Intl to Atlanta flights
O'Hare Intl to San Francisco flights
O'Hare Intl to Fort Myers flights
O'Hare Intl to Seattle flights
O'Hare Intl to Boston flights
Midway to Dallas/Fort Worth flights
O'Hare Intl to Dulles Intl flights
O'Hare Intl to Ontario flights
O'Hare Intl to Baltimore flights
Midway to John F Kennedy Intl flights
O'Hare Intl to New Orleans flights
O'Hare Intl to Reagan-National flights
O'Hare Intl to Santa Ana flights
Midway to Miami flights
Midway to LaGuardia flights
Midway to Los Angeles flights
Midway to Atlanta flights
O'Hare Intl to Austin flights
O'Hare Intl to George Bush Intcntl flights
O'Hare Intl to Hobby flights
O'Hare Intl to San Diego flights
O'Hare Intl to West Palm Beach flights
O'Hare Intl to Honolulu flights
Midway to Orlando flights
Midway to Baltimore flights
O'Hare Intl to Nashville flights
O'Hare Intl to Salt Lake City flights
O'Hare Intl to Philadelphia flights
Midway to Sky Harbor Intl flights
Midway to Hobby flights
Midway to Denver flights
Midway to Las Vegas flights
Midway to Tampa flights
O'Hare Intl to Sarasota flights
O'Hare Intl to Charlotte flights
O'Hare Intl to Love Field flights
O'Hare Intl to Raleigh flights
Midway to Dulles Intl 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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$210Average$454FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.