$101 Find Cheap Flights from Chicago Midway Airport to Montana

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Montana departing on 9/21. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Montana

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Montana, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Montana, as well as popular online travel agencies
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Flight Deals

Cheap Flights from Midway to Montana

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Bozeman
Bozemannonstop$215
Kalispell
Kalispell1 stop$347
Missoula
Missoula1 stop$274
Billings
Billings1 stop$264
Great Falls
Great Falls2 stops$504
Helena
Helena2 stops$858
West Yellowstone
West Yellowstone2 stops$1,139
Bozeman
Bozemannonstop$215
Kalispell
Kalispell1 stop$347
Missoula
Missoula1 stop$274
Billings
Billings1 stop$264
Great Falls
Great Falls2 stops$504
Helena
Helena2 stops$858
West Yellowstone
West Yellowstone2 stops$1,139

Book Cheap Midway to Montana Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to Montana that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to Montana

Sat, Sep 13 - Thu, Sep 18
Southwest Logo
8:20 am - 10:30 amMDW-BZN
3h 10mnonstop
Southwest Logo
11:20 am - 3:15 pmBZN-MDW
2h 55mnonstop
$215Southwest
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Sat, Sep 13 - Thu, Sep 18
Southwest Logo
8:20 am - 10:30 amMDW-BZN
3h 10mnonstop
Southwest Logo
2:25 pm - 11:25 pmBZN-MDW
8h 00m1 stop
$225Southwest
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Sun, Aug 31 - Sat, Sep 6
Southwest Logo
10:55 am - 1:05 pmMDW-BZN
3h 10mnonstop
Southwest Logo
11:10 am - 7:00 pmBZN-MDW
6h 50m1 stop
$231Southwest
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Sun, Aug 31 - Sat, Sep 6
Southwest Logo
10:55 am - 1:05 pmMDW-BZN
3h 10mnonstop
Southwest Logo
12:25 pm - 4:20 pmBZN-MDW
2h 55mnonstop
$236Southwest
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Mon, Sep 22 - Tue, Sep 23
Delta Logo
7:15 pm - 11:56 pmMDW-BZN
5h 41m1 stop
Delta Logo
6:00 am - 1:03 pmBZN-MDW
6h 03m1 stop
$237Delta
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Wed, Aug 27 - Sat, Sep 6
Southwest Logo
9:55 am - 12:05 pmMDW-BZN
3h 10mnonstop
Southwest Logo
12:25 pm - 4:20 pmBZN-MDW
2h 55mnonstop
$241Southwest
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Sun, Aug 31 - Sat, Sep 6
Delta Logo
6:00 am - 1:08 pmMDW-BZN
8h 08m1 stop
Delta Logo
6:05 am - 3:28 pmBZN-MDW
8h 23m2 stops
$242Delta
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Fri, Oct 31 - Tue, Nov 4
Delta Logo
6:00 am - 1:19 pmMDW-BZN
8h 19m1 stop
Delta Logo
6:10 am - 1:08 pmBZN-MDW
5h 58m1 stop
$243Delta
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Sat, Sep 6 - Fri, Sep 12
Southwest Logo
8:20 am - 10:30 amMDW-BZN
3h 10mnonstop
Southwest Logo
5:00 pm - 12:05 amBZN-MDW
6h 05m1 stop
$245Southwest
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Thu, Dec 18 - Mon, Dec 22
Logo
6:00 am - 5:52 pmMDW-MSO
12h 52m1 stop
Logo
1:11 pm - 2:32 pmMSO-MDW
24h 21m2 stops
$618
Find Deal
Booking Insights

KAYAK's insights & trends for Midway to Montana flights

Get data-powered insights and trends into flights from Midway to Montana to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Chicago Midway Airport to Montana flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Montana from Chicago Midway Airport found in the last 72 hours was to Bozeman, at $225 round-trip. The most popular route is from Chicago Midway Airport (MDW) to Bozeman (BZN), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $225.

Can I save money by flying with a layover from Chicago Midway Airport to Montana?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $240 on average.

What is the cheapest month to fly from Chicago Midway Airport to Montana?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago Midway Airport to Montana, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago Midway Airport to Montana is January, when tickets cost $210 (return) on average. On the other hand, the most expensive months are September and July, when the average cost of round-trip tickets is $786 and $547 respectively.

What’s the cheapest day of the week to fly from Chicago Midway Airport to Montana?

The average price of all round-trip flights from Chicago Midway Airport to Montana clicked on KAYAK for each day over the last 12 months.

For Chicago Midway Airport to Montana, Saturday is the cheapest day to fly on average and Wednesday is the most expensive. Flying from Montana back to Chicago Midway Airport, the best deals are generally found on Tuesday, with Sunday being the most expensive.

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Good to know

Low seasonJanuary
Cheapest flight$101
Best time to beat the crowds with an average 54% drop in price.
Most popular time to fly with an average 10% increase in price.
Flight from Chicago Midway Airport to Bozeman

FAQs - booking Montana flights

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to Montana?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago Midway Airport to Montana.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport to Montana?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago Midway Airport to Montana is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago Midway Airport to Montana?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Chicago Midway Airport to Montana with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway Airport to Montana?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Chicago Midway Airport to Montana up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Montana?

    The cheapest time of day to fly to Montana is generally in the morning, when round-trip flights cost $439 on average. Morning departures are around 14% cheaper than evening flights, on average. The most expensive time of day to fly to Montana is generally in the evening, which is peak travel time and where the average cost of a ticket is $510.

Reviews of the top airline flying from Midway to Montana

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Montana. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Midway to Montana? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4246 reviews
8.1Boarding
7.5Entertainment
8.0Comfort
8.6Crew
7.0Food
Airline reviews

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

6.0 GoodDavid, Aug 2025MCO - DEN
Read more Southwest reviews

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

Southwest's seats are the least comfortable I have ever sat in.

The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.

Southwest like most American domestic airlines, is a mediocre airline. But it is among the cheapest. Oh well.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

Other than a bit of a delay, everything was good. Again, the boarding process and picking seats is the only thing I don't enjoy.

If we are going to have to pay for luggage, make it easier to do. Put something on the app during check-in so I don't need to do it at the kiosk. I've done it twice recently and I ended up having to pay at the desk because something went wrong at the kiosk in Tampa.

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

The quality of Southwest Airlines continues to degrade each time I fly with them. If it were not for the free luggage, I would probably choose another airline. Their prices are a little bit competitive, but way too high for the quality of the service. Southwest is not unique in this way. Domestic flight in the United States of America has continued to be a lower and lower quality product. Very sad when you compare the quality of domestic airlines to that of many international airlines around the world.

Everything you need to know for your flight from Midway to Montana

Information on your arrival and departure airports

Chicago Midway Airport (MDW)

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