$177 Find Cheap Flights from Chicago Midway Airport to Montana - Compare and Save

1 adult
1 adult, Economy, 0 bags

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Cheap Flights from Midway to Montana

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Bozeman
Bozeman1 stop$355
Kalispell
Kalispell1 stop$364
Missoula
Missoula1 stop$379
Billings
Billings2 stops$306
Great Falls
Great Falls2 stops$1,169
Helena
Helena2 stops$619
Bozeman
Bozeman1 stop$355
Kalispell
Kalispell1 stop$364
Missoula
Missoula1 stop$379
Billings
Billings2 stops$306
Great Falls
Great Falls2 stops$1,169
Helena
Helena2 stops$619
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?

The cheapest ticket to Montana from Chicago Midway Airport found in the last 5 days was to Bozeman, at $395 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 5 days was $395.

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 $415 on average. The most expensive time of day to fly to Montana is generally in the morning, which is peak travel time and where the average cost of a ticket is $415.

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

No, with an average price for the route of $434, prices are generally cheapest when you fly direct.

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

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

Good to know

Cheapest flight

$177
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.

Reviews of the top airline flying from Midway to Montana

 
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 4195 reviews
7.5Entertainment
8.6Crew
8.0Comfort
8.1Boarding
7.0Food
Airline reviews

Boarding process of asking for volunteers to check bags goes against the system you had before with 2 bags checked free. This process is more of a guilt trip than a caring attitude toward the customer. In addition bag-size scrutiny has increased which also slows down the process of boarding. My wife said she will not fly on your airline again unless there is no other option.

10.0 ExcellentDenis, Aug 2026
Read more Southwest reviews

Boarding process of asking for volunteers to check bags goes against the system you had before with 2 bags checked free. This process is more of a guilt trip than a caring attitude toward the customer. In addition bag-size scrutiny has increased which also slows down the process of boarding. My wife said she will not fly on your airline again unless there is no other option.

Overall good, just screaming kids in the area the whole flight.

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

My flight to Chicago left and landed early. My return flight left two minutes late and arrived 2 minutes late. My seat selections were ideal! There were no snacks going to Chicago and no snacks on the return trip. There are no charging outlets on board.

More options for your flight from Midway to Montana

Complete your trip to Montana with a hotel stay or car rental