$109 Find Cheap Flights from Chicago Midway Airport to Montana - Compare and Save

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 9/8. 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, 0 bags

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
Bozeman1 stop$294
Kalispell
Kalispell1 stop$329
Missoula
Missoula1 stop$329
Billings
Billings1 stop$271
Great Falls
Great Falls2 stops$424
Helena
Helena2 stops$634
West Yellowstone
West Yellowstone2 stops$525
Bozeman
Bozeman1 stop$294
Kalispell
Kalispell1 stop$329
Missoula
Missoula1 stop$329
Billings
Billings1 stop$271
Great Falls
Great Falls2 stops$424
Helena
Helena2 stops$634
West Yellowstone
West Yellowstone2 stops$525

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

Tue, Sep 1 - Tue, Sep 8
Delta Logo
1:51 pm - 8:12 pm
MDW
-
BIL
7h 21m
1 stop
Delta Logo
6:15 am - 1:11 pm
BIL
-
MDW
5h 56m
1 stop
$271Delta
Sat, Sep 5 - Tue, Sep 8
Delta Logo
9:59 am - 5:48 pm
MDW
-
BIL
8h 49m
2 stops
Delta Logo
6:15 am - 1:11 pm
BIL
-
MDW
5h 56m
1 stop
$276Delta
Fri, Aug 21 - Thu, Aug 27
Southwest Logo
6:15 am - 2:50 pm
MDW
-
BZN
9h 35m
1 stop
Southwest Logo
3:30 pm - 11:45 pm
BZN
-
MDW
7h 15m
1 stop
$294Southwest
Tue, Jul 21 - Wed, Jul 29
Southwest Logo
6:40 pm - 12:50 am
MDW
-
BZN
7h 10m
1 stop
Southwest Logo
6:40 am - 10:30 am
BZN
-
MDW
2h 50mnonstop
$295Southwest
Mon, Aug 24 - Mon, Aug 31
Delta Logo
9:59 am - 2:50 pm
MDW
-
BZN
5h 51m
1 stop
Delta Logo
6:19 am - 1:10 pm
BZN
-
MDW
5h 51m
1 stop
$297Delta
Fri, Aug 21 - Sun, Sep 6
Southwest Logo
6:15 am - 2:50 pm
MDW
-
BZN
9h 35m
1 stop
Southwest Logo
4:15 pm - 4:30 am
BZN
-
MDW
11h 15m
1 stop
$298Southwest
Wed, Aug 26 - Tue, Sep 1
Southwest Logo
2:15 pm - 8:00 pm
MDW
-
BZN
6h 45m
1 stop
Southwest Logo
2:00 pm - 7:50 pm
BZN
-
MDW
4h 50m
1 stop
$300Southwest
Sun, Aug 23 - Sat, Aug 29
Delta Logo
7:25 pm - 11:16 pm
MDW
-
BZN
4h 51m
1 stop
Delta Logo
6:19 am - 1:10 pm
BZN
-
MDW
5h 51m
1 stop
$301Delta
Mon, Aug 24 - Mon, Aug 31
Delta Logo
7:25 pm - 11:16 pm
MDW
-
BZN
4h 51m
1 stop
Delta Logo
6:00 am - 6:01 pm
BZN
-
MDW
11h 01m
2 stops
$302Delta
Sun, Aug 30 - Wed, Sep 9
Delta Logo
7:25 pm - 11:30 pm
MDW
-
BIL
5h 05m
1 stop
Delta Logo
6:15 am - 1:11 pm
BIL
-
MDW
5h 56m
1 stop
$302Delta
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 5 days was to Bozeman, at $345 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 $345.

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

The average price for all round-trip flights from Chicago Midway Airport to Montana depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Montana is generally in the morning, when round-trip flights cost $425 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 $425.

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 $382 on average.

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 Wednesday, with Friday being the most expensive.

Find deals

Good to know

Cheapest flight$109
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

 
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.
7.9
SouthwestOverall score based on 4235 reviews
8.1Boarding
8.0Comfort
7.0Food
8.6Crew
7.5Entertainment
Airline reviews

there were two flight attendants that were up front...that were the best! They get KUDOs for making my trip only fantastic. Tell them Jeff said that!

10.0 ExcellentAnonymous, Jun 2026
OKC - LAS
Read more Southwest reviews

there were two flight attendants that were up front...that were the best! They get KUDOs for making my trip only fantastic. Tell them Jeff said that!

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.

Flight coming out of Buffalo was delayed, so we had to be rescheduled on another flight from Baltimore to Phoenix which means we had a long layover and got home 3.5 hours late. Shuttle to parking stopped at 10pm, so we had to pay for an Uber to the parking lot and got charged an extra day of parking since it was after midnight. Not the best experience. Long day!

Was fine, delayed and feels like southwest is always late

I don't know why flying out of Sarasota requires two plane changes.

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.

The flight was smooth. The Southwest experience has degraded overall, but this one was okay.

No gluten free snacks. Seats felt worn or bare bones even though it was a new 737 MAX 8.

One major problem that was very unprofessional and uncalled for. Plane landed and we had to wait 20 minutes to get off the plane since they were waiting for someone to come to the gate to drive the jetway. Southwest couldn't have someone available and waiting for the plane to land? Is there only one person in Hobby airport who knows to drive the jetway? Was he at lunch? In the bar? Uncomfortable and uncalled for!

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

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

Information on your arrival and departure airports

Chicago Midway Airport (MDW)