$107 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 8/11. 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$250
Kalispell
Kalispell1 stop$329
Missoula
Missoula1 stop$329
Billings
Billings1 stop$271
Great Falls
Great Falls2 stops$404
Helena
Helena2 stops$414
West Yellowstone
West Yellowstone2 stops$456
Bozeman
Bozeman1 stop$250
Kalispell
Kalispell1 stop$329
Missoula
Missoula1 stop$329
Billings
Billings1 stop$271
Great Falls
Great Falls2 stops$404
Helena
Helena2 stops$414
West Yellowstone
West Yellowstone2 stops$456

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

Thu, Aug 20 - Tue, Aug 25
Southwest Logo
6:15 am - 2:50 pm
MDW
-
BZN
9h 35m
1 stop
Southwest Logo
12:55 pm - 4:50 pm
BZN
-
MDW
2h 55mnonstop
$250Southwest
Mon, Aug 24 - Fri, Aug 28
Southwest Logo
10:50 am - 12:55 pm
MDW
-
BZN
3h 05mnonstop
Southwest Logo
2:30 pm - 11:45 pm
BZN
-
MDW
8h 15m
1 stop
$251Southwest
Wed, Jun 3 - Wed, Jun 10
Southwest Logo
6:05 pm - 12:15 am
MDW
-
BZN
7h 10m
1 stop
Southwest Logo
6:40 am - 10:30 am
BZN
-
MDW
2h 50mnonstop
$260Southwest
Wed, Jun 10 - Mon, Jun 15
Delta Logo
7:16 pm - 11:58 pm
MDW
-
BZN
5h 42m
1 stop
Delta Logo
6:00 am - 1:09 pm
BZN
-
MDW
6h 09m
1 stop
$261Delta
Wed, Sep 9 - Sat, Sep 12
Southwest Logo
2:15 pm - 8:00 pm
MDW
-
BZN
6h 45m
1 stop
Southwest Logo
7:10 am - 11:05 am
BZN
-
MDW
2h 55mnonstop
$263Southwest
Mon, Aug 24 - Fri, Aug 28
Southwest Logo
10:50 am - 12:55 pm
MDW
-
BZN
3h 05mnonstop
Southwest Logo
12:20 pm - 4:15 pm
BZN
-
MDW
2h 55mnonstop
$264Southwest
Sat, Jun 6 - Tue, Jun 9
Southwest Logo
12:50 pm - 9:55 pm
MDW
-
BZN
10h 05m
2 stops
Southwest Logo
7:05 pm - 5:25 am
BZN
-
MDW
9h 20m
1 stop
$265Southwest
Wed, Jun 10 - Mon, Jun 15
Delta Logo
7:16 pm - 11:58 pm
MDW
-
BZN
5h 42m
1 stop
Delta Logo
6:00 am - 4:16 pm
BZN
-
MDW
9h 16m
2 stops
$266Delta
Wed, May 27 - Wed, Jun 3
Delta Logo
7:13 pm - 11:14 pm
MDW
-
BIL
5h 01m
1 stop
Delta Logo
6:30 am - 1:19 pm
BIL
-
MDW
5h 49m
1 stop
$271Delta
Sat, Jun 6 - Sat, Jun 13
Delta Logo
7:13 pm - 11:44 pm
MDW
-
BZN
5h 31m
1 stop
Delta Logo
6:00 am - 1:09 pm
BZN
-
MDW
6h 09m
1 stop
$273Delta
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 $311 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 $311.

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 $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?

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 $298 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 Sunday being the most expensive.

Good to know

Cheapest flight$107
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.
8.0
SouthwestOverall score based on 4327 reviews
7.5Entertainment
8.0Comfort
8.1Boarding
7.0Food
8.6Crew
Airline reviews

The crew was very kind and made going to Hawaii relaxing and fun to look forward to! Thank you Southwest for a pleasant flight!

10.0 ExcellentJasmine, Apr 2026
LGB - HNL
Read more Southwest reviews

The crew was very kind and made going to Hawaii relaxing and fun to look forward to! Thank you Southwest for a pleasant flight!

This leg was much better, but we did have to have a 3 hour lay o er after coming from a very exhausting hiccup with our flight from BNA to Den

We waited in the airplane for over 45 min for a southwest employee to make the flight. This cause over half the plane to miss their connecting flight in Denver. When we confronted the desk upon arrival, they told us the only flight they had was the next day leaving at 8:50 pm!!! Or they offered to get us to Burbank or LA, but after that we were on our own to get back to Santa Barbara. I paid for a flight from sba to bna bna to sba. My re entry into mom mode has been 💯 rough because of southwest mistake with my flight. And now I’m leaving to Reno tomorrow for a vballl tournament and just discovered that my leg in Vegas has me and my 3 kids on a stand by flight even though I had booked these ticket last year November!! Do better southwest!

Southwest is kind of a slum airline. It’s gotten more expensive over the years for less and less service. I am a Southwest Chase Visa card holder and was forced to choose a seat in the 26th row in the middle seat. However my wife who is a rewards member but doesn’t hold a card or anything else, gets randomly assigned a normally paid seat in row 6! How does that work?

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

The seat was not comfortable. 1D. My back was sore all night and the next day.

Great flight. I didn't get a drink because I was asleep whole on the flight.

Great flight from Seattle to Phoenix and to Chicago-Midway from Phoenix

The new boarding process was easy and straightforward. Very pleasant.

The flight was okay. The pilots did an amazing job and kept us updated on the flight. The flight attendants were okay. They found time to be chatty with each other rather than focus on the guests. One of the attendants was a little less warm when asking about my bag I had on my lap that I was using during latter part of the mid- flight. Mind you, it was not the departure descent. I’m respectful to each and every attendant, it was the tone in her voice reminding me to place my carryon bag on the floor. I hope to have a better experience next time.

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

Information on your arrival and departure airports