$68 Find Cheap Flights from Chicago 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 Chicago to Montana departing on 1/28. 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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Cheap Flights from Chicago to Montana

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Bozeman
Bozeman1 stop$182
Kalispell
Kalispell2 stops$205
Missoula
Missoula1 stop$249
Billings
Billings2 stops$223
Great Falls
Great Falls1 stop$227
Bozeman
Bozeman1 stop$182
Kalispell
Kalispell2 stops$205
Missoula
Missoula1 stop$249
Billings
Billings2 stops$223
Great Falls
Great Falls1 stop$227

Book Cheap Chicago 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 Chicago 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 Chicago to Montana

Sun, Jan 25 - Tue, Jan 27
Southwest Logo
1:45 pm - 10:40 pm
MDW
-
BZN
9h 55m1 stop
Southwest Logo
3:50 pm - 9:50 pm
BZN
-
MDW
5h 00m1 stop
$182Southwest
Wed, Feb 11 - Tue, Feb 17
Delta Logo
7:30 am - 2:20 pm
ORD
-
BZN
7h 50m1 stop
Delta Logo
3:05 pm - 11:52 pm
BZN
-
ORD
7h 47m1 stop
$189Delta
Sun, Feb 22 - Fri, Feb 27
American Airlines Logo
5:50 pm - 8:21 pm
ORD
-
BZN
3h 31mnonstop
American Airlines Logo
1:36 pm - 5:51 pm
BZN
-
ORD
3h 15mnonstop
$199American Airlines
Sun, Jan 25 - Fri, Jan 30
Multiple Airlines Logo
6:41 am - 8:16 pm
ORD
-
FCA
14h 35m2 stops
Multiple Airlines Logo
11:16 am - 4:51 pm
FCA
-
ORD
28h 35m1 stop
$205Multiple Airlines
Wed, Jan 14 - Tue, Jan 20
Alaska Airlines Logo
8:00 am - 11:56 pm
ORD
-
BZN
16h 56m1 stop
Alaska Airlines Logo
7:20 am - 11:50 pm
BZN
-
ORD
15h 30m1 stop
$208Alaska Airlines
Mon, Jan 12 - Wed, Jan 21
United Airlines Logo
9:11 am - 11:44 am
ORD
-
BZN
3h 33mnonstop
United Airlines Logo
6:15 am - 1:24 pm
BZN
-
ORD
6h 09m1 stop
$209United Airlines
Sat, Feb 7 - Tue, Feb 10
American Airlines Logo
7:37 pm - 10:02 pm
ORD
-
BZN
3h 25mnonstop
American Airlines Logo
1:42 pm - 5:49 pm
BZN
-
ORD
3h 07mnonstop
$211American Airlines
Sat, Jan 17 - Wed, Jan 28
Multiple Airlines Logo
6:02 pm - 9:49 am
ORD
-
BIL
40h 47m2 stops
Multiple Airlines Logo
11:20 am - 5:56 pm
BIL
-
ORD
29h 36m1 stop
$223Multiple Airlines
Wed, Jan 7 - Tue, Jan 13
Alaska Airlines Logo
8:00 am - 3:31 pm
ORD
-
MSO
8h 31m1 stop
Alaska Airlines Logo
6:23 am - 2:38 pm
MSO
-
ORD
7h 15m1 stop
$249Alaska Airlines
Mon, May 25 - Sat, May 30
United Airlines Logo
8:50 am - 11:41 am
ORD
-
FCA
3h 51mnonstop
United Airlines Logo
5:00 pm - 11:57 pm
FCA
-
ORD
5h 57m1 stop
$275United Airlines
Booking Insights

KAYAK's insights & trends for Chicago to Montana flights

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

How much is a round-trip flight from Chicago to Montana?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago to Montana departing in January.

What is the cheapest Chicago 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 found in the last 72 hours was to Bozeman, at $223 round-trip. The most popular route is from Chicago O'Hare Intl Airport (ORD) to Bozeman (BZN), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $223.

Can I save money by flying with a layover from Chicago 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.

No, with an average price for the route of $390, prices are generally cheapest when you fly direct.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago 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 to Montana is September, when tickets cost $295 (return) on average. On the other hand, the most expensive months are December and March, when the average cost of round-trip tickets is $474 and $466 respectively.

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

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

If you are looking for a flight deal from Chicago to Montana, look for departures on Tuesdays and avoid leaving on a Thursday, as it's usually the priciest day. When flying back from Montana, Thursday is the cheapest day to fly and Monday is the most expensive.

How far in advance should I book a flight from Chicago to Montana?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago to Montana, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago to Montana, you should book around 3 weeks before departure, which saves you about 34% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 11 weeks before departure.

Good to know

Low seasonNovember
Cheapest flight$68
Best time to beat the crowds with an average 6% drop in price.
Flight from Chicago O'Hare Airport to Bozeman

FAQs - booking Montana flights

  • What are some common layovers on the route from Chicago to Montana?

    When flying from Chicago, either from O'Hare International Airport (ORD) or Midway International Airport (MDW) to Montana, you may encounter layovers, especially when heading to smaller Montana cities. Common layover locations include Denver International Airport (DEN) and Minneapolis-Saint Paul International Airport (MSP). These layovers depend on the airline you choose and your specific destination within Montana.

  • Which airlines offer Wi-Fi onboard during flights from Chicago to Montana, and is it free or does it come with a fee?

    On flights from Chicago to Montana, airlines such as United Airlines and Southwest Airlines typically offer onboard Wi-Fi. United Airlines usually provides Wi-Fi at a fee, with different pricing based on the flight duration and type of access. Southwest Airlines also offers Wi-Fi, often charging a flat fee for the service regardless of the flight length.

  • How can I make my flight from Chicago to Montana more sustainable?

    To enhance the sustainability of your flight from Chicago to Montana, consider flying with airlines that have demonstrated a commitment to environmental stewardship. United Airlines, for instance, which operates out of Chicago, has been investing in fuel-efficient aircraft and supporting sustainable aviation fuel initiatives. They also offer a carbon offset program for passengers.

  • If I want to visit Glacier National Park, which airport should I fly to?

    For visiting Glacier National Park in Montana, the most convenient airport is Glacier Park International Airport (FCA) in Kalispell. Located close to the park, Glacier Park International Airport offers easy access and is a short drive from one of Montana's most renowned natural attractions.

  • How does KAYAK find such low prices on flights from Chicago 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 to Montana.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago 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 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 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 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 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 afternoon, when round-trip flights cost $289 on average. Morning departures are around 5% 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 $404.

Top tips for finding cheap flights to Montana

  • Chicago O'Hare International Airport (ORD), a hub for United and American Airlines, offers a wide range of direct and connecting flights to Montana. It's ideal for more destination choices within the state. Chicago Midway International Airport (MDW), mainly served by Southwest Airlines, may have fewer Montana flights but is a good option if you prefer Southwest or if it's more conveniently located for you.
  • Montana's key airports include Bozeman Yellowstone International Airport (BZN) for access to central and southern Montana, including Yellowstone National Park, and Glacier Park International Airport (FCA) near Kalispell for the northern regions, including Glacier National Park. Billings Logan International Airport (BIL) in Billings is another option, especially for eastern Montana.
  • Airlines such as United Airlines, American Airlines, and Delta Air Lines operate flights from Chicago to these Montana destinations. United Airlines often provides direct flights to Bozeman, while other airlines may offer routes with stopovers, typically in their hub cities.
  • When flying from Chicago to Montana with your family, both Chicago O'Hare International Airport and Chicago Midway International Airport offer amenities to make your trip more comfortable. O'Hare International Airport is equipped with children's play areas, nursing rooms for mothers, and family restrooms, providing convenience and comfort while you wait for your flight. Chicago Midway International Airport also caters to families with similar facilities, including family restrooms and a straightforward layout for easy navigation.
  • For a more comfortable and relaxed flight, consider upgrading your seat. Airlines like Delta and United offer options for more spacious seating and added benefits such as priority boarding and better in-flight service. These upgrades, which can be especially appealing on longer flights, can be obtained at the time of booking or through upgrade offers.

Reviews of the top 5 airlines serving from Chicago 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 Chicago 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
Alaska AirlinesOverall score based on 11408 reviews
7.1Food
8.5Crew
7.8Comfort
7.0Entertainment
8.1Boarding
Airline reviews

The flight was delayed so we didn’t get into San Diego until almost 1 AM. Otherwise, it was lovely.

8.0 ExcellentAnonymous, Dec 2025
ORD - SAN
Read more Alaska Airlines reviews

The flight was delayed so we didn’t get into San Diego until almost 1 AM. Otherwise, it was lovely.

The plane was old so the seats were very worn out. The seats were hard, uncomfortable, and caused me actual pain. The lights were too bright. The flight itself was fine.

Flight was delayed but still made it to Phoenix on time. Boarding went quickly, the flight was smooth.

1. Denial of Basic Needs (SEA): Upon arrival in Seattle, the wheelchair attendant refused my urgent request to use the restroom, insisting on scanning documents first. She eventually took me to a restroom but then abandoned me and my autistic son at an unstaffed, deserted gate for over four hours. When I called the accommodation line for help, I was told to "get someone's attention," which was impossible. My son, traumatized by the prospect of me yelling for help, was forced to wander the terminal to find assistance. 2. Revocation of Accommodations & Threats: At the gate, an agent stated I had no accommodations on file, despite my previous leg having them. When I showed the app (where my bulkhead seat was erased and replaced with Row 14), he denied the evidence. When I attempted to advocate for my immobilized leg, he threatened to "yank me from the flight" if I said one more word. He coerced me into agreeing that I was "asking for accommodations for the first time" before he would allow assistance, effectively forcing me to falsify the situation under duress. I complied only out of fear of being stranded in a strange city. 3. On-Board Negligence and Injury: Because my bulkhead seat was revoked, I was forced into Row 14. With my leg immobilized and unable to bend, it extended into the aisle. During boarding and the flight: 16 different passengers tripped over my injured leg. 6 rolled luggage bags were pulled over my injured leg. The Flight Attendant (FA) was one of the people who tripped and drove luggage over me. I reported the issue to the FA after 10 trips and 3 luggage impacts. He ignored me. He only addressed me later to ask me to move my immobilized leg for beverage service. I informed him again: "16 people have tripped, 6 luggage runovers, I cannot bend it." He provided no medical aid and no incident report. 4. Resolution and Trauma: Eventually, a different employee noticed my distress and my original paper boarding pass showing the correct bulkhead assignment. He asked me to move up. I broke down in tears, terrified that moving would cause the gate agent to remove me from the plane as threatened. We were eventually moved to the bulkhead, but the damage was done. My autistic son was traumatized by watching his mother be trampled and threatened. 5. Post-Flight: I called to report these injuries, but was disconnected after a 45-minute hold. I require a formal record of this injury and these violations.

They were so kind to us! The entire staff were so good to us when we had our service dog join our trip and we couldn't be more grateful!

Larger seats with a bit more room would be good! Thanks for all your hard work. I think we are all feeling a bit down these days economically and your positive attitudes, both from SJC to Seattle and from Seattle to Bozeman makes more of a difference than you can see! Thank you and Merry Christmas! I hope all your financial needs are met and that very good things come your way.

I purchased a 1st class ticket and unfortunately the main flight attendant was not the best and seemed more interested in her phone than the passengers at times. Then the plane didn’t get restocked and the only snacks for this flight were pretzels. However I would like to say that the rest of the flight crew and ground crew at the airport we’re great, especially the people that wheeled me around the airport some and then the one getting me to the plane and the automated wheelchair that wheeled me through the airport.

My flight got canceled never left san diego and miss out my fam event

Flight was delayed as it always is with Alaska airlines. Particularly to smaller airports. No AC on the plane so it was miserably hot.

I liked that it didn't take 10 hours to drive here. Super short trip!

The lead steward kept singing about "San Francisco" and hotel California---more annoying than humorous....needs work. Flight was smooth and on time.

Still a fan of open seating. Flight was on schedule and arrived on time. The 737 MAX is very comfortable.

Airline travel is always too cramped to really be pleasant, but the cabin crew on this flight did a pretty good job of making up for it by putting on some music during boarding and sprinkling a few funny remarks into the safety briefing and announcements, and just generally being friendly and helpful. It definitely reminded me of why I prefer the in-flight experience on Southwest!

No delays and arrived to destination 30 min early. Staff was super friendly.

San Diego airport is brand new, spacious, airy and very smooth checkin at SW baggage drop.

It was rough. The staff was unprofessional, the choice of on board drinks terrible, it was cramped in space at every airport, they always ran out of overhead bin space so they pressured people to check bags for free or we couldn’t leave on the plane— so I did check my bag to help, and they nearly lost my bag. My bag did not arrive on the luggage belt, another man on my flight and I had to waste our time going to the baggage office to search for our bags. I would only fly southwest again if it was my last choice. Also, my flights were consistently delayed over and over again— at one point they straight up told us we were waiting for the pilot to arrive.

Crew could have been friendlier, maybe I'm spoiled by SW crews. In flight wifi was good. Would be nice to have more food offerings on a 4 plus hour flight

Had to get off plane from prior flight even though I had to reboard same plane to continue to my final destination.

Everything a cheap airline should be at normal airline rates.

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

The food is terrible. The staff is wonderful. Comfort is good.

Left on time, a bit delayed due to headwinds most of the trip.

I fly Delta all the time, have Platinum Medallion status. But this route seems to have major problems with delays and seems to never leave on time! Have only taken it twice in the last two weeks, and each time it had delays of more than 1 hour... very disappointed!!!!

Good seats in Main cabin, excellent service and excellent landing

My flight was cancelled with no explanation after I had already cleared security. I was given 4 options to rebook, only one being non-stop like I had paid for. I grabbed it. It was 4 plus hours later and then took off even later. Biggest complaint is that I booked early and had an aisle seat. They gave me a "window" seat in front of the exit row, so the seat did not decline. I weigh all of 103 #s and it was tight for me! For what I paid, I feel I was kind of ripped off. I think they should have given me the empty comfort seat for the inconvenience. There was no apology nor any explanation as to why the flight was cancelled. My guess is it benefitted Delta in some way.

Very smooth, on-time, and pleasantly uneventful flight. The team at the gate and on board were professional and genuinely courteous. The pilot kept us well updated throughout, and both takeoff and landing were steady and enjoyable without any drama. Just a good, solid flight. Thank you! 💗

Staff was exceptional! Everyone was kind, professional and friendly making the trip very pleasant. Thank you!

No lunch on a x-country flight scheduled for 10:50 am departure, arrived 5+ hrs later. That requires a black box label before you pay for the tickets. Worst, when I checked in online, it's specifically said that lunch was served on his flight for economy Plus passengers.

We had a lot of really rough weather but that was not Delta's fault. Pilot was amazing.

First, Delta needs more flights to/from Miami. Second, a 1000pm leaving at 1230pm is unacceptable from their biggest airport world hub. Another aircraft could have been used such as the aircraft scheduled to be used in the morning for that exact same route. Yes, I did get me there but the lack of sleep the next day didn't help me enjoy my entire trip since I was busy with activities during the weekend. This can be and is expected from Spirit (going bankrupt) and Frontier (despite they're nickel and dimers). But from Delta's World Hub? That's totally unacceptable!

After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.

Very thoughtful flight attendant offered me water immediately since I had run to make my connection.

Always wish for more healthy, gluten free options. We have to bring our own.

Having a long layover, I was very appreciative of the ability to stand by for an earlier flight. Other airlines like Delta have refused this to me in the past, just to be mean (because my ticket class wasn't high enough). United went out of their way to help me get to my destination early, which I really appreciated given that it was the third leg of a 24+ hour journey for me.

Other than a way way too cold cabinets for the entire flight, all was great

One bag is incorrect and not acceptable for an international flight. The food was not just good. I won't fly with them again.

Excellent flight. Smooth, efficient boarding. Quick flight. Arrived early at STL.

I will never book a flight through Cheap fare. They booked me from Portland Main . And would not give me a refund, so I bought 2 tickets one for 299. From Portland Main to ORD. Then I had to buy a ticket from Oregon PDX to ORD that was another 440. So Just so you know they even told me it was there fault but no refund. Bad bussniess. I did inform United but they said they couldn't help me due to the fact I booked through Cheap Tickets. Never again. And I'm spreding the word. I let everyone know at my 50th class reunion

Crew and customer service were excellent. This flight also had plenty of leg room and seat mounted screens for entertainment. A very pleasant flight all around!

It would have been better if the crew has supported my husband's reasons for needing to keep the space clear around his feet, rather than insisting that he put his knapsack in that space.

We loved the steward on the plane. He made the night enjoyable

The plane was late, when we did board the plane was as cold as a freezer. I was freezing the entire flight, no blankets. Lost miserable flight I’ve ever had.

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

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

Cabin class types available on flights to Montana

Cabin classes available on flights to Montana. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.