$134 Find Cheap Flights from Chicago 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 Chicago to Montana departing on 9/23. 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.
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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
Bozemannonstop$305
Kalispell
Kalispell1 stop$329
Missoula
Missoulanonstop$309
Billings
Billingsnonstop$261
Great Falls
Great Falls1 stop$318
Bozeman
Bozemannonstop$305
Kalispell
Kalispell1 stop$329
Missoula
Missoulanonstop$309
Billings
Billingsnonstop$261
Great Falls
Great Falls1 stop$318

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

Sat, Aug 29 - Sat, Sep 5
United Airlines Logo
8:40 am - 11:02 am
ORD
-
BIL
3h 22mnonstop
United Airlines Logo
2:29 pm - 10:46 pm
BIL
-
ORD
7h 17m
1 stop
$261United Airlines
Sat, Sep 5 - Wed, Sep 9
United Airlines Logo
8:40 am - 11:02 am
ORD
-
BIL
3h 22mnonstop
United Airlines Logo
2:29 pm - 9:30 pm
BIL
-
ORD
6h 01m
1 stop
$271United Airlines
Wed, Dec 2 - Wed, Dec 9
Delta Logo
1:00 pm - 7:48 pm
MDW
-
BIL
7h 48m
2 stops
Delta Logo
6:15 am - 11:51 am
BIL
-
MDW
4h 36m
1 stop
$276Delta
Wed, Dec 2 - Tue, Dec 8
Delta Logo
1:00 pm - 7:48 pm
MDW
-
BIL
7h 48m
2 stops
Delta Logo
5:45 am - 4:50 pm
BIL
-
MDW
10h 05m
2 stops
$281Delta
Sun, Aug 23 - Tue, Aug 25
American Airlines Logo
9:45 am - 12:05 pm
ORD
-
BZN
3h 20mnonstop
American Airlines Logo
4:15 pm - 12:18 am
BZN
-
ORD
7h 03m
1 stop
$305American Airlines
Sun, Aug 23 - Mon, Aug 31
Southwest Logo
10:25 am - 12:35 pm
MDW
-
BZN
3h 10mnonstop
Southwest Logo
5:05 pm - 12:25 am
BZN
-
MDW
6h 20m
1 stop
$305Southwest
Sat, Sep 19 - Sat, Oct 3
American Airlines Logo
10:00 am - 12:56 pm
ORD
-
MSO
3h 56mnonstop
American Airlines Logo
12:45 pm - 5:25 pm
MSO
-
ORD
3h 40mnonstop
$309American Airlines
Sun, Aug 23 - Mon, Aug 31
Southwest Logo
10:25 am - 12:35 pm
MDW
-
BZN
3h 10mnonstop
Southwest Logo
7:20 am - 5:00 pm
BZN
-
MDW
8h 40m
2 stops
$310Southwest
Sat, Sep 12 - Sat, Sep 19
Alaska Airlines Logo
8:00 am - 3:17 pm
ORD
-
MSO
8h 17m
1 stop
Alaska Airlines Logo
4:16 pm - 11:59 pm
MSO
-
ORD
6h 43m
1 stop
$329Alaska Airlines
Sat, Sep 12 - Sat, Sep 19
Alaska Airlines Logo
8:00 am - 3:17 pm
ORD
-
MSO
8h 17m
1 stop
Alaska Airlines Logo
4:16 pm - 11:59 pm
MSO
-
ORD
6h 43m
1 stop
$339Alaska 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 August.

Flight prices are typical for this route right now.

Flights to Montana from Chicago usually cost between $305 and $466 in August.
The lowest price found in the past 5 days was $305 on American Airlines (Aug 23-Aug 25).

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 5 days was to Billings, at $251 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 5 days was $285.

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

The average price for all round-trip flights from Chicago 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 afternoon, when round-trip flights cost $346 on average. Morning departures are around 2% 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 $381.

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.

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 $454 on average.

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 January, when tickets cost $320 (return) on average. On the other hand, the most expensive months are July and February, when the average cost of round-trip tickets is $449 and $419 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 Sunday 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 28% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 25 weeks before departure.

Good to know

Low season

November

Cheapest flight

$134
Best time to beat the crowds with an average 18% drop in price.
Most popular time to fly and prices are also 8% lower on average.
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.

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
SouthwestOverall score based on 4236 reviews
8.0Comfort
7.5Entertainment
7.0Food
8.6Crew
8.1Boarding
Airline reviews

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

8.0 ExcellentAnonymous, Jul 2026
MDW - MHT
Read more Southwest reviews

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.

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.

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.

The seat was comfortable, but I paid for upgraded seats and they did not state that there was no outlets for devices.

Extremely professional crew there are very friendly and first class. Everything worked well on the plane. Food was to be expected. Drinks were very good. Shout out to Charlie in first class who was an excellent flight attendant.

Thanks for all you do to keep us safe and on time!

I like flying Alaska Airlines. I think the staff are happy, the plane is comfortable, the entertainment reasonable, the food acceptable.

No WiFi. Terrible food. Very long walk to the gate and from the gate after landing. Gate changed without notice.

I really hate the seat assignment at the gate. I understand it is so families can sit together but it caused me and others a lot of unnecessary stress and confusion, enough for me to not fly Alaska again. The app is so awful that it did not even update my seat assignment on the boarding pass but sent me a notification of my seat... it showed in Apple Wallet but not in the Alaska app itself. That only made the stress worse. I think most people like myself prefer to know where they are seated at check in 24 hours before so they don't have to anxiously hang out at the gate the entire time. This is not a good use of your agents time either to be dealing with all of us asking where we are sitting. You should automatically assign the multiple seat purchases to be together before they check in and fill us solo travelers in those gaps as we check in.

Great. Went right to the desk and the people were helpful and kind. I was able to get my boarding pass in under 5minutes. They made sure I received the text.

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

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

Would have been nice if my flight was on time and I didn't miss my connection and had to spend the night in Seattle, losing one night at the VRBO I paid for in Sitka. And, my connecting flight was still at the gate when my flight was taxiing to it's gate. But, it took off. Too bad for me. I really can't believe you even want me to review or comment on my experience.

The crew was very inconsiderate and rude. My flight was scheduled to depart at 6:00am. I received a call from the crew at 5:40am, asking if I was going to make the flight because I was the only one that hasn't boarded yet and boarding ends at 5:50am. I let them know that I will be at the gate in a few minutes, before the 5:50am cutoff. When I arrived at the gate at 5:45am the gate was closed. Departing early on last minute notice without having all passengers on board is inconsiderate and unprofessional.

Very easy to use and convenient, you can perform any action within the same portal

Okay considering we had weather delays which the Pilot notified us of immediately!

The boarding was organized and informative but the plane was tight meaning that you were sitting on one another and extremely uncomfortable. It’s disappointing that can’t have common seating comfort on the plane.

Everything could have benn better. Short fly, no food, no entertainment and no wifi.

Stop changing gates. Stop cancelling flights Stop moving my seat.

The staff was frielndly. The plane was terrible, it was too small and should be decommissioned. There were no back seat screens at all. The only beverages we had a choice from was coffee, tea or water. The only bathroom in the back was behind the flight attendant's jump seat and wasn't working. And I literally felt like I was sitting on top of the guy next to me. It was terribly hot in the plane and we had to sit on the tarmac in Chicago for 1/2 hour due to congestion in Mpls. Wouldn't they have know that before they even boarded us so that we could have sat in comfort in the terminal?

This was one of the worst flights I’ve been on in years. I upgraded to comfort and had such an uncomfortable experience. The person next to me was oversized - which I understand - however, they took up their space and mine. I could only use about 50% of my seat space to not be physically touching this person the entire flight and there was no spatial awareness. I also could not use the seat outlet because their body was obstructing it. It was very inconvenient. Their body kept touching me repeatedly during the flight and I felt very uncomfortable. To pay more for an upgraded space and then not even being able to use it was highly disappointing.

It was very cold because the air conditioner was on high power, and my son got sick.

The boarding process was terrible especially with an indirect flight Chicago to Seattle to San Diego was terrible talking about we overbooked a flight idk if I’d take this airline ever again we got off our flight from Chicago to Seattle and we traveled for business and they told us our connecting flight was over booked and their was no seats asking people to take a delayed next flight and they don’t tell anyone coughing to wear masks seats 30A-B were terrible during the flight no one wants to sit next to people coughing all around I don’t want to be sick traveling for work or get sick anytime it’s very upsetting the staff doesn’t take this stuff serious to tell them to wear masks when they see people coughing and sneezing

It was extremely hot in the cabin the entire flight, vent air was worn

Have not had a flight out or returning to Norfolk that has not required maintenance, and a gate delay. Properly staff the crew so maintenance can be performed without last minute emergencies on each flight and there is enough staff to have gates prepared for inbound flights. Staff to ensure the safety and on time service vs. profit.

My original flight was cancelled and that affected my trip and my plans and I got no compensation and customer service was hard to reach as well

The flight was delayed by a hour and I wish they had communicated it sooner. No issues on the plane, it did take a while for food to come.

Know that the movies that you are going to be offered are the oldest be rated movies they could possibly get. They may have one or two new movies that they keep advertising but when you’re flying 15 hours, there is nothing to see past the first new movie.

Great experience. Boarding was fast, staff were very nice and funny, everything at the seat worked well.

Horrible! Several delays and then was cancelled! I spent over 24 hours in the airport and was unable to get a hotel or food voucher.

Boarded early; and arrived home 40 mins early. After a long flight, it’s nice to be back home early. These flights have no amenities; no snacks. So need to bring your own

A long delay. Don't travel late in the day.

Super friendly with lots of drink options an entertainment. Friendly crew.

I had my flight of Cedar Rapids. THen Chicago to Boston. Flight out of Cedar rapids was delayed by 12 hrs. Had to drive to Chicago to catch my flight

Long delays to board due to mechanical issues with plane.

Flight was delayed, boarded, sat at the gate for more than 30 minutes, left the gate then waited on the pad for another 30 to 60 minutes then returned to the gate, deboarded and was cancelled... alternative flight was not booked automatically. Waited in line for 30 minutes but fortunately an alternate flight to a different destination was found ... no thanks to the travel agent used by kayak

The flight from Milwaukee to Dallas was great the staff absolutely amazing. After that EVERYTHING WENT DOWN HILL!!! ABSOLUTELY HORRIBLE!!! WILL NOT FLY THIS AIRLINE AGAIN

I was very unhappy with the lack of communication from the cockpit. It took close to a half an hour before we took off after the doors were closed, and we got no announcements as to progress. It would be nice to get some acknowledgement of the situation and updates as to when we are taking off.

The seat was not even cleaned. It has full of cookie crums probably from last flight's passenger. Its basic expectation that, seats are clean.

Very turbulent flight, no drinks, very little service, unorganized boarding, gate changed multiple times

The flight was delayed significantly. Communication during the flight was abrupt and caused some panic as we were navigating turbulence. It was also too loud and every announcement felt startling. The flight attendants did not offer any assurances and I felt unsettled most of the flight. The seats, floor and tray table was very dirty. The seat next to me was broken and the passenger sitting there was very uncomfortable. He had a spring in his back and his seat made terrible squeaking noises through the flight.

Significant delays on my trip to Chicago and my trip back to NY

You were more on time than United. I'm so over united delays.

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.