$96 Find Cheap Flights from Chicago to Big Sky

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 Big Sky departing on 11/1. 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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Flight Deals

Cheap Flights from Chicago to Big Sky (CHI-BZN)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Big Sky 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.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Big Sky

Sat, Nov 1 - Sat, Nov 8
American Airlines Logo
10:36 am - 1:08 pmORD-BZN
3h 32mnonstop
American Airlines Logo
1:31 pm - 9:21 pmBZN-ORD
6h 50m1 stop
$201American Airlines
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Sat, Nov 1 - Sat, Nov 8
Alaska Airlines Logo
7:00 am - 1:02 pmORD-BZN
7h 02m1 stop
Alaska Airlines Logo
4:02 pm - 5:01 amBZN-ORD
11h 59m1 stop
$210Alaska Airlines
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Sat, Sep 6 - Sat, Sep 13
Hawaiian Airlines Logo
6:20 am - 2:14 pmORD-BZN
8h 54m1 stop
Hawaiian Airlines Logo
3:08 pm - 12:03 amBZN-ORD
7h 55m1 stop
$215Hawaiian Airlines
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Thu, Oct 30 - Sun, Nov 2
Hawaiian Airlines Logo
7:00 am - 1:02 pmORD-BZN
7h 02m1 stop
Hawaiian Airlines Logo
11:16 am - 9:40 pmBZN-ORD
9h 24m1 stop
$219Hawaiian Airlines
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Wed, Dec 10 - Sun, Dec 14
Delta Logo
7:30 am - 4:38 pmORD-BZN
10h 08m1 stop
Delta Logo
5:45 am - 12:24 pmBZN-ORD
5h 39m1 stop
$237Delta
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Mon, Sep 8 - Sat, Sep 13
United Airlines Logo
5:00 am - 9:52 amORD-BZN
5h 52m1 stop
United Airlines Logo
8:00 am - 12:05 pmBZN-ORD
3h 05mnonstop
$239United Airlines
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Sun, Sep 21 - Fri, Sep 26
Southwest Logo
9:40 am - 11:50 amMDW-BZN
3h 10mnonstop
Southwest Logo
5:00 pm - 12:05 amBZN-MDW
6h 05m1 stop
$239Southwest
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Mon, Aug 25 - Tue, Aug 26
Southwest Logo
8:25 am - 10:35 amMDW-BZN
3h 10mnonstop
Southwest Logo
8:05 am - 12:00 pmBZN-MDW
2h 55mnonstop
$241Southwest
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Sat, Nov 1 - Sat, Nov 8
Delta Logo
5:15 pm - 10:54 pmORD-BZN
6h 39m1 stop
Delta Logo
11:56 am - 9:19 pmBZN-ORD
8h 23m2 stops
$242Delta
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Thu, Oct 30 - Sun, Nov 2
United Airlines Logo
9:15 am - 11:43 amORD-BZN
3h 28mnonstop
United Airlines Logo
4:35 pm - 11:59 pmBZN-ORD
6h 24m1 stop
$256United Airlines
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Good to know

Low seasonNovember
Cheapest flight$96
Best time to beat the crowds but there is an average 19% increase in price.
Most popular time to fly and prices are also 16% lower on average.
Flight from Chicago O'Hare Airport to Bozeman

When to book flights from Chicago to Big Sky

Are your dates flexible? Find out the best times to travel from Chicago to Big Sky based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

FAQs for booking flights from Chicago to Big Sky

  • Which airports will I be using when flying from Chicago to Big Sky?

    When flying out of Chicago you’ll be using one of these airports: Chicago Midway or Chicago O'Hare Intl. Big Sky does not have its own airport so you’ll be flying into nearby Bozeman Gallatin Field airport, which is 37.5 mi away.

  • How long does a flight from Chicago to Big Sky take?

    Direct flights cover the 1,198 miles separating Chicago and Big Sky in about 3h 10m.

  • How many flights are there between Chicago and Big Sky?

    11 direct flights run between Chicago and Big Sky on a daily basis. On average, there are about 77 departures each week.

  • What’s the cheapest day of the week to fly between Chicago and Big Sky?

    Consider leaving on a Saturday and avoid Mondays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Thursdays and the most expensive ones on Tuesdays.

  • How does KAYAK find such low prices on flights from Chicago to Big Sky?

    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 Big Sky.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Big Sky from Chicago 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 Big Sky?

    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 to Big Sky with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Big Sky?

    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 to Big Sky from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • Which airlines provide the cheapest flights from Chicago to Big Sky?

    In the last 72 hours, the cheapest one-way ticket between Chicago and Big Sky found on KAYAK was with American Airlines for $96. American Airlines offered a round-trip connection from $201 and Alaska Airlines from $210.

Top tips for finding cheap flights from Chicago to Big Sky

  • There is no airport in Big Sky. Instead, you’ll be flying into Gallatin Field Airport when flying between Chicago and Big Sky.
  • The cheapest flight from Chicago to Big Sky was found 58 days before departure, on average.
  • Book at least 1 week before departure in order to get a below-average price.
  • High season is considered to be November, December and January. The cheapest month to fly is August.

Reviews of the top 5 airlines serving Chicago to Big Sky

 
Need help choosing which airline to fly with from Chicago to Big Sky? 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 10000 reviews
7.8Comfort
8.1Boarding
7.0Entertainment
8.5Crew
7.1Food
Airline reviews

There was a very drunk man behind me who kept talking loudly to no one in particular. He was slurring his words and at times he didn’t know where we were going or whether or not we landed. He was also loudly using a lot of profanity. The attendants didn’t seem to notice or care and in fact continued to serve him alcohol. He was allowed to purchase 4 little bottles.

6.0 GoodAnonymous, Aug 2025PDX - PSP
Read more Alaska Airlines reviews

There was a very drunk man behind me who kept talking loudly to no one in particular. He was slurring his words and at times he didn’t know where we were going or whether or not we landed. He was also loudly using a lot of profanity. The attendants didn’t seem to notice or care and in fact continued to serve him alcohol. He was allowed to purchase 4 little bottles.

Didn't care for the crowding at the gate area at SEA TAC. Not a fault of the airline.

Flight was switched to a different airline. Caused scheduling issues. Flight delayed an hour, but arrived only 20 minutes late thanks to tail winds.

Loved the staff ease of flying snacks and free movies and WiFi

you could have gotten me there on the day I was supposed to be there, not a day later. Paid for 3 nights at a VRBO and got to spend only 2 nights there.

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.

We did not realize there wasn't any food apart from a small packet of pretzels - I dropped one and nearly cried.

boarding was late worst was going back LAX to SFO delayed not once ? but TWICE😡I was at the airport practically almost 5 hours of previous time , very inconvenient! i would have spend longer time with family , I was wanting to avoid TSA line? but it just got me to spend unwanted time @ d airport

Flight crew and gate staff were very polite and professional. They were very helpful and made my trip smooth and trouble free

Upon arrival I was disappointed that the assist I requested to get to the baggage claim wasn't provided. The entire baggage area was not clearly marked and I wanted to store my baggage overnight, that wasn't available. I had to take it on the shuttle to the hotel!

Southwest's seats are the least comfortable I have ever sat in.

The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.

Southwest like most American domestic airlines, is a mediocre airline. But it is among the cheapest. Oh well.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

Other than a bit of a delay, everything was good. Again, the boarding process and picking seats is the only thing I don't enjoy.

If we are going to have to pay for luggage, make it easier to do. Put something on the app during check-in so I don't need to do it at the kiosk. I've done it twice recently and I ended up having to pay at the desk because something went wrong at the kiosk in Tampa.

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

The quality of Southwest Airlines continues to degrade each time I fly with them. If it were not for the free luggage, I would probably choose another airline. Their prices are a little bit competitive, but way too high for the quality of the service. Southwest is not unique in this way. Domestic flight in the United States of America has continued to be a lower and lower quality product. Very sad when you compare the quality of domestic airlines to that of many international airlines around the world.

Very smooth checking in our luggage with a super pleasant SW agent. I enjoyed a fun entertaining movie.

On this flight I felt the food offering was not as complete as on previous flights. The tomato salad was a bit off and there was nothing additional such a bread or butter. The breakfast was only one option, so you either ate what they had or ate nothing. The crew was efficient, but most seemed frustrated throughout the flight. The flight arrived early and was obstacle-free, so I’m overall quite happy, but the shine in the rest of the experience just wasn’t there.

The seats got pretty uncomfortable pretty fast. The armrests are bigger than on other planes, so I had less room in the actual seat. My butt hurt by the end of the flight. :/ comfort was the primary issue. The crew were fantastic!

I believe that a four-hour trip should have a meal. Delta had none.

Great flight with Delta! Boarding was quick and easy, the amenities were solid, and the plane was in great shape. The flight attendants had a fun, lively energy while staying professional. All in all, a smooth trip — even managed to catch up on some rest. Thanks, Delta!

I was uncomfortably cold on the plane. Other than that it was uneventful and therefore as enjoyable as a plane ride can be.

There was supposed to be a meal served, but there wasn’t and the major toilet was out of order

They made us board and then deboard due to mechanical issue which delayed the departure by almost 2 hours and we barely made our connecting flight. These quality checks should've been done before boarding not after.

Having to up charge for a seat assignment is not good. Delta can do better

I liked the friendliness of the staff. The cleanliness of all 3 planes.

Was charged for my luggage despite having been on one ticket from an international flight. Too tired to argue after 15 hours on flight. Was charged for rechecking it at JFK airport. Not sure why those off Kenya Airways were required to do that.

Excellent flight. Boarding was efficient and departure was on time. Smooth flight with on time arrival. Deplaning was also efficient.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

A bit rush for transit. Food and entertainment are not available

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

My flight was scheduled for about 6:05 departure. There were 11 gate changes from 4-7pm and the flight was 3 hours delayed due to operational issues. The plane taxied around the airport for about half an hour before stopping to be de-iced. It would have been nice if we were alerted of the plan to de-ice prior to the 30 minute drive around the airport. The flight attendant was friendly, which was the only redeeming thing about this flight. As a former flight attendant for United, I was extremely disappointed.

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.

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

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

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