$114 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 2/10. 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

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Everything you should know

Cheapest round-trip
$199
Overall average: $491
United Airlines
Thu 3/26Wed 4/1
ORD - BZN • Non-stop
Cheapest non-stop
$229
Typical prices: $223-$401
American Airlines
Sun 1/4Sat 1/10
ORD - BZN • Non-stop
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Flight Deals
Useful Info
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.

Recent round-trip flight deals from Chicago to Big Sky

Thu, Mar 26 - Wed, Apr 1
United Airlines Logo
7:40 pm - 10:11 pm
ORD
-
BZN
3h 31mnonstop
United Airlines Logo
8:10 am - 12:20 pm
BZN
-
ORD
3h 10mnonstop
$199United Airlines
Tue, Mar 31 - Wed, Apr 1
Delta Logo
7:20 am - 2:34 pm
ORD
-
BZN
8h 14m1 stop
Delta Logo
5:20 am - 12:23 pm
BZN
-
ORD
6h 03m1 stop
$217Delta
Tue, Mar 31 - Wed, Apr 1
Delta Logo
3:59 pm - 11:10 pm
ORD
-
BZN
8h 11m2 stops
Delta Logo
3:19 pm - 11:54 pm
BZN
-
ORD
7h 35m1 stop
$222Delta
Tue, Mar 3 - Sat, Mar 7
Alaska Airlines Logo
3:54 pm - 11:56 pm
ORD
-
BZN
9h 02m1 stop
Alaska Airlines Logo
7:00 am - 4:33 pm
BZN
-
ORD
8h 33m1 stop
$228Alaska Airlines
Sun, Jan 4 - Sat, Jan 10
American Airlines Logo
8:25 am - 11:09 am
ORD
-
BZN
3h 44mnonstop
American Airlines Logo
7:00 am - 11:14 am
BZN
-
ORD
3h 14mnonstop
$229American Airlines
Sat, Jan 3 - Fri, Jan 9
American Airlines Logo
10:10 am - 12:44 pm
ORD
-
BZN
3h 34mnonstop
American Airlines Logo
1:42 pm - 5:49 pm
BZN
-
ORD
3h 07mnonstop
$231American Airlines
Thu, Mar 26 - Tue, Mar 31
Delta Logo
7:20 am - 2:34 pm
ORD
-
BZN
8h 14m1 stop
Delta Logo
5:50 am - 11:35 am
BZN
-
ORD
4h 45m1 stop
$233Delta
Sat, Feb 7 - Tue, Feb 10
Alaska Airlines Logo
8:00 am - 2:09 pm
ORD
-
BZN
7h 09m1 stop
Alaska Airlines Logo
7:20 am - 5:10 pm
BZN
-
ORD
8h 50m1 stop
$239Alaska Airlines
Sat, Jan 3 - Fri, Jan 9
Southwest Logo
5:15 am - 9:40 am
MDW
-
BZN
5h 25m1 stop
Southwest Logo
7:40 am - 4:45 pm
BZN
-
MDW
8h 05m1 stop
$249Southwest
Wed, Jan 7 - Sun, Jan 11
Southwest Logo
6:10 am - 3:05 pm
MDW
-
BZN
9h 55m1 stop
Southwest Logo
12:45 pm - 9:00 pm
BZN
-
MDW
7h 15m1 stop
$295Southwest
Useful Info

Good to know

Low seasonNovember
Cheapest flight$114
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly and prices are also 9% 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 25m.

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

    14 direct flights run between Chicago and Big Sky on a daily basis. On average, there are about 98 departures each week.

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

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

  • 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 $105. Southwest offered a round-trip connection from $152 and Delta from $169.

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 74 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 February, March and April. The cheapest month to fly is September.

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 11451 reviews
7.1Food
8.1Boarding
8.5Crew
7.8Comfort
7.0Entertainment
Airline reviews

I liked that I made it onto the flight rather than “missing” the connection. We left PDX early in the morning along with half of Portland arriving at about the same time as we did- 2 hours prior to our flight leaving. The layover was for less than an hour and we were concerned that we would not make the connection, but as it turns out, the flight leaving LAX was even more delayed in departure due to needing some maintenance repair for the a/c of the plane. As for the food- it seems not so very nice that you are not feeding people and offering complementary alcohol on the international flights any more.

8.0 Excellentjanelle, Dec 2025
PDX - LAX
Read more Alaska Airlines reviews

I liked that I made it onto the flight rather than “missing” the connection. We left PDX early in the morning along with half of Portland arriving at about the same time as we did- 2 hours prior to our flight leaving. The layover was for less than an hour and we were concerned that we would not make the connection, but as it turns out, the flight leaving LAX was even more delayed in departure due to needing some maintenance repair for the a/c of the plane. As for the food- it seems not so very nice that you are not feeding people and offering complementary alcohol on the international flights any more.

I was standing in line to use the restroom. A First Class passenger wanted to use the restroom after me, but Jaques made me wait on Flight 3418 from BOI to SJC on December 12, 2025. I felt this was inappropriate and rude.

The flight was fine. The connecting flight was a nightmare. Gate change without text or email notification was super frustrating and I ended up missing my connecting flight. Return flight was delayed and had I not quadruple checked flight time, gate and refreshed the Alaska Airlines app every 5 minutes, I would have taken a flight that would not arrive in time for my connecting flight. Ended up flying Delta home.

Short trip from Honolulu to Kauai. Not a major issue. Only concern was the drop off of the luggage for departure. Only one person handling all of the passengers. She was busting her butt.

There was no food or entertainment so quit asking about that! Everything else was fine.

There was no food or entertainment. I was in the middle seat which was uncomfortable. The flight and crew were fine.

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

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

The boarding and seat assignment system no longer works for me, but I know it is being replaced. Otherwise, I am good with the overall experience.

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.

Original flight was cancelled and when i was rebooked by the airline, they couldn't seat me in the same type of seat as I had originally booked (went from window/aisle to middle/middle and one was a bulkhead seat, and other wasn't in the same class)

Lady Pilot was perfect in every way wheels up to wheels down communication, professionalism, excellent on time departure and on time arrival, excellent communication! Fantastic job with Superb attitude!!

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.

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 Big Sky

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