$98 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 9/6. 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 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

Sat, Sep 6 - Fri, Sep 12
Hawaiian Airlines Logo
7:00 am - 1:14 pmORD-BZN
7h 14m1 stop
Hawaiian Airlines Logo
3:08 pm - 11:59 pmBZN-ORD
7h 51m1 stop
$196Hawaiian Airlines
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Wed, Sep 17 - Wed, Sep 24
Alaska Airlines Logo
2:07 pm - 12:15 amORD-BZN
11h 08m1 stop
Alaska Airlines Logo
11:26 am - 10:04 pmBZN-ORD
9h 38m1 stop
$197Alaska Airlines
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Sat, Sep 6 - Fri, Sep 12
American Airlines Logo
11:54 am - 7:17 pmORD-BZN
8h 23m1 stop
American Airlines Logo
3:04 pm - 7:21 pmBZN-ORD
3h 17mnonstop
$207American Airlines
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Mon, Oct 13 - Fri, Oct 17
United Airlines Logo
4:40 pm - 6:58 pmORD-BZN
3h 18mnonstop
United Airlines Logo
12:50 pm - 4:55 pmBZN-ORD
3h 05mnonstop
$211United Airlines
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Mon, Sep 1 - Tue, Sep 30
American Airlines Logo
10:25 am - 12:39 pmORD-BZN
3h 14mnonstop
American Airlines Logo
3:06 pm - 7:23 pmBZN-ORD
3h 17mnonstop
$213American Airlines
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Mon, Oct 13 - Fri, Oct 17
United Airlines Logo
4:40 pm - 6:58 pmORD-BZN
3h 18mnonstop
United Airlines Logo
2:42 pm - 11:59 pmBZN-ORD
8h 17m1 stop
$221United Airlines
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Wed, Jul 30 - Wed, Aug 6
Delta Logo
7:11 am - 4:34 pmORD-BZN
10h 23m1 stop
Delta Logo
5:30 am - 11:53 amBZN-ORD
5h 23m1 stop
$237Delta
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Mon, Aug 11 - Fri, Aug 22
Delta Logo
7:17 pm - 11:29 pmMDW-BZN
5h 12m1 stop
Delta Logo
11:28 am - 5:37 pmBZN-MDW
5h 09m1 stop
$237Delta
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Tue, Aug 12 - Wed, Aug 13
Southwest Logo
6:00 am - 10:05 amMDW-BZN
5h 05m1 stop
Southwest Logo
8:05 am - 12:00 pmBZN-MDW
2h 55mnonstop
$239Southwest
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Sat, Jul 5 - Thu, Jul 10
Southwest Logo
8:05 am - 10:20 amMDW-BZN
3h 15mnonstop
Southwest Logo
12:20 pm - 4:15 pmBZN-MDW
2h 55mnonstop
$244Southwest
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Good to know

Low seasonNovember
High seasonJuly
Cheapest flight$98
Best time to beat the crowds but there is an average 15% increase in price.
Most popular time to fly and prices are also 8% 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?

    10 direct flights run between Chicago and Big Sky on a daily basis. On average, there are about 70 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 Thursdays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Fridays and the most expensive ones on Thursdays.

  • 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 Hawaiian Airlines for $98. Hawaiian Airlines offered a round-trip connection from $196 and Alaska Airlines from $197.

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 2 weeks 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 April.

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

Food and entertainment aren’t a thing on these regional flights. But it was a smooth flight. Could see gorgeous countryside through the large windows. The earplugs are a nice touch for the prop engines but the hum of the engines did not bother me. Grateful the option exists to easily get from A to B.

10.0 ExcellentAnonymous, Jun 2025SEA - BIL
Read more Alaska Airlines reviews

Food and entertainment aren’t a thing on these regional flights. But it was a smooth flight. Could see gorgeous countryside through the large windows. The earplugs are a nice touch for the prop engines but the hum of the engines did not bother me. Grateful the option exists to easily get from A to B.

Both flights were delayed going to our destination and leaving, and communication about the delays was not great by the airlines, now the crews were phenomenal and great to be around!!

Both flights were delayed due to an incident at SEA. The problem really rests with inadequate customer & plane facilities for Skywest at SEA. You feel like you are in a cattle enclosure. And planes were sitting on taxiways waiting for parking so every plane was late. SEA appears to be over capacity. It is not a fun passenger experience waiting. But crews and flights were all fine. Alaska needs to step up.

Really good except my daughter's tv broke during the flight so she could watch tv

Staff are helpful and patient. I don’t appreciate the almost 5 hours delay and also the delay of our luggage and being switched from one carousel to another to pick them up.

Delayed. It's not our first flight with them either, it's actually our 3rd and all 3 were delayed by hours each time. It was a myriad of delays. On one flight we boarded after being delayed for a little over an hr, only to be told we were going to sit in the plane for another hour before departing. Once landed, we waited another 40ish min to get to our gate. On another flight, flight was delayed just under 3 hrs but atleast we got to wait it out at the airport terminal. Its just a bad experience overall flying with Alaska Airlines.

Flight was delayed for weather, then delayed for mechanical, then just cancelled. Once mechanical problems started I wish you had just started offering rebooking options (at the same airport). I felt my trip was not a priority for you. I called you, I asked for a better option (than changing airports), then I had to literally run around the airport making it happen. Do better.

Staff were great but we were delayed on the tarmac for over an hour.

Great crew, smooth flight and landing. Wish they would offer Dr. Pepper and a choice of flavors of pretzels.

I would've liked to have the seat tablets like before to view movies, with long travels not everyone carries tablets to view movies. And phones are not worth it because screens to small.

Southwest is Southwest. No frills. If you're luck enough to get a happy crew (we did), then it makes for a nicer flight.

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

We sat on the plane on the tarmac for 4 hours.

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

Flight crew and cabin crew were great. I had to rearrange flights because my original flight was 3hrs delayed for weather, the rub is the flight I moved to boarded on time then we sat at the gate for 2 hours because scheduling stole our first officer for another flight, TWICE. Then our actual FO was an hour delayed. To make it worse my original flight went from a 3 hour delay to departing 15min EARLY. Just poor scheduling operations all around.

Bring back peanuts Take our drink orders when were all seated, especially after you switch to assigned seating.

Staff was far less than helpful at all times. Departure and arrival times mean nothing to Southwest. Extremely disappointed, will never fly with them again, and I’ll be sure to share my experience with all.

It is southwest seat was ok. Not the most comfortable seat

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

The flight was scheduled for 2:30 PM. Early in the morning we got a text message saying the flight was delayed and rescheduled for 3:00 PM. We got to the airport with that in mind. Then we got a message during check-in at the flight was rescheduled again for 2:30 PM. We almost missed our flight. In fact, our bags Were told that they would not make it. At the end, everything worked out. But it is very stressful.

Most aspects were good however if they assign boarding zones they ought to enforce them or why bother? My luggage from SAN-JFK-MAD was lost in NY so I without my main bag for two days upon arrival in Spain. They were helpful in tracking it and eventually delivered it to my hotel. The flub was because of a delay upon arrival in NYC. I had booked 2 1/2 hours between flights but we had to hold on the taxiway for an hour after landing while waiting for a clear gate which likely caused the baggage error.

Excellent check-in. Crew was good. Excellent communication from flight deck.

Great overall. There was a bit of turbulence so they could only serve water because too much turbulence for the carts. Was glad they prioritized safety though

Excellent flight, the planes were newer, they did a nice job with boarding, great service overall.

Great service. Flight was delayed while we sat on the runway for a couple of hours. Weather related. Staff made is very bearable. The steward servicing the first class cabin was exceptional. Thank you! 💗

5 hours of delay that could've been much shorter if Delta had taken the 1 hour delay they imposed on the flight before boarding to run any of the plane checks required for flight to find the hydraulic issue that required nearly 3 hours to fix. $24 of meal credit buys a sandwich and a soft drink. Poor communication within the terminal about what gate we'd be re-boarding from and when we'd be re-boarding.

Amazing flight! I have never noticed the uniforms of the attendants before in twenty years of flying except today when one female had the most amazing dress on. It was beautifully designed and showed she was in charge. I never dreamed I would google who designed Delta uniforms . The ultimate compliment is when another woman admires your outfit. . I hope your designer puts it on the market

It would be nice if was given wires ear buds. Overall was a good experience was able to sleep on the plane

My flight was 6 pm 6/6. Every hour they delayed it again - air condition issues then no pilot then the crew had worked too many hours and cancelled the flight at 11 pm. Sent customers to NJ a 45 minutes uber ride to a hotel. Had to be back by 5 am for a 7 am flight and again no pilot etc with another three hours of delays.

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.

Delays took 2hours and thirty minutes making me miss my connecting flight and make me sit in the Chicago airport for 9 hours

Had a short delay once we boarded the aircraft in Chicago, but it was fixed in no time flat then we were on our way. The pilot was able to make up the time lost and we landed 5 minute later then schedualed . Great service

Our seats were all the way in back of the plane,

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.

The meals were mediocre and the alcohol selection was poor. I enjoyed the selection of movies and other entertainment.

I chatted with the captain before the flight, and similarly during the welcome announcement, he warned of a turbulent flight that may impact the in-flight service. However, once at altitude, he announced that the weather changed and he immediately turned off the seatbelt sign. But it appeared the cabin crew had already decided to take off this flight. They remained seated and then just chatted in the galley. The flight was fully catered, but only first class received service.

My flight attendant was attentive! The elderly person next to me was flatulent and the flight attendant could see that I was in distress and brought me some face masks

My boarding pass wouldn't pull up in the app very easily and had to really dig through my email. That caused a delay in TSA..

I had a TERRIBLE experience with the AA crew. I believe it was disability-related. It’s unlikely I will fly AA again.

Everything you need to know for your flight from Chicago to Big Sky

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