$138 Find Cheap Flights from Chicago to Big Sky - 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 Big Sky departing on 9/15. 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
$301
Typical prices: $244-$323
United Airlines
Tue 10/20Sat 10/24
ORD - BZN • Non-stop
Cheapest non-stop
$316
Typical prices: $244-$323
United Airlines
Fri 10/23Mon 10/26
ORD - BZN • Non-stop
Arrival airport
You can't fly directly to Big Sky. It is served by Bozeman (BZN), located 37.5 miles from Big Sky.
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Flight Deals
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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.

Recent round-trip flight deals from Chicago to Big Sky

Tue, Oct 20 - Sat, Oct 24
United Airlines Logo
4:45 pm - 7:12 pmORD  Chicago O'Hare Intl-BZN Bozeman Gallatin Field
3h 27mnonstop
United Airlines Logo
2:37 pm - 10:46 pmBZN  Bozeman Gallatin Field-ORD Chicago O'Hare Intl
7h 09m1 stop Denver Intl
$301United Airlines
Sat, Dec 12 - Fri, Dec 18
United Airlines Logo
5:00 am - 9:47 amORD  Chicago O'Hare Intl-BZN Bozeman Gallatin Field
5h 47m1 stop Denver Intl
United Airlines Logo
8:00 am - 12:08 pmBZN  Bozeman Gallatin Field-ORD Chicago O'Hare Intl
3h 08mnonstop
$305United Airlines
Mon, Oct 26 - Fri, Oct 30
American Airlines Logo
5:00 am - 12:57 pmORD  Chicago O'Hare Intl-BZN Bozeman Gallatin Field
8h 57m1 stop Dallas/Fort Worth
American Airlines Logo
1:47 pm - 11:59 pmBZN  Bozeman Gallatin Field-ORD Chicago O'Hare Intl
9h 12m1 stop Dallas/Fort Worth
$315American Airlines
Mon, Sep 14 - Thu, Sep 17
American Airlines Logo
1:46 pm - 8:43 pmORD  Chicago O'Hare Intl-BZN Bozeman Gallatin Field
7h 57m1 stop Dallas/Fort Worth
American Airlines Logo
6:30 am - 4:00 pmBZN  Bozeman Gallatin Field-ORD Chicago O'Hare Intl
8h 30m1 stop Dallas/Fort Worth
$315American Airlines
Tue, Sep 22 - Wed, Sep 30
Alaska Airlines Logo
8:00 am - 2:46 pmORD  Chicago O'Hare Intl-BZN Bozeman Gallatin Field
7h 46m1 stop Seattle/Tacoma Intl
Alaska Airlines Logo
9:20 am - 7:21 pmBZN  Bozeman Gallatin Field-ORD Chicago O'Hare Intl
9h 01m1 stop San Diego
$315Alaska Airlines
Fri, Sep 11 - Tue, Sep 15
Alaska Airlines Logo
3:52 pm - 10:59 pmORD  Chicago O'Hare Intl-BZN Bozeman Gallatin Field
8h 07m1 stop Seattle/Tacoma Intl
Alaska Airlines Logo
2:21 pm - 11:59 pmBZN  Bozeman Gallatin Field-ORD Chicago O'Hare Intl
8h 38m1 stop Seattle/Tacoma Intl
$315Alaska Airlines
Tue, Sep 15 - Tue, Sep 22
Southwest Logo
6:00 pm - 10:30 pmMDW  Chicago Midway-BZN Bozeman Gallatin Field
5h 30m1 stop Denver Intl
Southwest Logo
6:55 am - 5:35 pmBZN  Bozeman Gallatin Field-MDW Chicago Midway
9h 40m1 stop Las Vegas Harry Reid Intl
$315Southwest
Sat, Sep 19 - Thu, Sep 24
Southwest Logo
5:05 pm - 9:20 pmMDW  Chicago Midway-BZN Bozeman Gallatin Field
5h 15m1 stop Denver Intl
Southwest Logo
1:35 pm - 8:15 pmBZN  Bozeman Gallatin Field-MDW Chicago Midway
5h 40m1 stop Denver Intl
$315Southwest
Tue, Sep 22 - Wed, Sep 30
Delta Logo
7:13 pm - 11:19 pmMDW  Chicago Midway-BZN Bozeman Gallatin Field
5h 06m1 stop Minneapolis St Paul
Delta Logo
6:17 am - 1:20 pmBZN  Bozeman Gallatin Field-MDW Chicago Midway
6h 03m1 stop Minneapolis St Paul
$315Delta
Tue, Oct 20 - Sat, Oct 24
Delta Logo
6:04 am - 1:21 pmMDW  Chicago Midway-BZN Bozeman Gallatin Field
8h 17m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:00 am - 11:47 amBZN  Bozeman Gallatin Field-MDW Chicago Midway
4h 47m1 stop Minneapolis St Paul
$315Delta
Useful Info

Good to know

Low season

November

Cheapest flight

$138
Best time to beat the crowds with an average 9% drop 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 05m.

  • 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 Friday and avoid Wednesdays 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 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 5 days, the cheapest one-way ticket between Chicago and Big Sky found on KAYAK was with Delta for $108. Delta offered a round-trip connection from $216 and American Airlines from $225.

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 52 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 September, October and November. The cheapest month to fly is April.

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
SouthwestOverall score based on 4218 reviews
8.1Boarding
8.0Comfort
8.6Crew
7.5Entertainment
7.0Food
Airline reviews

Boarding process of asking for volunteers to check bags goes against the system you had before with 2 bags checked free. This process is more of a guilt trip than a caring attitude toward the customer. In addition bag-size scrutiny has increased which also slows down the process of boarding. My wife said she will not fly on your airline again unless there is no other option.

10.0 ExcellentDenis, Aug 2026
Read more Southwest reviews

Boarding process of asking for volunteers to check bags goes against the system you had before with 2 bags checked free. This process is more of a guilt trip than a caring attitude toward the customer. In addition bag-size scrutiny has increased which also slows down the process of boarding. My wife said she will not fly on your airline again unless there is no other option.

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.

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 a good experience, unfortunately my checked baggages were come late and not arrived on time.

Very stressful to locate United Airline boarding area, delayed flight, changing boarding area again to another location with all tiredness 😩. But flying was fine.

It was hot and not as comfortable as the flight to Chicago. Must have been a different plane that needs to be worked on or replaced.

The SFO lounge closes at 12 midnight. My flight took off at 2AM

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.

The power outlets were not working for my row. Also felt like the seats have gotten smaller. I was in the window seat and felt like suffocated, as the two passengers next to me were tall and wide.

Terrible. The flight I booked had a convenient departure time. Quick layover. And an arrival timed that worked for the people who had to pick me up. Thanks to delays and rebooking I got none of those things

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

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

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

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