$115 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 2/24. 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
$250
Overall average: $461
American Airlines
Sat 2/21Fri 2/27
ORD - BZN • 1 stop
Cheapest non-stop
$250
Typical prices: $335-$482
American Airlines
Thu 6/4Mon 6/8
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

Sat, Feb 21 - Fri, Feb 27
American Airlines Logo
5:00 am - 10:43 am
ORD
-
BZN
6h 43m
1 stop
American Airlines Logo
3:36 pm - 11:36 pm
BZN
-
ORD
7h 00m
1 stop
$250American Airlines
Mon, Feb 23 - Sat, Feb 28
Delta Logo
2:05 pm - 11:15 pm
ORD
-
BZN
10h 10m
2 stops
Delta Logo
6:00 am - 11:45 am
BZN
-
ORD
4h 45m
1 stop
$254Delta
Sat, May 2 - Tue, May 5
Delta Logo
2:12 pm - 10:02 pm
MDW
-
BZN
8h 50m
2 stops
Delta Logo
2:53 pm - 10:28 pm
BZN
-
MDW
6h 35m
1 stop
$254Delta
Thu, Jun 4 - Sun, Jun 7
United Airlines Logo
8:13 pm - 10:40 pm
ORD
-
BZN
3h 27mnonstop
United Airlines Logo
4:20 pm - 8:32 pm
BZN
-
ORD
3h 12mnonstop
$259United Airlines
Fri, Feb 27 - Mon, Mar 2
American Airlines Logo
7:45 pm - 10:14 pm
ORD
-
BZN
3h 29mnonstop
American Airlines Logo
3:36 pm - 11:36 pm
BZN
-
ORD
7h 00m
1 stop
$260American Airlines
Wed, Feb 18 - Wed, Feb 25
Delta Logo
1:49 pm - 11:15 pm
MDW
-
BZN
10h 26m
2 stops
Delta Logo
6:00 am - 5:37 pm
BZN
-
MDW
10h 37m
2 stops
$260Delta
Wed, Jun 10 - Mon, Jun 15
United Airlines Logo
8:13 pm - 10:40 pm
ORD
-
BZN
3h 27mnonstop
United Airlines Logo
2:26 pm - 10:44 pm
BZN
-
ORD
7h 18m
1 stop
$265United Airlines
Fri, Feb 27 - Mon, Mar 2
Alaska Airlines Logo
5:29 pm - 11:56 pm
ORD
-
BZN
7h 27m
1 stop
Alaska Airlines Logo
3:02 pm - 11:56 pm
BZN
-
ORD
7h 54m
1 stop
$269Alaska Airlines
Wed, Mar 4 - Thu, Mar 5
Southwest Logo
6:10 am - 3:05 pm
MDW
-
BZN
9h 55m
1 stop
Southwest Logo
7:10 pm - 5:20 am
BZN
-
MDW
9h 10m
1 stop
$270Southwest
Sat, Feb 28 - Tue, Mar 3
Southwest Logo
3:15 pm - 10:50 pm
MDW
-
BZN
8h 35m
1 stop
Southwest Logo
7:40 am - 4:45 pm
BZN
-
MDW
8h 05m
2 stops
$275Southwest
Useful Info

Good to know

Low seasonNovember
Cheapest flight$115
Best time to beat the crowds with an average 8% drop in price.
Most popular time to fly and prices are also 2% 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?

    16 direct flights run between Chicago and Big Sky on a daily basis. On average, there are about 112 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 11807 reviews
8.1Boarding
8.5Crew
7.0Entertainment
7.8Comfort
7.1Food
Airline reviews

We left about 30 minutes late due to ramp issues. It did not impact me, but I know others on the flight had very tight connections to Maui.

8.0 ExcellentBrian, Jan 2026
MCO - SAN
Read more Alaska Airlines reviews

We left about 30 minutes late due to ramp issues. It did not impact me, but I know others on the flight had very tight connections to Maui.

The stewardess are very nice and pleasant, Someone onboard had a medical attention, and they attended that person non-stop all throughout the flight, and yet, did not forget to serve and help other passengers.

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.

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

Flight was delayed as it always is with Alaska airlines. Particularly to smaller airports. No AC on the plane so it was miserably hot.

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

Everything went smoothly and we even arrived a little bit early.

Great vacation. Can't wait till next year for another one.

Great flight but super high price. Glad it was a business trip and not personal

On time. Friendly staff. Took to long to pre bord all the specialty groups. Cramped small plane

The seats were comfortable, and the boarding process was pretty smooth.

3 hour delay. Had to change plans and was still delayed.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

The crew canceled the complementary snack and drink in anticipation of turbulence that never materialized. I was counting on the drink (water) to take the the doses of medication - prescribed for my heart condition - that were due during the flight. Since no snack or meal was served on this flight, I cannot rate the food quality. Otherwise, this flight was excellent.

Departure was delayed more than 1/2 hour while we waited for luggage (only) transfer from another flight/plane. Once approved for takeoff, the flight was excellent.

Timing, quality of service, promptness and courtesy of the staff

It was last minute due to weather - considering - it was amazing! Good smiles, friendly staff and they were making sure we knew what was going on when and where.

delta last minute gave me a boarding pass for a different flight with no confirmation that they were changing it

The service from the flight attendants were of supreme quality. They greeted and treated everyone with a wide smile. This is totally absent nowadays. Kudos to them!!!!

Excellent flight and got us around tough weather. Only issue was seat TV did not work and crew tried to reboot.

Very large passenger too space from my own seat. Arm board couldn’t be lowered because of his size. It wads very uncomfortable trip, as the flight was full couldn’t move anywhere having back pain because of the position in which I was the entire flight.

was sitting in the jet bridge for 10 minutes in -20 degree weather waiting for my bag

Outdated equipment in disrepair, wifi inoperable. Broken seats, taped air vents, generally poor condition, the 717 showed its age and lack of upkeep.

My flight out of Baton Rouge to Atlanta was delayed by a half hour. This got us into Atlanta airport 30 minutes late. I ran through the airport to get to my connecting flight. As I approached the boarding gate, I saw the boarding door was still open and a passenger was being checked in. But when I got to the gate, the boarding agent told me they had already given away my seat and there were no empty seats on that flight. So I had to take a later flight. That has never happened to me before. Very frustrating.

Connection through Atlanta was difficult. Mechanical issue on plane caused a two hour delay. New gate was a mile away.

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

I understand weather is an issue, but making us chase our plane down at five scheduled gates across three terminals in an airport the size of O'Hare was unfair. They'd have probably been better off to leave gates as TBD until the inbound plane is in final approach instead of running us all over the place. Also, props to the consistently-unprepared ground crew in Richmond for once again leaving my lane parked short of the gate because they couldn't have a crew in place on time with 2 hours notice...

cabin crew was OK, food was OK, the trip from the US to Munich was actually pretty bad comfort wise. Noisy aircraft, lights never dimmed even in Business class (night flight) barely sufficient amenities for the price. I have millions of miles with United but TBH American is gaining ground and Delta has always been marginally better then United although on paper United has more longes and cheaper upgrades.

Essy to get on. The hostess gave very little pop, the plane was late getting in, and we are still waiting for our bags. This sucks. :/

Great flight. On time boarding. Smooth flight and on time arrival at EWR. The flight crew was marvelous and there was a great selection of movies on the entertainment system. Our bags were at the carousel before we got there. Another excellent flight from United.

I liked the snacks and the flight attendants were friendly.

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.

The aircraft had several problems - from excess fuel to non operational ac. Two hours of delay in Chicago could have been avoided with proper planning and aircraft maintenance.

Crew in Columbia was not prepared for landing. It was a bit of a disaster and getting bags took forever.

We were upgraded to First Class and it was a great flight

We experienced gate changes and a long delay. My seat was dirty when I boarded and I had to use wipes to clean it myself. There was an unpleasant and overpowering cleaning product scent on the plane as well that lingered through the flight.

My carry on baggage was damaged. Entire trip, I had to carry the baggage. When complained to the boarding crew, they got mad at me and still asked me to valet check in the cabin baggage. Rude boarding crew!!!

Crew were all friendly and helpful. It was a short flight so just a beverage service with a cookie. After we were boarded the plane took about 45 minutes to leave the gate but it was New Year’s Eve so not shocking there was some delay. Overall good experience and very grateful.

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

The boarding by groups is pointless. The first two groups worked fine, but almost Noone boarded in goups three thru five leaving the vast majority boarding when group six was called. It defeated the purpose of spreading out the crowd.

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.

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

Complete your trip to Big Sky with a hotel stay or car rental