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Find cheap flights from Chicago to Big Sky from $88

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 7/31. 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
0 bags
Thu 7/11
Thu 7/18

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Good to know

Low season

November

High season

August

Cheapest flight

$88
Best time to beat the crowds but there is an average 4% increase in price.
Most popular time to fly and prices are also 5% 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 15m.

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

    6 direct flights run between Chicago and Big Sky on a daily basis. On average, there are about 47 departures each week.

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

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

  • 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 Sun Country Air for $88. Sun Country Air offered a round-trip connection from $175 and American Airlines from $231.

See more FAQs

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 42 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 January.
See more tips

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 9267 reviews
7.3Food
8.6Crew
7.9Comfort
7.3Entertainment
8.2Boarding
Airline reviews

I like the big picture of the Eskimo on the tail of the plane.

10.0 ExcellentAnonymous, Jun 2024SMF - SAN
Read more about Alaska Airlines reviews

I like the big picture of the Eskimo on the tail of the plane.

The crew members were wonderful. When we encountered a little turbulence, the pilots let us know and provided an estimate of how long it would last. Another nice amenity: every seat has AC power outlets and USB ports. It was a 6-hour flight, which seems a bit much for a single-aisle jet: over 200 passengers with access to only 3 restrooms (assuming you time it right and won't be blocked in by beverage carts); food is mediocre, over-priced, and (if you failed to reserve a meal ahead of time) the flight attendants have to process food/meal sales in the aisle. To access any entertainment, you must use your own device to log on to the plane's wi-fi (or bring your own entertainment).

The crews on Alaska Airlines are really wonderful. They clearly know how to treat passengers with kindness and respect. During my trip, I discovered that my upgraded seat had been changed when reviewing my electronic boarding pass. When I questioned the change at the gate, the two staff members acknowledged that the change was odd, checked on their computer, and confirmed that I still had my upgraded seat (i.e., the electronic boarding pass was incorrect). I was impressed by how they seemed to be "in my corner" from the start, quickly investigated, and provided me with a paper boarding pass with the correct information "just in case." All that said, I was a bit disappointed that Alaska Airlines uses single-aisle jets with only four restrooms (3 at the back of the plane, one at the front (ostensibly reserved for crew and first class travelers). I would understand for short flights, but for a 6-hour flight from Seattle to Honolulu...really? I will stick with Hawaiian Airlines from now on.

Seats are more spacious than other airlines that have you packed like sardines.

Barbara at JFK terminal for Alaska was very helpful in retrieving our boarding passes for our connecting and quite pleasant!! Thanks

The TSA line took over an hour and half to get through due to being understaffed and only having one scanner open. I got to my gate with five minutes to spare only to find out my flight left 8 minutes early. I needed help rebooking and had to pay to get a new ticket and was grounded for 24 hours. Not the greatest experience to start things off and had to completely rework my trip to accommodate the situation.

Being seated next to the engine was awful! I was nauseous the entire trip from pre-take-off, flying to landing. The engine vibration was very strong!

Everything was great but there were no entertainment options available.

The crew was the best I’ve had the experience of flying with. A misbehaving child was making things difficult for me with bopping my tray table, taking my snack, and continually tapping or bumping me. The crew quietly and respectfully moved me to another seat, and thanked me for my patience. They couldn’t have been more kind. Their professionalism really stood out to me and I am more than happy to leave a great review for them!

It was okay. Gate crew could be better organized. Wheelchair service for my mother was late as we deplaned. Flight crew was alright. I’ve seen better and worse.

3 hours late and all they have is was a $12 meal voucher. That’s not even enough to cover fast food.

Among the poorest flights I’ve had with Delta in a while. Entertainment system failed completely on a 7.5 hr flight. Crew seemed distracted and not the normal friendly crew. Flight overbooked it seemed… very crowded.

If I can, I always fly Delta. I’ve found their service to always be reliable and pleasant.

You could have not cancelled the flight (AA, which I will be flying from now on) left for BOS despite the fictitious weather issues (that no one in my Boston family could see). You could have rebooked my direct flight to another direct flight instead of sending me though JFK, the worst US airport after O’Hara You could have rebooked me on a Main Cabin seat (like the one I paid for in my original ticket instead of putting me a the last row on JFK->BOS leg, pocketing the difference in ticket price But I do not really care whether you will ever do that in a future because in a future neither I nor anyone from my company (unless they pay out of pocket) nor an of my clients and partners (if they heed my advice) will ever be caught dead on any of Delta flights

Really bad baggage handling. Had my Rimowa bag badly damaged at the latches.

It was pretty good I was worried with the short Layover that I might not catch my connection but the gate was there

It was good until there was a 3 hour delay because there was not any pilots to fly the plane.

There was plenty of overhead room but half of the passengers were told they had to check their carryon bags. My partner and I checked in as early as possible and our seats were split across the aisle.

Friendly flight attendants. Comfort plus seats were very comfortable and had lots of leg room. 10A and 10 B.

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

Flighty delayed on boarding - then group 1 had to check their carry on bags but groups 3 and beyond could carry bags on - very inconvenient for weekend business trip with no checked baggage. Then delayed on the runway - before take off. No communication from pilot on why or how long. Wifi/Entertainment didn't work for 4+ flight. Upon arrival, attendants announced wrong carousel for baggage claim - everyone was waiting at the wrong place for their checked bags. This was a mess united!

There was no screens on board AND the WiFi didn’t work. My seat was broken and couldn’t recline so I couldn’t even sleep. The flight attendants didn’t offer anything to make it more comfortable. It was such an old cramped plane, when the person in front of me reclined I couldn’t even open my tray table. All the United ads talk about guaranteeing everyone gets a screen!

I’ve had a couple flights this week on United that were delayed by an hour or more

Great! The plane was decently sized and comfortable. The staff was nice and there was great in flight entertainment

Last minute gate change nearly caused us to miss our flight. Change was not announced or displayed in the main board at the old gate. Terrible communication. When we landed we had to wait 20 minutes because there was another plane at the assigned gate. Not the crew’s fault, but adding 20 minutes to a 45 minute flight sucked.

delay several times and wait extra long to board. no entertainment service because there are problem for some rows. always encounter some delays for the last flight of the day.

The flight experience was very good! Especially the United Club!

I was not able to buy food in the flight. They refer to include your Credit card in the APP, and if you are not from USA (i have a credit card form Canada) it is not possible

The flight from Ottawa to Chicago took a lot longer due to DC in Ottawa. We got to Chicago and went to our gate to catch our flight. We only had nine minutes I found that very stressful.

Good boarding. Crew started quick with drinks and food. They came around several times for trash which I really liked. Other than turbulence due to storms in the area, flight was great.

My husband and I pre-ordered our food, but they did not have my husband’s order, and my cheese plate was very average. I asked for a blanket and was told they don’t carry blankets on domestic routs. The flight was on time and smooth!

Good flights. Departure and arrivals were on time. DFW was a little problematic in that the Skytrain without prior notice bypassed the Echo terminal so that delayed my arrival at my connecting flight.

Because I can’t stand very long in one place, I was allowed to reword.

5 hour flight - full flight - not enough room to use my computer - slightly delayed - Admirals club was excellent quality food, drink made up for flight seating. No food offerred on flight, you ahd to prebook.

Excellent- plan was barely populated. I cannot remember a flight where I was able/encouraged to stretch out!

Great flight. Boarding was efficient and quick. On time departure and smooth flight. Flight arrived early at destination. Good experience.

Had technical issue which delayed the flight period. Flight crew knew there was 5 passengers that the connecting flight was within 15 minutes once at the gate. Rather than identify the 5 passengers to assure they got first. The flight attended mentioned it but didn't assist to assure passengers with connecting flights off first. This caused a hardship and our party of 3 missed the connecting flight.

I don't like that I have to pay if I want extra leg room. The seats are so expensive; I sit in normal seats and my legs and knees cramp the entire flight. I never feel comfortable on AA flights.

Flight was delayed at departure due to weather and the need for de-icing. The flight was smooth but there was a delay at arrival due to weather. We were in a hold for 20 minutes or more. The flight arrived more than 30 minutes late. Airlines have no control over the weather and I'm glad that they follow all safety procedures. Had to wait a long time for my checked luggage. Whole process was slow and the bags arrived wet due to the rain. The onboard wifi and entertainment access was spotty and the signal was dropped several times. Otherwise the crew was great and friendly. They tried to get everyone's bags stowed and seated so we could take off.

Regarding the boarding: it needs more efforts to make it more convenient

They were flexible and let my daughter and I sit in the back of the plane.

A flight attendant appeared to not be in a good mood that served us; felt she was being short. Overhead announcements were very loud compared to other airlines and the message was not friendly and was a little confusing. This flight was particularly over all was not satisfying compared to previous Sun Country flights.

Airlines should have to add their fees to their fares

I am upset with the hidden fees for bringing on an overhead carryon onto flight and also having to pay for my seat selection. This should all be part of the original price of the ticket. Very poor customer service

Sun country Wi-Fi was not working. Flight was overbooked by two people. Had to pay extra for carryons day before flight and I don’t like hidden fees like that.

WiFi did not work. Woman flight attendant in the rear of the plane was moody.

Flight delayed over 3 hrs due to unexplained issue. No text message to notify.

Well we did not realize at first it was a ground transfer, but we really enjoyed it and would definitely recommend to friends and family. Our driver was awesome and the ride was wonderful. A bathroom on board would have been nice, but at least we were warned that there wasn't one so we went ahead of time.

We were on a fairly long flight and they offered nothing for a snack (unless you paid) and then quickly gave you a drink and were never to be seen again. I would have loved a refill on my water but that was not an option. The flight attendants were standing on ther phone when we boarded and left and never even greeted us. Any other flight I have been on they would have welcomed us on the plane and again greeted us as we got off. Our landline transfer from MSP to Rochester on the other hand was FANTASTIC! We would highly recommend!

Took forever to get the plane loaded and unloaded. Longest I have ever had. I was in the middle of the plane and it almost took a hour after landing to get off of the plane.

Book cheap flights from Chicago to Big Sky

Recent round-trip flight deals

7/9Tue
1 stopSun Country Air
15h 52mORD-BZN
7/17Wed
1 stopSun Country Air
5h 39mBZN-ORD
$175
8/19Mon
1 stop
7h 09mORD-BZN
8/22Thu
1 stop
7h 14mBZN-ORD
$212
9/25Wed
nonstopAmerican Airlines
3h 19mORD-BZN
10/1Tue
nonstopAmerican Airlines
3h 04mBZN-ORD
$231
8/19Mon
1 stopAmerican Airlines
7h 16mORD-BZN
8/22Thu
nonstopAmerican Airlines
3h 00mBZN-ORD
$241
10/7Mon
1 stopAlaska Airlines
28h 41mORD-BZN
10/15Tue
1 stopAlaska Airlines
20h 30mBZN-ORD
$262
8/19Mon
1 stopAlaska Airlines
7h 09mORD-BZN
8/22Thu
2 stopsAlaska Airlines
12h 25mBZN-ORD
$282
8/16Fri
nonstopUnited Airlines
3h 20mORD-BZN
8/19Mon
1 stopUnited Airlines
16h 12mBZN-ORD
$311
8/13Tue
1 stopDelta
5h 17mORD-BZN
8/20Tue
1 stopDelta
7h 10mBZN-ORD
$320
8/19Mon
1 stopDelta
6h 07mORD-BZN
8/22Thu
2 stopsDelta
10h 31mBZN-ORD
$325
7/25Thu
nonstopUnited Airlines
3h 20mORD-BZN
7/29Mon
nonstopUnited Airlines
3h 03mBZN-ORD
$371

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Recent one-way flight deals

7/31Wed
1 stopSun Country Air
15h 48mORD-BZN
$88
8/2Fri
1 stopSun Country Air
14h 02mORD-BZN
$98
8/12Mon
1 stopDelta
5h 45mORD-BZN
$125
8/12Mon
2 stopsDelta
11h 15mORD-BZN
$130
8/7Wed
1 stopAlaska Airlines
10h 09mORD-BZN
$157
7/23Tue
nonstopAmerican Airlines
3h 31mORD-BZN
$176
7/12Fri
nonstopUnited Airlines
3h 20mORD-BZN
$186
7/15Mon
1 stopAlaska Airlines
10h 09mORD-BZN
$190
7/6Sat
nonstopAmerican Airlines
3h 25mORD-BZN
$196
7/23Tue
1 stopUnited Airlines
5h 38mORD-BZN
$225

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Last minute flights from Chicago to Big Sky

Last minute flight, train and bus deals

6/14Fri
multi-stop
14h 04mORD-BZN
6/27Thu
multi-stop
7h 16mBZN-ORD
$419
6/14Fri
multi-stop
14h 04mORD-BZN
6/26Wed
multi-stop
17h 55mBZN-ORD
$434
6/15Sat
multi-stopAlaska Airlines
10h 09mORD-BZN
6/27Thu
multi-stopAlaska Airlines
9h 45mBZN-ORD
$500
6/14Fri
multi-stopAlaska Airlines
7h 09mORD-BZN
6/17Mon
multi-stopAlaska Airlines
8h 00mBZN-ORD
$540
6/15Sat
multi-stopDelta
11h 23mORD-BZN
6/25Tue
multi-stopDelta
7h 27mBZN-ORD
$545
6/16Sun
multi-stopDelta
8h 03mORD-BZN
6/23Sun
multi-stopDelta
5h 09mBZN-ORD
$580
6/14Fri
nonstopAmerican Airlines
3h 26mORD-BZN
6/27Thu
nonstopAmerican Airlines
3h 04mBZN-ORD
$611
6/14Fri
multi-stopAmerican Airlines
7h 03mORD-BZN
6/26Wed
nonstopAmerican Airlines
3h 04mBZN-ORD
$621
6/16Sun
multi-stopUnited Airlines
6h 15mORD-BZN
6/22Sat
nonstopUnited Airlines
3h 03mBZN-ORD
$656
6/13Thu
nonstopUnited Airlines
3h 21mORD-BZN
6/19Wed
nonstopUnited Airlines
3h 03mBZN-ORD
$779

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Flights to Big Sky

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