Find cheap flights from Illinois to Aspen

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Find cheap flights from Illinois to Aspen

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Round-trip
Economy
Boston (BOS)
Aspen Pitkin County
Fri 5/14
Fri 5/21
Any month
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Good to know

Low season

AugustBest time to beat the crowds with an average 4% drop in price.

High season

NovemberMost popular time to fly with an average 14% increase in price.

Average price round-trip

$507(avg. price over the last 2 weeks)

Good deal round-trip

$264or less

Good deal one-way

$146or less

FAQs for booking flights from Illinois to Aspen

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Top 3 airlines serving Illinois to Aspen Pitkin County

Scores according to KAYAK customer reviews

8.3
Alaska Airlines
Overall score based on 29,359 reviews
8.5
Boarding
8.3
Comfort
8.8
Crew
7.9
Entertainment
7.9
Food
Airline reviews

Cons: "Alaska is great I love theM"

Cons: "It was a little chilly."

Cons: "Better snacks. No cost for checked first luggage"

Cons: "Nothing. I've flown on worse."

Pros: "It’s not American, United, or Delta."
Cons: "The Gogo Internet access was much worse than non-existent, causing me to pay and waste literally hours trying to get a single flight search done on [This idiotic form is broken—the search engine that starts with “Kaya”], and now I have to waste more time and effort to demand a refund from Gogo."

Pros: "Alaska is a great airline."
Cons: "Free food would be awesome."

Pros: "Good communication re: the delay, comfy seats, super friendly gate staff, great free movie selection"
Cons: "Not sitting at the gate on the plane for 2+ hours:("

Pros: "Average"
Cons: "Seat back screens. More space."

Pros: "The crew did very well. The seats could have been a little more comfortable, the lumbar could have been a bit more stiff for lower back support, the arm rest up and down function did not work, and a little more space between rows and seats would have made it more comfortable."
Cons: "The seats could have been a little more comfortable, the lumbar could have been a bit more stiff for lower back support, the arm rest up and down function did not work, and a little more space between rows and seats would have made it more comfortable. The bathroom was too narrow."

Cons: "I really wish you guys told me that in permium seating that the snacks you guys offer had nuts. You guys up sold me by telling me how much I'm going to enjoy the free drinks and snacks on the phone. So I said screw these people seemed nice and not pushy. Very upset that this wasn't giving to me."

Pros: "Timing-Fasrer than scheduled"

Pros: "Everything was great, flights were on time."

Pros: "Great! Decent."

Cons: "Delayed. Flue season folks. If your sick just don’t travel!"

Pros: "Great crew as usually"
Cons: "Hated ORD"

Pros: "Everything went smooth and was great besides the boarding."
Cons: "Boarding seemed to take quite quite awhile, not sure what the deal was but once we were boarded they kicked it into high gear"

Pros: "All good"

Cons: "Delayed"

Pros: "Time of flight is not delayed and arrival time is even ahead of the estimated time."

Cons: "The delay due to mechanical failure and not being compensated"

Pros: "The crew were very friendly, and gave the kids extra cookies!"

Cons: "They did not provide sanck for 4 hr flight and they should keep a few spare head phone"

Pros: "Nice movies Comfortable seats"
Cons: "Noisy air con Seat not reclining Headphone jack not working No storage space"

Cons: "Nothing"

Pros: "I was in premium sitting, very comfortable. I didn’t use airline food or entertainment so rated those lower."
Cons: "Nothing."

Pros: "Alaska airlines much better than United or American in terms of friendly service, wifi and battery charge, and entertainment options"

Pros: "We especially liked the in flight movies which you could rent on a tablet like device similar in size to an iPad. Also, we appreciate airlines that still board the plane by row starting in the rear. That is the most sensible way to board a plane. Also, I had plenty of legroom while seated."
Cons: "Nothing to complain about."

Pros: "This was a completely booked flight during Xmas week, and the flight was delayed an hour. Alaska Air did a great job of accommodating these difficulties. When I checked in online they had a notice asking if we would volunteer to check bags for free because they knew overhead space would be tight. Once the flight was underway they announced they'd been able to reroute to save us some of that time. And the Alaska Air/Horizon connecting flight was also delayed, most likely to accommodate this large flight. The aircraft is wonderful--the plugs for devices at every seat plus free entertainment piped to our devices really helps to pass the time."
Cons: "Person announcing the boarding needs some enunciation lessons. She spoke too quickly and on top of (or below) other announcements and even kept talking when she was doing something beneath the podium, so no chance to read lips."

Pros: "Friendly staff, comfortable seats"

Pros: "Flight crew was pleasant, pilot came on loudspeaker to talk throughout the flight, food food for purchase."
Cons: "No free WiFi, no free snacks."

Cons: "The USB charger on my seat was broken"

Pros: "Excellent experience all around on all flights."

Pros: "Professional flight attendants"
Cons: "N/A"

Pros: "Love the amount of space availabile for my legs!!"

Pros: "First time flying Alaskan. Out of all the US-based airlines I flew with, Alaskan was the cleanest, friendliest, and quickest."

Pros: "Friendliness"

Pros: "The flight attendants made quite a few passes through to make sure everyone had drinks."
Cons: "We were very delayed in taking off because the copilot wasn't there. Many people had connecting flights and the crew did nothing to help them get off the plane first or give any kind of reasrrances that they could make the flight."

Pros: "LOVE the free WiFi for messaging."

Pros: "Free movies!"

Cons: "Customers should be made aware that animals are on the flight before boarding to safe guard against allergies."

Pros: "First off Bonnie at the boarding gate was phenomenal , She has an amazing disposition ( especially at 5:00 in the morning ) she greeted each and every customer by name and with a smile ! Our flight was delayed for 2 hours as we sat at the gate while problems were fixed . The Captain made sure he kept us informed as each problem occurred and was fixed . The rest of the flight crew remained patient and attentive , which of course kept all the customers onboard calm and patient as well . My daughter just moved to Seattle and if this is the norm for this airline I will continue to use them for my future visits ! Elizabeth"

Cons: "Can I have a refund? My flight has been delayed 3 1/2 hours and then they add another delayed flight to leave from my gate ahead of us. Wonderful."

Pros: "Efficient and comfortable"

Pros: "The plane was new but with no bells let alone whistles."
Cons: "No monitors/screens at all on plane."

Cons: "My initial flight was at 0800; I got to the gate before 0800 and was told I couldn't board the flight even though it was still at the gate and was still before the flight time. I had to pay to rebook my flight, spent over $200 in rides to and from airport, had additional parking fees and was several hours late to work. I have many family members who work in flight service so I understand that employees don't like to re-do paperwork; however, being there before the flight time and being denied cost a lot of work time and money. I have always had great experiences with Alaska so this one was quite a disappointment compared to their usual great service. :("

Pros: "Very accommodating staff"

Pros: "The staff was extremely pleasant. Plenty of leg room. Departed on time and arrived ahead of schedule."
Cons: "Nothing."

Pros: "Captain's flight commentary good Crew fine. Plane fine."
Cons: "slow, untimely, disorganized boarding Couldn't get seat assignment online or at airport."

Pros: "New equipment"
Cons: "Sparse food."

Pros: "Free novies"
Cons: "Food service and better social distancing"

Pros: "Yes"
Cons: "Blankets"

Cons: "Baggage delivery was slow and then split between 2 different terminals"

Pros: "Seat room is limited, especially when you are in the middle seat."
Cons: "Seat space"

Pros: "Great price!"
Cons: "More food."

Pros: "The place to charge the phone is easily accessible on the back of the seat in front (as opposed to underneath)."
Cons: "Did not like that I had to check my bag at the gate"

Cons: "Had to clean my seat before seating."

Cons: "The legroom is not sufficient for taller people"

Pros: "On time. Fast boarding. Comfortable seating."

Cons: "Unable to play entertainment on my compatible device."

Cons: "The terrible communication for delays and boarding."

Cons: "Feeling of being cramped"

Pros: "All was good"
Cons: "Nothing to complain about."

Cons: "Delayed multiple times"

Cons: "Extraordinarily rude staff, no information, mess with gates, staff not willing to help. Really rude and awful-worst experience ever!"

Cons: "I will never, ever book with Kayak again"

Pros: "Busy but kind stewardesses"
Cons: "Please offer another snack option besides carboard flavored pretzels."

Cons: "Pushy crowd.."

Cons: "I tried to change my seat to an available window seat several times after online check in opened using the app and consistently received error messages so ended up stuck in a middle seat."

Cons: "Kept the lights on for too long serving dinner. Forgot to serve the middle section beverages during breakfast."

Pros: "Nothing"
Cons: "Cancelled"

Pros: "Nothing"
Cons: "Incredibly uncomfortable. I even paid extra for more room. Meals were a joke"

Cons: "It was not clear that I needed a different 6 letter code to checkin using the AA website. I finally got frustrated and called AA only to find out the code was different. The codes should have been the same or you should have referenced it on the website when I tried to check in"

Pros: "Great service"

Pros: "Amazing entertainment selection, comfortable."

Pros: "Almost empty in economy"
Cons: "I liked everything"

Cons: "For our delay with no information"

Pros: "Food was surprisingly good. Smooth ride could have been just good weather, but it was nice. We got in early!!!"
Cons: "Legroom was ok for me because I'm short. Others may have needed more."

Pros: "The airplale MD 80 are old"

Pros: "Excellent service. Loved the tv screens with the remote. Exclennt flignt"

Cons: "They were late because of bad scheduling and the gate agent was rude"

Cons: "I loved everything"

Pros: "was a pain checking extra baggage. No one seemed to know what to do.. Apart from that AA was good."

Cons: "Indian vegetarian rice uncooked vegetables cold inedible when asked about different food no protein no vegetables Please have better food more options for vegetarian"

Pros: "Everything was great. Easy boarding great comfortable seating and friendly efficient stewardship"

Cons: "Boarding was a little chaotic. Could have been more organized."

Pros: "staff was amazing, entertainment great, dasani sparkling lime water tasty, very clean and reasonably comfortable"
Cons: "the breakfast was made of 90% sugar - this was very disappointing."

Pros: "Everything was on time!"

Pros: "Extra blanket and pillow. Empty seat to sleep in. Fairly clean interior for the most part."

Pros: "All good! Nice staff. Easy travel."

Cons: "Three gate changes and 45 minute delay. Same happened two years ago"

Pros: "Free alcohol and good passenger friends and friendly service."
Cons: "No outlets for phones"

Pros: "All the movies"
Cons: "Legroom"

Cons: "Could not read paper when passenger in front reclined seat. No space between rows."

Pros: "Clean environment of the terminals and the speed of the shuttle."
Cons: "no comment."

Pros: "It took off on time and life was good."

Cons: "No complaints."

Pros: "Everything"

Cons: "Requested for wheelchair assistance but none provided?!!"

Pros: "Timing and transit time was excellent"

Pros: "Getting a meal and drink"

Pros: "The crew was friendly and patient"
Cons: "The seats aren't very comfortable, but it was a short flight"

Pros: "I liked that I knew in advance to download the United app so I could actually watch a movie!! This was the second leg of the trip, and I didn’t know this the first flight and couldn’t use the United entertainment."
Cons: "An hour and half layover is fine, but add an3 hour delay on top of that, Kinda stunk. But hey, me and all my bags made it this trip!"

Pros: "Fast & efficient"
Cons: "Not much"

Cons: "Plane too small"

Cons: "The $25 each way for piece of luggage"

Pros: "Nothing"
Cons: "Delayed, rude stewadess"

Pros: "Everything ran on time"
Cons: "Would love healthier snacks"

Pros: "nothing"
Cons: "crying babies & no food"

Pros: "Same as above"
Cons: "Same as above"

Pros: "It was on time"
Cons: "Nothing was bad, completely average. Nothing impressive either."

Pros: "The personal tv"
Cons: "Having to pay an extra fee just to watch whatever I wanted"

Pros: "Late boarding, other then that ok."

Pros: "That I arrived to Memphis on time!"
Cons: "That the air isn't on until its time to board, instead of being a lil before its time to board."

Pros: "Same as above"

Cons: "Long waiting to take off other than that good"

Cons: "Arrived at 1:30 AM"

Cons: "N/a"

Cons: "Very long delay"

Pros: "Yes"
Cons: "All"

Cons: "The boarding gate changed but the gate information did not. I thought I would save money and time flying United at Ohare. That's a mistake I will never make again."

Cons: "In an effort to maximize profit you give up comfort. I bet you could charge more if it were comfortable."

Pros: "i liked the fact that it was a short trip so i could make my way home from there."

Cons: "Same as above."

Pros: "On time!!!!"
Cons: "Only water served"

Cons: "The delays"

Cons: "Same as first leg of the trip"

Pros: "coffee was good"
Cons: "Only got to serve it once due to turbulence"

Pros: "I made it to my destination and was offered a beverage"
Cons: "Everything else. No one greeted me. No TVs. Luggage was ruined. Ppl were rude"

Pros: "Was given a couple of blankets that I asked for. Everyone was very professional. Very accommodating."

Cons: "no outlets, no tv, no wifi"

Pros: "Early boarding for passengers with children under age of 2 was super helpful for me as I was traveling by myself with baby for the first time!"

Cons: "Wifi did not work. Limited food & beverage choices."

Pros: "Comfortable"
Cons: "Cat meowing loudly in seat in front of us"

Pros: "I made it alive"

Cons: "Crowded seating."

Pros: "Delayed a lot"

Pros: "Nothing"
Cons: "Everything"

Pros: "Early arrival"
Cons: "No free snacks"

Pros: "Early"

Pros: "Fast and easy yo use"
Cons: "None"

Cons: "Poor seat selection options."

Pros: "On-time flights"

Pros: "On time"

Cons: "Same as the first one"

Cons: "Delays"

Cons: "Weather delay but then sat at the gate for nearly an hour waiting for "fuel". Give me a break! No update as to why we were waiting, just said we would leave in 15 min an hour before we left."

Cons: "Didn't make it"

Cons: "Paid for first class, didn't get offered dinner"

Pros: "See above"
Cons: "See above. Stewartists were rude both ways."

Read more about Alaska Airlines
COVID-19 information

Safety measures for airlines flying from Illinois to Aspen

Airlines flying from Illinois to Aspen have enacted additional safety measures and adjusted policies to better accommodate travelers. Policies vary by airline.

Heightened sanitation

Daily cleaning, installation of cabin HEPA filters on flights from Illinois to Aspen

Mandatory masks

Masks required on board, masks provided on flights from Illinois to Aspen

Social distancing seating

Middle seats unavailable to book on flights from Illinois to Aspen

Pre-flight testing

Testing for antibodies, testing for symptoms for flights from Illinois to Aspen

Book cheap flights from Illinois to Aspen

Recent round-trip flight deals

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