Find cheap flights from Aspen to Chicago

ASE - CHI

Find cheap flights from Aspen to Chicago

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Aspen (ASE)
Chicago All airports
Fri 1/15
Fri 1/22
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Good to know

Low season

May Best time to beat the crowds with an average 44% drop in price.

High season

November Most popular time to fly with an average 28% increase in price.

Average price round-trip

$404 (avg. price over the last 2 weeks)

Good deal round-trip

$371 or less

Good deal one-way

$232 or less

When to book flights from Aspen to Chicago

Estimated round-trip price
Average price per month
Flight prices as travel date approaches
-1 day
-2 days

Top tips for finding a cheap flight

  • Looking for a cheap flight? 25% of our users found flights on this route for $232 or less one-way and $371 or less round-trip.
  • The cheapest flight from Aspen to Chicago was found 38 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 October, November and December. The cheapest month to fly is May.
  • Morning departure is around 7% more expensive than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

FAQs for booking flights from Aspen to Chicago

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Top airlines flying Aspen Pitkin County to Chicago

Scores according to KAYAK customer reviews

7.2
American Airlines
Overall score based on 45,043 reviews
7.5
Boarding
7.1
Comfort
7.8
Crew
6.8
Entertainment
6.7
Food
Airline reviews

Pros: "We liked the effiency and politeness of the staff. We enjoyed the movies, the food was better than normal."
Cons: "We were very unhappy at having to pay extra for our seats after we had booked the airfare. Especially on the way to Paris when there were so many extra available seats! I counted 50 available seats!"

Pros: "Cerainly boarding is easy and the seats are quite comfort in business class."
Cons: "the service, considering this was the highest level of service on these flights was less than I would have expected"

Pros: "First class on TUS to ORD flight - very good flight attendant who was very pleasant, attentive and knowledgeable... she remembered which drink I was having."

Cons: "Horrible long delays."

Cons: "The seats were so close together! I was between two men, and one was spitting tabaco into a cup. It was terrible."

Cons: "Not much offered on domestic flights."

Pros: "I wish I could remember the names of our flight attendants- but they were wonderful and really took time to get to know passengers! They were so friendly and went above and beyond in any of our requests. Loved them!"
Cons: "It would have been nice to have individual screens for such a long flight, but I wouldn't say that's a complaint. The flight was fine."

Pros: "Nothing"
Cons: "Personnel; lack of customer service"

Cons: "Kayak repeatedly listed the departure gate as D36 when it was D17."

Cons: "It was cancelled"

Cons: "The tsa in chicago was very unorganized. The tsa workers were extremely rude."

Cons: "Flight connection was too close. Delays in leaving Nairobi made us almost miss this flight"

Pros: "The new clean plane. The pilot and crew were great."
Cons: "Nothing"

Pros: "On time"
Cons: "Very cold on board"

Pros: "Was able to store my carry on and arrived early"

Pros: "Having flown long haul with American numerous times, this time I was pleasantly surprised by several things. Firstly, the brand new plane with excellent in-seat entertainment choices, power points at every seat, more comfortable chairs with better head rests and even window dimmers vs. window shades, allowing you to look outside the whole flight. Secondly, the food was much improved...definitely better quality and tastier than typical airline food. And thirdly, better service from flight attendants who actually smiled. Keep up the good work. This represents a real step change."

Pros: "The food, entertainment and crew were satisfactory."
Cons: "I did not like that my original flight was flat out cancelled. It made for a stressful trip."

Pros: "Flight was on time"
Cons: "There was water dripping from the vents. When I tried to inform the flight attendant, she shut me down so fast I couldn't believe it. All she had to do was reassure me that it wasn't a safety issue. Her attitude was like she was tired of telling passengers that it was perfectly normal. Very unprofessional!"

Cons: "Allergic to cat/dog dander. Had dog with no kennel in window seat of my row. I was on aisle seat. As we all got up to let the owner go to the bathroom a dog followed walking on my seat. For the last hour and a half of the flight the dog Sat on the owners lap. My allergies and asthma begin to flare up prior to landing . Not a pleasant flight ."

Cons: "The flight was cancelled, there is nothing to rate except the inconvenience it caused me and my fiancee who were traveling back home for a business meeting."

Pros: "Flight crew was excellent."
Cons: "We booked flights through British Airways but flew American Airlines. The check in process was a stressful mess: we were forced to stand in long customer service lines both on our first flight from LAX to Chicago and again during our very short layover in Chicago to Dublin to ensure that our bags were checked all the way to our final destination. Very stressful, and it didn't help that the gate crew was extremely rude and unprofessional. It is very inconvenient that we could not choose our seats beforehand."

Pros: "Individual entertainment. Wowww!"
Cons: "Seat was a bit tiny. Free food snacks were not quite good."

Pros: "Nothing"
Cons: "Everything"

Pros: "American Airlines was amazing fed you a good meal fun crew good entertainment had 3 glasses of wine desert , and hot biscuits and coffee before landing was a great flight."

Pros: "Great staff and leg room/comfort. Food, drinks and entertainment was superb! Comfortable Boeing 787."
Cons: "Nothing"

Pros: "When the arrival time of the connecting flight was changed, we chose another set of flights."

Pros: "ON TIME!!!!! Nice folks, smooth and safe."
Cons: "Got through the extensive security lines to USA one hour before scheduled departure and looked at the screen which said 'final boarding' which was not true and made us panic a bit, running for the gate. It did board and leave on time but not an hour early. This flight was night and day different than our ORD to Dublin flight of 5.12.17 which was 5 hours delayed and do stressful."

Pros: "Crew was very pleasant, boarding efficient."
Cons: "Food was very mediocre but nothing new in air travel. The biggest complaint is that there was no individual light available for each person to sue to read. On a transatlantic flight of 10+ hours that is not overnight, it is a bit much to expect customers to fill that much time if one cannot read because the lights aren't working. The flight attendant said it was a very old plane as the reason why, not exactly what one wants to hear. Also, the plane was different than the one I prepaid my seats for, thus the money I spent on bulkhead seats was wasted as we just got two normal seats. Not a good experience."

Pros: "wifi was great"

Pros: "Clean plane . excellent staff"
Cons: "Nothing."

Pros: "Flight on time."

Pros: "Awesome crew. Comfortable seats. Great entertainment options. Good food."

Pros: "Nice crew. Chairs were comfortable."
Cons: "Not enough movies! No individual screens. Plans had dirt stuck all along the air vents"

Pros: "Fast check in, timely take off & arrival Excellent and friendly service"
Cons: "NA"

Pros: "One of the crew members, Walt, was amazing."
Cons: "Everything else was a NIGHTMARE. We bought our tickets in Nov. I paid for an upgrade and assigned seats in FEBRUARY. We flew May 13. Not only did they RESELL and REASSIGN our seats to someone else -- we could not get a refund for the upgrade we paid for. To add insult to injury, the only seats they could give us were in the back of the plane next to the toilet. Having heard so many similar nightmare stories about American Air I can say I will never ever fly American Air again. We now have to spend our firrst few days home from vacation disputing that charge, writing letters and making calls to get that damn refund. I will be sharing my discontent far and wide. Whoever at corporate thinks it's best practice to sell and sell and sell seats and live with the aggravation of the customers has an upside down notion of how to run a successful business. NIGHTMARE."

Pros: "Left and arrived on time. Crew was friendly and professional."
Cons: "Passengers are packed in like sardines. All carry on bags must be checked at the gate as the overhead bins are too small to accommodate anything except a small personal bag or jacket."

Pros: "Flight was fine"
Cons: "After traveling on 9 flights during a 2.5 week period, this crew mishandled my bag leaving damage to the handle and top of my bags."

Pros: "The staff were very friendly and informative"
Cons: "It felt a bit cramped, but overall nice seats and movie screens"

Pros: "Arrived early. Smooth flight."

Cons: "The flight attendant was arrogant. This is her job... just for $$$"

Pros: "The in flight entertainment was perfect, new, and relevant. I also had an empty seat between myself and another passenger so my legs weren't as cramped."

Pros: "My flight was very short. It was a straight flight and there was no turbulence. Flight pulled off when it was supposed and early landing."

Pros: "Nothing"
Cons: "Delayed flights, rude agents, no pre-boarding for families, no stroller delivery at the arrival gate and 20 year old planes with mechanical issues. Nightmare!"

Pros: "The new Dreamliner was amazing. However my great experience was also directly a result of the unfilled nature of the plane. This gave so much room to the passengers, food service was fast and plentiful, and crew was in a good mood."

Pros: "10 hour flight with entertainment system in main cabin that had no sound. Made the flight feel a lot longer."

Pros: "The gentlemen from the wheelchair service who was there to pick us up when we arrived in Heathrow went above and beyond his duties. Instead of passing us over to another wheelchair attendant as we needed to switch terminals, he stayed with us thru the terminal change until we were on the airplane. We needed to get our boarding passes at Heathrow from a different airline and he helped us with this. Kudos to him!! The attendants on this flight were very helpful when my husband was having a diabetic reaction and I was vomiting form air motion sickness. We were a mess!! However the flight attendants were sure we had a wheelchair in Chicago and helped us with our bags as we were exiting the plane. Nice Job"

Pros: "Nice plane, very friendly pilot."
Cons: "Delayed flight."

Cons: "They had no record of this portion of my trip, after a few people checked they found the Chicago to Ammon part so they added me onto a flight from Washington to Chicago. All should of went well from there but they sent me to the wrong gate. Luckily I just made it to the correct gate for boarding. Upon arriving at Chicago there was no one available to provide information on how to get to Royal Jordanian gates. Also on my AA portion of my flight coming into The U S in New York the flight was cancelled and I was told the next flight Available was next day (18hr delay) at the other NY airport. I had to have someone drive from D.C. (My destination) to pick me up"

Pros: "The crew was friendly and did their best, the flight took off my schedule"
Cons: "They didn't have individual tvs which was disappointing but showed three movies instead on screens. They announced the movies being shown on the flight at the beginning and then proceeded to show three completely different things, some just being random tv shows. The whole middle section of the plan had static in their headphones so they were unable to watch the movies. The crew was friendly but seemed very confused as if it was their first time working together. Announcements were choppy And confusing. They also asked me to pay 190 dollars extra to sit with my husband. Not the best experience"

Pros: "The crew was fine."
Cons: "United is consistently late and unhelpful with addressing travel delays. The first leg of my flight was delayed which would have caused me to miss my connection. United staff could not have been less helpful. In the future, I will try to avoid flying United wherever possible."

Pros: "Flight was cancelled twice. United lied about luggage. Had to purchase toiletries and hotel room."

Pros: "Great in flight service. On time. Easy upgrades using United mobile app."

Pros: "Nothing"
Cons: "Our plane departed on time, 6:05 AM. About 6:40 A E turned back towards Boston. There was a problem with the wing. It got repaired. We deplaned. And waited. And waited. Then we needed fuel to be removed. And we waited. And waited. Then we got back on board, got to the runway, and the RIGHT ENGINE didn't start. So they tried to repair it, couldn't (didn't want to fly on that old, broken plane anyway at this point), and we had our flight canceled. All told, I spent 10+ hours at Logan Airport. It was an absolute disaster."

Pros: "Boarding was much more organized with lines marked for each boarding group. The crew was super friendly. Also, I received a whole can of cran-apple juice, which was much nicer than just a small cup. The tv options were also fairly priced for the options available."

Pros: "Great customer service.. Comfortable flight and smooth landing!"
Cons: "Paying for one check in bag..."

Pros: "Crew- very efficient on the ground andon the air"
Cons: "Inner flights no entertainment. Maybe dhould go wifi like LH"

Cons: "Easy for check-in and on time"

Pros: "The trip TO the United States was bearable."
Cons: "This flight was a complete disaster. I ended up b=on a different flight to Newark, as my flight to Chicago got canceled. Then that fight was unable to land, so I spent hours in baltimore, and missed my connecting flight to Brussels. By the time I finally arrived, 4 hours late, to Newark, I had to spend 2 hours in a line to get re-book, for a flight the next night. I was compensated for all this mess with a $10 food voucher, and had to get a cab from the airport to the closest and cheapest hotel. My flight to Brussels was uneventful, save one rude flight attendant, and I got to school a day late."

Pros: "The crew was very kind to everyone and it was a very pleasant flight!"

Pros: "Staff was friendly and helpful. Flight was smooth."

Cons: "Entertainment could have been better."

Pros: "The crew , living on time"
Cons: "I had no dislikes"

Cons: "O'Hare airport. Bad signage to economy parking."

Pros: "The flight was on time."
Cons: "The wifi for the entertainment worked perfectly, a power jack is needed to charge the device."

Pros: "United got me from point A to point B"
Cons: "Crew was rude, not just to me, but to other patrons. Flight was packed going and the man scanning boarding passes spoke to those of us asking simple questions as if we were stupid and defiant. Was he a prison guard in his previous job? On the way to Newark, I had an aisle seat. One of the stewardesses blazed by me with a cart ramming it into my shoulder without so much as a, "sorry." I'm not a big woman but maybe as I dozed off I leaned over a bit...There is no way she didn't feel her cart hit me. Rudeness, it seems is a part of the culture at United because the flight attendants coming back squeezed past the long line for the bathroom without saying, "excuse me." They did however, say, "I need to get by," and one of them brushed by the gentlemen sitting next to me and bumped his laptop and coffee. Overall it seems that the crew working these particular United flights have forgotten that we pay hard earned money to fly. Some of us are going on vacation, to see loved ones, and some are flying to deal with unpleasant circumstances. The staff may fly several times a day, but most passengers do not. There's a lot of prep and anxiety, that goes into taking a flight and a surly flight crew multiplies that anxiety. No one wants to fly with a crew that hates their job."

Cons: "Our flight home we couldn't land in Chicago due to storms and diverted to Madison. Sat on Tarmac 2 hours and some passengers from Madison allowed to end journey there. We had to wait for that approval and again had to wait for their luggage to be removed from the plane. My opinion is let them disembark but not the luggage. It was too long to be in that plane"

Pros: "Bad good, good service but 5 hours delay"
Cons: "The airplane food and the delay in Chicago"

Pros: "The staff was pleasant tho"
Cons: "I missed my connecting flight in Chicago due to my first flight being delayed an hour, which in turn forced me to stay overnight because the next available flight wasn't until the next day"

Pros: "The onboard crew was lovely, I especially appreciated them asking those who were not transferring to another plane to wait until those who were got off as we were 45 minutes late"
Cons: "The male gate agent in pittsburgh was the rudest and least helpful person I have every met in all my travels. When flight was delayed for weather reasons, and looking like we might not connect in ORD he could only say 'call united'"

Pros: "Crew took special care of my guitar -- much appreciated."
Cons: "Small plane. Kept bumping my head when I got up."

Pros: "They had movies you could watch, for a price"
Cons: "I think united pays it's staff to be unnecessarily rude. It's so much rudeness that is almost ridiculous. Their demands, censure and dismissals of customers would make you think that you are their servants instead of customers."

Cons: "During my round trip my flight was delayed 4 times and canceled twice. On the first cancellation I had to get a hotel room because the next flight wasn't for 24 hours. Then, that flight was canceled but the booked me on another airlines. At first they were going to make me wait another 24 hours until I had told her that I had already did that once. The desk clerks were rude on every encounter."

Pros: "I'm handicapped and the help getting from terminal to terminal. The people were very helpful."
Cons: "I have metal leg braces. I had to remove them to get in the seat. So the flight was uncomfortable. It would be nice if the plane could have handicapped seating.I know I wouldn't have minded paying a little more for comfortable seating."

Cons: "My itinerary had to completely change."

Pros: "Pilots and some flight attendants were kind and friendly."
Cons: "On the return home, I was seated in the last row right next to the lavatory. I was bumped into at least 25 times by other passengers and flight attendants. I would suggest removing the aisle seat on both sides."

Pros: "The crew was the most polite, calm and reassuring crew I've ever come across. When faced with the mounting frustrations of a cabin full of delayed passengers, these guys were smooth as silk. Bravo!"
Cons: "Being grounded due to weather is unfortunate, but the team did so well in managing expectations, it's hard to be mad."

Cons: "Grant flight , i flew with my daughter in business class the service was very good , food was great , missed watching direct tv as the Olympic Games was going on , but over top notch"

Pros: "Everyone was very friendly"

Pros: "Was nice"

Pros: "When l got to airport I was advised my flight had been canceled. Rerouted on United airlines thru Washington Dulles. Waited on Tarmac 2 1/2 hours due to bad weather, etherwise everything was good."

Pros: "I liked when I got home 12 plus hours later than I was supposed to!"
Cons: "The three canceled flights and 7 delays that I was out through were awful!"

Cons: "We got on board, waited 20 minutes. Capt said it was a bad reverser, and we were waiting on paperwork for 15 minutes. Long story short, they make us leave the plane after 2.5 hours. Then we wait in the airport for another 2.5 hours. I missed my connection and spent 10 hours in Chicago."

Pros: "Nothing!!"
Cons: "Everything. Delays were inexcusable, staff ridiculously unfriendly and just bad attitudes all round. Very unpleasant experience, won't be using this airline ever again."

Cons: "My connection to YYZ was cancelled and I was not even rebooked to the next flight. I needed to buy a ticket on Air Canada in order to get there. Every time I fly United I find myself asking "why in the hell am I flying United?""

Cons: "The seats on the flight from LAX to ORD are built for people who are under 6' tall. You need to disclose the fact that your seats cannot accomodate a person who is 6'2" and 200 lbs. or you will need to accept medical responsibility for the damage done to a persons musculoskeketal system."

Pros: "I know it's some sort of miracle. But there was only 40 people on an airbus. We all had about 3 seats each and we made full beds for ourselves."

Cons: "Boarded and left late for many to miss connections. No real help to get to new connection both on plane and off."

Pros: "Overall good flight. Very quick! :) nice pilot"
Cons: "Nothing in particular."

Cons: "The plane was absolutely filthy.. crumbs on seats debris on floors. Dirty arm rest and seat backs"

Cons: "VERY UPSET THAT MY FLIGHT WAS DELAYED AND I MISSED MY CONNECTION AS WELL AS MY LUGGAGE DID NOT ARRIVE IN LONDON UNTIL YESTERDAY-June 18 after leaving Oklahoma to London on June 14 also my luggage was damaged when it was finally delivered here in London... Broken wheel and zipper!!! I also had to go out and buy a pair of pants, shirt, socks, underwear and a jacket for meetings on Thursday and Friday."

Pros: "I havd to buy a whole new flight. from mechanical errors. it was horrible. I have no help"

Pros: "Nothing"
Cons: "Held up at check in because of understaffing. Long TSA line. When we finally got to gate wouldn't let us board. Then agent was extremely rude about putting us on a different flight. Have always flown Delta and am sorry I ever strayed. It will never happen again."

Pros: "A everything was fine other than..."

Pros: "I did not like anything. Please people don't book through kayak. Scam website"
Cons: "Flight delayed. Stayed at airport for more than 2 hours. Baggage lost."

Cons: "It took almost 15 minutes to get my bag back that I had to gate check. We were not allowed to carry on."

Pros: "Easy flight"
Cons: "Very bumpy!"

Pros: "Short flight , every thing was good f"
Cons: "Flight was likeable short flight"

Cons: "Had to sit on runway for over 2 hours causing me to miss connecting flight in Chicago. Then no more flights to Little Rock so had to spend the nite in airport very uncomfortable!! Kept changing gate numbers causing me to walk all over airport while having severe knee pain!! Very upsetting and painful"

Pros: "On time; uneventful flight. Perfect!"
Cons: "Instead of pretzels they handed out ranch flavored items; I have food allergies to seasonings. I prefer just plain pretzels"

Read more about American Airlines
COVID-19 information

Safety measures for airlines flying from Aspen to Chicago

Airlines flying from Aspen to Chicago 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 Aspen to Chicago

Mandatory masks

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

Social distancing seating

Middle seats unavailable to book on flights from Aspen to Chicago

Pre-flight testing

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

Book cheap flights from Aspen to Chicago

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