ASE - ORD

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ASE — ORD
Dec 9 — Dec 161
Round-trip
1 adult
Economy
0 bags
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Fri 12/9
Fri 12/16

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Good to know

Low season

December

High season

April

Cheapest flight

$244

Average price round-trip

$600

Good deal round-trip

$399
Best time to beat the crowds with an average 44% drop in price.
Most popular time to fly with an average 57% increase in price.
Flight from Aspen Pitkin County to Chicago O'Hare Intl
(avg. price over the last 2 weeks)
or less

When to book flights from Aspen to O'Hare Intl

Estimated round-trip price
Average price per month
Flight prices as travel date approaches

Top tips for finding a cheap flight from ASE to Chicago O'Hare Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $399 or less round-trip.
  • High season is considered to be March, April and May. The cheapest month to fly is December.
  • Morning departure is around 5% cheaper 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 Aspen to Chicago O'Hare Airport flights

Top 3 airlines serving Aspen Pitkin County to Chicago O'Hare Intl

Scores according to KAYAK customer reviews
7.9
DeltaOverall score based on 31880 reviews
8.1Boarding
7.8Comfort
8.5Crew
7.8Entertainment
7.5Food
Airline reviews

TsA was fast and efficient. Boarding was effortless, fast. Having a new and clean plane only amplified the experience

Read more about Delta

TsA was fast and efficient. Boarding was effortless, fast. Having a new and clean plane only amplified the experience

Crew was super helpful storing my bag, seating people, etc And now they’ve started thanking their Delta frequent flyer members !! Two crew came to find me and thanked me by name

Pros: "Kosher snacks! Thank you! Very safe and controlled Covid procedures. Made me feel safe."
Pros: "Very controlled and safe Covid procedures. Outlets and screens at every seat."
Pros: "Felt very clean and so glad they are not selling every seat"
Pros: "great everything!"
Cons: "Not delayed"
Pros: "It was all good glad the last leg of the trip was pleasant."
Cons: "Small plane, feels cramped"
Cons: "The unfortunate delay prevented me from attending my grandmother’s wake. Fewer delays would be helpful."
Pros: "Crew was friendly"
Cons: "The boarding process was rough and haphazard"
Cons: "No sandwiches for sale just snack boxes"
Pros: "Taco"
Cons: "Taco"
Pros: "Crew very friendly and courteous"
Cons: "Would’ve been nicer to have lunch rather than breakfast"
Pros: "The crew and the comfort plus seat"
Cons: "Announcements were too loud in earphones (could damage ear drums) and entertainment was turned off while waiting 30 min for the gate to open."
Cons: "Smooth on time flight"
Pros: "The crew really kept us updated on the many delays."
Cons: "There were SO many delays and they kept changing. At one point we got on and off the plane."
Pros: "Nothing."
Cons: "Flight was delayed 2 hours. Even though I had carry on, they checked it and this made me waste my time at baggage claim rather than gate checking. Flight attendants were miserable. Power supply didn’t work at seats."
Pros: "The seats were ok."
Cons: "The flight was delayed over 3 hours so I missed my connection in Chicago to Seattle. I’m now stick in Chicago overnight and have to be on a 6 am flight tomorrow. The Delta staff at LaGuaurdia was extremely rude and not helpful at all. Hate Delta......"
Pros: "Amazing crew and clean cabin."
Pros: "Fast boarding, friendly crew, and comfy seats"
Cons: "It was pretty bumpy and a few times we changed altitude very quickly"
Pros: "I loved the flight attendants and the desk staff everyone was so friendly and made me want to travel delta again."
Cons: "Delta doesn’t offer military spouses free checked bags and I found this out at the airport. It was disheartening, but at least it’s Delta and not the airline that is supposed to represent America."
Pros: "Clean plane, the seat felt roomy. Smooth ride and the captain communicated clearly."
Cons: "It felt super hot and I wish there was food included in such a long flight."
Pros: "Quick flight"
Cons: "Flight attendant spoke like a robot. Could not understand her."
Pros: "On time"
Cons: "Small aircraft"
Pros: "Staff, service, options"
Cons: "Over an hour delay before boarding due to supposedly bad weather. Because flight was overbooked they were offering $400 gift card to change to standby on another flight. If you didn’t make that flight (evening), you’d be confirmed on a flight the following morning with one stop in Detroit (we booked a nonstop to Chicago). Uh, no thanks. Then to top it off, we’ve landed and been told that it will be at least an hour before we can deplane due to no availability at the gate (it’s 1145 pm right now). All this plus their new policy of not allowing us to select our seats because we bought the cheapest tickets. Really Delta? You go ahead and cater to the rich and I’ll choose to fly with another airline."
Pros: "Crew friendly"
Cons: "Middle seat with no option for me to move"
Pros: "Flight attendants were pleasant."
Pros: "Friendly service, comfortable seat, on time, no issues."
Cons: "Everything"
Pros: "The crew was great"
Cons: "The flight was 4 hours delayed"
Pros: "i liked that staff and crew were very communicative and pleasant."
Cons: "one crew member didn't show up and caused delayed flight."
Pros: "Flight was on time. Boarded quickly with no fuss."
Pros: "Flt on time, very nice and friendly gate agent and flight attendant"
Cons: "Too tight and seats not comfortable."
Cons: "Delayed"
Cons: "The delta studio didn't work with Android 8"
Pros: "We were traveling with a toddler and infant but put in different row because the tickets were purchased separately. Gate staff promptly put us together and even bumped us up to delta comfort. Was a very pleasant trip. Thanks delta!"
Pros: "Ease of flight"
Cons: "N/A"
Pros: "Accident on way to airport, so I showed up to check bags 45 minutes before flight time. They said they couldn't get the bag to the plane..in 45 minutes? So, they put on the next flight... 6 hours later. Said I could fly without the bag... uh, no thanks. They would not look for alternatives without charging me more. Flight attendants were crabby, otherwise everything was fine. I flew British Airways a few months ago. Night and day. Seriously. Delta does not even approach having good service. There was no comparison to British Air--- Delta is not in the same league."
Pros: "Entertainment options weren't bad. Most of the crew was polite other than one flight attendant who seemed ambivalent and unhappy to be there."
Cons: "Three hour+ flight and just one tiny bag of pretzels? And no lemon or lime wedges on the beverage cart? Plus, I have to pay extra for one checked bag. I will only fly Delta if I have to in the future. Subpar airline."
Pros: "What I liked: Sky Priority privilege came with separate luggage check-in queues and early boarding"
Cons: "What I disliked: Seats were too small No beverages or snacks offered No USB or power outlets available Three different groups board before Delta Comfort (e.g. those needing more time, travelers with children, first/business class) Didn't see the value compared to a less expensive main cabin ticket"
Pros: "I was notified about the delay via text before I left for the airport, which was nice. I would not have checked my email."
Cons: "Delayed for over 2 hours. I have never flown Delta before this flight and it wasn't a great representation. The flight attendants were nice but I was in a seat near the engine and it was making really weird noises. I fly almost every two weeks, so I'm used to engine noises but this was one of the loudest/most rickety sounding flights I have ever been on.. and I have flown Spirit a few times. It just didn't feel safe. Landing scared me a little too as I have landed in O'Hare countless times and have never flown so low to the highway upon entry. It felt like we were only a couple hundred feet above the cars."
Pros: "Great short trip with an attentive crew."
Cons: "Seats were a bit uncofortable and small compared to previous flights."
Pros: "Delta has failed in trying to break into the Aspen market. Their "personal ground crew" was hapless. Half the passenger bags didn't make it on to the plane. When we checked in the ticketing agent was randomly stacking bags in a heap behind her, and not putting them on the conveyor belt. The flight attendant was loud and screechy, saying that it was easier to leave off the bags than take people off the plane. What?? How was this not accounted for before the flight. On the way out, they forgot to build in time to de-ice the plane. SMH"
Cons: "The flight attendant looked like she was mad throughout the whole flight"
Pros: "Everything went well"
Cons: "I was late from first flight"
Pros: "First time flying DELTA and to New York City. Really liked flying into Marine Terminal for it's smallness and easiness to collect luggage and catch a taxi."
Pros: "Fantastic crew"
Cons: "Great trip"
Pros: "Easy no hassle check in and board."
Cons: "Absolutely nothing. Thank you!"
Pros: "Seats seem to get smaller but overall a good experience"
Cons: "Seat room"
Cons: "The crew was outstanding and the aircraft was new and comfy"
Cons: "The airport experience was horrible. American Airlines did not have enough personnel on duty to process all the waiting passengers."
Pros: "Nothing"
Cons: "American airlines needs to improve their inter hub options"
Pros: "Was not long enough"
Cons: "Boarding at Heathrow is horribly inefficient."
Pros: "Customer service"
Cons: "Nothing"
Cons: "There was no entertainment at all, and pretzels are gross"
Pros: "Nice plane and entertainment"
Cons: "Booked flight through British air for a reason. Didn’t anticipate American Airlines being used for our flights. The Flight was also delayed but it was never explained why despite dozens of questions from passengers. This caused a missed connection flight and forced us to stay overnight in Chicago with nothing but a $12 food voucher. When we tried t ask what other options were, American Airlines personal offered no sympathy and said the best we would get is the food vouchers and we should be grateful. No other travel reimbursement or vouchers were offered other than a replacement flight. Overall it was a huge inconvenience and caused numerous other expenditures for us."
Pros: "The TV's on the back of the seats were nice."
Cons: "The threatening tone of the counter associates about last minute checking of your bags because they don't have enough space in the overhead cabins. Why offer everyone that option if they will force groups 7-9 to check them?"
Cons: "Left Newark 2 hours late which mean missing connections in Chicago by 20 minutes. From that point on American was inept in getting me to MSP."
Pros: "Great flight"
Cons: "everyone was friendly"
Cons: "Small seats."
Cons: "Fast flight"
Pros: "Boarding was on time, and landing was smooth."
Cons: "No entertainment."
Pros: "One cabin crew went the extra mile for me...rescued a partial dental plate which I had inadvertently tossed in the trash."
Pros: "This trip was short and sweet.. Uneventful +Praise God!"
Pros: "Everything was good."
Cons: "Movies selection"
Pros: "On time, good service."
Cons: "Delayed flight, multiple gate changes"
Pros: "Finish currently use were the most courteous and caring I ever was serviced by."
Cons: "Not much to recall"
Pros: "Nothing"
Cons: "When I purchased my tickets, American decided it would be reasonable to separate my husband, our 1 year old daughter, and myself which I was notified of only when I asked the customer service agent over the phone prior to our flight. She explained that she was unable to do anything about it. I then called American during my trip and spoke with another agent who said it was out of her hands as well and to take it up with an agent at the desk at the airport. When I checked in online, I was able to change our seats myself which was nothing that either agent even suggested. The lack of ability of these agents on the phone to help two parents traveling internationally with a toddler was unbelievable. American has terrible customer service."
Pros: "Everyone was so friendly and helpful, especially Ricardo at the check in desk. Our flight was delayed for 2 hours but the friendly staff made it easier to deal with the delay!"
Pros: "I would like if for my return from Paris to Chicago, Chicago Seattle I would be greeted by the personal and offered to flight first class without extra charge to compensate for the bad experience on my way going in. Thank you"
Cons: "I was told I would be able to choose the seats only 24 hours before the flight by going online. I tried to choose the seats online but could not have access to the site. I then called the number provided to ask for more help, and was told that I could then only choose the seats at the check in time. I was at the airport 2 hours before the flight schedule to book my seat and was told them that I could only choose the seats at the gate. Once I got at the gate I asked the person to please give me a seat at the aisle for medical reasons but after waiting until the boarding process had started I was giving a middle seat. Not only I was treated as a stand by passenger that had not purchased the tickets I was put nt on group 8 and at the moment of boarding the gate personal aggressively grabbed my carry-on bag because they insisted there was no more spaces in the compartment above heads. Once I got inside of airplane I saw many empty compartments available for carry-on luggage. I wish I had not purchased my ticket with Iberia Airlines operated by American Airlines. It was not a good, pleasant experience and do not recommend. I wil certainly avoid in the future and not travel this way another time. Thanks"
Pros: "Price"
Cons: "Arrived 1 hr before my flight and they wouldn't check me in. I believe they overbook the flight and turn customer down. They even gave me hard time during rebooking us. Never again."
Pros: "The flight was equal to AA service I have had on a regular basis."
Cons: "Nothing"
Pros: "Full flight, crew worked timely"
Pros: "All good, except poor prep on food"
Cons: "As above"
Pros: "Crew was great. Boarding was quick. Food was good."
Cons: "The entertainment on a cross Atlantic flight was not family friendly. Playing 'Dark Knight Rises' and 'Guardians of the Galaxy' while my 6 year old is on the flight is not appropriate. While I didn't let him listen to the program, he could still watch violent scenes I would not allow at home. There are plenty of family friendly good quality PG or G rated movies that appeal to everyone. Would it be too hard to get individual screens in 2017?"
Pros: "Our flight was delayed by almost three hours due to weather in Chicago, the crew was very helpful and the pilot kept us informed about the updates that he was receiving."
Pros: "Quick and easy boarding"
Cons: "Uncomfortable seats"
Pros: "Courteous crew"
Cons: "The plane was tiny and old"
Pros: "Clean plane . excellent staff"
Cons: "Nothing."
Pros: "Flight on time."
Pros: "Arrived early. Smooth flight."
Pros: "They were absolutely fantastic on checking on me, food, service, flight in general. Would recommend to anyone!!!"
Pros: "On time"
Cons: "All well"
Pros: "What I enjoyed about this flight is that I eventually made it to Chicago."
Cons: "Flight was delayed several times - blamed on Chicago ATC. The food offered was not suitable for First Class - there was chicken and vegetarian option. The FA was rather slow in serving and clearing trays. She was not interested in going around and asking for refills - when I inquired about it at dessert time, she didn't come back for 15 minutes and I had to ring the call button - she informed me they didn't have my drink of choice, so it was OK for her not to come back and tell me that. Service was terrible in First Class. American should seriously do something about that."
Pros: "The flight from San Diego to Chicago went well. We left on time and arrived a little earlier than expected. I was worried about the weather delaying our flight once we go to Chicago but we encounter different problems. as I will explain next."
Pros: "our original flight was cancel due to snow, and we were placed at a hotel and food vouchers were given as well"
Cons: "no head set were passed out making video entertainment useless"
Cons: "We fly from London to Dallas and Dallas to Albuquerque but we miss our connecting flight because of the delay leaving London and because of weather. So we got mid sets from Dallas to Albuquerque."
Cons: "Would at least like a choice of a snack instead of cookies I don't care for."
Pros: "Worst customer service I have ever experience"
Cons: "They canceled my flight to Florida due to hurricane then refused to refund my return flight ticket. How can I fly back if I never made it there. Bunch of thiefs kept my money and they never got me to my destination."
Cons: "The fact that people carry-on luggage that exceeds the max requirements for carry on luggage so they can avoid the checked luggage fee. It's a disgrace. It time to live by your rules, the same for everyone. I had to be rebooked out a different airport as PGV was flooded. I was seated in 21F which does not recline. AA cancelled my flight out of PGV, a better seat would have been nice since I had to drive an hour to EWN whereas I was staying only 10 mins from PGV."
Cons: "We could not check in online because we refused to pay for seats that I felt that already purchased or was entitled to one so I bought a ticket. When we got to the airport and checked in they did not put me and my traveling partner together meaning they didn't see them together not to mention. Our flight was delayed and we only have 4 minutes to get from gate a to gate. We got to the gate collected our boarding passes found out we were seated at the very very very back of the plane right next to the restrooms.........NICE"
Pros: "Good flight."
Cons: "A little crowded"
Pros: "After traveling on a budget airline to Las Vegas and having a horrific experience, I couldn't have been more pleased with the comfort and cleanliness of the aircraft as well as the friendliness of the flight crew!"
Cons: "The plane was pretty chilly and I was FREEZING, but when I asked for a blanket they told me they only hand them out to the first-class passengers. In addition, they did forget to download our in-flight movie, but we all make mistakes :)"
Pros: "Seats were ok."
Cons: "Crew was very grumpy and not accommodating to families (ours and others). No wifi or outlets."
Cons: "The actual flight was fine. It was the delay, followed by what seemed changing info on when it was happening. Every 30 minutes it changed. Five minutes before the flight, the info board said it had been moved to 9:40pm and was changed from Gate 3 to Gate 30, a very long distance to get to. However t"
Cons: "With the exception of delays due to thunderstorms all was excellent."
Cons: "My name was on both reservations, i did not notice this until my wife and i tried to check in. They would not change the name on one of the tickets to my wife, Kathleen. So we had to cancel the entire reservation. I have trip insurance with Allianz, and am trying to get a refund for the tickets. If"
Pros: "Amazing crew"
Cons: "Tight seats, no access to actual WiFi unless you purchase a yearly or monthly plan"
Cons: "The flight was a little early which I truly love! Everything else was just fine."
Cons: "Boarding could have been better. If you have 5 groups you should have 5 lines — not 2. Also the terminal in Holland was extraordinarily cold."
Pros: "The crew was very helpful and kind."
Cons: "The entertainment app did not allow me to watch any of the quality programming and my seat to Chicago was extremely cramped and did not recline."
Cons: "Several delays for maintenance and then plane in our gate when we landed"
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: "Economy plus was so roomy and the crew was very attentive and nice."
Pros: "On time"
Cons: "Space a little cramped.for spmepne 6'3""
Pros: "Everything was really smooth sailing."
Cons: "Everything was great! The Charleston airport is small yet very nice inside"
Pros: "Check-in process was smooth"
Pros: "Lots of leg room for a regional jet."
Cons: "AC was not very good. Very warm on flight."
Pros: "The flight was actually with United not Lufthansa."
Cons: "It was like they changed our Lufthansa flight to United. I was not able to get our seat until the last minute at the counter. Luckily the crew was good and helpful atherwise I could not even sit with my husband. My chair was broken so I had to sit very straight. The screen was very tiny like only half size of the one on Luthansa flight. The food was only so so as well but that was just my personal taste."
Cons: "Delayed due to a late crew member. Arrived 2 hours late into O'Hare making for a very tight connection. Other than the delay, all was fine."
Cons: "Flight attendants seemed completely unwilling to accommodate any requests outside of their "service time"."
Pros: "Staff are so nice"
Pros: "Staff in Syracuse where awsome from the guy at the united check in Guest to the TSA Gal who had to give us a patdown super sweet and helpful."
Cons: "In both airports I was wheeled to gates and left in the way of people coming and going. I tried to get the attention of airline employees and when I did they told someone else and so I sat for between 40-60 minutes."
Pros: "The actual crew on the flight was lovely and apologetic, did everything they could to help us despite the delays. At least that's something."
Cons: "Delayed for over an hour but not notified of the length of the delay in a fashion which would allow me to drive the 2 hours to Chicago in order to make my connection. Repeatedly told the connecting flight was the last one out of the entire airport to my final destination. Heard other travelers discussing that they had been rebooked onto an alternate airline and then found a later flight on Kayak, walked up to podium and asked to be rebooked on that specific flight, which they grudgingly did. Of note, I was repeatedly reassured that they were "sure" I would make my connection without a problem and to stop worrying so much. My flight left out of Madison 2 minutes after my connection departed Chicago. I usually fly a different airline, whose flights out of Madison were all on time that day, and will do so in the future despite more expensive ticket. The actual crew on the flight was lovely and apologetic, did everything they could to help us despite the delays. At least that's something."
Pros: "Flight was on time and boarding was smooth."
Cons: "The crew weren’t as welcoming. No leg room at all."
Cons: "Extremely small plane. No tv in headrests or on plane, Not enough room for everyone's carry on, no usb charging ports, don't offer unlimited snacks and beverages. They did not offer ANY drinks or snack on this flight which is ridiculous."
Pros: "I was impressed that he came into the cabin to talk to us face-to-face instead of just over the intercom. He was friendly and humorous at boarding, and completely serious when he needed to divert. Explained clearly why and kept us informed of next steps."
Cons: "Other than sitting in the airport for 4 hour and changing to 3 different gate and not getting in till 7:30. Need I say more"
Cons: "One of the crew members was late to arrive, so boarding was delayed. However, The gate crew was amazing, very communicative and apologetic. During the flight the attendants seemed very agitated, I think a smile would go along way to improve the attitude of everyone. I also work with the public, I get that it is challenging, but I do believe that the simple gesture of a smile sets the tone."
Pros: "Clean aircraft, swift flight"
Cons: "Seat was changed to last row/middle seat (not what initially booked or confirmed with online check-in). Before takeoff, attendant moved all passengers in back row to alternate seats. Which meant that I was no longer traveling with my colleague. Unfortunately, that made our intended meeting time impossible."
Pros: "United Provide good service"
Cons: "The flight delayed"
Pros: "Very short flight seating was normal for what I expect as a guy my size"
Cons: "I couldnt figure out their wifi to check on my connecting flight. I could get other stuff to work on it but couldnt find flight information"
Pros: "The crews and staff were competent and helpful."
Cons: "The seat pitch and width isn't worth the price of the flight. Some passengers winced some when they saw where they would be seatied in the cramped cabin. For the plane type, I would think not much can be done for the width, but the tight seat pitch is very tight for most of the people that fly."
Cons: "I'm 5'3 and could not even lean forward to rest my head on the table in front of me because there wasn't enough room. I shouldn't have to pay an additional 95 dollars to have what was previously considered a normal seat with normal leg room, especially after loosing 6 hours of my life due to United flight delays during the course of my trip."
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: "very kind flight crew, no complaints coming back!"
Cons: "We did have one seemingly annoyed flight attendant on the way to NOLA from Chicago, and older woman. Seemed like every question we had was a burden. Everyone else was really nice, though."
Cons: "My flight to LAX was delayed by over two hours and I had to call and reschedule. I was rescheduled to an AA flight connecting in Chicago. The flight from Chicago to LAX was delayed by over four hours!"
Cons: "I never made it on the flight due to weather conditions they couldn't even hold the flight, and then when I have to get my own accommodations had to pay for my own hotel that is not cool"
Pros: "Flight and service were great."
Cons: "United it terrible at letting you know flights are delayed. Got to the airport and found out my flight wasn't going to take off till 2:45 which was 4 hours later then my scheduled flight. I asked the ticketing associate why it was delayed and she said that it was due to crew issues. At least let me know that the flight is delayed so I didn't have to get to the airport 5 hours before my flight took off."
Pros: "Some gate agents were very helpful and friendly with making (gratis) layover changes due to weather issues in my original layover city."
Cons: "They don't assign seats ahead of time, in FCA...too much "juggling" people around prior to boarding."
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: "Crew was great."
Cons: "Unfortantely their was a mechanical problem that delayed the flight. I understand that failures occur, but only having one mechanic available to work this problem is not good. What happend to the two person concept when working on critical aircraft systems? Pretty hard landing at Chicago."
Pros: "Nothing."
Cons: "No alternative options given. Slow response. No retrieval of email confirmation after purchase of trip. Flight was delayed and no notice was given. Rental car had to ordered last minute and was left without room and board for the night. Had to call again for actual co formation of second flight because no notice was given,"
Cons: "The seats are so narrow in coach that the man with broad shoulders that sat next to me could not help being in my seat. I needed to be able to sleep, since it was an overnight flight. This was not possible."
Pros: "The flight attendents were attentive and did a great job."
Cons: "Customer service was rude to us about our carry on. It was fine on the way to Boston, but made to pay and check it on the way back. other customers had bags our size but we we're rudely told "you need to go pay for your bag that's it". The bag fit effortlessly in the top on the way there."
Pros: "guess that the only thing I liked is that there was no problem during the flight."
Cons: "When we landed un Houston it took forever to get off the plane. It was unclear where to get my luggage. I had to leave it to pass through TSA to run and try to catch my flight from Houston to Chicago. When I arrived at my gate I got there just in time because they were starting to board the plane. I was uconfortable sitting between two men. I traveled alone. When we landed in Chicago, took forever to get to the gate so we can get off the plane. There was no entertainment, at least for me. My phone was way low in battery and ai couldn't watch anything."
Cons: "Delays, had to stay overnight in Chicago since we arrived 6 hours late"
Cons: "For reasons known only to them, United managed to separate the reservations of my wife and mine. Having paid for the trip with the Mileage Plus Explorer card, the first checked bag is free for each traveler. At the kiosk check-in at Logan, the machine wanted to bill us $25 to check my wife's bag. It took another 20 minutes to get this rectified."
Pros: "Crew was very nice."
Cons: "Plane aisle was a tight squeeze with carry on bag plus seats were very close together, and I'm a small person at 5'1". Otherwise flight was good."
Cons: "There was no air circulating on the plane the entire flight. The plane was over 90 degrees when we got on. Everyone on the flight asked for the air to be on and we were told it was. No air was coming out of the vents. Horrible flight."
Pros: "The availability of free entertainment on the plane was a positive. The stewardess also was accommodating in giving me both a soda and water."
Cons: "We arrived 1 hour early to a line for checking bags that did not move for nearly 1 hour. There were staff behind the desk that were standing around on their phones and meanwhile there were lines longer than I have ever seen just waiting to be helped. The fact that check in etc was all in one place at the MSY is baffling. I paid ahead of time to check my bags but still had to wait in line behind people who had not even checked in for flights that appeared to be stopping in at least two destinations. Once we finally got to the counter, the staff member informed us that they were re-routing our trip. No apology was offered. When I conferred with my travel companion about the best option to re-route, the employee said "Sir I am speaking to you. Not that man." I tried to explain that this man was my travel companion who I needed to travel with because we were in-fact going to the same destination and had planned additional transportation together and that I needed to know if there was room for two people on this flight so that we could proceed onto our route together. After being interrogated about why my companion was not on my reservation, the employee told us that 12 people would not make the flight we were supposed to be on. She then took our bags (we have now been in line to check bags for almost 1.5 hours). Fast-forward to the return flight. We are supposed to depart at 7:15, but were delayed to 8pm, then 8:30, then back to 8pm, then to 8:25, then 8:40, then 9pm between the times of 11am and 8pm. Our trip to the airport that included two trains was significantly more stressful as these projected times were changed because we went from being on time to late to on time all within the span of an hour. The employees on the return flight were helpful in making up for the numerous delays but the confusion that seemed to hover over the company made me feel like nobody cared about whether we reached our destination."

Book cheap flights from Aspen to Chicago O'Hare Airport

Recent round-trip flight deals

1/6Fri
nonstopAmerican Airlines
2h 58mASE-ORD
1/22Sun
nonstopAmerican Airlines
3h 23mORD-ASE
$380
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nonstopAmerican Airlines
2h 58mASE-ORD
1/22Sun
1 stopAmerican Airlines
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7h 49mASE-ORD
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nonstopUnited Airlines
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nonstopUnited Airlines
3h 14mORD-ASE
$400
1/4Wed
1 stopAmerican Airlines
7h 49mASE-ORD
1/20Fri
nonstopAmerican Airlines
3h 23mORD-ASE
$409
1/4Wed
1 stopAmerican Airlines
7h 49mASE-ORD
1/20Fri
1 stopAmerican Airlines
16h 58mORD-ASE
$418
12/26Mon
nonstopUnited Airlines
3h 03mASE-ORD
12/31Sat
nonstopUnited Airlines
3h 09mORD-ASE
$440
12/26Mon
1 stopUnited Airlines
4h 44mASE-ORD
12/30Fri
nonstopUnited Airlines
3h 06mORD-ASE
$449
1/4Wed
nonstopAmerican Airlines
2h 58mASE-ORD
1/20Fri
nonstopAmerican Airlines
3h 23mORD-ASE
$454
1/10Tue
1 stopUnited Airlines
4h 53mASE-ORD
1/14Sat
2 stopsUnited Airlines
18h 57mORD-ASE
$456
12/26Mon
1 stopUnited Airlines
4h 44mASE-ORD
12/31Sat
1 stopUnited Airlines
4h 53mORD-ASE
$458
12/20Tue
nonstopUnited Airlines
2h 52mASE-ORD
12/23Fri
nonstopUnited Airlines
3h 09mORD-ASE
$460
12/20Tue
1 stopUnited Airlines
8h 36mASE-ORD
12/23Fri
nonstopUnited Airlines
3h 06mORD-ASE
$469
1/4Wed
nonstopMultiple Airlines
3h 05mASE-ORD
1/22Sun
nonstopMultiple Airlines
3h 23mORD-ASE
$488
1/4Wed
1 stopMultiple Airlines
4h 41mASE-ORD
1/23Mon
nonstopMultiple Airlines
3h 23mORD-ASE
$497
12/21Wed
1 stopAmerican Airlines
7h 49mASE-ORD
12/24Sat
1 stopAmerican Airlines
17h 52mORD-ASE
$503
1/4Wed
1 stopMultiple Airlines
4h 41mASE-ORD
1/22Sun
1 stopMultiple Airlines
7h 18mORD-ASE
$506
1/4Wed
nonstopMultiple Airlines
2h 58mASE-ORD
1/21Sat
nonstopMultiple Airlines
3h 14mORD-ASE
$508
1/6Fri
1 stopMultiple Airlines
7h 49mASE-ORD
1/21Sat
nonstopMultiple Airlines
3h 14mORD-ASE
$517
1/4Wed
1 stopMultiple Airlines
13h 59mASE-ORD
1/21Sat
nonstopMultiple Airlines
3h 14mORD-ASE
$522

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Recent one-way flight deals

1/6Fri
nonstopAmerican Airlines
2h 58mASE-ORD
$244
1/6Fri
1 stopAmerican Airlines
7h 49mASE-ORD
$253
1/9Mon
nonstopAmerican Airlines
2h 58mASE-ORD
$264
1/8Sun
1 stopAmerican Airlines
7h 49mASE-ORD
$273
2/5Sun
1 stopAmerican Airlines
22h 18mASE-ORD
$279
1/9Mon
2 stopsMultiple Airlines
22h 19mASE-ORD
$305
12/18Sun
1 stopDelta
6h 06mASE-ORD
$313
1/6Fri
2 stopsAmerican Airlines
17h 06mASE-ORD
$372
1/3Tue
1 stopUnited Airlines
23h 45mASE-ORD
$373
12/17Sat
nonstopUnited Airlines
3h 03mASE-ORD
$374
12/17Sat
1 stopDelta
7h 26mASE-ORD
$383
1/3Tue
2 stopsUnited Airlines
16h 30mASE-ORD
$418
12/18Sun
3 stopsMultiple Airlines
26h 00mASE-ORD
$443
12/18Sun
2 stopsMultiple Airlines
16h 08mASE-ORD
$475
12/17Sat
2 stopsMultiple Airlines
16h 08mASE-ORD
$482
12/18Sun
2 stopsAmerican Airlines
15h 11mASE-ORD
$493
12/17Sat
3 stopsMultiple Airlines
41h 47mASE-ORD
$506
12/17Sat
2 stopsMultiple Airlines
16h 08mASE-ORD
$508
1/8Sun
2 stopsUnited Airlines
14h 03mASE-ORD
$515
12/18Sun
2 stopsUnited Airlines
21h 05mASE-ORD
$523

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Aspen - Chicago O'Hare Airport Flights

Departure:

Aspen (ASE)United States

Destination:

Chicago O'Hare Airport (ORD)United States

Return flight deals:

Chicago O'Hare Airport - Aspen

Cabin classes:

$399

Browse origins:

$508