ASE - MDW

Find cheap flights from Aspen to Chicago Midway Airport

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ASE — MDW
Dec 2 — Dec 91
Round-trip
1 adult
Economy
0 bags
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Fri 12/2
Fri 12/9

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When to book flights from Aspen to Midway

Estimated round-trip price
Average price per month
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Top tips for finding a cheap flight from ASE to Chicago Midway Airport

  • Morning departure is around 49% 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 Midway Airport flights

Top airline flying Aspen Pitkin County to Chicago Midway

Scores according to KAYAK customer reviews
7.9
DeltaOverall score based on 31847 reviews
8.1Boarding
7.8Comfort
8.5Crew
7.8Entertainment
7.5Food
Airline reviews

The seat provides more space for legs to stretch than other airlines.

Read more about Delta

The seat provides more space for legs to stretch than other airlines.

Delays really ruin days, excitement, the overall experience of traveling. Having inaccurate times and poor communication sucks.

Everything was very good no complaints

Crew was rude, and continued to bang into me as they passed and ram the cart into my seat.

Thanks

Pros: "the scheduled time offers, the fast boarding time"
Cons: "offer lactose intolerance snacks"
Pros: "Crew was night seat sucked plane was cramped"
Pros: "Nassau security line was quick. US Customs line was quick."
Cons: "The Delta line to drop my bags was long and unorganized. The ticket agents were moving in slow motion. I waited over an hour to drop my bag. I thought I was going to miss my flight."
Cons: "Food was terrible. Paid for first class, expected something better than coach. Our food choice was a ham sandwich, there were better choices but the crew took them for themselves so nothing left for the 1st class passengers. Similar situation on our eastbound flight the week earlier. I doubt if Delta knows or cares that this occurs. After paying more than twice the coach fare, we expect something better than a ham sandwich on a coast to coast flight."
Pros: "The crew was great. The flight was on time."
Cons: "The cabin temperature was very hot"
Cons: "WiFi"
Pros: "Nice on board crew."
Cons: "More arm & leg room in basic seating. Tray tables are flimsy and seem worn."
Pros: "Food was great. Movie selection was good."
Cons: "When we booked our flight, we were not informed by KAYAK that we have to pay for our luggage! I t was very unpleasant surprise both ways."
Pros: "Crew very friendly and courteous"
Cons: "Would’ve been nicer to have lunch rather than breakfast"
Cons: "On time flight"
Pros: "Crew was very friendly and efficient. Flight was pretty smooth."
Cons: "On time departure would have been nice. 2.5 hours late."
Pros: "Nothing exceptional stands out"
Cons: "Flight was not on time"
Pros: "Crew was great. Planes with built in TV was even better."
Cons: "One really obnoxious kid kept screaming the entire time. Instead of charging for earbuds maybe give them out for those of us that don’t have any."
Pros: "Wonderful friendly crew. Comfy seat. Very pleasantly impressed with the comfort on a CRJ900 -- windows are large and closer to eye level, standing room is enough."
Cons: "Basic economy is just another way for the airlines to provide low service and nickel and dime everyone while charging the same prices."
Pros: "The boarding was very quick"
Pros: "Zero turbulence"
Cons: "Nothing"
Pros: "see above"
Pros: "The crew was friendly and we arrived earlier than expected"
Cons: "Seats are too tight and too expensive to upgrade."
Cons: "I did not like that they would not assign me a seat because the flight appeared to be oversold. Finally I was allowed to board (and it was a good seat location but the seat back was locked in the upright position and I wanted to knap)"
Pros: "Standard Air France flight. My wife and I like the Airbus 380."
Cons: "The flight left two hours late. Apparently this happens a lot with this flight these days because it's an Airbus 380 coming from Paris to Dulles and turning around. The incoming flight was two hours late, so the departure was late. Our arrival in Paris was late. We made the flight, but our luggage didn't. Our return flight from Paris to Dulles was half an hour late because of people from connecting flights. We arrived about 30 minutes late, but no big deal (unless you had a connection)"
Cons: "flight rerouted to LAX!"
Pros: "All good"
Pros: "liked the main meal"
Cons: "didn't like the pastrami sandwich snack before landing."
Pros: "Flight went off pretty well. On time no complaints."
Cons: "Somewhere somehow you need to know that, although partners, Delta and West Jet do not share computer systems and that they are two completely different airlines. This affects ,sometimes, how luggage is handled especially when you land in another country and you have to manually transfer your own - and nobody tells you. You actually change airlines. Itinerary implies West Jet controls the entire thing. Not the case. Better job economic explaining what to With luggage and that, while itinerant implies 1 airline, they are only partners and should be treated separately."
Pros: "The entertainment"
Cons: "Did not like that they still made me pay a fee to bring my support dog aboard. Stood at the special services counter just to pay a fine for my medical animal."
Cons: "Flight delayed 2 hrs"
Pros: "After almost every airline cancelled. Delta still took me to where I needed to go with not one single problem. That pilot was amazing. I forget his name. But the plane didn't slide or anything during take off. Amazing."
Cons: "What was there not to like. We were a little bit late but I wasn't in a rush. I planned well ahead. Delta moved my flight from 10 a.m. to 6 a.m. and that was perfectly fine with me."
Pros: "Despite a delay, we arrived in White Plains on or close to schedule."
Cons: "The gate agent just kept going on and on about trying to make up the time from a delay (18 minutes ...hardly world ending). The lead flight attendant wasn’t much better"
Pros: "Our Delta plane was brand spanking new. Everything worked and the inflight entertainment system was fantastic with many movies to choose from, free headphones, games, tv shows, etc. The crew was polite and the seating at least as comfortable as expected for a 4 hour flight."
Cons: "The restrooms in the rear of the plane were remarkably small, even by airline standards. I'm a somewhat larger person and I fit, but I know a lot of people who would literally not be able to fit on the toilet without touching both of the sidewalls or risk getting stuck in there. The boarding process at San Jose Del Cabo was the most ridiculous setup I've ever experienced. There were numerous flights boarding out of the same gates and at least 3 or 4 lines for different destinations forming on a ramp just outside the gates. There were guys with signs trying to herd people into the correct lines and then loading the people onto buses which took you out to the planes. The planes were loading from both the front and rear doors and people were getting tangled up inside because of the haphazard loading process. Very easy for a person to end up on an incorrect plane!!"
Pros: "The weather was bad in Atlanta. We were rerouted to Minneapolis and made a connection to Philadelphia. No problems."
Pros: "Was initially hoping to fly a US airline but will now look for Aeromexico first. Exceeded my expectations!"
Cons: "The layover in Mexico City was a bit long and the airport was not so great"
Pros: "Left on time, got here early and the capitan was just super nice"
Pros: "Good"
Cons: "Seats"
Pros: "Boarding, checking in etc. The usual stuff, nothign spectacular."
Cons: "Seats are getting too crowded!"
Cons: "Delayed"
Pros: "The crew was beyond friendly and courteous. Lots of leg room."
Cons: "I was an older plane, it was louder than our flight down to Atlanta. Nothing they could do about it, but a slight annoyance."
Pros: "Service and staff."
Cons: "No entertainment system on a very new A320. Gate G14 and G15 in Minniapolis is always vey contested"
Pros: "Friendly and informative flight attendants kept the passengers in reasonable spirit."
Cons: "Left nearly an hour late after confusion related to oversold seats and upgrades. The gate agent entered the plane multiple times. The landing was rough, the brakes were loud."
Pros: "The gate agents and flight attendants were nice."
Cons: "We were not able to choose our seats until we got to the airport. Which was a waste of time since we did online check in but still needed to go to the self check for seat assignment. Then by that time it was too late to try to get a seat with my wife who is very afraid to fly. Overall not a good experience"
Pros: "The crew was friendly and accommodating, and service was good"
Cons: "I purchased a basic economy ticket and upon checking in, my Delta app said my seat was unassigned and I had to get my boarding pass at the airport. I checked back later and the app had me as number 7 on the standby list. I called Delta (wait time 3+ hours... my flight was in 3), and then the Delta app support where I was able to get through to someone. She told me that the ticket I purchased over a month in advance did not guarantee me a seat on the plane (???). She said that if I was bumped from the flight they would reschedule me for the next morning. She was pretty rude and made it seem like I had a 50/50 shot of getting on this plane. I rushed to the airport in hopes that I would be the first from Standby there, and the gate agent told me that I was fine and would board right after first class and be assigned a seat then. Great. Once I got my seat assignment, I board to find out there is someone else sitting in my seat...... They eventually called the desk and had her moved, but it was the weirdest boarding experience I've had.. and I've flown Spirit. These planes that Delta fly's are SO OLD. Both times I have flown Delta the "turbulence" has been so bad and cold air was blowing right on my the whole flight with no option to turn it off (it wasn't from one of the vents, but from the side). Someone close to me works for Delta and I know for a fact that some of their engines blow mid-flight.. and they tell the passengers that it's turbulence.. so that doesn't make me feel very safe. I won't fly Delta again if there is another comparable option."
Pros: "Did not eat or use entertainment."
Pros: "Service"
Cons: "Long delay"
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"

Book cheap flights from Aspen to Chicago Midway Airport

Recent one-way flight deals

1/11Wed
1 stopDelta
8h 57mASE-MDW
$253
12/18Sun
1 stopDelta
8h 13mASE-MDW
$313
3/13Mon
3 stopsMultiple Airlines
22h 04mASE-MDW
$399
3/13Mon
3 stopsMultiple Airlines
22h 04mASE-MDW
$406
2/4Sat
1 stopDelta
7h 38mASE-MDW
$483
2/4Sat
2 stopsMultiple Airlines
9h 00mASE-MDW
$508
3/13Mon
2 stopsMultiple Airlines
15h 00mASE-MDW
$617
3/13Mon
2 stopsMultiple Airlines
15h 00mASE-MDW
$633
12/12Mon
2 stopsMultiple Airlines
18h 32mASE-MDW
$634
3/13Mon
1 stopDelta
6h 46mASE-MDW
$649
1/3Tue
2 stopsMultiple Airlines
28h 41mASE-MDW
$691
12/27Tue
1 stopDelta
6h 49mASE-MDW
$743
12/11Sun
2 stopsMultiple Airlines
14h 29mASE-MDW
$749
2/19Sun
1 stopDelta
6h 46mASE-MDW
$779
1/16Mon
2 stopsMultiple Airlines
9h 23mASE-MDW
$791
12/27Tue
2 stopsMultiple Airlines
17h 23mASE-MDW
$812
2/19Sun
2 stopsDelta
19h 08mASE-MDW
$833
12/26Mon
2 stopsMultiple Airlines
17h 23mASE-MDW
$848
3/12Sun
2 stopsMultiple Airlines
17h 49mASE-MDW
$862
12/26Mon
1 stopDelta
6h 49mASE-MDW
$1,099

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Aspen - Chicago Midway Airport Flights

Departure:

Aspen (ASE)United States

Destination:

Chicago Midway Airport (MDW)United States

Return flight deals:

Chicago Midway Airport - Aspen

Cabin classes:

Browse origins:

$1,205