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Reliable Flight Search results

Chicago (ORD) → Aspen (ASE)

Best trips

2 nonstop, 24 with 1 connection · ranked by overall best · published legroom for 26 of 26 · showing the top 3

  1. Our best overall pick

    71% chance you arrive on time · nonstop · 30 in legroom · planes about 2 years old · 3h 15m

    Top pick#1 · Nonstop · 3h 15m

    7:45 PM → 10:00 PM

    50

    score

    price

    live on Aviasales

    71%

    arrive on time

    7:45 PM ORD → 10:00 PM ASE3h 15m

    SkyWest 5254 · sold as United Express, Delta Connection, American Eagle or Alaska

    Embraer E175 · 1–12 yrs oldLegroom 30–32 in · 18–19.3 in wide · Main Cabin
    73% on time · 2.4% cancel
    Find 7:45 PM flight fares Opens this date on Aviasales
  2. #2 · 1 connection · 5h 01m · one ticket (United)

    5:00 AM → 8:59 AM

    41

    score

    price

    live on Aviasales

    92%

    connections made

    74%

    arrive on time

    5:00 AM ORD → 6:41 AM DEN2h 41m

    United 2666

    Airbus A321neo · 1–13 yrs oldLegroom 30–31 in · 16.3–18.4 in wide · United Economy
    93% on time · 0.5% cancel
    Connect in DEN · 1h 19m · 96% chance to make it · same ticket: the airline rebooks you if you miss it

    8:00 AM DEN → 8:59 AM ASE1h 01m

    SkyWest 5782 · sold as United Express

    Embraer E175 · 2–12 yrs oldLegroom 31 in · 18–18.2 in wide · United Economy
    81% on time · 3.7% cancel
    Find this United trip Look for United 2666 + SkyWest 5782 on Aviasales
  3. #3 · 1 connection · 7h 09m · one ticket (United)

    5:00 AM → 11:09 AM

    36

    score

    price

    live on Aviasales

    94%

    connections made

    77%

    arrive on time

    5:00 AM ORD → 6:41 AM DEN2h 41m

    United 2666

    Airbus A321neo · 1–13 yrs oldLegroom 30–31 in · 16.3–18.4 in wide · United Economy
    93% on time · 0.5% cancel
    Connect in DEN · 3h 24m · 99% chance to make it · same ticket: the airline rebooks you if you miss it

    10:05 AM DEN → 11:09 AM ASE1h 04m

    SkyWest 5444 · sold as United Express

    Embraer E175 · 2–12 yrs oldLegroom 31 in · 18–18.2 in wide · United Economy
    82% on time · 5.0% cancel
    Find this United trip Look for United 2666 + SkyWest 5444 on Aviasales

Aircraft and ages come from the planes each flight number actually flew in the last 3 months of data (FAA registry build years); airlines can swap planes. Legroom is the seat pitch the airline or a seat-map source publishes for that aircraft and cabin; we never estimate it, and seat maps change, so check the airline’s seat map when you book.

ORD → ASE

Chicago to Aspen: 1,042 nonstop flights a year

On time (12 months)

61%

Cancelled

2.6%

avg delay 40 min

Best time to leave

6 to 9 PM

74% on time vs 50% noon to 3 PM

Most reliable airline

SkyWest

60% chance on time

Check ORD to ASE fares

Fares open on our travel partner (Aviasales). Pick the flight number you chose here.

Airlines on this route

Season-adjusted chance of operating and arriving on time.

  • SkyWest Airlines (sold as United Express, Delta Connection, American Eagle or Alaska)60%

    1,042 flights · 61% on time as flown · 2.6% cancel

On time by departure time

All airlines, scheduled local departure, Jun 2025 to May 2026.

  • Before 9 AM65%

    140 flights · avg delay 36 min

  • 9 AM to noon58%

    464 flights · avg delay 36 min

  • Noon to 3 PM50%

    154 flights · avg delay 50 min

  • 3 to 6 PM63%

    127 flights · avg delay 30 min

  • 6 to 9 PM74%

    157 flights · avg delay 56 min

Best day: Wednesday (71%). Worst: Friday (55%).

Historical odds, not a guarantee. Built from the US DOT Bureau of Transportation Statistics on-time reports (Jun 2025 to May 2026), FAA ground stop and delay program advisories, and 20 years of airport weather observations. Covers US airlines that report to the DOT; schedules are flights operated recently, so confirm times when you book. ATIS Alerts is not affiliated with any airline. Fares are what Aviasales travelers saw in recent searches (USD, one way, 1 adult), not live quotes; the partner site shows the current price. Fare links go to our travel partner and may earn us a commission at no cost to you. Affiliate disclosure