$222 Find Cheap Flights from Aspen to Chicago - Compare and Save

These are the earliest and latest flight times currently scheduled from Aspen to Chicago:

• Earliest: departs at 7:50 am and lands at 10:59 am
• Latest: departs at 4:39 pm and lands at 7:48 pm.

The flight takes about 3h 09m.

Two cabin classes are available on flights from Aspen to Chicago:

• Economy Class
• First Class

A nonstop flight from Aspen to Chicago takes about 3h 09m, covering 1,024 miles.

No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID or another TSA-accepted form of identification.

Round-trip flights from Aspen to Chicago range from $343 to $533, with an average of $416 over the past 12 months. Anything below $343 counts as a good deal.

On this route, nonstop flights are cheaper than layover options on average. Nonstop fares average $414 round-trip, compared to $604 via a layover through Denver Intl (DEN).

There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $40–$100 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

Afternoon is most often the busiest departure period on Aspen to Chicago flights, with 66% of flights leaving in that window. The rest depart in the morning.

Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $443 to $1,821. That means the highest observed fare was about 4x higher than the lowest one.

American Airlines is typically the only airline on the Aspen to Chicago route offering in-flight Wi-Fi. Pricing depends on fare class.

One-way fares from Aspen to Chicago are currently higher than usual. Average one-way flight prices are about $320, which is 5% above the typical average for this route.

Since Chicago is served by multiple airports, car rental options and rates can vary depending on which one you fly into.
Near Chicago O'Hare Intl Airport (ORD) — daily rates averaging $63:

• Routes Car & Truck Rentals
• Europcar
• Hertz
• Ace
• Dollar

Near Chicago Midway Airport (MDW) — daily rates averaging $86:

• Hertz
• Dollar
• Budget
• Alamo
• Rent-A-Wreck

Near Chicago Greater Rockford Airport (RFD) — daily rates averaging $81:

• Alamo
• Enterprise Rent-A-Car
• Budget
• Avis
• National

Flights from Aspen to Chicago usually depart from Aspen Pitkin County (ASE) and may arrive at several airports in Chicago area, including Chicago Midway (MDW), Chicago O'Hare Intl (ORD) and Chicago Greater Rockford (RFD).

Most connecting flights from Aspen to Chicago pass through Denver Intl (DEN), which handles 100% of one-stop traffic on this route.

Yes. Flexible dates can save you up to 42% on flights from Aspen to Chicago. Tuesday is the cheapest departure day at $381 round-trip on average, while Saturday is the most expensive at $646, a difference of $265.

KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

Only United Airlines and American Airlines currently operate flights between Aspen and Chicago on a regular basis.

Chicago is 1 hour ahead of Aspen (Central Time vs Mountain Time). Plan for the time shift when scheduling connections or first-day activities.

Some of the most popular sights in Chicago are Magnificent Mile, Grant Park and Soldier Field. These are among the most viewed places in Chicago on KAYAK.

American Airlines and United Airlines offer free seat selection on this route. Availability depends on fare class.

Only American Airlines currently offers extra legroom on this route. Availability can vary by aircraft type and fare class.

Here are some options for this route, based on selected ticket types and cabin classes:

• American Airlines: a cabin bag and a checked bag in First Class
• United Airlines: a cabin bag in Economy Class class

Bag allowance can vary by ticket type, cabin class, route and airline, so always check the fare details before booking.