$207 Find Cheap Flights from Aspen to Chicago - Compare and Save

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

• Earliest: departs at 8:15 am and lands at 11:23 am
• Latest: departs at 4:22 pm and lands at 7:30 pm.

The flight takes about 3h 08m.

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

• Economy Class
• First Class

A nonstop flight from Aspen to Chicago takes 3h 08m, 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 $353 to $522, with an average of $416 over the past 12 months. Anything below $353 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 $495 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.

Morning is the busiest departure period on Aspen to Chicago flights, with 50% of flights leaving in that window. Afternoon departures account for 50%, evening flights for 0%, and night flights for 0%.

Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $413 to $1,239. That means the highest observed fare was about 3x higher than the lowest one.

American Airlines is 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 lower than usual. Average one-way flight prices are about $222, which is 28% below 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 from around $17:

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

Near Chicago Midway Airport (MDW) — daily rates from around $32:

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

Near Chicago Greater Rockford Airport (RFD) — daily rates from around $28:

• 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.

2 airlines operate flights between Aspen and Chicago. The airlines offering nonstop flights on this route include:

• United Airlines
• American Airlines

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.

Among airlines operating Aspen to Chicago flights:

• American Airlines: offers extra legroom; offers free seat selection
• United Airlines: offers extra legroom; offers free seat selection

Extra legroom and free seat selection availability depends on fare class and route.

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

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