$187 Find Cheap Flights from Aspen to Chicago - Compare and Save

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.

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

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).

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 travelers should check the fare details before booking.

Only Economy Class is available on flights from Aspen to Chicago.

On this route, layover flights are cheaper than nonstop options on average. Layover fares average $385 round-trip via Denver Intl (DEN), compared to $406 for nonstop.

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.

Connecting flights from Aspen to Chicago most commonly pass through:

• Denver Intl (DEN) - 50% of one-stop connections
• Dallas/Fort Worth (DFW) - 50% of one-stop connections
Together, these airports account for 100% of one-stop bookings on this route.

Yes. Being flexible with your travel dates can save you up to 43% on the Aspen to Chicago route. Thursday is the cheapest departure day at $369 round-trip on average, while Saturday is the most expensive at $646, a difference of $277. KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

Morning is the busiest departure period on Aspen to Chicago flights, with 100% of flights leaving in that window. Afternoon departures account for 0%, evening flights for 0%, and night flights for 0%.

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

A nonstop flight from Aspen to Chicago takes 3h 08m, covering 1,024 miles.

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

• Earliest: departs at 7:00 am and lands at 10:08 am
• Latest: departs at 1:54 pm and lands at 5:02 pm.

The flight takes about 3h 08m.

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.

Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $373 to $2,953. That means the highest observed fare was about 8x higher than the lowest one.

One-way fares from Aspen to Chicago are currently lower than usual. Average one-way flight prices are about $192, which is 40% below the typical average for this route.

Flying via Denver Intl (DEN) gives the shortest average 1-stop total travel time at 4h 34m, compared with 7h 24m via Dallas/Fort Worth (DFW).

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

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
· Dollar
· Ace

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 $30:

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

Round-trip flights from Aspen to Chicago range from $365 to $509, with an average of $405 over the past 12 months. Anything below $365 counts as a good deal.

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