C$251 Cheap Flights from Chicago (CHIA) to Aspen (ASE)

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Flight deals from Chicago to Aspen

Looking for a cheap last-minute deal or the best return flight from Chicago to Aspen Airport? If you want to travel next month, return fares start from C$474. Find the lowest prices on one-way and return tickets right here.

Find the cheapest month to fly from Chicago to Aspen

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago to Aspen flights are currently cheapest in June.

Which airlines fly from Chicago to Aspen?

Chicago to Aspen: Alternative routes

Compare routes from Chicago to Aspen below. You may find an airport to fly into that's cheaper, faster, or easier than Aspen.

Chicago to Aspen: Flight information

The things to know before you go.
Cheapest flight foundC$251
Cheapest month to flyJune
Average flight time3 hrs, 18 mins
Most popular airlineSkyWest Airlines
Average flights per week76

Finding cheap flights from Chicago to Aspen: Frequently asked questions

The best price we found for a return flight from Chicago to Aspen is C$474. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
3 hours and 18 minutes is the average flight time from Chicago to Aspen.
SkyWest Airlines, American Airlines and United fly direct from Chicago to Aspen.
As of April 2026, there are 76 flights per week flying from Chicago to Aspen.
The cheapest month to fly from Chicago to Aspen is usually May.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Aspen Airport on Monday, May 25, 2026.
Yes – the average flight time is 3 hours and 18 minutes.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Aspen but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Aspen is around 40 days in advance, so don’t leave your flight to the last minute.
The cheapest airline that flies to Aspen is United .

Flying from Chicago to Aspen Airport (ASE): what you need to know

  • All great adventures start at one of Chicago's main airports, O'Hare International Airport (ORD) or Chicago Midway International Airport (MDW). Explore your options for booking a flight from Chicago to Aspen Airport (ASE) taking off from either of these bases.

  • The average length of a direct flight from Chicago to Aspen Airport is 3 hours 8 minutes.

  • Aspen is 1 hour behind Chicago. Aspen Airport is located in Aspen, which operates on the UTC-6 timezone.

  • O'Hare International Airport (ORD) to Aspen Airport (ASE) is the most popular route. There are 22 direct weekly flights to choose from. If you prefer starting your day later, hop on the last flight with United at 20:00. Choose the first ORD to ASE departure with American Airlines at 08:15 if you want to get going earlier.

  • Arriving two hours before an international flight and one hour ahead of a domestic departure are travel rules worth sticking to. Get to the airport on time to board your flight from Chicago to ASE.

  • With more travellers during peak months like August, be at your terminal even earlier. Two hours for domestic flights and as much as four for international journeys will allow for extra wait times. Remember things also get busy during major holidays like July Fourth.

Airports in Chicago

O'Hare International Airport (ORD)

  • You can book a direct flight from Chicago to Aspen Airport (ASE) out of O'Hare International Airport (ORD).

  • When leaving from ORD, you can take a direct flight from Chicago to Aspen Airport with United.

  • From central Chicago, ORD is approximately 40 kilometres away. Use navigation apps or visit the official airport website to find the best way to get there.

  • Have an early flight from Chicago to Aspen Airport? Avoid the last-minute rush to the terminal (and enjoy a little extra shut-eye) by choosing one of these hotels near O'Hare International Airport:

Chicago Midway International Airport (MDW)

  • Chicago Midway International Airport (MDW) offers nonstop flights from Chicago to Aspen Airport (ASE).

  • United operates direct flights from Chicago to ASE departing from MDW. Book your preferred aisle (or window) seat and reach your destination in a single journey.

  • On public transport, you can travel from central Chicago to MDW in around 46 minutes. The airport is roughly 19 kilometres away, and making the journey by car takes approximately 21 minutes.

  • You're off on vacation, so why not extend it with an extra night away? Consider checking in to one of these hotels near Chicago Midway International Airport the day before your flight from Chicago to ASE:

About Aspen Airport (ASE)

Getting from Aspen Airport (ASE) to central Aspen

  • Aspen Airport to the centre of Aspen is about 10 minutes in a car. It's approximately 6 kilometres away. See what options are available, such as cabs, car rentals or ride-sharing.

  • Travelling to the centre by public transport will take you around 26 minutes.

How to find the cheapest flights from Chicago to Aspen Airport (ASE)

  • Pick up a one-way ticket from Chicago to Aspen Airport from C$251 or travel return from just C$474. The prices shown are based on availability and could change when you book.

  • Score flight tickets from Chicago to ASE by booking at least 10 months ahead. Based on flight price data, that's the sweet spot for picking up a bargain.

  • Organize your trip for July. That's the cheapest month for tickets from Chicago to Aspen Airport. If you're flexible with your travel dates, use the 'Whole month' tool to find the lowest price across each month.

  • Log into your online account or use the app to set up a Price Alert. We'll notify you right away if there's a better deal on this route. It doesn't take long, and it'll save you time searching for a cheap ticket from Chicago to ASE every day.

  • Tailor your flights with filters. Choose your ideal arrival and departure times, total journey duration and airlines. You can also sort the results by 'Best,' 'Fastest' or 'Cheapest' flights from Chicago to Aspen Airport.

The best time to fly from Chicago to Aspen Airport (ASE)

  • April is the quietest time to travel to Aspen. Alternatively, follow the crowds and take off in July. This is the most popular month for flights from Chicago to Aspen Airport, but the best time to go is your call.

  • The warmest month in Aspen is July, with temperatures ranging between 4ºC and 26ºC. Lock in your flights from Chicago to ASE in this month if this is the type of weather you enjoy.

  • Look for cheap flights from Chicago to Aspen Airport in December if you want to travel in cooler conditions. Temperatures are at their lowest around then, ranging between -19ºC and 1ºC on average.

More about Aspen

  • Start your Aspen trip off on the right foot by choosing the ideal place to stay. Once you've booked your flight from Chicago to Aspen Airport, browse our range of accommodation options including:

  • All great vacations should include some sightseeing. Aspen Mountain Ski Resort - Aspen Skiing Company, Aspen Art Museum and Wheeler Opera House are attractions you won't want to skip in Aspen.

Complete your Aspen trip with a car rental

  • Shut down all those tabs and leave the hard work to us. We can also help you find deals on car rentals in Aspen once you've booked your hotel and cheap flight from Chicago to Aspen Airport. Instantly compare prices all in one place and drive off with a bargain that fits your budget.

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.