Cheap Flights from Aspen to Chicago

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Find the cheapest month or even day of the year to fly to Chicago

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Find the cheapest month to fly from Aspen to Chicago

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

Direct flights from Aspen to Chicago

Alternative Aspen to Chicago routes

Looking for the cheapest, fastest or easiest route from Aspen to Chicago? You could fly into the following airports instead.

Aspen to Chicago: Flight information

The things to know before you go.
Cheapest flight foundRs40,718
Cheapest month to flyJune
Average flight time2 hrs, 59 mins
Most popular airlineSkyWest Airlines
Average flights per week63

Finding cheap flights from Aspen to Chicago: Frequently asked questions

There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.
The best price we found for a return flight from Aspen to Chicago is Rs66,594. 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.
2 hours and 59 minutes is the average flight time from Aspen to Chicago.
SkyWest Airlines, United and American Airlines fly direct from Aspen to Chicago.
As of April 2025, there are 63 flights per week flying from Aspen to Chicago.
The cheapest month to fly from Aspen to Chicago is usually April 2025.
If you're flying from Aspen Airport, the cheapest airport near Chicago is Chicago O'Hare International – which is 25.4 km away from the centre of Chicago. We've found flights into this airport from Rs66,594.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Aspen Airport to Chicago on Friday, 6 June 2025.
Yes – the average flight time is 2 hours and 59 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 Chicago 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 Chicago is around 40 days in advance, so don’t leave your flight to the last minute.
In April, the average temperature is usually around 8°C. July is typically the warmest month in Chicago, when it usually averages around 26°C. You can expect the least rain in January. The coldest month is January, with temperatures averaging -8°C. The rainiest month is August.
Currently, American Airlines offers the cheapest flight tickets to Chicago.

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

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

  • The timezone in Chicago is UTC-5. The city is 1 hour ahead of Aspen, where Aspen Airport is located.

  • Aspen Airport (ASE) to O'Hare International Airport (ORD) is the most popular route, with 45 flights a week to pick from. If you have things to finalize before heading off, the last flight from ASE to ORD is with United at 16:00. Opt for the first departure with United at 08:00 if you want to get on your way earlier.

  • For stress-free travel, turn up at the airport two hours ahead of international flights and an hour before domestic departures. This way, you'll have plenty of time to board your flight from ASE to Chicago.

  • Travelling during a peak month like July? Popular seasons (like summer, Thanksgiving, Christmas and spring break) can easily add another hour at security. Be extra safe and arrive up to four hours before international flights and two hours before a domestic departure.

  • You can book a direct flight from Aspen Airport to Chicago that lands at O'Hare International Airport (ORD).

  • Keep an eye out for promotions from United. This airline operates direct flights from Aspen Airport to Chicago.

  • You won't need your passport or a visa to fly within United States. You will need a valid identity document however, such as a driver's licence or an ID card. Put them on your packing list after booking your cheap tickets from Aspen Airport to Chicago.

  • ASE is around 6 kilometres from central Aspen. If you're ride-sharing, catching a cab or driving from the centre, it'll take you 10 minutes or so to get there, depending on the traffic. If you're planning to take public transport, expect the journey time to be around 26 minutes.

  • In search of a handy hotel near ASE? If you're catching an early flight from Aspen Airport to Chicago, these accommodation options will put you moments from your check-in counter:

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

  • The lowest price we've seen for a one-way ticket from Aspen Airport to Chicago is Rs40,718. The cheapest price for a return flight is Rs66,594. Keep in mind fares may change due to demand at the time of booking.

  • To pick up cheap tickets from ASE to Chicago, book your journey 10 months before the departure date.

  • The cheapest month for tickets from Aspen Airport to Chicago is June. Compare prices using the 'Whole month' tool to find the dates with the lowest fares.

  • Set up a Price Alert for flight tickets from ASE to Chicago. There's no need to look every day to see if prices have fallen. We'll update you the moment the price changes.

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

Airports in Chicago

O'Hare International Airport (ORD)

Chicago Midway International Airport (MDW)

Best time to go to Chicago

  • It's time to plan your dates for your flight from Aspen Airport to Chicago. August is the busiest month for a trip to Chicago. If you like a more peaceful vibe, go in February.

  • Lock in your flight from Aspen Airport to Chicago for July to visit the city during its warmest month. Expect temperatures to range from 15ºC to 29ºC.

  • If you like travelling in cooler conditions, search for a cheap flight from ASE to Chicago in January when temperatures average between -12ºC and 3ºC.

More about Chicago

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

  • There are so many things to discover in this city it can be tricky to work out where to start. Millennium Park, Art Institute of Chicago and LandShark Beer Garden at Navy Pier are leading attractions which should be on every Chicago itinerary.

Complete your Chicago trip with a car rental

  • Choose one of our car rentals in Chicago and explore the city on your own schedule. Easily compare options in one go to find the ideal ride once you've booked your hotel and cheap flights from Aspen Airport to Chicago.

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