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296 € Cheap Flights from Chicago to Aspen

Compare Chicago to Aspen flight deals

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

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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 338 €. Find the lowest prices on one-way and return tickets right here.
Aspen.296 € per passenger.Departing Mon, 4 Jan, returning Thu, 7 Jan.Return flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Mon, 4 Jan, arriving in Aspen.Inbound direct flight with United departs from Aspen on Thu, 7 Jan, arriving in Chicago O'Hare International.Price includes taxes and charges.From 296 €, select.
Aspen.305 € per passenger.Departing Tue, 15 Sep, returning Thu, 1 Oct.Return flight with United.Outbound indirect flight with United, departs from Chicago O'Hare International on Tue, 15 Sep, arriving in Aspen.Inbound indirect flight with United, departs from Aspen on Thu, 1 Oct, arriving in Chicago O'Hare International.Price includes taxes and charges.From 305 €, select.
Aspen.338 € per passenger.Departing Sun, 5 Jul, returning Tue, 14 Jul.Return flight with United.Outbound indirect flight with United, departs from Chicago O'Hare International on Sun, 5 Jul, arriving in Aspen.Inbound indirect flight with United, departs from Aspen on Tue, 14 Jul, arriving in Chicago O'Hare International.Price includes taxes and charges.From 338 €, select.
Aspen.351 € per passenger.Departing Sun, 2 Aug, returning Fri, 7 Aug.Return flight with United.Outbound indirect flight with United, departs from Chicago O'Hare International on Sun, 2 Aug, arriving in Aspen.Inbound indirect flight with United, departs from Aspen on Fri, 7 Aug, arriving in Chicago O'Hare International.Price includes taxes and charges.From 351 €, select.
Aspen.361 € per passenger.Departing Mon, 6 Jul, returning Wed, 15 Jul.Return flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Mon, 6 Jul, arriving in Aspen.Inbound direct flight with United departs from Aspen on Wed, 15 Jul, arriving in Chicago O'Hare International.Price includes taxes and charges.From 361 €, select.
Aspen.362 € per passenger.Departing Mon, 29 Jun, returning Fri, 3 Jul.Return flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Mon, 29 Jun, arriving in Aspen.Inbound direct flight with United departs from Aspen on Fri, 3 Jul, arriving in Chicago O'Hare International.Price includes taxes and charges.From 362 €, select.
Aspen.363 € per passenger.Departing Mon, 1 Feb, returning Mon, 8 Feb.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Mon, 1 Feb, arriving in Aspen.Inbound indirect flight with Delta, departs from Aspen on Mon, 8 Feb, arriving in Chicago Midway.Price includes taxes and charges.From 363 €, select.
Aspen.369 € per passenger.Departing Sun, 21 Jun, returning Tue, 23 Jun.Return flight with United.Outbound indirect flight with United, departs from Chicago O'Hare International on Sun, 21 Jun, arriving in Aspen.Inbound indirect flight with United, departs from Aspen on Tue, 23 Jun, arriving in Chicago O'Hare International.Price includes taxes and charges.From 369 €, select.
Aspen.391 € per passenger.Departing Sat, 5 Sep, returning Tue, 8 Sep.Return flight with United.Outbound indirect flight with United, departs from Chicago O'Hare International on Sat, 5 Sep, arriving in Aspen.Inbound indirect flight with United, departs from Aspen on Tue, 8 Sep, arriving in Chicago O'Hare International.Price includes taxes and charges.From 391 €, select.
Aspen.395 € per passenger.Departing Fri, 6 Nov, returning Sun, 8 Nov.Return flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Fri, 6 Nov, arriving in Aspen.Inbound direct flight with United departs from Aspen on Sun, 8 Nov, arriving in Chicago O'Hare International.Price includes taxes and charges.From 395 €, select.
Aspen.428 € per passenger.Departing Fri, 26 Jun, returning Tue, 30 Jun.Return flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Fri, 26 Jun, arriving in Aspen.Inbound direct flight with United departs from Aspen on Tue, 30 Jun, arriving in Chicago O'Hare International.Price includes taxes and charges.From 428 €, select.
Aspen.433 € per passenger.Departing Tue, 15 Dec, returning Sun, 20 Dec.Return flight with United.Outbound indirect flight with United, departs from Chicago O'Hare International on Tue, 15 Dec, arriving in Aspen.Inbound indirect flight with United, departs from Aspen on Sun, 20 Dec, arriving in Chicago O'Hare International.Price includes taxes and charges.From 433 €, select.
Aspen.450 € per passenger.Departing Fri, 9 Oct, returning Sun, 11 Oct.Return flight with United.Outbound indirect flight with United, departs from Chicago O'Hare International on Fri, 9 Oct, arriving in Aspen.Inbound indirect flight with United, departs from Aspen on Sun, 11 Oct, arriving in Chicago O'Hare International.Price includes taxes and charges.From 450 €, select.
Aspen.473 € per passenger.Departing Sat, 20 Mar, returning Wed, 24 Mar.Return flight with United.Outbound indirect flight with United, departs from Chicago O'Hare International on Sat, 20 Mar, arriving in Aspen.Inbound indirect flight with United, departs from Aspen on Wed, 24 Mar, arriving in Chicago O'Hare International.Price includes taxes and charges.From 473 €, select.
Aspen.575 € per passenger.Departing Thu, 30 Jul, returning Sun, 2 Aug.Return flight with United.Outbound indirect flight with United, departs from Chicago O'Hare International on Thu, 30 Jul, arriving in Aspen.Inbound indirect flight with United, departs from Aspen on Sun, 2 Aug, arriving in Chicago O'Hare International.Price includes taxes and charges.From 575 €, select.

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 January.
Jun
from 369 €
Jul
from 338 €
Aug
from 351 €
Sep
from 391 €
Oct
from 450 €
Nov
from 395 €
Dec
from 433 €
Jan
from 296 €
Feb
from 363 €
Mar
from 473 €
Apr
Find prices
May
Find prices

Direct flights 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.

Aspen

6km from central Aspen
ClosestCheapest
from 296 €
Search flights

Vail Eagle County

51km from central Aspen
from 365 €
Search flights

Gunnison

73km from central Aspen
from 328 €
Search flights

Chicago to Aspen: Flight information

The things to know before you go.
Cheapest flight found296 €
Cheapest month to flyJanuary
Average flight time3 hrs, 16 mins
Most popular airlineSkyWest Airlines
Average flights per week237

Finding cheap flights from Chicago to Aspen: Frequently asked questions

The best price we found for a return flight from Chicago to Aspen is 296 €. 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 16 minutes is the average flight time from Chicago to Aspen.
SkyWest Airlines, American Airlines and United fly direct from Chicago to Aspen.
As of June 2026, there are 79 flights per week flying from Chicago to Aspen.
The cheapest month to fly from Chicago to Aspen is usually January.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Aspen Airport on Monday, 4 January 2027.
Yes – the average flight time is 3 hours and 16 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 .

Travelling from Chicago to Aspen Pitkin County Airport (ASE): What you need to know

  • Chicago's main airport is Chicago O'Hare International Airport (ORD). Check out your options for departing from here when searching for flights from Chicago to Aspen Pitkin County Airport (ASE).

  • Expect to be travelling for 3 hours 20 minutes. That's the average duration of a direct Chicago to Aspen Pitkin County Airport flight.

  • The timezone in Aspen is UTC-7, which is one hour behind Chicago. Aspen Pitkin County Airport is located in Aspen.

  • The busiest route is from Chicago O'Hare International Airport (ORD) to Aspen Pitkin County Airport (ASE), with 23 direct services every week. If you're not one for hanging around, the earliest flight from ORD to ASE is the 8am American Airlines option. If a later start suits your schedule, the last departure is at 8:20pm with United Airlines.

  • To ensure you get on your flight from Chicago to ASE, allow plenty of time for things like check-in and baggage drop. Turning up two hours ahead of international departures and an hour before domestic flights is the general rule.

  • July is a busy travel month. If you're heading away then or during a major holiday like Thanksgiving, be there even earlier. Aim for at least two hours ahead for domestic flights and up to four hours for international journeys.

Airports in Chicago

Chicago O'Hare International Airport (ORD)

  • Go straight to your destination from Chicago O'Hare International Airport (ORD). Nonstop flights from Chicago to Aspen Pitkin County Airport (ASE) operate from here.

  • United Airlines is a leading airline that offers direct flights from Chicago to Aspen Pitkin County Airport jetting out of ORD.

  • Most travellers prefer to book seats with United from ORD to ASE.

  • Among carriers on this route, United has the best record for on-time arrivals.

  • Located around 27 kilometres from the centre of Chicago, ORD can be reached in about 30 minutes by car, depending on traffic. The journey by public transport will take roughly 45 minutes.

  • In search of a convenient hotel near Chicago O'Hare International Airport? If you're catching an early flight from Chicago to Aspen Pitkin County Airport, these stays will put you just around the corner from the terminal:

  • When it comes to the on-time performance of Chicago O'Hare International Airport, data shows 70% of flights arrive within the scheduled time frame.

  • ORD is located at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • You can get to MDW from central Chicago in approximately 25 minutes by car, depending on traffic conditions. The journey by public transport will take roughly 30 minutes to cover the 16 kilometres or so.

  • Want to treat yourself to an extra night away before your Chicago to ASE flight? Kick back in a hotel near Chicago Midway International Airport before your adventure officially starts. These stays are expecting you:

  • 76% of flights taking off from Chicago Midway International Airport make it to their destination as expected.

  • The street address for MDW is 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • RFD is roughly 145 kilometres from central Chicago. Driving from the city centre to the terminal takes about 1 hour 40 minutes. If you're considering public transport, expect a journey of around 2 hours.

  • Make catching an early Chicago to Aspen Pitkin County Airport flight the easiest part of your trip. Stay at one of these accommodation options close to Chicago Rockford International Airport and get to your departure gate without rushing:

  • Flights departing from RFD land at their destination as scheduled 71% of the time.

  • The street address of Chicago Rockford International Airport is 2 Airport Cir.

About Aspen Pitkin County Airport (ASE)

  • Have a late flight from Chicago to Aspen Pitkin County Airport? Don't let it leave you bleary-eyed. Stay at one of these hotels near ASE and hit the lights earlier:

  • To lock in the lowest price, book your vehicle around four weeks ahead of your Chicago to Aspen Pitkin County Airport flight.

  • ASE is located at 233 East Airport Road.

Getting from Aspen Pitkin County Airport (ASE) to central Aspen

  • Aspen Pitkin County Airport is roughly 5 kilometres from central Aspen. How long it takes to get there in a taxi or car hire depends on the time of day. Do a little research before your trip.

  • Travelling by public transport takes around 20 minutes.

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

  • Right now, 148 € is the best price we've found for a one-way ticket from Chicago to Aspen Pitkin County Airport. The cheapest price for a return flight is 296 €. Remember fares can change due to demand at the time of booking.

  • To score cheap flights from Chicago to ASE, book your ticket two months before your planned departure.

  • Schedule your trip for July. That's the best month for landing the biggest deals on Chicago to Aspen Pitkin County Airport tickets. If you're flexible with your dates, use the 'Whole month' tool to find the cheapest price across each month.

  • Never miss a deal on plane tickets from Chicago to ASE by setting up a Price Alert. We'll send you an email or notification through the app when fares go down.

  • Filters make it easier to dig up a deal for your flight from Chicago to Aspen Pitkin County Airport. Choose the airlines, flight times and stops that make sense for you. Then sort the results by 'Cheapest' to find the best price quickly.

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

  • It's time to work out your travel dates for your flight from Chicago to Aspen Pitkin County Airport (ASE). March is when most people travel to Aspen. If you prefer a quieter vibe, head there in May.

  • The warmest month in Aspen is July, with temperatures ranging between 4ºC (39ºF) and 26ºC (79ºF). Book your Chicago to ASE plane ticket then if you enjoy this type of weather.

  • Search for cheap tickets from Chicago to Aspen Pitkin County Airport in January if you like travelling in cooler conditions. Temperatures are at their lowest then, ranging between -20ºC (-4ºF) and 0ºC (32ºF).

More about Aspen

  • Once you've booked your flight from Chicago to Aspen Pitkin County Airport, choose a hotel that puts you where you want to be. Make one of these accommodation options your base for exploring Aspen:

  • Your visit to Aspen wouldn't be complete without a bit of sightseeing. Top attractions worth exploring include Aspen Mountain Ski Resort - Aspen Skiing Company, Aspen Mountain and Conundrum Hot Springs.

Explore more of the United States

  • Denver is just one of the many places in the United States waiting to be discovered after you've seen Aspen. Around 177 kilometres away to the east, popular attractions include Denver Art Museum, Meow Wolf Denver's Convergence Station and Ballpark.

  • Colorado Springs is another standout destination in the United States and is around 177 kilometres east of Aspen. No journey is complete without visiting Garden of the Gods, Pikes Peak Region Attractions and Red Rock Canyon.

Plan the rest of your trip from Chicago to Aspen

Prices shown on this page are estimated lowest prices only. Found in the last 12 days.