Cheap flight tickets from Aspen to Chicago

Compare Aspen to Chicago flight deals

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

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Flight deals from Aspen to Chicago

Looking for a cheap last-minute deal or the best return flight from Aspen to Chicago? Find the lowest prices on one-way and return tickets right here.

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 March.

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 foundRM1,259
Cheapest month to flyMarch
Average flight time3 hrs, 5 mins
Most popular airlineSkyWest Airlines
Average flights per week86

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 RM1,259. 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 5 minutes is the average flight time from Aspen to Chicago.
SkyWest Airlines, United and Lufthansa fly direct from Aspen to Chicago.
As of December 2025, there are 86 flights per week flying from Aspen to Chicago.
The cheapest month to fly from Aspen to Chicago is usually March.
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 RM1,259.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Aspen Airport to Chicago on Thursday, 12 March 2026.
Yes – the average flight time is 3 hours and 5 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 December, the average temperature is usually around -2°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, United offers the cheapest flight tickets to Chicago.

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

  • Expect to be travelling for 3 hours 15 minutes. That's the average duration of a direct flight from Aspen Airport to Chicago.

  • Aspen Airport is located in Aspen. Following the UTC-5 timezone, Chicago is one hour ahead of Aspen.

  • With 18 weekly flights between the two airports, Aspen Airport (ASE) to O'Hare International Airport (ORD) is the most popular route. United Airlines operates the earliest flight at 08:00. If you're eager to make the most of your day before you fly, the latest departure from ASE to ORD is with United Airlines at 16:30.

  • Give yourself plenty of time to get on your ASE to Chicago flight. Generally, it's best to arrive two hours before international departures and an hour ahead for domestic flights.

  • If you're travelling during a bank holiday or another peak period, give yourself more time. A good general rule is two hours before domestic flights and up to four hours before international departures. Lines at check-in and security will be longer.

  • You can book a direct Aspen Airport to Chicago ticket. Begin your journey at ASE and land at O'Hare International Airport (ORD).

  • United Airlines is a well-known carrier that offers direct flights from Aspen Airport to Chicago.

  • ASE is about 5 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 traffic. If you're planning to take public transport, expect the journey time to be around 25 minutes.

  • Looking for a hotel close to ASE? If you're boarding an early flight from Aspen Airport to Chicago, these stays will put you moments from your departure gate:

  • Of the departures from Aspen Airport, 56.67% land on time at their destination.

  • You'll find ASE at 233 East Airport Road.

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

  • RM891 is the lowest price we've found for a one-way Aspen Airport to Chicago flight. A return flight ticket right now is RM1,259. Depending on the availability and when you book, these fares may change.

  • Book two months before you want to fly. Pricing trends show that this is the ideal window for finding cheap flights from ASE to Chicago.

  • The best month for scoring cheap Aspen Airport to Chicago tickets is June. Use the 'Whole month' tool to compare flight prices, then choose the dates that offer the biggest savings.

  • Cut down on the time spent looking for cheap flights from ASE to Chicago by creating a Price Alert. You'll get an email or push notification on the app when a lower fare pops up.

  • Find an affordable flight from Aspen Airport to Chicago with the help of our filters. Select your preferred departure time, duration and airlines, then sort the results by 'Cheapest' for the best deals.

Airports in Chicago

O'Hare International Airport (ORD)

  • O'Hare International Airport (ORD) to the centre of Chicago takes about 35 minutes to reach by car. The centre is roughly 40 kilometres away.

  • If you're taking public transport, expect a journey time of around 55 minutes.

  • If you have a late flight from Aspen Airport to Chicago, few things beat the convenience of staying near the terminal. Grab your luggage from the carousel and then be showered and relaxing not long after at one of these hotels near ORD:

  • Grab an O'Hare International Airport rental car and discover Chicago and beyond with your own wheels. Routes Car Rentals, Dollar and Budget are well-known companies to choose from here.

  • Booking your ride from O'Hare International Airport about four weeks in advance of your flight from ASE to Chicago can help you lock in the best possible rate.

  • You'll find ORD at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • The centre of Chicago is located around 19 kilometres from Chicago Midway International Airport (MDW). After your flight from Aspen Airport to Chicago has touched down and you've made your way out of the airport, expect a drive of about 20 minutes.

  • If you're catching public transport, it'll take about 45 minutes.

  • After stepping off your ASE to Chicago flight, rest your head at a hotel close to MDW. These are some comfortable options that'll help you slip into relaxation mode:

  • Forget about public transport schedules or long cab queues. Pick up a Chicago Midway International Airport rental car and let your trip unfold on your terms. Compare availability and rates from Dollar, Hertz and Budget.

  • Get what you want, not just what's left over. Securing your ride from MDW four weeks in advance often means lower prices and a bigger choice of vehicles.

  • Chicago Midway International Airport can be found at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • Make your way to the city centre after your flight from Aspen Airport to Chicago has arrived. Central Chicago is about 137 kilometres from Chicago Rockford International Airport (RFD) and takes roughly 1 hour 25 minutes to reach by car.

  • If you're using public transport, the journey takes around 4 hours 15 minutes.

  • If you don't want to make the trip into the centre, head for a hotel near RFD. Make yourself comfortable at one of these options after your ASE to Chicago flight:

  • Take control of the next part of your trip by picking up a Chicago Rockford International Airport rental car. Budget, Alamo and National will get you on the road.

  • Rental companies sometimes offer promotions on early bookings, so reserve your vehicle from RFD well ahead of your flight from Aspen Airport to Chicago. A little prep work can make a big difference in cost.

  • Chicago Rockford International Airport's official address is 2 Airport Cir.

Best time to go to Chicago

  • Carefully consider your dates before securing your flight from Aspen Airport to Chicago. The city buzzes in high season, but hotel prices are typically higher and major attractions can get busy. Plan your trip to Chicago in the low season if you like a more relaxed vibe.

  • The warmest month in Chicago is July, with temperatures ranging between 15ºC (59ºF) and 29ºC (84ºF). Book your Aspen Airport to Chicago flight ticket then if you enjoy this type of weather.

  • Search for cheap tickets from ASE to Chicago in January if you'd rather travel during cooler conditions. Temperatures are at their lowest then, ranging between -12ºC (10ºF) and 3ºC (37ºF) on average.

More about Chicago

Explore more of United States

  • You've seen Chicago, now it's time to discover other parts of United States. Travel around 451 kilometres south-east to Columbus to tick off its leading attractions. From Franklin Park Conservatory and Botanical Gardens to Ohio Statehouse and German Village, you'll have a full itinerary ahead.

  • Around 257 kilometres south-east of Chicago, Indianapolis is another essential stop in United States. Experience major highlights starting with The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo.

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