Cheap flights from Aspen to Chicago (ASE - CHI)

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The best prices from Aspen Pitkin County to Chicago are usually found in May or August, booked 40 days in advance, depart on a Thursday or Saturday and return on a Monday

How to find the cheapest flight from
Aspen (ASE) to Chicago (CHI)

All the information you need to plan the best ASE to CHI flight in 2022: compare Aspen to Chicago flight prices with the expected peak season, weather and rainfall in Chicago.
ASE - CHI
Price
$226 - $559
CHI
Temperature
23 - 73.4 °F
CHI
Precipitation
1.7 - 4.9 inches

Popular in

November

High demand for flights, 28% potential price rise

Cheapest in

May

Best time to find cheap flights, 44% potential price drop

Average price

$521

Average for round-trip flights in January 2022

Round-trip from

$226

From Aspen Pitkin County to Chicago (CHI)

Flight route prices based on searches on Cheapflights within the last 3 days, monthly prices based on aggregated historical data.
When is the cheapest time to fly from Aspen to Chicago (ASE - CHI)?

It’s optimal to fly from Aspen to Chicago in the afternoon. By choosing this option you can save up to 6% on the cost of your flight, compared to a flight at noon.

What is the cheapest day to fly round-trip from Aspen to Chicago?

Departing on a Wednesday is a good option for securing a great price. You can expect to save up to 55% when planning your travel around this day of the week.

How far in advance should I book a flight from Aspen to Chicago?

Travelers have found it’s best to book a flight 39 days in advance to save up to 47% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 39 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from Aspen to Chicago 1-2 weeks in advance for as low as $454, or $592 for flights within the next 24 hours.

What is the cheapest month to fly from Aspen to Chicago?

May can be a great time to fly to Chicago from Aspen with a flight ticket averaging about $404. Cheapflights users have found deals in the month of May for as cheap as $226. The most expensive prices can be found in the month of November.

Cheap flights from Aspen to Chicago in January, February 2022

The best prices found for ASE to CHI flights for January, February
9 Feb - 11 Feb
$249pp
ASE
Aspen Pitkin County
American Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
ASE
Aspen Pitkin County
10 Feb - 14 Feb
$270pp
ASE
Aspen Pitkin County
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
ASE
Aspen Pitkin County
10 Feb - 13 Feb
$279pp
ASE
Aspen Pitkin County
United Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
ASE
Aspen Pitkin County

Aspen Pitkin County to Chicago 2022 flight deals

Cheap flights to Chicago from Aspen found for this year
9 Feb - 11 Feb
$249pp
ASE
Aspen Pitkin County
American Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
ASE
Aspen Pitkin County
10 Feb - 14 Feb
$270pp
ASE
Aspen Pitkin County
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
ASE
Aspen Pitkin County
10 Feb - 13 Feb
$279pp
ASE
Aspen Pitkin County
United Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
ASE
Aspen Pitkin County

Non-stop flights to Chicago from Aspen

Save time with Aspen to Chicago direct flight deals
10 Feb - 14 Feb
$270pp
ASE
Aspen Pitkin County
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
ASE
Aspen Pitkin County
10 Feb - 15 Mar
$294pp
ASE
Aspen Pitkin County
American Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Non-Stop
ASE
Aspen Pitkin County
3 Mar - 7 Mar
$298pp
ASE
Aspen Pitkin County
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
ASE
Aspen Pitkin County

Last minute flights from Aspen to Chicago

Late deals on round-trip flights to Chicago from Aspen, departing today and this week
26 Jan - 28 Jan
$490pp
ASE
Aspen Pitkin County
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
ASE
Aspen Pitkin County
26 Jan - 28 Jan
$499pp
ASE
Aspen Pitkin County
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
 
1 STOP
ASE
Aspen Pitkin County
26 Jan - 28 Jan
$508pp
ASE
Aspen Pitkin County
United Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
 
1 STOP
ASE
Aspen Pitkin County

One-way flights to Chicago from Aspen

The cheapest one-way flights from Aspen to Chicago
11:18 am - 6:28 am
American Airlines
1 Stop
18h 10m
ASE - ORD
American Airlines
10:02 am - 5:05 pm
Delta
1 Stop
6h 03m
ASE - MDW
Delta
$419
Delta
7:34 am - 5:59 pm
Multiple Airlines
2 Stops
9h 25m
ASE - MDW
Multiple Airlines
$458
United

Related info for your journey

Useful info, stats and facts about <span class="emphasized">Aspen</span> to <span class="emphasized">Chicago</span> flights.

Flight FAQs

From Aspen to Chicago

What airport do you fly from for flights from Aspen to Chicago?

Most people fly from Aspen Pitkin County (ASE) if they book a flight from Aspen to Chicago. On average, Pitkin County has 7 outbound flights to Chicago per day from 3 airlines. Aspen Pitkin County is conveniently located just 3.5 mi from Aspen’s city center.

Which airlines flying from Aspen Pitkin County to Chicago have flexible cancellations due to COVID-19?

United Airlines, American Airlines, and Delta are some of the carriers that may have flexible cancellation policies. You can use our site to filter for other airlines that may also have this kind of flexibility.

Can I find flights from Aspen to Chicago for under $300 on Cheapflights?

Yes, there are multiple flights from Aspen to Chicago for under $300. The cheapest flight booked recently is on American Airlines for just $249, but on average you can expect to pay $299.

Are there nonstop flights from Aspen to Chicago for under $300 on Cheapflights?

Cheapflights has at least 20 direct flights from Aspen to Chicago under $300. A good price for a nonstop flight from Aspen to Chicago is less than $376.

Are there last-minute flights available from Aspen to Chicago for under $500?

There are currently 18+ open flights from Aspen to Chicago within the next 7 days for less than $500.

What are the cheapest airlines flying from Aspen to Chicago round-trip?

According to our current data, American Airlines ($249), and United Airlines ($270) offers the cheapest pricing from Aspen to Chicago. Users have found that American Airlines is 38% cheaper than the other options available to this destination.

What are the cheapest airlines to fly from Aspen to Chicago one-way?

$219 is the cheapest one-way deal found within the past few days, from United Airlines. You may also be able to find cheap deals on American Airlines and Delta, with prices starting from $228 and $358, respectively.

What are the cheapest flights from Aspen to Chicago?

While on average a flight from Aspen to Chicago is generally $427, our data shows the cheapest flight currently is $98. When looking at the most popular route, (Aspen Pitkin County - Chicago O'Hare Intl), you can expect to pay $394 for that flight.

What are the most reliable airlines from Aspen to Chicago?

Before booking your flight to Chicago from Aspen, check out the most reliable airlines to get you to your destination on time: Lufthansa (43%), United Airlines (38%), SkyWest Airlines( 36%).

What are the most popular airlines that fly from Aspen to Chicago?

The most popular airlines flying from Aspen to Chicago are American Airlines, Delta and United Airlines. Something to consider prior to booking your flight.

COVID Restrictions

View COVID Travel Restrictions for Chicago, IL

Do I need a COVID test to fly to Chicago from Aspen?

Information is based on travel restrictions for travel to Chicago within the United States

Most visitors from Aspen Pitkin County need to provide a negative COVID-19 test result and/or quarantine to enter Chicago.

COVID-19 testing requirements
Visitors from Aspen Pitkin County must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 24 hours before departing to Chicago.

Quarantine requirements
Visitors from Aspen Pitkin County are not required to quarantine after entering Chicago.

Do I need a test to fly back to Aspen from Chicago?

Returning to Aspen Pitkin County from Chicago

COVID-19 testing requirements
Visitors from Chicago must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 24 hours before departing to Aspen Pitkin County.

Quarantine requirements
Visitors from Chicago are not required to quarantine after entering Aspen Pitkin County.

Hide COVID Travel Restrictions for Chicago, IL

Alternative routes for Aspen to Chicago

See prices for flight routes from nearby airports that may be better suited for you.

Destination information for Chicago

Things to know before you go - useful duration and weather info for your trip from Aspen to Chicago.
Flight duration from ASE to Chicago
3h 04m
Average temperature for January in Chicago
33.8 °F
Avg rainfall for January in Chicago
0.7 ″

Airports servicing Aspen

Airports servicing Chicago

Midway (MDW)
Rockford (RFD)

Top 3 airlines flying from Aspen Pitkin County to Chicago

The chart below displays the airlines Cheapflights users traveling from Aspen to Chicago choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
Airline Cheapest Average Flexibility On-time COVID-19 safety
American Airlines
$297 $397 No cancel fee 71%
United Airlines
$342 $463 No cancel fee 69%
Delta
$370 $476 No cancel fee N/A

Hourly flight availability from Aspen to Chicago

See what time of day planes typically take off from Aspen towards Chicago.
Morning 6 AM to noon 52% of ASE to CHI departures
Afternoon Noon to 6 PM 47% of ASE to CHI departures
Early morning Midnight to 6 AM 1% of ASE to CHI departures
Evening 6 PM to midnight 0% of ASE to CHI departures
Midnight
6 AM
Noon
6 PM
Weekly flight availability
from Aspen to Chicago
See how many times per day planes take to the skies headed from Aspen to Chicago.
Sunday
8 daily flights
Monday
7 daily flights
Tuesday
8 daily flights
Wednesday
7 daily flights
Thursday
8 daily flights
Friday
8 daily flights
Saturday
6 daily flights
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