Cheap flights from Aspen (ASE) to Chicago (CHI)

ASE — CHI
Oct 9 — Oct 161

The best prices from Aspen Pitkin County to Chicago are usually found in October or November, booked 60 days in advance, depart on a Saturday or Friday and return on a Friday

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

$374 - $791

CHI

Temperature

23 - 73.4 °F

CHI

Rainfall

1.7 - 4.9 inches

Popular inFebruaryHigh demand for flights, 32% potential price rise
Cheapest inOctoberBest time to find cheap flights, 30% potential price drop
Average price$374Average for round-trip flights in October 2022
Round-trip from$374From Aspen Pitkin County to Chicago (CHI)

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

Departing on a Friday is a good option for securing a great price. You can expect to save up to 99% 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 61 days in advance to save up to 67% 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 61 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 $662, or $787 for flights within the next 24 hours.

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

October can be a great time to fly to Chicago from Aspen with a flight ticket averaging about $538. Cheapflights users have found deals in the month of October for as cheap as $286. The most expensive prices can be found in the month of February.

When is the cheapest time to fly from Aspen to Chicago (ASE - CHI)?

It’s optimal to fly from Aspen to Chicago at noon. By choosing this option you can save up to 19% on the cost of your flight, compared to a flight in the evening.

Cheap flights from Aspen to Chicago in October, November 2022

The best prices found for ASE to CHI flights for October, November
Nov 1 - Nov 8
ASE

Aspen Pitkin County

ORD

Chicago O'Hare Intl

1 stop

5h 56m
ORD

Chicago O'Hare Intl

ASE

Aspen Pitkin County

1 stop

6h 13m
$378

United Airlines

Pick Dates

Deal found 10/3/22

Oct 27 - Oct 28
ASE

Aspen Pitkin County

ORD

Chicago O'Hare Intl

Nonstop

2h 58m
ORD

Chicago O'Hare Intl

ASE

Aspen Pitkin County

Nonstop

3h 04m
$380

United Airlines

Pick Dates

Deal found 10/1/22

Oct 27 - Oct 28
ASE

Aspen Pitkin County

ORD

Chicago O'Hare Intl

Nonstop

2h 58m
ORD

Chicago O'Hare Intl

ASE

Aspen Pitkin County

1 stop

6h 30m
$389

United Airlines

Pick Dates

Deal found 10/1/22

Aspen to Chicago 2022 flight deals

Cheap flights to Chicago from Aspen found for this year
Nov 1 - Nov 8
ASE

Aspen Pitkin County

ORD

Chicago O'Hare Intl

1 stop

5h 56m
ORD

Chicago O'Hare Intl

ASE

Aspen Pitkin County

1 stop

6h 13m
$378

United Airlines

Pick Dates

Deal found 10/3/22

Oct 27 - Oct 28
ASE

Aspen Pitkin County

ORD

Chicago O'Hare Intl

Nonstop

2h 58m
ORD

Chicago O'Hare Intl

ASE

Aspen Pitkin County

Nonstop

3h 04m
$380

United Airlines

Pick Dates

Deal found 10/1/22

Dec 17 - Jan 3
ASE

Aspen Pitkin County

ORD

Chicago O'Hare Intl

1 stop

4h 42m
ORD

Chicago O'Hare Intl

ASE

Aspen Pitkin County

Nonstop

3h 18m
$389

United Airlines

Pick Dates

Deal found 10/3/22

Cheap United Airlines flights from Aspen to Chicago

Nov 1 - Nov 8
ASE

Aspen Pitkin County

ORD

Chicago O'Hare Intl

1 stop

5h 56m
ORD

Chicago O'Hare Intl

ASE

Aspen Pitkin County

1 stop

6h 13m
$378

United Airlines

Pick Dates

Deal found 10/3/22

Oct 27 - Oct 28
ASE

Aspen Pitkin County

ORD

Chicago O'Hare Intl

Nonstop

2h 58m
ORD

Chicago O'Hare Intl

ASE

Aspen Pitkin County

Nonstop

3h 04m
$380

United Airlines

Pick Dates

Deal found 10/1/22

Dec 17 - Jan 3
ASE

Aspen Pitkin County

ORD

Chicago O'Hare Intl

1 stop

4h 42m
ORD

Chicago O'Hare Intl

ASE

Aspen Pitkin County

Nonstop

3h 18m
$389

United Airlines

Pick Dates

Deal found 10/3/22

Cheap American Airlines flights from Aspen to Chicago

Dec 17 - Jan 3
ASE

Aspen Pitkin County

ORD

Chicago O'Hare Intl

1 stop

5h 39m
ORD

Chicago O'Hare Intl

ASE

Aspen Pitkin County

1 stop

8h 35m
$483

American Airlines

Pick Dates

Deal found 10/1/22

Dec 17 - Jan 3
ASE

Aspen Pitkin County

ORD

Chicago O'Hare Intl

2 stops

15h 00m
ORD

Chicago O'Hare Intl

ASE

Aspen Pitkin County

1 stop

9h 41m
$487

American Airlines

Pick Dates

Deal found 10/1/22

Nov 12 - Nov 14
ASE

Aspen Pitkin County

ORD

Chicago O'Hare Intl

1 stop

17h 43m
ORD

Chicago O'Hare Intl

ASE

Aspen Pitkin County

2 stops

15h 53m
$503

American Airlines

Pick Dates

Deal found 10/2/22

Non-stop flights to Chicago from Aspen

Save time with Aspen to Chicago direct flight deals
Oct 27 - Oct 28
ASE

Aspen Pitkin County

ORD

Chicago O'Hare Intl

Nonstop

2h 58m
ORD

Chicago O'Hare Intl

ASE

Aspen Pitkin County

Nonstop

3h 04m
$380

United Airlines

Pick Dates

Deal found 10/1/22

Oct 19 - Oct 25
ASE

Aspen Pitkin County

ORD

Chicago O'Hare Intl

Nonstop

2h 58m
ORD

Chicago O'Hare Intl

ASE

Aspen Pitkin County

Nonstop

3h 04m
$400

United Airlines

Pick Dates

Deal found 10/3/22

Dec 17 - Jan 3
ASE

Aspen Pitkin County

ORD

Chicago O'Hare Intl

Nonstop

2h 52m
ORD

Chicago O'Hare Intl

ASE

Aspen Pitkin County

Nonstop

3h 09m
$425

United Airlines

Pick Dates

Deal found 10/4/22

Last minute flights from Aspen to Chicago

Late deals on return flights to Chicago from Aspen, departing today and this week
Oct 12 - Oct 16
ASE

Aspen Pitkin County

ORD

Chicago O'Hare Intl

1 stop

6h 25m
ORD

Chicago O'Hare Intl

ASE

Aspen Pitkin County

Nonstop

3h 04m
$489

United Airlines

Pick Dates

Deal found 10/1/22

Oct 12 - Oct 16
ASE

Aspen Pitkin County

ORD

Chicago O'Hare Intl

1 stop

6h 25m
ORD

Chicago O'Hare Intl

ASE

Aspen Pitkin County

1 stop

4h 38m
$498

United Airlines

Pick Dates

Deal found 10/1/22

Oct 12 - Oct 14
ASE

Aspen Pitkin County

ORD

Chicago O'Hare Intl

1 stop

6h 25m
ORD

Chicago O'Hare Intl

ASE

Aspen Pitkin County

Nonstop

3h 04m
$529

United Airlines

Pick Dates

Deal found 10/1/22

One-way flights to Chicago from Aspen

The cheapest one-way flights from Aspen to Chicago
Dec 16
ASE

Aspen Pitkin County

ORD

Chicago O'Hare Intl

Nonstop

2h 58m
$234

American Airlines

Pick Dates

Deal found 10/4/22

Jan 13
ASE

Aspen Pitkin County

MDW

Chicago Midway

1 stop

6h 46m
$243

Delta

Pick Dates

Deal found 10/3/22

Oct 28
ASE

Aspen Pitkin County

ORD

Chicago O'Hare Intl

1 stop

8h 16m
$243

American Airlines

Pick Dates

Deal found 10/4/22

Related info for your journey

Useful info, stats and facts about Aspen to Chicago flights.

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 2 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 $400 on Cheapflights?

Yes, there are multiple flights from Aspen to Chicago for under $400. The cheapest flight booked recently is on United Airlines for just $378, but on average you can expect to pay $449.

Are there nonstop flights from Aspen to Chicago for under $400 on Cheapflights?

Cheapflights has at least 7 direct flights from Aspen to Chicago under $400. A good price for a nonstop flight from Aspen to Chicago is less than $473.

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

There are currently 19+ 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, United Airlines ($378), and American Airlines ($483) offers the cheapest pricing from Aspen to Chicago. Users have found that United Airlines is 29% cheaper than the other options available to this destination.

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

$234 is the cheapest one-way deal found within the past few days, from American Airlines. You may also be able to find cheap deals on Delta and United Airlines, with prices starting from $243 and $279, respectively.

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.

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: Qatar Airways (93%), American Airlines (82%), SkyWest Airlines( 75%).

What are the cheapest flights from Aspen to Chicago?

While on average a flight from Aspen to Chicago is generally $703, our data shows the cheapest flight currently is $260. When looking at the most popular route, (Aspen Pitkin County - Chicago O'Hare Intl), you can expect to pay $378 for that flight.

Alternative routes for Aspen to Chicago

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

Top 3 airlines flying from Aspen 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.
AirlineCheapestAverageFlexibilityOn-timeCOVID-19 safety
American AirlinesCheapest$244Average$409FlexibilityNo cancel feeOn-time71%COVID-19 safety
Search American Airlines flights
United AirlinesCheapest$287Average$523FlexibilityNo cancel feeOn-time69%COVID-19 safety
Search United Airlines flights
DeltaCheapest$370Average$476FlexibilityNo cancel feeOn-timeN/ACOVID-19 safety
Search Delta flights

Hourly flight availability from Aspen to Chicago

See what time of day planes typically take off from Aspen to Chicago
0%of flight departuresEarly morningMidnight to 6 am
100%of flight departuresMorning6 am to noon
0%of flight departuresAfternoonNoon to 6 pm
0%of flight departuresEvening6 pm to midnight
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
Sunday2daily flights
Monday2daily flights
Tuesday4daily flights
Wednesday2daily flights
Thursday2daily flights
Friday2daily flights
Saturday2daily flights