$121 Find Cheap Flights from Aspen to Illinois

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Aspen to Illinois departing on 3/17. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Illinois

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Aspen to Illinois, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Aspen to Illinois, as well as popular online travel agencies
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Flight Deals

Cheap Flights from Aspen to Illinois

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Chicago
Chicago1 stop$275
St. Louis
St. Louis1 stop$269
Chicago
Chicago1 stop$275
St. Louis
St. Louis1 stop$269

Book Cheap Aspen to Illinois Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Aspen to Illinois that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Aspen to Illinois

Fri, Mar 6 - Mon, Mar 9
United Airlines Logo
7:56 am - 2:43 pm
ASE
-
STL
5h 47m
1 stop
United Airlines Logo
5:55 pm - 9:42 pm
STL
-
ASE
4h 47m
1 stop
$269United Airlines
Fri, Apr 10 - Sun, Apr 19
United Airlines Logo
6:19 pm - 12:30 am
ASE
-
ORD
5h 11m
1 stop
United Airlines Logo
9:14 am - 11:33 am
ORD
-
ASE
3h 19mnonstop
$275United Airlines
Fri, Apr 10 - Sun, Apr 19
United Airlines Logo
6:19 pm - 12:30 am
ASE
-
ORD
5h 11m
1 stop
United Airlines Logo
7:00 am - 12:25 pm
ORD
-
ASE
6h 25m
1 stop
$285United Airlines
Wed, Mar 11 - Mon, Mar 16
American Airlines Logo
3:46 pm - 7:47 pm
ASE
-
ORD
3h 01mnonstop
American Airlines Logo
7:15 am - 9:37 am
ORD
-
ASE
3h 22mnonstop
$289American Airlines
Wed, Mar 11 - Mon, Mar 16
American Airlines Logo
2:47 pm - 11:36 pm
ASE
-
ORD
7h 49m
1 stop
American Airlines Logo
10:18 am - 12:49 pm
ORD
-
ASE
3h 31mnonstop
$299American Airlines
Wed, Mar 11 - Mon, Mar 16
American Airlines Logo
3:46 pm - 7:47 pm
ASE
-
ORD
3h 01mnonstop
American Airlines Logo
12:24 pm - 2:52 pm
ORD
-
ASE
3h 28mnonstop
$304American Airlines
Wed, Jun 10 - Mon, Jun 15
United Airlines Logo
3:25 pm - 9:39 pm
ASE
-
ORD
5h 14m
1 stop
United Airlines Logo
5:00 am - 8:46 am
ORD
-
ASE
4h 46m
1 stop
$309United Airlines
Wed, Jun 10 - Mon, Jun 15
Delta Logo
8:05 am - 4:25 pm
ASE
-
MDW
7h 20m
1 stop
Delta Logo
6:00 am - 11:29 am
MDW
-
ASE
6h 29m
1 stop
$629Delta
Wed, Jun 10 - Mon, Jun 15
Delta Logo
8:05 am - 6:31 pm
ASE
-
MDW
9h 26m
2 stops
Delta Logo
6:00 am - 11:29 am
MDW
-
ASE
6h 29m
1 stop
$724Delta
Fri, Apr 10 - Mon, Apr 20
Delta Logo
1:45 pm - 10:31 pm
ASE
-
MDW
7h 46m
1 stop
Delta Logo
6:00 am - 11:38 am
MDW
-
ASE
6h 38m
1 stop
$784Delta
Booking Insights

KAYAK's insights & trends for Aspen to Illinois flights

Get data-powered insights and trends into flights from Aspen to Illinois to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Aspen to Illinois flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Illinois from Aspen found in the last 72 hours was to Chicago, at $268 round-trip. The most popular route is from Aspen (ASE) to Chicago O'Hare Intl Airport (ORD), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $268.

Can I save money by flying with a layover from Aspen to Illinois?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $402 on average.

What’s the cheapest day of the week to fly from Aspen to Illinois?

The average price of all round-trip flights from Aspen to Illinois clicked on KAYAK for each day over the last 12 months.

Your flight ticket price will generally be cheaper if you fly to Illinois on a Thursday and more expensive on a Monday. On your return trip to Aspen, you should consider flying back on a Sunday, and avoid Thursdays for better deals.

Good to know

Low seasonApril
Cheapest flight$121
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly and prices are also 7% lower on average.
Flight from Aspen to Chicago O'Hare Airport

FAQs - booking Illinois flights

  • How does KAYAK find such low prices on flights from Aspen to Illinois?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Aspen to Illinois.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Aspen to Illinois?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Aspen to Illinois is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Aspen to Illinois?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Aspen to Illinois with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Aspen to Illinois?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Aspen to Illinois up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Illinois?

    The cheapest time of day to fly to Illinois is generally in the afternoon, when round-trip flights cost $444 on average. Morning departures are around 4% more expensive than evening flights, on average. The most expensive time of day to fly to Illinois is generally in the morning, which is peak travel time and where the average cost of a ticket is $496.

Top tips for finding cheap flights to Illinois

  • Looking for a cheap flight? 25% of our users found tickets from Aspen to the following destinations at these prices or less: Chicago $303 one-way - $311 round-trip

Reviews of the top airlines flying from Aspen to Illinois

 
See real verified KAYAK customer reviews for airlines flying from Aspen to Illinois. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Aspen to Illinois? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.4
United AirlinesOverall score based on 9325 reviews
7.7Boarding
8.1Crew
7.3Comfort
6.6Food
7.1Entertainment
Airline reviews

Crew was great (professional, attentive, prompt). Snacks for 4 hrs flight is deplorable.

8.0 ExcellentDarly, Feb 2026
LAX - ORD
Read more United Airlines reviews

Crew was great (professional, attentive, prompt). Snacks for 4 hrs flight is deplorable.

United Airlines is my preferred airlines and I am thankful for Gary who also help support me on the phone to switch my flight literally last min.

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

It was a pretty standard flight... until the almost hour and a half spent on the taxi way. I get that the weather has been poor but the delay had nothing to do with the weather and more to do with a plane with several issues tying up the gate. I get that that happens from time to time but this has been EVERY flight I've been on for the past 5 years and I fly 3 to 5 times a year. This isn't just United... it's American, it's Delta. It's an issue with the entire industry. I work for UPS and packages on a cargo plane get better service than people do these days. Anymore I HATE flying.

Perfect flight. Smooth flight. Arrived 20 minutes early at destination. Excellent service.

The flights were on time which was great give. It was holiday travel season and there’d been some weather issues. The only complaint and this is every time with United is the terrible seat design. The head rest is not built for comfort and having my neck bent forward for a cross country trip reminded me while I try not to take United flights as a rule.

Everything was absolutely wonderful from check in to baggage claim. Staff was very professional and sweet. Will definitely recommend United to family and friends.

They did the one thing that really matters - got to Chicago early.

The flight was on time. I generally don’t drink or eat on short flights and the seats were good and the flight attendants were friendly. That’s all I expect

It was nice to have gotten up upgraded to first class with a meal on a three hour flight

The gate agent had a really bad attitude and refused to help me get on the standby list. She just handed me a card and said I needed to call a number. I asked her to help with the AA app on my phone and she just shrugged and said she didnt know. After a few phone calls, I eventually just went to a different gate agent on the other side of the terminal and got the help I needed.

Overall, my last three trips on American Airlines have all been either delayed or "rescheduled" due to mechanical issues. At least on delay caused me to miss two possible connecting flights each later than the first. My last option for my last connection required the assistance of the onsite service desk (O'Hare Airport). The wait time for the service desk was such that it jeopardized getting booked on the last connecting flight available for the night. Suffice it to say, my latest experiences with American Airlines have caused me extensive loss of productive business and personal time and can therefore be classified as significantly less than satisfactory.

Waiting for gate in RDU for more than 20mins is crazy.

American Airlines was great and worked very hard to change my ticket so I could get an earlier, direct flight back to Dallas. However, I was informed that Kayak made mistakes with my itinerary and classified my ticket as desiring to be on the earlier flight instead of taking the necessary step of calling AA to get me on the standby list. This ended up keeping me from being added to the standby list and delayed me getting home by 6 hours. I am happy to discuss this further with Kayak so they can correct their procedures so this won't happen again.

Waited for oxygen tanks for 30 minutes after boarding was complete.

We flew in first class. The crew did not offer drinks before the flight took off, but they treated us well during the flight. The food was excellent. There was actually too much food served, but it was nice to have all the options.

Update to handle the delay was very bad, crews no smiles or welcome or thanks. Don’t care attitude

Pilot navigated severe weather/snow storm with skill. Described his intentions clearly

Little warm on the plane and delayed for an hour

So excited very proud first of all I wanna thank kayak all updates very professional and fast alart And amazing cabin crew so nice to me they deserve big salute

Everything you need to know for your flight from Aspen to Illinois

Information on your arrival and departure airports