Cheap flights from Aspen to Chicago

Aspen
ASE
Chicago FSS
CHI

Flight deals from Aspen to Chicago

Below you can see the best deals on flights Aspen — Chicago for upcoming dates. Direct and connecting flights from various airlines — compare prices and choose the right ticket.

The lowest price for the next 2 months is on 30 September, from $208.

Top 10 cheap flights from Aspen to Chicago

UA
$ 234

Aspen — Chicago

08:21—12:29
24 Sep 2026
3 h 8 m
Direct flight
AA
$ 235

Aspen — Chicago

07:00—11:05
24 Sep 2026
3 h 5 m
Direct flight
DL
DL
DL
$ 244

Aspen — Chicago

07:20—18:33
3 Sep 2026
10 h 13 m
2 stops
DL
DL
DL
$ 244

Aspen — Chicago

07:20—18:29
3 Sep 2026
10 h 9 m
2 stops
UA
$ 274

Aspen — Chicago

12:10—16:11
27 Aug 2026
3 h 1 m
Direct flight
UA
$ 274

Aspen — Chicago

09:00—13:08
27 Aug 2026
3 h 8 m
Direct flight
UA
$ 274

Aspen — Chicago

12:10—16:11
28 Aug 2026
3 h 1 m
Direct flight
UA
$ 274

Aspen — Chicago

09:00—13:08
28 Aug 2026
3 h 8 m
Direct flight
UA
$ 274

Aspen — Chicago

12:20—16:24
15 Sep 2026
3 h 4 m
Direct flight
UA
$ 274

Aspen — Chicago

12:10—16:11
26 Aug 2026
3 h 1 m
Direct flight

Prices were found in the last 72 hours and may change — check the exact price when you continue.

About the Aspen — Chicago flight

Looking for cheap flights from Aspen to Chicago? Compare fares from different airlines, check the flight schedule and travel time — and book your Aspen — Chicago ticket online at the best price.

The route has direct flights — around 45 flights per week, flights are operated by United Airlines, American Airlines, a nonstop flight takes about 3 h 4 min, the distance between the cities is around 1,649 km.

Planning your trip? You may find our Chicago travel guide, how to get from the airport into town and Chicago weather forecast useful. To catch a low fare, use the low-price calendar and the monthly price chart on this page.

Facts about this route

from $208Min. price
SeptemberCheapest
MarchPeak season
YesDirect flights
1,649 kmDistance
3 h 4 minTravel time
2Airlines
45 / wkFlights

Flight schedule from Aspen to Chicago

The table shows direct flights from Aspen to Chicago on the selected date. The flight takes approximately 3 h 4 min. Regular flights are operated by United Airlines and American Airlines. Departures from Aspen Airport airports, arrivals at O'Hare International Airport, Chicago Midway International Airport and Midway International Airport.

For each flight, the following details are shown: departure time (local), arrival city and airport, flight number and airline, terminal or gate, and status. Click on a flight to open its details and go to ticket search. To view flights on a different day, change the date above the table.

Today
Any time
Last update: 25 Aug 2026

Flight ticket prices by day: Aspen — Chicago

Below is a calendar of the lowest flight ticket prices for Aspen — Chicago by day. Pick a convenient date and instantly see the fare. The cheapest flights on this route start from $208 in September, and the most expensive are around $326 in March. If your travel dates are flexible, the calendar will help you find the best price for your preferred period. To view round-trip fares, switch to the "Round trip" tab above the calendar, select your departure date — and the right-hand calendar will highlight the lowest prices for return flights on each day.

 
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Prices by month

Average one-way fares from Aspen to Chicago by month. Tickets are usually cheapest in May (around $423) and priciest in January (about $629) — use the table and chart below to pick the best time to fly.

MonthAverage priceLevelMonthAverage priceLevelMonthAverage priceLevel
Jan$629highMay$423lowSep$617high
Feb$604highJun$508mediumOct$447low
Mar$532mediumJul$580highNov$435low
Apr$435lowAug$592highDec$629high

Some values are estimated based on seasonality.

When to fly

Weather in Chicago: it is warmest in July (up to 27 °C on average) and coolest in January (around 0 °C). The driest month is November.

Tickets are usually cheapest in September and most expensive in March. Compare prices and weather by month in the charts below to pick the best time to fly.

Temperature · Chicago

Dry and wet days · Chicago

Wind speed and direction · Chicago

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How to get the best deal on a Aspen — Chicago ticket

  • Book ahead: fares for Aspen — Chicago are usually lower 3–8 weeks before departure than at the last minute.
  • Play with your dates — Tuesday, Wednesday and Saturday departures are often cheaper than Friday and Sunday.
  • Flights Aspen — Chicago operate on Mondays, Tuesdays, Wednesdays, Thursdays, Fridays and Saturdays — keep that in mind when picking your travel dates.
  • The cheapest month to fly to Chicago is usually September — plan your trip around it if your dates are flexible.
  • Compare direct and connecting flights: nonstop is faster, while a connection is sometimes noticeably cheaper.
  • Watch the low-price calendar and the monthly price trend on this page — they make it easier to catch a good date.
  • Travelling light? Pick a cabin-baggage-only fare — tickets without checked luggage are noticeably cheaper.
  • Get to the airport in good time — about 2–3 hours before an international departure and roughly an hour before a domestic one.

Airlines

Flights on the Aspen — Chicago route are operated by 2 airlines; United Airlines runs the most flights (around 53% of all flights). Compare carriers, flight shares and schedules below.

  • United AirlinesUA
    8x/week
    WebsiteFleet: 956165M pax/year
    • Direct flight ASE → ORD8x/week
      Duration
      3h 7m
      Days
      MTWTFSS
    53.3%Open →
  • American AirlinesAA
    7x/week
    WebsiteFleet: 965211M pax/year
    • Direct flight ASE → ORD7x/week
      Duration
      3h 4m
      Days
      MTWTFSS
    46.7%Open →

Cities and airports on the Aspen — Chicago route

Flights Aspen — Chicago depart from Aspen Airport and arrive at O'Hare International Airport, Chicago Midway International Airport, Midway International Airport and Chicago Rockford International Airport. Below are pages for the cities, countries, and airports on the route: airlines, schedules, and travel guides.

Departure

Aspen

ASE
United States
About the cityHow to get thereWeatherAll about the country United States
Arrival

Chicago

CHI
United States
About the cityHow to get thereWeatherAll about the country United States
Departure airports
Arrival airports

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Frequently asked questions about the Aspen — Chicago flight

How long is the flight from Aspen to Chicago?

A nonstop Aspen — Chicago flight takes about 3 h 4 min — the distance between the cities is around 1,649 km.

How far is it from Aspen to Chicago?

The distance from Aspen to Chicago is about 1,649 km, which a nonstop flight covers in around 3 h 4 min.

Are there direct flights from Aspen to Chicago?

Yes, there are nonstop flights Aspen — Chicago — around 45 flights per week.

Which airlines fly from Aspen to Chicago?

Airlines operating Aspen — Chicago include United Airlines, American Airlines. See the full list with schedules in the "Airlines" section on this page.

Which airports do Aspen — Chicago flights use?

Flights from Aspen depart from Aspen Airport, and arrive at O'Hare International Airport, Chicago Midway International Airport, Midway International Airport. If a city has more than one airport, check which one your ticket uses before you travel.

How much is a ticket from Aspen to Chicago?

The price of a Aspen — Chicago ticket depends on your travel date, season and demand: it is usually cheapest to fly in September, and most expensive in March. Tickets typically cost between $208 and $326. Check the current lowest fare and low-price calendar on this page.

When is the best time to book flights Aspen — Chicago?

Flights Aspen — Chicago are usually cheaper when booked in advance — a few weeks before departure and away from peak dates; the most budget-friendly month to fly is September. Compare prices by month in the price trend chart on this page.

How can I find the cheapest flights from Aspen to Chicago?

To catch a low fare Aspen — Chicago, book a few weeks in advance, keep your dates flexible, and compare airlines and connecting options. The low-price calendar and monthly price chart on this page show the cheapest days and months at a glance: the most budget-friendly month to fly is usually September.

How early should I arrive at the airport?

For international flights, plan to be at the airport about 2–3 hours before departure, and around an hour before a domestic flight. Allow extra time during busy travel seasons and at large hubs, where check-in and security lines can be longer.

Where else you can fly from Aspen

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DenverLos AngelesDallasAustinHoustonAtlantaSan FranciscoPhoenixCharlotteLexingtonProvoManhattanRapid CityLas VegasLincoln

Where else you can fly from Chicago

See all
New York CityTorontoDetroitWashington, D.C.AtlantaMinneapolisLos AngelesSeattleBostonDallasHoustonOrlandoDenverLondonNashvilleIndianapolisSan DiegoMontrealSt. LouisMilwaukeeCharlottePhiladelphiaColumbusKansas CityMiamiPhoenixLas VegasCincinnatiGrand RapidsDes MoinesRaleighSan FranciscoMadisonDaytonGreen BayTampaPittsburghLouisvilleKnoxvilleRochester

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