Flight Routes from Aspen to Chicago

Compare cheap outbound and return flights from Aspen (ASE) to Chicago (CHI) and find the best offer from numerous airlines and travel agencies.

Cheapest roundtrip flight: from€560
Fastest flight: 2h 47min
non-stop flights: 37x / week
Flight distance: 1,650 km
Time difference: +1 hour
Airports in Chicago: O'Hare International Airport, IL
Midway International Airport, IL
Rockford, IL

Cheap flight offers from Aspen to Chicago

sorted by price and recency

filtersRound tripnon-stop flight

Thu, Dec 31, 2026 – Fri, Jan 29, 2027
13:00 – 21:29
ASE–CHI
7h 29min
1 stopover
09:10 – 11:48
CHI–ASE
3h 38minnon-stop flight
€574
Thu, Dec 31, 2026 – Fri, Jan 29, 2027
11:07 – 19:30
ASE–CHI
7h 23min
1 stopover
16:00 – 18:31
CHI–ASE
3h 31minnon-stop flight
€572
Thu, Dec 31, 2026 – Fri, Jan 29, 2027
15:26 – 21:29
ASE–CHI
5h 3min
1 stopover
12:59 – 15:30
CHI–ASE
3h 31minnon-stop flight
€560
Thu, Dec 31, 2026 – Fri, Jan 29, 2027
12:47 – 16:50
ASE–CHI
3h 3minnon-stop flight
12:36 – 16:27
CHI–ASE
4h 51min
1 stopover
€3,114
Thu, Dec 31, 2026 – Fri, Jan 29, 2027
15:44 – 20:03
ASE–CHI
3h 19minnon-stop flight
11:45 – 14:29
CHI–ASE
3h 44minnon-stop flight
€725

Important flight information

Discover more flights around Aspen and Chicago

Departure airport	Airport Aspen Pitkin County Airport, CO (ASE)
Arrival airport	Airport Chicago-IL, all airports (CHI)
Destination country	Flights to United States
Departure airport - Destination country	Aspen Pitkin County Airport, CO - United States

Alternative routes to United States

Flight Aspen - Atlanta from 677 $
Flight Aspen - Chicago O'Hare from 560 $
Flight Aspen - Charlotte from 608 $
Flight Aspen - White Plains-NY from 628 $
Flight Aspen - Milwaukee from 556 $
Flight Aspen - Los Angeles from 518 $
Flight Aspen - Rapid City from 1.172 $
Flight Aspen - Phoenix - Sky Harbor from 612 $
Flight Aspen - Gillette from 536 $
Flight Aspen - Midland-Odessa from 496 $

Alternative flights to Chicago

Flight New York - Chicago from 273 $
Flight Los Angeles - Chicago from 328 $
Flight Las Vegas - Chicago from 333 $
Flight Boston - Chicago from 94 $
Flight Washington-DC - Chicago from 267 $
Flight Atlanta - Chicago from 120 $
Flight Orlando - Chicago from 210 $
Flight Miami - Chicago from 426 $
Flight Denver - Chicago from 200 $
Flight Fort Myers - Chicago from 493 $

Flight destinations with a similar price

Flight Chicago - Amman from 886 $
Flight Chicago - Madrid from 572 $
Flight Chicago - London from 303 $
Flight Chicago - Cancun from 409 $
Flight Chicago - Guadalajara from 321 $
Flight Chicago - Morelia from 375 $
Flight Chicago - Puerto Vallarta from 389 $
Flight Chicago - Durango from 632 $
Flight Chicago - Rome from 608 $
Flight Chicago - San Jose, Costa Rica from 430 $

Flight destinations with a similar price

Flight Aspen - Chicago O'Hare from 560 $
Flight Aspen - Charlotte from 608 $
Flight Aspen - Milwaukee from 556 $
Flight Aspen - Los Angeles from 518 $
Flight Aspen - Phoenix - Sky Harbor from 612 $
Flight Aspen - Gillette from 536 $
Flight Aspen - Lexington from 567 $
Flight Aspen - Salt Lake City from 555 $
Flight Aspen - Boise from 558 $
Flight Aspen - Traverse City from 583 $