Chicago to Vail flights in October 2027
Saved fares include round trips from $373 and one-way flights from $215 for one adult in economy. Fare observations: October 29, 2026.
Departure airports: Chicago (ORD,MDW). Destination: Vail (EGE).
ORD → EGE · October 2027 · One adult in economy
| Travel dates | Airline | Stops | Total (USD) |
|---|---|---|---|
| Oct 1, 2027 · One way | Delta Air Lines | Up to 1 stop each way | $215.10 |
| Oct 1, 2027 · One way | American Airlines | Nonstop | $224.10 |
| Oct 1, 2027 – Oct 4, 2027 · 3 nights | Delta Air Lines | Up to 1 stop each way | $377.10 |
| Oct 1, 2027 – Oct 4, 2027 · 3 nights | American Airlines | Nonstop | $386.10 |
| Oct 1, 2027 – Oct 8, 2027 · 7 nights | Delta Air Lines | Up to 1 stop each way | $377.10 |
| Oct 1, 2027 – Oct 8, 2027 · 7 nights | American Airlines | Nonstop | $386.10 |
| Oct 2, 2027 · One way | Delta Air Lines | Up to 1 stop each way | $215.10 |
| Oct 2, 2027 · One way | American Airlines | Nonstop | $224.10 |
| Oct 2, 2027 – Oct 5, 2027 · 3 nights | American Airlines | Up to 1 stop each way | $372.60 |
| Oct 2, 2027 – Oct 5, 2027 · 3 nights | Delta Air Lines | Up to 1 stop each way | $377.10 |
| Oct 3, 2027 · One way | Delta Air Lines | Up to 1 stop each way | $215.10 |
| Oct 3, 2027 · One way | American Airlines | Nonstop | $224.10 |
| Oct 3, 2027 – Oct 6, 2027 · 3 nights | Delta Air Lines | Up to 1 stop each way | $377.10 |
| Oct 3, 2027 – Oct 6, 2027 · 3 nights | American Airlines | Nonstop | $386.10 |
| Oct 4, 2027 · One way | Delta Air Lines | Up to 1 stop each way | $215.10 |
| Oct 4, 2027 · One way | American Airlines | Nonstop | $224.10 |
| Oct 4, 2027 – Oct 7, 2027 · 3 nights | Delta Air Lines | Up to 1 stop each way | $377.10 |
| Oct 4, 2027 – Oct 7, 2027 · 3 nights | American Airlines | Nonstop | $386.10 |
| Oct 5, 2027 · One way | United Airlines | Up to 1 stop each way | $215.10 |
| Oct 5, 2027 · One way | American Airlines | Nonstop | $224.10 |
| Oct 5, 2027 – Oct 8, 2027 · 3 nights | Delta Air Lines | Up to 1 stop each way | $377.10 |
| Oct 5, 2027 – Oct 8, 2027 · 3 nights | American Airlines | Nonstop | $386.10 |
| Oct 6, 2027 · One way | Delta Air Lines | Up to 1 stop each way | $215.10 |
| Oct 6, 2027 · One way | American Airlines | Nonstop | $224.10 |
| Oct 7, 2027 · One way | Delta Air Lines | Up to 1 stop each way | $215.10 |
| Oct 7, 2027 · One way | American Airlines | Nonstop | $224.10 |
| Oct 8, 2027 · One way | Delta Air Lines | Up to 1 stop each way | $215.10 |
| Oct 8, 2027 · One way | American Airlines | Nonstop | $224.10 |
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Hotels in Vail with Axel
Axel books the hotel too, at private rates shown beside the public rate for the same stay. Hotels in Vail has the best recent deals, and a flight booked with Axel can make the hotel cheaper through the bundle.
Where to stay: Where to stay in Vail: the 2 best neighborhoods, ranked
Hotel details in Vail: Antlers at Vail · Four Seasons Resort and Residences Vail · Marriott's StreamSide Birch at Vail · Residence Inn by Marriott Vail · The Hythe, a Luxury Collection Resort, Vail · All 30 hotels in Vail
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