Cheap flights from Chicago to Vail

One-way fares from $322 · CHI → EGE · prices found by travellers in the last 48 hours

Compare all dates Vail → Chicago
Cheapest fare
$322

United Airlines · Tue, Nov 10

Cheapest month
November

from $322

Direct flights
Not recently

Usually 1+ stop

Quickest trip
3h 43m

1,590 km

Get a price alert

We'll email you when Chicago → Vail drops to your price. It's free, and you can stop any time.

Today's cheapest fare is $322. We'll send one email to confirm. See our privacy policy.

Cheapest month to fly from Chicago to Vail

Lowest one-way fare per person in each month. Choose a month to see every date.

  1. November 2026 Cheapest $322

Cheapest dates in November 2026

The lowest fares we've seen for each day, cheapest first.

United Airlines
Depart10:55 Tue, Nov 10ORD → EGE 3h 48m · 1 stop
$322one way, per person
View deal
United Airlines
Depart07:00 Thu, Nov 26ORD → EGE 3h 43m · 1 stop
$382one way, per person
View deal
See every date in November 2026 →

Plan the rest of your trip to Vail

Where to stay, what to do and getting around, from our travel partners.

Where to stay

Hotels in VailCompare places to stay on Booking.com Find hotels →

Things to do

Things to do in VailTours, attractions and day trips on Klook Explore →

Getting around

Airport transfer in VailPre-book a driver to meet you at arrivals, with Kiwitaxi Book a transfer → Car hire in VailCompare rental cars from major brands on EconomyBookings Compare cars →

About flights from Chicago to Vail

Chicago (CHI) and Vail (EGE) are about 1,590 km apart. We haven't seen direct fares on this route recently, so expect at least one stop; the quickest journey we've seen takes about 3h 43m. Over the next few months, one-way fares start from $322, and November 2026 is currently the cheapest month to fly.

These prices come from searches travellers made in the last 48 hours, so they move quickly. If you see a good fare, it's worth booking soon. FlightsExp is free to use: you book directly with our travel partner.

Frequently asked questions

How much is a flight from Chicago to Vail?

The cheapest one-way fare we've seen recently is $322 with United Airlines, departing Tuesday, November 10, 2026.

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

November 2026 currently has the lowest fares, from $322 one way.

Are there direct flights from Chicago to Vail?

We haven't seen direct fares recently, so most journeys include at least one stop.

How long is the flight from Chicago to Vail?

The quickest journey we've seen takes about 3h 43m. Chicago and Vail are around 1,590 km apart.

Which airlines fly from Chicago to Vail?

Recent fares on this route were with United Airlines.

More cheap flights from Chicago

Compare flights to Vail from other cities →